Registration Statement by Foreign Issuer – Business Combinations (Form F-4)

As filed with the Securities and Exchange Commission on March14, 2025

Registration No. 333-

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, D.C. 20549

FORM F-4

REGISTRATION STATEMENT
UNDER

THE SECURITIES ACT OF 1933

Fairfax Financial Holdings Limited	Allied World Assurance Company Holdings, Ltd
(Exact name of registrant as specified in its charter)	(Exact name of registrant as specified in its charter)
Canada (State or other jurisdiction of incorporation or organization)	Bermuda (State or other jurisdiction of incorporation or organization)
Not Applicable (I.R.S. Employer Identification No.) 6331 (Primary Standard Industrial Classification Code Number)	98-1603554 (I.R.S. Employer Identification No.) 551112 (Primary Standard Industrial Classification Code Number)
95 Wellington Street West, Suite 800 M5J 2N7 Toronto, Ontario (416) 367-4941	27 Richmond Road Pembroke HM 08 Bermuda +1 (441) 278-5400
(Address and telephone number of Registrant's principal executive offices)	(Address and telephone number of Registrant's principal executive offices)
Fairfax (US) Inc. 401 East Corporate Drive, Suite 200 Lewisville, TX 75057 U.S.A. (972) 318-6100
(Name, Address (Including Zip Code) and Telephone Number (Including Area Code) of Agent for Service in the United States)

Copies to:

Derek Bulas  Vice President, Chief Legal Officer and Corporate Secretary Fairfax Financial Holdings Limited Suite 800, 95 Wellington St. W. Toronto, Ontario  M5J 2N7 (416) 367-4941

Mile T. Kurta, Esq. Christopher R. Bornhorst, Esq. Torys LLP 1114 Avenue of the Americas, 23rd Floor New York, New York 10036 (212) 880-6000

David Chaikof Robbie Leibel Torys LLP 79 Wellington St. W. Suite 3000 Toronto, Ontario M5K 1N2 (416) 865-0040

Approximate date of commencement of proposed sale of the securities to the public: as soon as practicable after this registration statement becomes effective.

If this Form is filed to register additional securities for an offering pursuant to Rule 462(b) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering. ¨

If this Form is a post-effective amendment filed pursuant to Rule 462(d) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering. ¨

If applicable, place an X in the box to designate the appropriate rule provision relied upon in conducting this transaction:

Exchange Act Rule 13e-4(i) (Cross-Border Issuer Tender Offer) ¨

Exchange Act Rule 14d-1(d) (Cross-Border Third-Party Tender Offer) ¨

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933.

Emerging growth company ¨

If an emerging growth company that prepares its financial statements in accordance with U.S. GAAP, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards† provided pursuant to Section 7(a)(2)(B) of the Securities Act. ☐

†	The term "new or revised financial accounting standard" refers to any update issued by the Financial Accounting Standards Board to its Accounting Standards Codification after April 5, 2012.

The registrants hereby amend this registration statement on such date or dates as may be necessary to delay its effective date until the registrants shall file a further amendment which specifically states that this registration statement shall thereafter become effective in accordance with Section 8(a) of the Securities Act, or until this registration statement shall become effective on such date as the Securities and Exchange Commission, acting pursuant to said Section 8(a), may determine.

The information in this prospectus is not complete and may be changed. We may not sell these securities until the registration statement filed with the Securities and Exchange Commission is effective. This prospectus is not an offer to sell these securities and it is not soliciting an offer to buy these securities in any state where the offer or sale is not permitted.

PRELIMINARY PROSPECTUS - SUBJECT TO COMPLETION - DATED MARCH 14, 2025

Fairfax Financial Holdings Limited

Allied World Assurance Company Holdings, Ltd

Offer to Exchange

$600,000,000 aggregate principal amount of 6.100% Senior Notes due 2055

for

$600,000,000 aggregate principal amount of 6.100% Senior Notes due 2055

that have been registered under the

Securities Act of 1933, as amended (the "Securities Act")

The Exchange Offer will expire at 5:00 p.m.,

New York City time, on     , 2025, unless extended.

Fairfax Financial Holdings Limited ("Fairfax" or the "Company") and the Company's subsidiary, Allied World Assurance Company Holdings, Ltd ("Allied World"), as co-obligors of the 6.100% Senior Notes due 2055 (the "Notes"), hereby offer, upon the terms and subject to the conditions set forth in this prospectus and the accompanying letter of transmittal, to exchange up to $600,000,000 aggregate principal amount of the outstanding Notes (the "Initial Notes") that are validly tendered and not validly withdrawn for an equal principal amount of new Notes (the "Exchange Notes") that will be registered under the Securities Act pursuant to this prospectus. This offer is referred to as the "Exchange Offer".

The terms of the Exchange Notes will be identical to the terms of the Initial Notes, except that, unlike the Initial Notes, the Exchange Notes will be freely tradable in the United States by persons not affiliated with us, will not bear legends restricting their transfer and will not contain the registration rights provisions of the Initial Notes. The payment obligations of each of Fairfax and Allied World in respect of the Notes are full and unconditional.

The Exchange Offer will expire at 5:00 p.m., New York City time, on       , 2025, unless we extend the Exchange Offer, in which case, the Exchange Offer will expire at 5:00 p.m., New York City time, on the date to which the Exchange Offer is extended (the "Expiration Date").

We will not receive any cash proceeds from the issuance of the Exchange Notes in the Exchange Offer.

No public market currently exists for the Initial Notes. We do not intend to list the Exchange Notes on any securities exchange and, therefore, no active public market is anticipated.

Before participating in the Exchange Offer, please carefully read this prospectus, including the section entitled "Risk Factors" commencing on page 10.

THESE SECURITIES HAVE NOT BEEN APPROVED OR DISAPPROVED BY THE U.S. SECURITIES AND EXCHANGE COMMISSION (THE "SEC") OR ANY CANADIAN SECURITIES REGULATORY AUTHORITY, NOR HAS THE SEC PASSED UPON THE ACCURACY OR ADEQUACY OF THIS PROSPECTUS. ANY REPRESENTATION TO THE CONTRARY IS A CRIMINAL OFFENCE.

The date of this prospectus is      , 2025

TABLE OF CONTENTS

	Page
ABOUT THIS PROSPECTUS	ii
PRESENTATION OF FINANCIAL INFORMATION	iii
DOCUMENTS INCORPORATED BY REFERENCE	iii
WHERE YOU CAN FIND MORE INFORMATION	iii
ENFORCEABILITY OF CIVIL LIABILITIES AGAINST FOREIGN PERSONS	iv
FORWARD-LOOKING INFORMATION	iv
SUMMARY	1
RISK FACTORS	10
USE OF PROCEEDS	29
CONSOLIDATED CAPITALIZATION	30
THE EXCHANGE OFFER	31
INSURANCE REGULATORY MATTERS	39
DESCRIPTION OF THE NOTES	58
CERTAIN ERISA CONSIDERATIONS	70
CERTAIN UNITED STATES FEDERAL INCOME TAX CONSIDERATIONS	72
CERTAIN BERMUDA CONSIDERATIONS	73
CERTAIN CANADIAN FEDERAL INCOME TAX CONSIDERATIONS	75
PLAN OF DISTRIBUTION	76
LEGAL MATTERS	77
INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM	78

Unless the context otherwise requires, the term "Fairfax" or the "Company" refers to Fairfax Financial Holdings Limited and its subsidiaries; the term "Allied World" refers to Allied World Assurance Company Holdings, Ltd, our majority-owned Bermuda-based holding company that, through its subsidiaries, provides global property, casualty and specialty insurance and reinsurance; the term "Brit" refers to our wholly-owned specialty insurance and reinsurance company operating in the Lloyd's market, Brit Group Holdings Limited and its subsidiaries; the term "Bryte" refers to our wholly-owned South African property and casualty insurance business, Bryte Insurance Company Ltd.; the term "Colonnade" refers to our wholly-owned Luxembourg-based insurance company, Colonnade Insurance S.A.; the term "Crum & Forster" refers to our wholly-owned U.S. property and casualty insurance business, Crum & Forster Holdings Corp. and its subsidiaries; the term "Fairfax Asia" refers to our property and casualty insurance and reinsurance business conducted through our subsidiaries in Hong Kong, Sri Lanka, Indonesia, Malaysia, Singapore and Thailand; the term "Fairfax Brasil" refers to our wholly-owned Brazilian property and casualty insurance company, Fairfax Brasil Seguros Corporativos S.A.; the term "Fairfax Latam" refers to our property and casualty insurance business conducted in Argentina, Chile, Colombia and Uruguay; the term "Fairfax Ukraine" refers to our wholly-owned property and casualty insurance business conducted through our subsidiaries in Ukraine; the term "GIG" refers to our majority-owned Kuwait company with property and casualty insurance operations in the Middle East and North Africa ("MENA") region, Gulf Insurance Group K.S.C.P.; the term "Group Re" refers to our wholly-owned reinsurance business, conducted through certain other subsidiaries; the term "Hamblin Watsa" refers to our wholly-owned investment management subsidiary, Hamblin Watsa Investment Counsel Ltd.; the term "Ki Insurance" refers to our majority-controlled fully digital and algorithmically driven Lloyd's of London syndicate, Ki Financial Limited; the term "Northbridge" refers to our wholly-owned Canadian property and casualty insurance business, Northbridge Financial Corporation and its subsidiaries; the term "Odyssey Group" refers to our majority-owned U.S. reinsurance and insurance business, Odyssey Group Holdings Inc. and its subsidiaries; the term "Polish Re" refers to our wholly-owned Polish reinsurance company, Polskie Towarzystwo Reasekuracji Spólka Akcyjna; the term "Zenith National" refers to our wholly-owned U.S. workers' compensation insurance business, Zenith National Insurance Corp. and its subsidiaries; and the term "Eurolife" refers to our majority-owned Greek life and non-life insurer, Eurolife FFH Insurance Group Holdings S.A.

ABOUT THIS PROSPECTUS

You should rely only on the information contained in or incorporated by reference in this prospectus. We have not authorized any other person to provide you with different information. If anyone provides you with different or inconsistent information, you should not rely on it. You should not assume that the information provided by this prospectus is accurate as of any date other than the date on the front of this prospectus. Our business, financial condition, results of operations and prospects may have changed since then. The Exchange Notes are being offered only in jurisdictions in which offers and sales are permitted. When the term "Notes" is used in this prospectus, the term includes the Initial Notes and the Exchange Notes unless otherwise indicated or the context otherwise requires. The terms of the Exchange Offer and Exchange Notes are summarized below and are more fully described in this prospectus.

You should read this prospectus carefully before you invest. This prospectus contains important information you should consider when making your investment decision and incorporates by reference business and financial information about us that is not included in or delivered with this prospectus. Copies of the documents incorporated by reference herein and the Indenture (as defined below) may be obtained without charge by writing to us at 95 Wellington Street West, Suite 800, Toronto, Ontario, M5J 2N7. Attention: Corporate Secretary. Our telephone number at that address is (416) 367-4941. To ensure timely delivery of requested information, you must make your request to us no later than five business days prior to the Expiration Date of the Exchange Offer.

We are making the Exchange Offer as a foreign issuer in the United States. Prospective investors should be aware that such requirements are different from those in the United States. The financial statements incorporated herein by reference have been prepared in accordance with International Financial Reporting Standards as issued by the International Accounting Standards Board ("IFRS Accounting Standards"). Thus, such financial statements may not be comparable to financial statements of U.S. companies.

Each broker-dealer that receives Exchange Notes for its own account pursuant to the Exchange Offer must acknowledge that it will deliver a prospectus meeting the requirements of the Securities Act in connection with any resale or transfer of such Exchange Notes in the United States. The letter of transmittal states that by so acknowledging and by delivering a prospectus, a broker-dealer will not be deemed to admit that it is an "underwriter" within the meaning of the Securities Act. This prospectus, as it may be amended or supplemented from time to time, may be used by a broker-dealer in connection with resales or transfers of Exchange Notes in the United States received in exchange for Initial Notes where Initial Notes were acquired by such broker-dealer as a result of market-making or other trading activities. The Company has agreed that it will make this prospectus available to any broker-dealer for use in connection with any such resale or transfer for a period that ends the earlier of (i) 180 days after the date on which the Registration Statement (as defined herein) that includes this prospectus is declared effective by the SEC, and (ii) the date on which participating broker-dealers are no longer required to deliver a prospectus in connection with market-making or other trading activities. See "Plan of Distribution".

Prospective investors should be aware that owning the Exchange Notes may subject you to tax consequences in each of the United States, Canada and Bermuda. This prospectus may not describe these tax consequences fully and such consequences for investors who are resident in, or citizens of, the United States may not be described fully herein. You should read the tax discussion in this prospectus. You should consult your own counsel, accountant or other advisors for legal, tax, business, financial and related advice regarding the Exchange Offer.

The enforcement by investors of civil liabilities under U.S. federal or state securities laws or other laws of the United States may be affected adversely by the fact that the Company and Allied World are each formed outside the United States, that most of our directors and officers, as well as certain of the experts named in this prospectus, reside outside of the United States, and that many of our assets and the assets of such persons are located outside the United States.

PRESENTATION OF FINANCIAL INFORMATION

As the majority of our operations are in the United States or conducted in U.S. dollars, we report our consolidated financial statements in U.S. dollars in order to provide more meaningful information to users of our financial statements. Except where otherwise indicated, all dollar amounts in this prospectus are expressed in U.S. dollars, references to "$", "US$" and "dollars" are to U.S. dollars and references to "Cdn$" are to Canadian dollars.

We have prepared our audited consolidated financial statements in accordance with IFRS Accounting Standards.

DOCUMENTS INCORPORATED BY REFERENCE

The SEC allows us to incorporate by reference the information we file with them, which means that we can disclose important information to you by referring you to those documents. We incorporate by reference the following documents we have filed with the SEC:

(a)

our Annual Report on Form 40-F for the year ended December 31, 2024, filed with the SEC on March 7, 2025 (the "Annual Report"); and

(b)

our management proxy circular dated March 7, 2024 in connection with the annual meeting of shareholders to be held on April 10, 2025, filed with the SEC on our Current Report on Form 6-K on March 7, 2024.

In addition, we incorporate by reference the future filings we make with the SEC under Section 13(a), 13(c), or 15(d) of the Securities Exchange Act of 1934, as amended (the "Exchange Act"), after (i) the initial filing date of the registration statement and prior to effectiveness of the registration statement and (ii) the date of this prospectus until the date we consummate the Exchange Offer. Any Form 6-K that we file or furnish that is identified in such form as being incorporated by reference into the registration statement of which this prospectus forms a part, in each case, subsequent to the date of this prospectus, are incorporated by reference into this prospectus as of the date of the filing of such documents.

Any statement contained in a document incorporated or deemed to be incorporated by reference in this prospectus shall be deemed to be modified or superseded for the purposes of this prospectus to the extent that a statement contained in this prospectus, or in any other subsequently filed document which also is or is deemed to be incorporated by reference herein, modifies or supersedes that statement. The modifying or superseding statement need not state that it has modified or superseded a prior statement or include any other information set forth in the document that it modifies or supersedes.

WHERE YOU CAN FIND MORE INFORMATION

We have filed a registration statement on Form F-4 (the "Registration Statement") with the SEC regarding the Exchange Offer, which includes this prospectus as part of such Registration Statement. For further information about us and the Exchange Offer, you should refer to the Registration Statement and its exhibits. This prospectus summarizes material provisions of agreements and other documents to which we refer you. Copies of these agreements and documents have been included as exhibits to the Registration Statement and you are encouraged to read these in their entirety.

The SEC maintains an Internet website that contains reports and other information about issuers who file reports with the SEC. The address of that website is www.sec.gov. The Company also files information, such as periodic reports and financial information, with the Canadian Securities Administrators, which may be accessed at www.sedarplus.ca. These filings can also be found on the Company's website, which may be accessed at www.fairfax.ca. The information on our website is not incorporated by reference into this prospectus and should not be considered a part of this prospectus, and the reference to our website in this prospectus is an inactive textual reference only.

The Company is currently subject to the periodic reporting and other informational requirements of the Exchange Act and in accordance therewith files reports and other information with the SEC. However, the Company is a "foreign private issuer" as defined in Rule 405 of the Securities Act and therefore is not required to comply with Exchange Act provisions regarding the furnishing and content of proxy statements, and its officers and directors are exempt from the reporting and short swing profit recovery provisions contained in Section 16 of the Exchange Act. Additionally, under a multijurisdictional disclosure system adopted by the United States and Canada, public reporting documents and other information (including financial information) have been prepared in accordance with the disclosure requirements of the provincial and territorial securities regulatory authorities of Canada, which differ from those in the United States.

As described in "Description of the Notes" in this prospectus, on July 19, 2024, Allied World became a co-obligor of the Notes that are the subject of this Exchange Offer, and the Company remains a full and unconditional obligor in respect of the Notes for all purposes under the Indenture. Accordingly, Allied World is exempt from the reporting requirements of the Exchange Act in reliance on Rule 12h-5 thereunder. Disclosures required by Rules 3-10 and 13-01 of Regulation S-X have been included in Management's Discussion and Analysis included in the Annual Report, which is incorporated by reference herein.

ENFORCEABILITY OF CIVIL LIABILITIES AGAINST FOREIGN PERSONS

The Company is a corporation organized under the laws of Canada and some of its assets are located in, and most of its directors and officers are residents of, Canada. Further, Allied World is incorporated under the laws of Bermuda, and most of its directors and officers, and its assets, are located outside of the United States. As a result, it may be difficult for U.S. investors to effect service of process in the United States upon the Company's or Allied World's directors or officers, or to realize upon judgments of U.S. courts predicated upon civil liability of such directors or officers under U.S. securities laws.

We have been advised by our counsel that a monetary judgment of a U.S. court predicated solely upon civil liability provisions of U.S. federal securities laws would likely be enforceable in Canada if the U.S. court in which judgment was obtained had a basis for jurisdiction that was recognized by a Canadian court for such purposes. We have also been advised by our counsel that it is less certain that an original action could be commenced in Canada on the basis of liability predicated solely upon such laws.

Each of the Company and Allied World has irrevocably appointed CT Corporation System, 28 Liberty Street, New York, New York 10005, as its U.S. agent for service of process in any legal action or proceeding arising out of or relating to the Indenture and the Exchange Notes for actions brought under U.S. federal or state securities laws or for actions brought by either trustee or for any actions arising out of or related to the Indenture or the Exchange Notes in any New York court, and has irrevocably submitted to the jurisdiction of the New York courts for such purposes.

In addition, each of the Company and Allied World has appointed Fairfax (US) Inc., 401 East Corporate Drive, Suite 200 Lewisville, Texas 75057, as our U.S. agent for service of process in connection with the Registration Statement.

FORWARD-LOOKING INFORMATION

This prospectus contains "forward-looking statements" and "forward-looking information" (collectively, "forward-looking information") within the meaning of applicable securities laws. Any statements made by us or on our behalf may include forward-looking information that reflect our current views with respect to future events and financial performance. The words "believe," "anticipate," "project," "expect," "plan," "intend," "predict," "estimate," "will likely result," "will seek to" or "will continue" and similar expressions identify forward-looking information. This forward-looking information relates to, among other things, our plans and objectives for future operations and underwriting profits. We caution readers not to place undue reliance on this forward-looking information, which speak only as of their dates. We are under no obligation to update or alter such forward-looking information as a result of new information, future events or otherwise, except as may be required by applicable securities laws. This forward-looking information is subject to known and unknown risks, uncertainties and other factors that could cause our actual results, performance or achievements to be materially different from any future results, performance or achievements expressed or implied by such forward-looking information. These uncertainties and other factors, which we describe in more detail elsewhere in this prospectus, or in documents incorporated by reference herein, include, but are not limited to:

·

our ability to complete acquisitions and other strategic transactions on the terms and timeframes contemplated, and to achieve the anticipated benefits therefrom;

·

a reduction in net earnings if our loss reserves are insufficient;

·

underwriting losses on the risks we insure that are higher than expected;

·

the occurrence of catastrophic events with a frequency or severity exceeding our estimates;

·

changes in market variables, including unfavorable changes in interest rates, foreign exchange rates, equity prices and credit spreads, which could negatively affect our operating results and investment portfolio;

·

the cycles of the insurance market and general economic conditions, which can substantially influence our and our competitors' premium rates and capacity to write new business;

·

insufficient reserves for asbestos, environmental and other latent claims;

·

exposure to credit risk in the event our reinsurers fail to make payments to us under our reinsurance arrangements;

·

exposure to credit risk in the event our insureds, insurance producers or reinsurance intermediaries fail to remit premiums that are owed to us or failure by our insureds to reimburse us for deductibles that are paid by us on their behalf;

·

our inability to maintain our long-term debt ratings, the inability of our subsidiaries to maintain financial or claims paying ability ratings and the impact of a downgrade of such ratings on derivative transactions that we or our subsidiaries have entered into;

·

risks associated with implementing our business strategies;

·

the timing of claims payments being sooner or the receipt of reinsurance recoverables being later than anticipated by us;

·

risks associated with any use we may make of derivative instruments;

·

the failure of any hedging methods we may employ to achieve their desired risk management objective;

·

a decrease in the level of demand for insurance or reinsurance products, or increased competition in the insurance industry;

·

the impact of emerging claim and coverage issues or the failure of any of the loss limitation methods we employ;

·

our inability to access cash of our subsidiaries;

·

an increase in the amount of capital that we and our subsidiaries are required to maintain and our inability to obtain required levels of capital on favorable terms, if at all;

·

the loss of key employees;

·

our inability to obtain reinsurance coverage in sufficient amounts, at reasonable prices or on terms that adequately protect us;

·

the passage of legislation subjecting our businesses to additional adverse requirements, supervision or regulation, including additional tax regulation, in the United States, Bermuda, Canada or other jurisdictions in which we operate;

·

risks associated with applicable laws and regulations relating to sanctions and corrupt practices in foreign jurisdictions in which we operate;

·

risks associated with government investigations of, and litigation and negative publicity related to, insurance industry practice or any other conduct;

·

risks associated with political and other developments in foreign jurisdictions in which we operate;

·

risks associated with legal or regulatory proceedings or significant litigation;

·

failures or security breaches of our computer and data processing systems;

·

the influence exercisable by our significant shareholder;

·

adverse fluctuations in foreign currency exchange rates;

·

our dependence on independent brokers over whom we exercise little control;

·

financial reporting risks associated with IFRS 17 (as defined below);

·

financial reporting risks relating to deferred taxes associated with amendments to IAS 12 (as defined below);

·

impairment of the carrying value of our goodwill, indefinite-lived intangible assets or investments in associates;

·

our failure to realize deferred income tax assets;

·

technological or other change that adversely impacts demand, or the premiums payable, for the insurance coverages we offer;

·

disruptions of our information technology systems;

·

assessments and shared market mechanisms that may adversely affect our insurance subsidiaries;

·

risks associated with the conflicts in Ukraine and Israel and the development of other geopolitical events and economic disruptions worldwide; and

·

risks associated with tariffs, trade restrictions, or other regulatory measures imposed by domestic or foreign governments that may, directly or indirectly, affect our business.

See the "Risk Factors" section of this prospectus and the documents incorporated by reference into this prospectus for a further discussion of these risks and uncertainties.

Should one or more risk, uncertainty, contingency or other factor materialize or should any factor or assumption prove incorrect, actual results could vary materially from those expressed or implied in the forward-looking information. Accordingly, you should not place undue reliance on forward-looking information. We do not assume any obligation to update or revise any forward-looking information after the date of this prospectus or to explain any material difference between subsequent actual events and any forward-looking information, except as required by applicable law.

RISK FACTORS

An investment in the Exchange Notes involves risk. You should carefully consider the following risk factors, as well as the information contained in and incorporated by reference into this prospectus, including the risks described in our annual report on Form 40-F for the year ended December 31, 2024, which is incorporated by reference in this prospectus, before deciding whether to participate in the Exchange Offer. Any of these risks could materially adversely affect our business, financial condition or results of operations and could materially adversely affect your investment in the Exchange Notes. Additional risks and uncertainties not currently known to us or that we currently deem to be immaterial may also materially and adversely affect our business, financial condition or results of operations.

Risk Factor Summary

Risk Factors Relating to Our Business

	·	If our actual claims exceed our claim reserves, our financial condition and results of operations could be adversely affected.
	·	Unpredictable catastrophic events could reduce our net earnings.
	·	Our portfolio holdings are subject to fluctuations in the market, which could negatively affect their value. If we are unable to realize our investment objectives, our business, financial condition or results of operations may be adversely affected.
	·	Our business could be harmed because of our potential exposure to asbestos, environmental and other latent claims.
	·	We cannot assure you that our reinsurers and certain insureds will pay us on a timely basis or at all.
	·	We are exposed to credit risk in the event our insureds, insurance producers or reinsurance intermediaries fail to remit premiums that are owed to us or failure by our insureds to reimburse us for deductibles that are paid by us on their behalf.
	·	If our insurance and reinsurance subsidiaries are unable to maintain financial strength ratings, it may be more difficult for them to renew policies, retain business or write new business and a downgrade of our credit rating may affect the cost and availability of financing.
	·	We may not be successful in achieving our strategic objectives.
	·	We may hold derivative instruments, which could result in significant losses and volatility of our operating results.
	·	The methods we employ to hedge risks associated with certain of our financial instruments may fail to achieve their desired risk management objectives.
	·	We operate in a highly competitive environment, which could make it more difficult for us to attract and retain business.
	·	Emerging claim and coverage issues, or the failure of any of the loss limitation methods we employ, could adversely affect our business, financial condition or results of operations.
	·	We are a holding company and may not have access to the cash that is needed to meet our financial obligations.
	·	Our inability to obtain additional capital in the future as required could have a material adverse effect on our financial condition.
	·	Our business could be adversely affected by the loss of one or more key employees.
	·	We may be unable to obtain reinsurance coverage at reasonable prices or on terms that adequately protect us.
	·	Our operations could be adversely affected as a result of regulatory, political, economic or other influences in the insurance and reinsurance industries.
	·	Our international business is subject to applicable laws and regulations relating to sanctions and foreign corrupt practices, the violation of which could adversely affect our operations.
	·	Certain business practices of the insurance industry have been the subject of negative publicity and investigations by government authorities and the subject of class action litigation.
	·	Political and other developments in foreign jurisdictions in which we operate could adversely affect our business and assets.
	·	We may be subject to regulatory proceedings or significant litigation, which will be expensive and time consuming and, if decided against us, could require us to pay substantial judgments or settlements.
	·	Our significant shareholder may substantially influence our direction and operations.
	·	We may be adversely affected by foreign currency fluctuations.
	·	We rely on independent brokers over whom we exercise little control, which exposes us to certain risks.

	·	Financial reporting risks associated with IFRS 17 (as defined below).
	·	Financial reporting risks relating to deferred taxes associated with amendments to IAS 12.
	·	To the extent that the value of our goodwill, indefinite-lived intangible assets or investments in associates is impaired, we are required to write down the value of such assets.
	·	Our failure to realize deferred income tax assets could lead to a write-down or tax authorities may take differing positions from ours, either of which could adversely affect our results of operations.
	·	Canadian or foreign tax laws, or the interpretation thereof, could change in a manner that adversely affects us.
	·	Technological or other changes could adversely impact demand, or the premiums payable, for the insurance coverages we offer.
	·	Assessments and other surcharges for guaranty funds and second-injury funds and other mandatory pooling arrangements may reduce the profitability of our insurance subsidiaries.

Risk Factors Relating to the Exchange Notes

	·	The market value of the Exchange Notes may be affected by changes in credit ratings.
	·	The Exchange Notes are effectively subordinated to the indebtedness of our subsidiaries (other than Allied World).
	·	We may incur additional indebtedness that may adversely affect our ability to meet our financial obligations under the Exchange Notes.
	·	Holders of the Exchange Notes may not be protected in the event we are involved in a highly leveraged transaction, reorganization, restructuring, merger or similar transaction in the future.
	·	The price at which you may be able to resell your Exchange Notes may be adversely affected by factors that are beyond our control.
	·	There may be no active market for the Exchange Notes.
	·	The Exchange Notes may be redeemed prior to maturity.

Risk Factors Relating to the Exchange Offer

	·	If you do not validly tender your Initial Notes, you will not receive Exchange Notes in the Exchange Offer, and the resale restrictions applicable to the Initial Notes will continue to apply to those Initial Notes that are not validly exchanged.
	·	The market for the Initial Notes may be significantly more limited after the Exchange Offer.
	·	The Exchange Offer may be terminated, cancelled or delayed.
	·	Some persons who participate in the Exchange Offer must deliver a prospectus in connection with resales of the Exchange Notes.

General Risk Factors

	·	Our computer and data processing systems may fail or be perceived to be insecure, which could adversely affect our business and damage our customer relationships.
	·	A disruption of our information technology systems could significantly affect our business.
	·	We may continue to be adversely impacted by the conflicts in Ukraine and Israel and the development of other geopolitical events and economic disruptions worldwide.

Risk Factors Relating to Our Business

If our actual claims exceed our claim reserves, our financial condition and results of operations could be adversely affected.

We maintain reserves to cover our estimated ultimate unpaid liability for losses and loss adjustment expenses with respect to insurance and reinsurance policies underwritten by the Company at the end of each reporting period. Our success is dependent upon our ability to accurately assess the risks associated with the businesses that we reinsure or insure. If we fail to accurately assess the risks we assume, we may fail to establish appropriate premium rates and our reserves may be inadequate to cover our losses. This could adversely affect our net earnings and financial condition in future reporting periods.

Reserves do not represent an exact calculation of liability, but instead represent estimates at a point in time involving actuarial and statistical projections of our expectations of the ultimate settlement of claims incurred and the associated claims adjustment expense. Establishing an appropriate level of claims reserves is an inherently uncertain process. We utilize both proprietary and commercially available actuarial models, as well as historical insurance industry loss development patterns, to assist in the establishment of appropriate claim reserves.

In contrast to casualty losses, which frequently can be determined only through lengthy and unpredictable litigation, property losses tend to be reported promptly and usually are settled within a shorter period of time. Nevertheless, for both casualty and property losses, actual claims and claim expenses ultimately paid may deviate, perhaps substantially, from the reserve estimates reflected in our financial statements. Variables in the reserve estimation process can be affected by both internal and external events, such as changes in claims handling procedures, economic and social inflation, legal trends and legislative changes. Many of these items are not directly quantifiable, particularly on a prospective basis.

If our claim reserves are determined to be inadequate, we will be required to increase claim reserves with a corresponding reduction in our net earnings in the period in which the deficiency is rectified. It is possible that claims in respect of events that have occurred could exceed our claim reserves and have a material adverse effect on our results of operations in a particular period and/or our financial condition.

Even though most insurance contracts have policy limits, the nature of property and casualty insurance and reinsurance is such that losses can exceed policy limits for a variety of reasons and could significantly exceed the premiums received on the underlying policies. When this occurs, our financial results are adversely affected.

Unpredictable catastrophic events could reduce our net earnings.

Our insurance and reinsurance operations expose us to claims arising out of catastrophes. We have experienced, and will in the future experience, catastrophe losses that may materially reduce our profitability or harm our financial condition. Catastrophes can be caused by various events, including natural events such as hurricanes, windstorms, earthquakes, tornadoes, hailstorms, severe winter weather and fires, and unnatural events such as terrorist attacks and riots. Weather-related losses have increased in recent years, in part due to climate change, which represents a significant emerging risk that will continue to increase the inherent unpredictability of both the frequency and severity of weather-related catastrophe losses.

The extent of losses from a catastrophe is a function of both the total amount of insured exposure in the area affected by the event and the severity of the event. Most catastrophes are restricted to small geographic areas; however, hurricanes, windstorms and earthquakes may produce significant damage in large, heavily populated areas. Catastrophes can cause losses in a variety of property and casualty lines, including losses relating to business interruptions occurring in the same geographic area as the catastrophic event or in the other geographic areas. It is possible that a catastrophic event or multiple catastrophic events could have a material adverse effect upon our financial condition, profitability or cash flows.

We believe that increases in the value and geographic concentration of insured property, and higher construction costs due to labor and raw material shortages following a significant catastrophic event, could increase the number and severity of claims from catastrophic events in the future.

Our portfolio holdings are subject to fluctuations in the market which could negatively affect their value. If we are unable to realize our investment objectives, our business, financial condition or results of operations may be adversely affected.

Investment returns are an important part of our overall profitability and our operating results depend in part on the performance of our investment portfolio. We hold bonds and other debt instruments, common stocks, preferred stocks and derivative instruments in our portfolio.

Accordingly, fluctuations in the fixed income or equity markets could have an adverse effect on our financial condition, profitability or cash flows. We derive our investment income from interest and dividends, together with net gains or losses on investments. The portion derived from net gains or losses on investments generally fluctuates from year to year and is typically a less predictable source of investment income than interest and dividends, particularly in the short term.

The retuon our portfolio and the risks associated with our investments are also affected by our asset mix, which can change materially depending on market and industry-specific conditions and the creditworthiness of our counterparties.

The uncertainty around the ultimate amount and the timing of our claim payments may force us to liquidate securities, which may cause us to incur losses. If we structure our investments improperly relative to our liabilities, we may be forced to liquidate investments prior to its maturity or planned exit date at a significant loss to cover such liabilities. Realized and unrealized investment losses resulting from a decline in value could significantly decrease our net earnings.

The ability to achieve our investment objectives is affected by general economic conditions that are beyond our control. General economic conditions can adversely affect the markets for interest rate sensitive securities, including the extent and timing of investor participation in such markets, the level and volatility of interest rates and, consequently, the value of fixed income securities. Interest rates are highly sensitive to many factors, including governmental monetary policies, domestic and international economic and political conditions, trade restrictions and other factors beyond our control. General economic conditions, stock market conditions, environmental conditions, climate change, policy changes and many other factors can also adversely affect the equity markets and, consequently, the value of the equity securities we own.

Inflation rates in jurisdictions that we operate or invest in have increased significantly in recent years, rising above the target inflation rate ranges set by governing central banks. A significant portion of the upward pressure on prices has been attributed to the rising costs of labor, energy, food, motor vehicles and housing, as well as overall challenges involved in managing the economy throughout the COVID-19 pandemic and continuing global supply-chain disruptions. Inflationary increases may or may not be transitory and future inflation may be impacted by reductions or increases in labor market constraints, supply-chain disruptions, tariffs and commodity prices. To address rising inflation, central banks across the world have simultaneously increased interest rates, which have remained at elevated levels despite recent easing. Inflation and the corresponding rise in interest rates in recent years have not had a material adverse effect on our business, however, any further sustained upward trajectory in the inflation rate and corresponding increases to interest rates may have an adverse impact on our operating results and our investments. We continue to monitor inflationary pressures in the jurisdictions we operate or invest in and assess any potential effects on our operating results and investments.

In addition, defaults by third parties who fail to pay or perform on their obligations could reduce our investment income and net gains on investment or result in investment losses. The cycles of the insurance and reinsurance industries, general economic conditions and industry-specific factors relating to our asset mix may cause fluctuations in our operating results.

Historically, we have experienced fluctuations in operating results due to competition, frequency or severity of both catastrophic and non-catastrophic events, levels of capital and underwriting capacity, general economic conditions and other factors. Demand for insurance and reinsurance is influenced significantly by underwriting results of primary insurers and prevailing general economic conditions. Factors such as changes in the level of employment, wages, consumer spending, business investment and government spending, the volatility and strength of the global capital markets and inflation or deflation, all affect the business and economic environment and, ultimately, the demand for insurance and reinsurance products, and therefore may affect our net earnings, financial position or cash flows.

The property and casualty insurance business historically has been characterized by periods of intense price competition due to excess underwriting capacity, as well as periods when shortages of underwriting capacity have permitted attractive premium levels. We expect to continue to experience the effects of this cyclicality, which, during down periods, could significantly reduce the amount of premium we write and could harm our financial condition, profitability or cash flows.

In the reinsurance industry, the supply of reinsurance is related to prevailing prices and levels of underwriting capacity surplus that, in turn, may fluctuate in response to changes in rates of retubeing realized in the broader capital markets. If premium rates change or other reinsurance policy terms and conditions change expanding coverage, particularly if the present level of demand for reinsurance decreases because insurers require less reinsurance or the level of supply of reinsurance increases as a result of capital provided by existing reinsurers or alternative forms of reinsurance capacity enter the market, the profitability of our reinsurance business could be adversely affected.

Our business could be harmed because of our potential exposure to asbestos, environmental and other latent claims.

We have established loss reserves for asbestos and environmental and other latent claims that represent our best estimate of ultimate claims and claims adjustment expenses based upon all known facts and current law. As a result of significant issues surrounding liabilities of insurers, risks inherent in major litigation and diverging legal interpretations and judgments in different jurisdictions, actual liability for these types of claims could exceed the loss reserves set by us by an amount that could be material to our financial condition, profitability or cash flows in future periods.

We cannot assure you that our reinsurers and certain insureds will pay us on a timely basis or at all.

Most insurance and reinsurance companies reduce their exposure to any individual claim by reinsuring amounts in excess of their maximum desired retention. Reinsurance is an arrangement in which an insurer, called the cedent, transfers insurance risk to another insurer, called the reinsurer, which accepts the risk in retufor a premium payment. This third-party reinsurance does not relieve us, as a cedent, of our primary obligation to the insured. Recoverables from reinsurers balances reported in reinsurance contract assets held may become uncollectible due to reinsurer solvency and credit concerns, due to the potentially long time period over which claims may be paid and the resulting recoveries may be received from the reinsurers, or due to policy disputes. If reinsurers are unwilling or unable to pay us amounts due under reinsurance contracts, we will incur unexpected losses and our results of operations, financial condition and cash flows could be adversely affected.

We are exposed to credit risk in the event our insureds, insurance producers or reinsurance intermediaries fail to remit premiums that are owed to us or failure by our insureds to reimburse us for deductibles that are paid by us on their behalf.

Various insurance intermediaries collect premiums from our customers, which they then remit to us. We may be required to provide insurance coverage even if an intermediary fails to pay us. In addition, we write certain insurance policies, such as large deductible policies (policies where the insured retains a specific amount of any potential loss), in which the insured must reimburse us for certain losses. Accordingly, we bear credit risk on these policies and cannot assure you that intermediaries of our insureds will pay us on a timely basis or at all.

If our insurance and reinsurance subsidiaries are unable to maintain financial strength ratings, it may be more difficult for them to renew policies, retain business or write new business and a downgrade of our credit rating may affect the cost and availability of financing.

Financial strength and credit ratings by major North American rating agencies are important factors in establishing competitive position for insurance and reinsurance companies. Third-party rating agencies assess and rate the claims-paying ability of reinsurers and insurers based upon the criteria of such rating agencies. Periodically the rating agencies evaluate our insurance and reinsurance subsidiaries to confirm that they continue to meet the criteria of the ratings previously assigned to them. The claims-paying ability ratings assigned by rating agencies to insurance or reinsurance companies represent independent opinions of financial strength and ability to meet policyholder obligations. A downgrade in these ratings could lead to a significant reduction in the number of insurance policies our insurance subsidiaries write and could cause early termination of contracts written by our reinsurance subsidiaries or a requirement for them to post collateral at the direction of their counterparties.

A downgrade in our long-term debt ratings by the major rating agencies could require us and/or our subsidiaries to accelerate our or their cash settlement obligations for certain derivative transactions to which we or they are a party and could result in the termination of certain other derivative transactions. In addition, a downgrade of our credit rating may affect the cost and availability of unsecured financing. Ratings are subject to periodic review at the discretion of each respective rating agency and may be revised downward or revoked at their sole discretion. Rating agencies may also increase their scrutiny of rated companies, revise their rating standards or take other action. We have dedicated personnel that manage our relationships with our various rating agencies, however there can be no assurance that these activities will avoid a downgrade by rating agencies. We can provide no assurance that we will not experience such downgrades in the future.

We may not be successful in achieving our strategic objectives.

We may periodically and opportunistically acquire other insurance and reinsurance companies or execute other strategic initiatives developed by management. Although we undertake due diligence prior to the completion of an acquisition, it is possible that unanticipated factors could arise and there is no assurance that the anticipated financial or strategic objectives following an integration effort or the implementation of a strategic initiative will be achieved, which could adversely affect our financial condition, profitability or cash flows.

We may periodically explore opportunities to make strategic investments in all or part of certain businesses or companies. Acquisitions may involve a number of special risks, including failure to retain key personnel, unanticipated events or circumstances, increased exposure to industry-specific and credit risks and potential for legal liabilities and incurrence of indebtedness to finance the transactions, some or all of which could have a material adverse effect on our business, results of operations and financial position. We cannot be sure that any acquired businesses will achieve the anticipated revenues, income and synergies, or that acquisitions of loan portfolios will perform as anticipated. Failure on our part to manage our acquisition strategy successfully could have a material adverse effect on our business, results of operations and financial position. We cannot be sure that we will be able to identify appropriate targets, profitably manage additional businesses, investments and/or portfolios or successfully integrate any acquired business into our operations.

The strategies and performance of our subsidiaries, and the alignment of those strategies throughout our organization, are regularly assessed through various processes undertaken by senior management and our Board of Directors, however there can be no assurance that these efforts will be successful to mitigate the risks identified above.

We may hold derivative instruments, which could result in significant losses and volatility of our operating results.

We may hold significant investments in derivative instruments and the market value and liquidity of these investments are volatile or extremely volatile and may vary dramatically up or down in short periods, and these circumstances may be exacerbated by adverse economic conditions, fluctuations in interest rates and the volatility in the public markets. We may use derivative instruments to manage or reduce risks or as a cost-effective way to synthetically replicate the investment characteristics of an otherwise permitted investment. The market value and liquidity of these instruments are volatile and may vary dramatically up or down in short periods, and their ultimate value will therefore only be known upon their disposition or settlement. If the counterparties to our derivative instruments fail to honor their obligations under the derivative instrument agreements, we may lose the value of our derivative instruments. This failure could have an adverse effect on our financial condition and results of operations.

Our use of derivative instruments is governed by our investment policies and exposes us to a number of risks, including credit risk, interest rate risk, liquidity risk, inflation risk, equity market risk, foreign currency risk, basis risk and counterparty risk. If the counterparties to our derivative instruments fail to honor their obligations under the derivative instrument agreements, we may lose the value of our derivative instruments, which failure could have an adverse effect on our financial condition, profitability or cash flows.

We endeavor to limit counterparty risk through diligent selection of counterparties to our derivative instruments and through the terms of agreements negotiated with our counterparties. Pursuant to these agreements, we and the counterparties are required to deposit eligible collateral in collateral accounts for either the benefit of us or the counterparty depending on the then current fair value or change in the fair value of the derivative contract.

We may not be able to realize our investment objectives with respect to derivative instruments, which could have a material adverse effect on our financial position, profitability or cash flows.

The methods we employ to hedge risks associated with certain of our financial instruments may fail to achieve their desired risk management objectives.

We may use derivative instruments from time to time to manage or reduce our exposure to credit risk and various market risks, including interest rate risk, equity market risk, inflation/deflation risk and foreign currency risk. Our hedging strategies may be implemented to hedge risks associated with a specific financial instrument, asset or liability or at a macro level to hedge systemic financial risk and the impact of potential future economic crisis and credit related problems on our operations and the value of our financial assets. Credit default swaps, total retuswaps and consumer price index-linked derivative instruments have been used in the past to hedge our macro-level risks.

Our derivative instruments may expose us to basis risk. Basis risk is the risk that the fair value or cash flows of derivative instruments applied as economic hedges will not experience changes in exactly the opposite directions from those of the underlying hedged exposure. This imperfect correlation may adversely impact the net effectiveness of the hedge and may diminish the financial viability of maintaining the hedging strategy and therefore adversely impact our financial condition, profitability or cash flows.

We regularly monitor the prospective and retrospective effectiveness of our economic hedging instruments and will adjust the amount and/or type of hedging instruments as required to achieve our risk management goals.

We operate in a highly competitive environment which could make it more difficult for us to attract and retain business.

The property and casualty insurance industry and the reinsurance industry are both highly competitive and will likely remain highly competitive in the foreseeable future. Competition in these industries is based on many factors, including premiums charged and other terms and conditions offered, products and services provided, commission structure, financial ratings assigned by independent rating agencies, speed of claims payment, reputation, selling effort, perceived financial strength and the experience of the insurer or reinsurer in the line of insurance or reinsurance to be written. We compete, and will continue to compete, with a large number of Canadian, U.S. and foreign insurers and reinsurers, as well as certain underwriting syndicates, some of which have greater financial, marketing and management resources than we do. In addition, some financial institutions, such as banks, are now able to offer services similar to those offered by our reinsurance subsidiaries while in recent years, capital market participants have also created alternative products that are intended to compete with reinsurance products.

Consolidation within the insurance industry could result in insurance and reinsurance market participants using their market power to implement price reductions. If competitive pressures compel us to reduce our prices, our operating margins would decrease. As the insurance industry consolidates, competition for customers could become more intense and the importance of acquiring and properly servicing each customer could become greater, causing us to incur greater expenses relating to customer acquisition and retention and further reducing operating margins.

Emerging claim and coverage issues, or the failure of any of the loss limitation methods we employ, could adversely affect our business, financial condition or results of operations.

The liability for incurred claims for insurance contracts is an estimate and may be found to be deficient, perhaps very significantly, in the future as a result of unanticipated frequency or severity of claims or for a variety of other reasons including unpredictable judicial rulings, expansion of insurance coverage to include exposures not contemplated at the time of policy issue (as was the case with asbestos and pollution exposures), extreme weather events, civil unrest and pandemics. Unanticipated developments in the law as well as changes in social and environmental conditions could result in unexpected claims for coverage under insurance and reinsurance contracts. With respect to casualty lines of business, these legal, social and environmental changes may not become apparent until some time after their occurrence.

The full effects of these and other unforeseen emerging claim and coverage issues are extremely hard to predict and could harm our business. As a result, the full extent of our liability under our coverages, and in particular our casualty insurance policies and reinsurance contracts, may not be known until many years after a policy or contract is issued. Our exposure to this uncertainty is greatest in our "long-tail" casualty lines of business where claims can typically be made for many years, rendering them more susceptible to these trends than in the property insurance lines of business, which are more typically "short-tail". In addition, we could be adversely affected by the growing trend of plaintiffs targeting participants in the property-liability insurance industry in purported class action litigation relating to claims handling and other practices.

Although loss exposure is limited by geographic diversification and we seek to limit our loss exposure by employing a variety of policy limits and other terms and conditions and through prudent underwriting of each program written, there can be no assurance that such measures will be successful in limiting our loss exposure.

Fairfax and Allied World are holding companies and may not have access to the cash that is needed to meet their payment obligations under the Notes.

Fairfax and Allied World are both holding companies that conduct substantially all of their business through their subsidiaries and receive substantially all of their earnings from such subsidiaries. We control the operating insurance and reinsurance companies, each of which must comply with applicable insurance regulations of the jurisdictions in which it operates. Each insurance and reinsurance operating company must maintain reserves for losses and loss adjustment expenses to cover the risks it has underwritten. The reserves of one of our insurance or reinsurance companies are not available to be applied against the risks underwritten by other of such companies. The financial condition and results of operations of each of the insurance and reinsurance companies we control are included in our consolidated financial statements and, generally, losses incurred by any of our companies directly impact our consolidated results. Although a severe loss incurred by one insurance or reinsurance company should not have any adverse effect on any of our other insurance or reinsurance companies, such loss, even though not material to us when our financial condition is viewed as a whole, could have an adverse effect on us because it could affect adversely how our other insurance or reinsurance companies are treated by others, including rating agencies and insurance regulators.

In the event of the insolvency or liquidation of a subsidiary, following payment by such subsidiary of its liabilities, the subsidiary may not have sufficient remaining assets to make payments to us as a shareholder or otherwise, or may be restricted from doing so by insurance regulatory authorities, receiver, administrator or supervising court, as applicable. In the event of a default by a subsidiary under a credit agreement or other indebtedness, its creditors could accelerate the debt, prior to such subsidiary distributing amounts to us that we could use to make payments on our outstanding debt.

Although substantially all of our operations are conducted through our subsidiaries, none of our subsidiaries are obligated to make funds available to us for the payment of principal and interest on our outstanding debt (other than Allied World, which is a Co-Obligor). Accordingly, our ability to meet financial obligations, including the ability to make payments on outstanding debt, is largely dependent on the distribution of earnings from our subsidiaries. The ability of subsidiaries to pay dividends or distributions in the future will depend on their statutory surplus, on earnings and on regulatory restrictions. Our subsidiaries may incur additional indebtedness that may severely restrict or prohibit the making of distributions, the payment of dividends or the making of loans by our subsidiaries to the Company. We cannot assure you that the agreements governing the current and future indebtedness of our subsidiaries will permit our subsidiaries to provide us with sufficient dividends, distributions or loans to meet our financial obligations, including to fund payments on our outstanding debt when due. Dividends, distributions or returns of capital to us are subject to restrictions set forth in the applicable laws and regulations of the countries where the relevant company operates (principally the U.S., Canada, the United Kingdom and Bermuda) (in each case, including the provinces, states or other jurisdictions therein) and is affected by the subsidiaries' credit agreements and indentures, rating agencies, the discretion of insurance regulatory authorities and capital support agreements with subsidiaries. Although we strive to be soundly financed and maintain high levels of liquid assets, an inability of subsidiaries to pay dividends could have a negative impact on our liquidity and ability to meet our obligations.

Our inability to obtain additional capital in the future as required could have a material adverse effect on our financial condition.

We are required to maintain specified levels of capital to satisfy regulatory requirements, maintain our credit ratings and meet conditions in various commercial and financing agreements. These requirements and the methods for calculating capital may change as regulators or rating agencies revise their models. Our future capital requirements depend on many factors, including our ability to successfully write new business and to establish premium rates and reserves at levels sufficient to cover losses. Our liquidity needs could increase materially and rapidly for a variety of reasons, many of which are outside of our control. For example, our insurance subsidiaries may require us to make additional investments in the event that their regulatory capital levels decline below desired levels as a result of net investment losses and future impairments of investment securities, catastrophe losses or other conditions, including changes in regulatory capital requirements. To the extent that the funds generated by our business are insufficient to fund future operations, we may need to raise additional funds through equity or debt financings. Any equity or debt financing, if available at all, may be on terms that are not favorable to us, including being subject to higher interest rates. The cost and availability of debt financing is affected by credit ratings. Our ability to raise additional capital may be adversely affected by our credit ratings. If we cannot obtain adequate capital or if we fail to refinance our existing debt as it comes due, our business, financial condition and profitability would be materially adversely affected. In addition, certain of our financings are, and future financings may be exposed to, floating interest rate risks, and if interest rates increase, an increased proportion of our cash flow may be required to service indebtedness.

Our ability and/or the ability of our subsidiaries to obtain additional financing for working capital, capital expenditures or acquisitions in the future may also be limited under the terms of the Company's unsecured revolving credit facility (the "Credit Facility"). The Credit Facility contains various covenants that may restrict, among other things, our ability or the ability of our subsidiaries to incur additional indebtedness, to create liens or other encumbrances and to sell or otherwise dispose of assets and merge or consolidate with another entity. In particular, the Credit Facility restricts indebtedness (other than certain additional permitted indebtedness) of the Company's regulated insurance subsidiaries and their immediate and intermediate, if applicable, parent holding companies to a maximum aggregate amount of $1.5 billion (including a sublimit of $1.0 billion in aggregate for Crum & Forster, Odyssey Group, Northbridge, Zenith National, Allied World and Brit (and each of their respective direct and indirect subsidiaries) (the "Core Group")) unless the applicable subsidiary provides an unsecured guarantee, which overall limit reduces to $1.0 billion in aggregate upon any sale of more than 51% of the equity interests of any member of the Core Group. In addition, the Credit Facility contains certain financial covenants that require the Company to maintain a ratio of consolidated debt to consolidated capitalization not exceeding 0.35:1 and consolidated shareholders' equity of not less than $11.5 billion, both calculated as defined in the Credit Facility (including, in certain circumstances and subject to certain limits and conditions, calculating consolidated debt on the basis of net consolidated debt, taking into account up to $1.0 billion in consolidated cash and cash equivalents that are held in an account in Canada or the United States with a lender under the Credit Facility (or its affiliate)). A failure to comply with the obligations and covenants under the Credit Facility could result in an event of default under such agreement which, if not cured or waived, could permit acceleration of indebtedness, including other indebtedness of the Company or our subsidiaries. If such indebtedness were to be accelerated, there can be no assurance that the Company's assets would be sufficient to repay that indebtedness in full. Moreover, the Credit Facility could limit our ability to incur additional indebtedness in the future.

Our business could be adversely affected by the loss of one or more key employees.

We are substantially dependent on a small number of key employees, including our Chairman and significant shareholder, Mr. Prem Watsa, and the senior management of the Company and its operating subsidiaries. The industry experience and reputation of these individuals are important factors in our ability to attract new business and investment opportunities. Our success has been, and will continue to be, dependent on our ability to retain the services of our existing key employees and to attract and retain additional qualified personnel in the future. The loss of the services of any of these key employees, or the inability to identify, hire and retain other highly qualified personnel in the future, could adversely affect the quality and profitability of our business operations. At our operating subsidiaries, employment agreements have been entered into with key employees. We do not maintain key employee insurance with respect to any of our employees.

We may be unable to obtain reinsurance coverage at reasonable prices or on terms that adequately protect us.

We use reinsurance arrangements, including reinsurance of our own reinsurance business purchased from other reinsurers, referred to as retrocessionaires, to help manage our exposure to property and casualty risks. The availability of reinsurance and rates charged by reinsurers are subject to prevailing market conditions, both in terms of price and available capacity, which can affect our business volume and profitability. Reinsurance companies can also add or exclude certain coverages from, or alter terms in, the policies that we purchase from them. Some exclusions are with respect to risks which we cannot exclude in policies we write due to business or regulatory constraints, such as coverage with respect to acts of terrorism, mold and cyber risk. Reinsurers may also impose terms, such as lower per occurrence and aggregate limits, on primary insurers that are inconsistent with corresponding terms in the policies written by these primary insurers. As a result, our insurance subsidiaries, like other primary insurance companies, increasingly are writing insurance policies which to some extent do not have the benefit of reinsurance protection. These gaps in reinsurance protection expose us to greater risk and greater potential losses.

The rates charged by reinsurers and the availability of reinsurance to our subsidiaries will generally reflect our recent loss experience and the industry loss experience overall. Reinsurance pricing has continued to firm as a result of catastrophe losses in recent years, the threat of sustained high inflation and its impact on claim costs and the effects of social inflation in the United States and the low interest rate environment. The retrocession market continues to experience significant rate increases due to increased catastrophe activity in recent years. Each of our insurance and reinsurance subsidiaries continue to evaluate the relative costs and benefits of accepting more risk on a net basis, reducing exposure on a direct basis, and paying additional premiums for reinsurance. If we cannot obtain adequate reinsurance protection for the risks we underwrite, we may be exposed to greater losses from those risks or we may be forced to reduce the amount of business we underwrite, which will reduce our revenues. As a result, our inability to obtain adequate reinsurance protection could have a material adverse effect on our financial condition and operations.

Our operations could be adversely affected as a result of regulatory, political, economic or other influences in the insurance and reinsurance industries.

We are subject to government regulation in each of the jurisdictions in which our operating insurance and reinsurance subsidiaries are licensed or authorized to conduct business. Governmental bodies have broad administrative power to regulate many aspects of the insurance business, which may include accounting methods, governance, premium rates, market practices, policy forms and capital adequacy. The laws and rules behind this regulation are concerned primarily with the protection of policyholders rather than investors. Governmental bodies may impose fines, additional capital requirements or limitations on our insurance and reinsurance operations, and/or impose criminal sanctions for violation of regulatory requirements. The laws and regulations that are applicable to our insurance and reinsurance operations are complex and may increase the costs of regulatory compliance or subject our business to the possibility of regulatory actions or proceedings.

In recent years, the insurance industry has been subject to increased scrutiny by policymakers, legislatures and regulators alike. New laws and rules and new interpretations of existing laws and rules could adversely affect our financial results by limiting our operating insurance subsidiaries' ability to make investments consistent with our total retustrategy or requiring us to maintain capital in specific operating subsidiaries in excess of the amounts we consider to be appropriate, or causing us to make unplanned modifications of products or services, or imposing restrictions on our ability to enter or exit lines of insurance business or to utilize new methods of assessing and pricing risks or selling products and services. We cannot predict the future impact of changing law, regulation or government policy on our operations; any changes could have a material adverse effect on us or the insurance industry in general.

Our international business is subject to applicable laws and regulations relating to sanctions and foreign corrupt practices, the violation of which could adversely affect our operations.

We must comply with all applicable economic sanctions and anti-bribery laws and regulations, including those of Canada, the United States, the United Kingdom, the European Union and other foreign jurisdictions where we operate. U.S. laws and regulations applicable to us include the economic trade sanctions laws and regulations administered by the U.S. Department of the Treasury's Office of Foreign Assets Control, as well as certain laws administered by the U.S. Department of State. In addition, our business is subject to the Canadian Corruption of Foreign Public Officials Act, Foreign Corrupt Practices Act and other anti-bribery laws such as the U.K. Bribery Act that generally bar corrupt payments or unreasonable gifts to foreign governments or officials and the Bribery Act 2016 of Bermuda. We believe that our commitment to honesty and integrity, set out in our Guiding Principles and regularly communicated, and the large number of our executives and employees who have served the Company for a long time, significantly enhance the likelihood that we will comply with those laws and regulations. More specifically, we have policies and controls in place that are designed to ensure compliance with these laws and regulations, including policies distributed annually to employees, controls and oversight at individual operating companies and companywide, and whistleblower programs that are monitored by senior management and the Board of Directors. Despite these policies and controls, it is possible that an employee or intermediary could fail to comply with applicable laws and regulations, which could expose us to civil penalties, criminal penalties and other sanctions, including fines or other punitive actions. In addition, such violations could damage our business and/or reputation and therefore have a material adverse effect on our financial condition and results of operations.

Certain business practices of the insurance industry have been the subject of negative publicity and investigations by government authorities and the subject of class action litigation.

From time to time, the insurance industry has been subject to investigations, litigation and regulatory activity by various insurance, governmental and enforcement authorities, concerning certain practices within the industry. We sometimes receive inquiries and informational requests from insurance regulators or other government officials in the jurisdictions in which our insurance and reinsurance subsidiaries operate. Our internal and external legal counsels coordinate with operating companies in responding to information requests and government proceedings. From time to time, consumer advocacy groups or the media also focus attention on certain insurance industry practices. We cannot predict at this time the effect that investigations, litigation and regulatory activity or negative publicity from consumers or the media will have on the insurance or reinsurance industry or our business, or whether activities or practices currently thought to be lawful will be characterized in the future as unlawful or will become subject to negative scrutiny from consumer advocacy groups or the media. Our involvement in any investigations and related lawsuits would cause us to incur legal costs and, if we were found to have violated any laws, we could be required to pay fines and damages, perhaps in material amounts. In addition, we could be materially adversely affected by the negative publicity for the insurance industry related to any such proceedings, and by any new industry-wide regulations or practices that may result from such proceedings or publicity. It is possible that future investigations or related regulatory developments will mandate changes in industry practices in a fashion that increases our costs of doing business or requires us to alter aspects of the manner in which we conduct our business.

Political and other developments in foreign jurisdictions in which we operate could adversely affect our business and assets.

Our international operations are regulated in various jurisdictions with respect to licensing requirements, currency, amount and type of security deposits, amount and type of reserves, amount and type of local investment and other matters. We regularly monitor for political and other changes in each country where we operate. The decentralized nature of our operations generally permits quick adaptation to, or mitigation of, evolving regional risks. Furthermore, our international operations are widespread and therefore not dependent on the economic stability of any one particular region. International operations and assets held abroad may, however, be adversely affected by political and other developments in foreign countries, including possibilities of tax changes, trade protectionism measures, nationalization and changes in regulatory policy, as well as by consequences of terrorism, war, hostilities and unrest. The risks of such occurrences and their overall effect upon us vary from country to country and cannot easily be predicted.

Our operations and financial performance may be impacted by changes in tariffs, trade restrictions or other regulatory measures imposed by domestic or foreign governments. The announced imposition of tariffs by the United States (the "U.S. Tariffs") and retaliatory measures between governments may cause multifaceted effects on the economy. The U.S. Tariffs may adversely impact our operations by causing supply chain disruptions, economic downturn, inflationary pressures and uncertainty in capital markets. We are currently assessing the direct and indirect impacts to our operations of these tariffs and potential retaliatory tariffs and other trade protectionist measures that may arise, and such impacts may be significant, including inflationary pressures on loss costs, particularly for raw materials in the auto and construction industries. Failure to mitigate the negative effects of the U.S. Tariffs on our business could have a material adverse impact on our operating results and financial condition. While we are taking steps to seek to mitigate the potential impact on our business, given that developments are ongoing with respect to these tariffs and other measures, their impacts are uncertain and could adversely affect our business, financial condition and results of operations.

We may be subject to regulatory proceedings or significant litigation, which will be expensive and time consuming and, if decided against us, could require us to pay substantial judgments or settlements.

We may, from time to time, become party to a variety of legal claims and regulatory proceedings, including, but not limited to: disputes over coverage or claims adjudication; disputes regarding sales practices, disclosures, premium refunds, licensing, regulatory compliance and compensation arrangements; disputes with our agents, brokers or network providers over compensation and termination of contracts and related claims; regulatory actions relating to consumer pressure in relation to benefits realized by insurers; disputes with taxing authorities regarding our tax liabilities and tax assets; regulatory proceedings and litigation related to acquisitions or divestitures made or proposed by us or our subsidiaries or in connection with subsidiaries in which we hold an investment; and disputes relating to certain businesses acquired or disposed of by us. Operating companies manage day-to-day regulatory and legal risk primarily by implementing appropriate policies, procedures and controls. Internal and external legal counsels also work closely with the operating companies to identify and mitigate areas of potential regulatory and legal risk. The existence of such claims against us or our subsidiaries, affiliates, directors or officers could, however, have various adverse effects, including negative publicity and the incurrence of significant legal expenses defending claims, even those without merit.

Our significant shareholder may substantially influence our direction and operations.

Mr. Prem Watsa, our Chairman and Chief Executive Officer, owns, directly or indirectly, or exercises control or direction over shares representing approximately 43.3% of the voting power of the Company's outstanding shares. Mr. Watsa has the ability to substantially influence certain actions requiring shareholder approval, including approving a business combination or consolidation, liquidation or sale of the Company's assets, electing members of our Board of Directors and adopting amendments to the Company's articles of incorporation and by-laws.

Amendments were made to the terms of our multiple voting shares, which are controlled by Mr. Watsa, in August of 2015 having the effect of preserving the voting power represented by the multiple voting shares at 41.8% even if additional subordinate voting shares are issued in the future.

We may be adversely affected by foreign currency fluctuations.

Our reporting currency is the U.S. dollar. A portion of our premiums and our expenses are denominated in foreign currencies and a portion of our assets (including investments) and loss reserves are also denominated in foreign currencies. We may, from time to time, experience losses resulting from fluctuations in the values of foreign currencies (including when our foreign currency assets and liabilities are hedged) which could adversely affect our financial condition, profitability or cash flows.

We rely on independent brokers over whom we exercise little control, which exposes us to certain risks.

We use brokers to distribute our business and, in some instances, will distribute through agents or directly to customers. We may also conduct business through third parties such as managing general agents where it is cost effective to do so and where we can control the underwriting process to ensure our risk management criteria are met. Each of these channels has its own distinct distribution characteristics and customers. A large majority of our business is generated by brokers (including international reinsurance brokers with respect to our reinsurance operations), with the remainder split among the other distribution channels. This is substantially consistent across our insurance and reinsurance subsidiaries.

Our insurance operations have relationships with many different types of brokers including independent retail brokers, wholesale brokers and national brokers depending on the particular jurisdiction, while our reinsurance operations are dependent primarily on a limited number of international reinsurance brokers. We transact business with these brokers on a non-exclusive basis. These independent brokers also transact the business of our competitors and there can be no assurance as to their continuing commitment to distribute our insurance and reinsurance products. Our continued profitability depends, in part, on the marketing efforts of independent brokers and our ability to offer insurance and reinsurance products and maintain financial ratings that meet the requirements and preferences of such brokers and their policyholders.

Because the majority of our brokers are independent, there is limited ability to exercise control over them. In the event that an independent broker exceeds its authority by binding us on a risk that does not comply with our underwriting guidelines, we may be at risk for that policy until the application is received and a cancellation effected. Although to date we have not experienced a material loss from improper use of binding authority by our brokers, any improper use of such authority may result in losses that could have a material adverse effect on our business, financial condition, profitability or cash flows. Our insurance and reinsurance subsidiaries closely manage and monitor broker relationships and regularly audit broker compliance with our established underwriting guidelines.

Financial reporting risks associated with IFRS 17.

IFRS 17 Insurance Contracts ("IFRS 17") as issued by the IASB was retrospectively adopted by the Company on January 1, 2023 with restated comparative periods presented in the financial statements. IFRS 17 replaced IFRS 4 Insurance Contracts and introduced considerable change and additional complexity to the recognition, measurement, presentation and disclosure of insurance contracts within the Company's consolidated financial statements. The complex measurement requirements of IFRS 17 increased the potential volatility in the Company's consolidated statement of earnings and financial position, which affects financial reporting risk.

Financial reporting risks relating to deferred taxes associated with amendments to IAS 12.

On May 23, 2023, the IASB issued amendments to IAS 12 Income Taxes ("IAS 12") to provide temporary relief from accounting and disclosure for deferred taxes arising from the implementation of Pillar Two model rules published by the Organisation for Economic Co-operation and Development ("OECD"). The Pillar Two model rules provide a general framework for the implementation of a 15% global minimum tax, which is to be applied on a jurisdiction-by-jurisdiction basis. We retrospectively adopted this amendment during the second quarter of 2023 and have applied the exception to recognizing and disclosing information regarding Pillar Two deferred income tax assets and liabilities.

To the extent that the value of our goodwill, indefinite-lived intangible assets or investments in associates is impaired, we are required to write down the value of such assets.

The goodwill, indefinite-lived intangible assets and investments in associates on our consolidated balance sheet originated from various acquisitions and investments made by us or our operating subsidiaries. Continued profitability and achievement of financial plans by acquired businesses and associates is a key consideration for there to be no impairment in the carrying value of goodwill, indefinite-lived intangible assets and investments in associates. An intangible asset may be impaired if the economic benefit to be derived from its use is unexpectedly diminished. An investment in an associate is considered to be impaired if its carrying value exceeds its recoverable amount (the higher of the associate's fair value and value-in-use).

Management regularly reviews the current and expected profitability of operating companies and associates and their success in achieving financial plans when assessing the carrying value of goodwill, indefinite-lived intangible assets and investments in associates. The carrying values of goodwill and indefinite-lived intangible assets are tested for impairment at least annually or more often if events or circumstances indicate there may be impairment. Investments in associates with carrying values that exceed their fair values are tested for impairment using value-in-use discounted cash flow models at each reporting date.

Our failure to realize deferred income tax assets could lead to a write-down or tax authorities may take differing positions from ours, either of which could adversely affect our results of operations.

Realization of deferred income tax assets is dependent upon the generation of taxable income in those jurisdictions where the relevant tax losses and temporary differences exist. Failure to achieve projected levels of profitability could lead to a reduction in our deferred income tax asset if it is no longer probable that the amount of the asset will be realized.

We are subject to income taxes in Canada, the United States and many foreign jurisdictions where we operate, and our determination of our tax liability is subject to review by applicable domestic and foreign tax authorities. Tax legislation of each jurisdiction in which we operate is interpreted to determine the provision for income taxes and expected timing of the reversal of deferred income tax assets and liabilities. While we believe our tax positions to be reasonable, where our interpretations differ from those of tax authorities or the timing of realization is not as expected, the provision for income taxes may increase or decrease in future periods to reflect actual experience.

There is a risk that Canadian or foreign tax laws, or the interpretation thereof, could change in a manner that adversely affects us.

Canada, together with approximately 140 other countries comprising the OECD and the G20 Inclusive Framework on Base Erosion and Profit Shifting ("BEPS"), approved in principle in 2021 certain base erosion tax initiatives including the introduction of a 15% global minimum tax to be applied on a jurisdiction-by-jurisdiction basis. Future developments with respect to the BEPS proposals may result in an increase in future taxes and an adverse effect on the Company.

Canada enacted legislation implementing certain aspects of Pillar Two (the primary charging rule of the global minimum tax and a domestic minimum tax) on June 20, 2024, effective for the Company for taxation years beginning on or after January 1, 2024, and announced draft legislation on August 12, 2024 to implement an undertaxed profits rule (a minimum effective tax rate of 15% on profits wherever multinational corporations do business) proposed to be effective for the Company for taxation years beginning on or after January 1, 2025. Certain other jurisdictions in which we operate have enacted or substantively enacted Pillar Two legislation, certain aspects of which will generally be effective for us for taxation years beginning on January 1, 2024. A number of jurisdictions are implementing, or considering the implementation of, new domestic tax regimes, or are planning to revise existing tax regimes, in response to the global Pillar Two tax initiative.

Further, on December 27, 2023, Bermuda enacted the CIT Act. Entities subject to tax under the CIT Act are the Bermuda constituent entities of multi-national groups. A multi-national group is defined under the CIT Act as a group with entities in more than one jurisdiction with consolidated revenues of at least EUR750 million for two of the four previous fiscal years. If Bermuda constituent entities of a multi-national group are subject to tax under the CIT Act, such tax is charged at a rate of 15% of the net taxable income of such constituent entities as determined in accordance with and subject to the adjustments set out in the CIT Act. Tax is chargeable under the CIT Act for tax years starting on or after January 1, 2025. In addition, the CIT Act includes transition rules, including carryforward tax losses incurred in the five fiscal years preceding the effective date or increases in the tax basis of assets and liabilities. The CIT Act also provides relief from double taxation via foreign tax credit based on the adjusted amount of foreign taxes accrued by the group. The CIT Act is designed as a covered tax for the purposes of the OECD's Global Base Anti-Erosion Rules ("GloBE Model Rules"), meaning the CIT Act does not presently apply an income-inclusion rule or under taxed profits rule in the same way as the GloBE Model Rules do. While we expect that Allied World would be treated as a Bermuda constituent entity for the purposes of the CIT Act and therefore subject to taxation in Bermuda, we do not currently expect the CIT Act to have a material adverse effect on our results of operations going forward. Future developments and guidance under the GloBE Model Rules may impact Bermuda's implementation of its corporate tax regime, and any future changes to the Bermuda corporate income tax regime may impact our tax liability, financial condition and results of operations, and could increase our administrative expenses. This is generally expected to result in an increase in the Company's liability for taxes in Bermuda and to reduce any Pillar Two top-up taxes payable by the Company in respect of Bermuda.

The Company is also subject to the application of the Canadian excessive interest and finance expense limitation rules (enacted on June 20, 2024) that limit the deductibility of certain interest expenses in certain circumstances, which may result in an increase in the amount of taxable income incurred by the Company or its subsidiaries.

No assurance can be given that applicable tax laws, or the interpretation thereof, will not change or that new taxes will not be implemented which would adversely affect the Company.

Technological or other changes could adversely impact demand, or the premiums payable, for the insurance coverages we offer.

Technological changes could have unpredictable effects on the insurance and reinsurance industries. It is expected that new services and technologies will continue to emerge that will affect the demand for insurance and reinsurance products and services, the premiums payable, the profitability of such products and services and the risks associated with underwriting certain lines of business, including new lines of business. While we strive to maintain an innovation working group comprised of members with diverse backgrounds from across our global operating companies to regularly assess new services and technologies that may be applicable or disruptive to the insurance and reinsurance industries, failure to understand evolving technologies, or to position us in the appropriate direction, or to deploy new products and services in a timely way that considers customer demand and competitor activities could have an adverse impact on our business, financial condition, profitability or cash flows.

Assessments and other surcharges for guaranty funds and second-injury funds and other mandatory pooling arrangements may reduce the profitability of our insurance subsidiaries.

Virtually all U.S. states require insurers licensed to do business in their state to bear a portion of the loss suffered by some insureds as a result of impaired or insolvent insurance companies. Many states also have laws that establish second injury funds to provide compensation to injured employees for aggravation of a prior condition or injury. In addition, as a condition to the ability to conduct business in various jurisdictions, some of our insurance subsidiaries are required to participate in mandatory property and casualty shared market mechanisms or pooling arrangements, which provide various types of insurance coverage to individuals or other entities that otherwise are unable to purchase that coverage from private insurers. The effect of these assessments and mandatory shared market mechanisms or changes in them could reduce the profitability of our U.S. insurance subsidiaries in any given period or limit their ability to grow their business. Similarly, our Canadian insurance subsidiaries contribute to mandatory guaranty funds that protect insureds in the event of a Canadian property and casualty insurer becoming insolvent, and certain of our Asian insurance subsidiaries participate in mandatory pooling arrangements in their local markets.

Risk Factors Relating to the Exchange Notes

The market value of the Exchange Notes may be affected by changes in credit ratings.

The value of the Exchange Notes will be affected by the general creditworthiness of the Company. Real or anticipated changes in credit ratings on the Exchange Notes may affect the market value of the Exchange Notes. No assurance can be given that any credit rating assigned to the Exchange Notes will not be lowered or withdrawn entirely by the relevant rating agency or that negative trends will not be applied by any ratings agency.

The Initial Notes were assigned ratings by Morningstar DBRS, Moody's Ratings, Fitch Ratings, Inc. and S&P Global Rating. One or more other independent credit rating agencies may assign credit ratings to the Exchange Notes. The ratings may not reflect the potential impact of all risks related to the structure, market, additional risk factors discussed herein and other factors that may affect the value of the Exchange Notes. A credit rating is not a recommendation to buy, sell or hold securities and may be subject to revision, suspension or withdrawal by the rating agency at any time. No assurance can be given that a credit rating will remain constant for any given period of time or that a credit rating will not be lowered or withdrawn entirely by a credit rating agency if, in its judgment, circumstances in the future so warrant. A suspension, reduction or withdrawal at any time of the credit rating assigned to the Exchange Notes by one or more of the credit rating agencies may adversely affect the cost and terms and conditions of our financing and could adversely affect the value and trading of the Exchange Notes.

The Exchange Notes are effectively subordinated to the indebtedness of our subsidiaries (other than Allied World).

The Exchange Notes are effectively subordinated to any existing and future indebtedness and other liabilities of our subsidiaries (other than Allied World, which is a Co-Obligor of the Notes). You will not have any claim as a creditor against our subsidiaries or the assets of our subsidiaries, other than Allied World, in respect of the Notes. Therefore, in the event of the insolvency or liquidation of any such subsidiary, following payment by such subsidiary of its liabilities, the subsidiary may not have sufficient remaining assets to make payments to us as a shareholder or otherwise. In the event of a default by any such subsidiary under any credit agreement or other indebtedness, its creditors could accelerate the debt, prior to such subsidiary distributing amounts to us that we could use to make payments on the Exchange Notes. In addition, if we caused any such subsidiary to pay a dividend to us to make payments on the Exchange Notes, and the dividend was determined to be improperly paid, holders of the Exchange Notes who had received proceeds from such dividend payments could be required to retuthe payment to the subsidiary's creditors.

As of December 31, 2024, our subsidiaries (other than Allied World) had approximately $3.3 billion principal amount of indebtedness. Our subsidiary debt may increase in the future. The terms of the Exchange Notes do not limit the ability of our subsidiaries to incur additional indebtedness that is senior to the Exchange Notes.

We may incur additional indebtedness that may adversely affect our ability to meet our financial obligations under the Exchange Notes.

As of December 31, 2024, the Company and Allied World had approximately $8.6 billion aggregate principal amount of total outstanding senior unsecured indebtedness, all of which would rank equally to the Notes. The Company's other subsidiaries had approximately $3.3 billion aggregate principal amount of total outstanding indebtedness, all of which would be structurally senior to the Notes. The Indenture that will govethe Exchange Notes does not limit the amount of additional indebtedness that we may incur. We may incur additional indebtedness in the future, which could have important consequences to holders of the Exchange Notes, including the following:

·

we could have insufficient cash to meet our financial obligations, including our obligations under the Exchange Notes;

·

our ability to obtain additional financing for working capital, capital expenditures or general corporate purposes may be impaired; and

·

a significant degree of debt could make us more vulnerable to changes in general economic conditions and could also affect the financial strength ratings of our insurance and reinsurance subsidiaries.

The Indenture governing the Notes provides that certain restrictive covenants will be automatically eliminated or amended effective as of the Amendment Date, including in respect of the limitation on liens on capital stock of restricted subsidiaries. The Indenture also provides that if we grant any security interest to any collateral agent or trustee pursuant to such covenant in connection with any series created after the date of the Third Supplemental Indenture, such security interest shall be automatically released on the Amendment Date and any such collateral agent or trustee shall be authorized to take such further actions as we may reasonably request to give effect to such release.

As a result, once such restrictive covenants have been automatically eliminated or amended, we will no longer be restricted under the terms and conditions of the Notes from entering into transactions that could increase the total amount of our outstanding indebtedness, adversely affect our capital structure or our credit ratings or associated outlooks, or otherwise adversely affect the holders of the Notes. See "Description of the Notes - Certain Covenants".

Holders of the Exchange Notes may not be protected in the event we are involved in a highly leveraged transaction, reorganization, restructuring, merger or similar transaction in the future.

The Indenture under which the Initial Notes were issued may not sufficiently protect holders of the Exchange Notes if we are involved in a highly leveraged transaction, reorganization, restructuring, merger or similar transaction. The Indenture does not contain:

·

any provision restricting us or any of our subsidiaries from incurring, assuming or being liable with respect to any indebtedness or other obligations;

·

any provision restricting us or our subsidiaries from incurring, assuming or being liable with respect to any unsecured indebtedness or other unsecured obligations;

·

any provision restricting us or any of our subsidiaries from paying dividends or making other distributions on capital stock or from purchasing or redeeming capital stock;

·

any restrictions on the ability of our subsidiaries to issue securities that would be senior to the common shares of the subsidiaries held by us;

·

any financial ratios or specified level of net worth to which we or our subsidiaries must adhere; or

·

any specific restrictions on our ability to contribute our assets to our insurance subsidiaries.

The price at which you may be able to resell your Exchange Notes may be adversely affected by factors that are beyond our control.

If you are able to resell your Exchange Notes, the price you receive will depend on many factors that may vary over time, including:

·

the number of potential buyers;

·

the level of liquidity of the Exchange Notes;

·

our financial performance;

·

the amount of indebtedness we have outstanding;

·

the level, direction and volatility of market interest rates generally; and

·

the market for similar securities.

Prevailing yields on similar securities will affect the market value of the Exchange Notes. Assuming all other factors remain unchanged, the market value of the Exchange Notes would be expected to decline as prevailing yields for similar securities rise and would be expected to increase as prevailing yields for similar securities decline. Spreads over the U.S. treasury yields and comparable benchmark rates of interest for similar securities will also affect the market value of the Exchange Notes in an analogous manner.

As a result of these factors, you may only be able to sell your Exchange Notes at prices below those you believe to be appropriate, including prices below the price at which you acquired the Initial Notes.

There may be no active market for the Exchange Notes.

There is currently no public market for the Exchange Notes, and we do not intend to apply for listing of the Exchange Notes on any securities exchange or any automated quotation system. Accordingly, we cannot be sure that any active market for the Exchange Notes will develop, or if one does develop, that it will be maintained. If an active market for the Exchange Notes fails to develop or be sustained, the trading price of the Exchange Notes could decline.

The Exchange Notes may be redeemed prior to maturity.

The Exchange Notes may be redeemed, at our option, in whole at any time or in part from time to time on or after the closing of the Exchange Offer and prior to the maturity date for the Exchange Notes, or in whole but not in part in the event of certain developments affecting Canadian or Bermuda taxation. Holders of Exchange Notes should assume that our redemption option will be exercised if it is in our interest to redeem the Exchange Notes. Holders whose Exchange Notes are redeemed would not be entitled to participate in any future increase in the market price of the Exchange Notes and may not be able to reinvest their redemption proceeds in securities providing a comparable expected rate of retuto maturity as the Exchange Notes for a comparable level of risk. See "Description of the Notes - Optional Redemption" and "Description of the Notes - Redemption for Tax Reasons".

Risk Factors Relating to the Exchange Offer

If you do not validly tender your Initial Notes, you will not receive Exchange Notes in the Exchange Offer, and the resale restrictions applicable to the Initial Notes will continue to apply to those Initial Notes that are not validly exchanged.

Only Initial Notes that are validly tendered (and not validly withdrawn) will be exchanged in the Exchange Offer and registered under the Securities Act. The Initial Notes that are not so exchanged will continue to be subject to restrictions on transfer under applicable U.S. federal and state securities laws, and while subject to such restrictions, may not be offered, sold or transferred in the United States except pursuant to an exemption from the registration requirements of, or in a transaction not subject to, the Securities Act and applicable state securities laws, or pursuant to an effective registration statement. Upon consummation of the Exchange Offer, certain registration and other rights under the Registration Rights Agreement will terminate. We will issue Exchange Notes only in exchange for Initial Notes that are timely received by the exchange agent, together with all required documents, including a properly completed and duly signed letter of transmittal or book-entry confirmation or notice of guaranteed delivery. Therefore, you should allow sufficient time to ensure timely delivery of the Initial Notes and should carefully follow the instructions on how to tender your Initial Notes.

We and the exchange agent are not required to notify you of any defects or irregularities with respect to your tender of the Initial Notes. If you do not tender your Initial Notes or if we do not accept your Initial Notes because you did not tender your Initial Notes properly, then, after consummation of the Exchange Offer, you will continue to hold Initial Notes that are subject to existing transfer restrictions.

Although we may in the future seek to acquire unexchanged Initial Notes in open market or privately negotiated transactions, through subsequent exchange offers or otherwise, we have no present plans to acquire any unexchanged Initial Notes or to file with the SEC a shelf registration statement to permit resales of any unexchanged Initial Notes. In addition, holders who do not tender their Initial Notes (except for the initial purchaser or holders of Initial Notes (i) who are prohibited by applicable law or SEC policy from participating in the Exchange Offer, (ii) who may not resell the Exchange Notes acquired in the Exchange Offer without delivering a prospectus or (iii) for whom this prospectus is not appropriate or available for resales of Exchange Notes acquired in the Exchange Offer) will not have any further registration rights and will not have the right to receive additional interest on their Initial Notes.

The market for the Initial Notes may be significantly more limited after the Exchange Offer.

Because we anticipate that most holders of Initial Notes will elect to exchange their Initial Notes, it is likely that the liquidity of the market for any Initial Notes remaining after the completion of the Exchange Offer may be substantially limited. Any Initial Notes tendered and exchanged in the Exchange Offer will reduce the aggregate principal amount of the Initial Notes outstanding. Accordingly, the liquidity of the market for any remaining Initial Notes could be adversely affected and you may be unable to sell them. The extent of the market for the Initial Notes and the availability of price quotations would depend on a number of factors, including the number of holders of Initial Notes remaining outstanding and the interest of securities firms in maintaining a market in the Initial Notes. An issue of securities with a smaller number of units available for trading may command a lower, and more volatile, price than would a comparable issue of securities with a larger number of units available for trading; therefore, the market price for the Initial Notes that are not exchanged may be lower and more volatile as a result of the reduction in the aggregate principal amount of the Initial Notes outstanding.

If you do not properly tender your Initial Notes, you will not receive Exchange Notes in the Exchange Offer, and you may not be able to sell your Initial Notes.

The Exchange Offer may be terminated, cancelled or delayed.

The consummation of the Exchange Offer is subject to, and conditional upon, the satisfaction or waiver of the conditions discussed under "The Exchange Offer-Conditions". We may, at our option and in our sole discretion, waive any such conditions.

In addition, subject to applicable law, we reserve the right to terminate, withdraw or amend the Exchange Offer at any time prior to the Expiration Date, as further described under "The Exchange Offer-Expiration Date; Extensions; Amendments; Termination".

Some persons who participate in the Exchange Offer must deliver a prospectus in connection with resales of the Exchange Notes.

If you exchange your Initial Notes in the Exchange Offer for the purpose of participating in a distribution of the Exchange Notes, you may be deemed to have received restricted securities and, if so, will be required to comply with the registration and prospectus delivery requirements of the Securities Act in connection with any resale transaction.

Based on our understanding of interpretations of the Staff of the SEC set forth in no-action letters issued to third parties, including Exxon Capital Holdings Corporation (available May 13, 1988), Morgan Stanley & Co. Incorporated (available June 5, 1991) and Shearman & Sterling (available July 2, 1993), we believe that holders who (i) are not "affiliates" of the Company or Allied World within the meaning of Rule 405 under the Securities Act; (ii) acquire their Exchange Notes in the ordinary course of business; (iii) do not engage in, intend to engage in, or have arrangements to participate in a distribution (within the meaning of the Securities Act) of the Exchange Notes; and (iv) are not broker-dealers, may offer for resale, resell or otherwise transfer the Exchange Notes without compliance with the registration and prospectus delivery requirements of the Securities Act. Holders described in the preceding sentence must tell us in writing at our request that they meet these criteria.

Holders that do not meet these criteria could not rely on interpretations of the SEC in no-action letters, and will have to register the Exchange Notes they receive in the Exchange Offer and deliver a prospectus for them. If such a holder transfers any Exchange Notes without delivering a prospectus meeting the requirements of the Securities Act or without an applicable exemption from registration under the Securities Act, such a holder may incur liability under the Securities Act. We do not and will not assume, or indemnify such a holder against, this liability. In addition, holders that are broker-dealers may be deemed "underwriters" within the meaning of the Securities Act in connection with any resale of Exchange Notes in the United States acquired in the Exchange Offer. Holders that are broker-dealers that receive Exchange Notes for their own account in exchange for Initial Notes that were acquired as a result of market-making activities or other trading activities must acknowledge that they will deliver a prospectus (or, to the extent permitted by law, make available a prospectus to purchasers) in connection with any resale of Exchange Notes in the United States they acquire in the Exchange Offer in order not to be deemed an underwriter.

General Risk Factors

Our computer and data processing systems may fail or be perceived to be insecure, which could adversely affect our business and damage our customer relationships.

Our business is highly dependent upon the successful and uninterrupted functioning of our computer and data processing systems. We rely on these systems to perform actuarial and other modeling functions necessary for writing business, to process and make claim payments and to process and summarize investment transactions. Third parties provide certain of the key components of our business infrastructure such as voice and data communications and network access. Given the high volume of transactions processed daily, we are reliant on such third-party provided services to successfully deliver our products and services. We have highly trained information technology staff that is committed to the continual development and maintenance of our technology infrastructure. Security measures, including data security programs to protect confidential personal information, have been implemented and are regularly upgraded. We, together with our third- party service providers, also maintain and regularly test contingency plans for our technology infrastructure. Notwithstanding these measures, the failure of these systems could interrupt our operations or materially impact our ability to rapidly evaluate and commit to new business opportunities. If sustained or repeated, a system failure could result in the loss of existing or potential business relationships, or compromise our ability to pay claims in a timely manner.

In addition, a security breach of our computer systems could damage our reputation or result in liability to persons affected by the breach as well as regulatory penalties. We retain confidential information regarding our business dealings in our computer systems, including, in some cases, confidential personal information regarding our insureds. We may be required to spend significant capital and other resources to protect against security breaches or to alleviate problems caused by such breaches. Any well-publicized compromise of security could deter people from conducting transactions that involve transmitting confidential information to our systems. Therefore, it is critical that these facilities and infrastructure remain secure and are perceived by the marketplace to be secure. This infrastructure may be vulnerable to physical break-ins, computer viruses, programming errors, attacks by third parties or similar disruptive problems. In addition, we could be subject to liability if hackers were able to penetrate our network security or otherwise misappropriate confidential information.

A disruption of our information technology systems could significantly affect our business.

We rely on information technology in virtually all aspects of our business. A significant disruption or failure of our information technology systems could result in service interruptions, safety failures, security violations, regulatory compliance failures, inability to protect information and assets against intruders, and other operational difficulties. Attacks perpetrated against our information technology systems could result in loss of assets and critical information, potential breach of privacy laws, expose us to remediation costs, reputational damage, regulatory scrutiny, litigation and adversely affect our results of operations, financial condition and liquidity.

Cyberattacks, including those perpetrated through the use of artificial intelligence, could further adversely affect our ability to operate facilities, information technology and business systems, or compromise confidential customer and employee information. Cyberattacks resulting in political, economic, social or financial market instability or damage to or interference with our assets, or our customers or suppliers may result in business interruptions, lost revenue, higher commodity prices, disruption in fuel supplies, lower energy consumption, unstable markets, increased security and repair or other costs, any of which may affect our consolidated financial results. Furthermore, instability in the financial markets as a result of terrorism, sustained or significant cyberattacks, or war could also materially adversely affect our ability to raise capital.

We have taken steps intended to mitigate these risks, including implementation of cybersecurity and cyber resilience measures, business continuity planning, disaster recovery planning and business impact analysis, and regularly update these plans and security measures, however, there can be no assurance that such steps will be adequate to protect us from the impacts of a cyberattack.

We may continue to be adversely impacted by the conflicts in Ukraine and Israel and the development of other geopolitical events and economic disruptions worldwide.

Supply chain disruptions and volatility in commodity prices persist in many regions of the world, contributing to increased inflationary pressures, worsened by supply shocks arising from the conflicts in Ukraine and Israel and other geopolitical events worldwide. In response, central banks around the world had aggressively raised interest rates in an effort to ease rising inflation. Our business relies, to a certain extent, on free movement of goods, services and capital from around the world, and as a result, are facing upward cost pressures. Given the ongoing and dynamic nature of the circumstances surrounding the conflicts in Ukraine and Israel, and other geopolitical events worldwide, it is difficult to predict how significant these continuing events or the occurrence of any similar events will be on the global economy and our businesses, investments and employees, or for how long any further disruptions in the future are likely to continue. Such further developments could have a material adverse effect on our business, financial condition, results of operations, profitability or cash flows.

USE OF PROCEEDS

Neither the Company nor Allied World will receive any cash proceeds from the issuance of the Exchange Notes. We are making the Exchange Offer solely to satisfy our obligations under the Registration Rights Agreement entered into in connection with the offering of the Initial Notes. In consideration for issuing the Exchange Notes, we will receive Initial Notes in the same aggregate principal amount. We have agreed to pay the expenses of the Exchange Offer, other than certain taxes. The form and terms of the Exchange Notes will be identical in all material respects to the form and terms of the Initial Notes, except as otherwise described herein, including under "The Exchange Offer - Terms of the Exchange Offer". The Initial Notes surrendered in exchange for the Exchange Notes will be retired and cancelled and will not be reissued. Accordingly, the issuance of the Exchange Notes will not result in any change in our outstanding indebtedness.

CONSOLIDATED CAPITALIZATION

The table below sets forth the Company's holding company cash and investments and capitalization on a consolidated basis as of December 31, 2024 and does not reflect certain other transactions of the Company after December 31, 2024, as indicated in the footnotes to the table below. You should read this table in conjunction with the Company's audited consolidated financial statements as of and for the years ended December 31, 2024 and 2023, which are incorporated by reference into this prospectus. As no proceeds will be realized from the Exchange Offer, the completion of the Exchange Offer will have no material change on our capitalization.

		As of December 31, 2024
(in millions of U.S. dollars)
Holding company cash and investments (net of derivative obligations)(1)		$	2,502.1
Debt(2)
Borrowings - holding company		$	7,882.4
Borrowings - insurance and reinsurance companies			975.8
Borrowings - non-insurance companies			2,895.5
Total debt			11,753.7
Net debt(3)			9,251.6
Equity
Common shareholders' equity(4)		$	22,959.8
Preferred equity			1,108.2
Non-controlling interests			4,281.2
Total equity			28,349.2
Total capitalization		$	40,102.9
Total debt as a percentage of total capitalization			29.3	%
Net debt as a percentage of net total capitalization(5)			24.6	%

(1)

Holding company cash and investments (net of derivative obligations) does not reflect: i) dividends of $343.6 million on our multiple voting shares and subordinated voting shares paid on January 23, 2025; and ii) proceeds of $190.8 million on January 23, 2025 from the sale of an approximate 2.2% equity interest in Eurobank.

(2)

See note 15 to the Company's audited consolidated financial statements as of and for the years ended December 31, 2024 and 2023, incorporated by reference herein, for details of our borrowings and credit facilities.

(3)

Net debt is calculated by the Company as total debt less holding company cash and investments (net of derivative obligations).

(4)

Common shareholders' equity does not reflect dividends of $343.6 million on our multiple voting shares and subordinated voting shares paid on January 23, 2025.

(5)

Net total capitalization is calculated by the Company as the sum of total equity and net debt.

THE EXCHANGE OFFER

Terms of the Exchange Offer

General

In connection with the issuance of the Initial Notes, the Company entered into the Registration Rights Agreement with the initial purchasers of the Initial Notes. The following contains a summary of the provisions contained in the Registration Rights Agreement. We refer you to the Registration Rights Agreement, which has been filed as an exhibit to the Registration Statement of which this prospectus forms a part.

Under the Registration Rights Agreement, the Company agreed to file under the Securities Act and use its commercially reasonable efforts to cause to become effective under the Securities Act, on or prior to 360 days after the closing of the offering of the Initial Notes, a registration statement with respect to a registered offer to exchange the Initial Notes for Exchange Notes. The Registration Statement has been filed to satisfy our registration obligations with respect to the Registration Rights Agreement, and the Exchange Offer is intended to comply with the requirements of the Registration Rights Agreement. Accordingly, we are required to keep the Exchange Offer open for at least 20 business days (or longer if required by law) after the date notice of the Exchange Offer is given to holders of the Initial Notes. If the Company fails to comply with certain obligations under the Registration Rights Agreement with respect to the Initial Notes, we will be required to pay additional interest to holders of the Initial Notes.

Upon the terms and subject to the conditions set forth in the Registration Statement, which includes this prospectus, and in the letter of transmittal, all Initial Notes validly tendered and not validly withdrawn prior to the Expiration Date will be accepted for exchange. Exchange Notes will be issued in exchange for an equal principal amount of outstanding Initial Notes accepted in the Exchange Offer. This prospectus, together with the letter of transmittal, is being sent to all holders of Initial Notes upon effectiveness of the Registration Statement. The Exchange Offer is not conditioned upon any minimum principal amount of Initial Notes being tendered for exchange. However, our obligation to accept Initial Notes for exchange pursuant to the Exchange Offer is subject to certain customary conditions as set forth herein under "- Conditions".

Initial Notes shall be deemed to have been accepted as validly tendered when, as and if we have given written notice thereof to The Bank of New York Mellon, the exchange agent for the Exchange Offer. The exchange agent will act as agent for the tendering holders of Initial Notes for the purposes of receiving the Initial Notes and delivering Exchange Notes to such holders.

Based on our understanding of interpretations of the Securities Act by the staff of the SEC set forth in several no-action letters to third parties, including Exxon Capital Holdings Corporation (available May 13, 1988), Morgan Stanley & Co. Incorporated (available June 5, 1991) and Shearman & Sterling (available July 2, 1993), we believes that holders who (i) are not "affiliates" (within the meaning of Rule 405 under the Securities Act) of the Company or Allied World, (ii) acquire their Exchange Notes in the ordinary course of business, (iii) do not engage in, intend to engage in, or have arrangements to participate in a distribution (within the meaning of the Securities Act) of the Exchange Notes, and (iv) are not broker-dealers, may offer for resale, resell or otherwise transfer the Exchange Notes without compliance with the registration and prospectus delivery requirements of the Securities Act. Holders described in the preceding sentence must tell either the Company or Allied World in writing at our request that they meet these criteria.

By tendering Initial Notes in exchange for Exchange Notes and executing the letter of transmittal or delivering a book-entry confirmation, each holder will represent to us that:

·

it is neither an affiliate of the Company or Allied World nor a broker/dealer tendering Initial Notes acquired directly from the Company or Allied World for its own account;

·

any Exchange Notes to be received by it will be acquired in the ordinary course of its business;

·

at the time of commencement of the Exchange Offer, it is not engaged in, and does not intend to engage in, and has no arrangement or understanding with any person to participate in the distribution (within the meaning of the Securities Act) of the Exchange Notes to be issued in the Exchange Offer; and

·

it is not acting on behalf of any person who could not truthfully make the foregoing representations.

If such holder is a broker-dealer, it will also be required to represent that the Initial Notes were acquired as a result of market-making activities or other trading activities and that it will deliver a prospectus in connection with any resale of Exchange Notes in the United States. Each holder, whether or not it is a broker-dealer, shall also represent that it is not acting on behalf of any person that could not truthfully make any of the foregoing representations contained in this paragraph. If a holder of Initial Notes is unable to make the foregoing representations, such holder may not rely on the applicable interpretations of the Staff of the SEC and must comply with the registration and prospectus delivery requirements of the Securities Act in connection with any secondary resale transaction in the United States unless such sale is made pursuant to an exemption from such requirements.

Each broker-dealer that receives Exchange Notes for its own account in exchange for Initial Notes where such Initial Notes were acquired by such broker-dealer as a result of market-making or other trading activities, must acknowledge that it will deliver a prospectus meeting the requirements of the Securities Act and that it has not entered into any arrangement or understanding with the Company or Allied World or an affiliate of the Company or Allied World to distribute the Exchange Notes in connection with any resale of such Exchange Notes.

We have not entered into any arrangement or understanding with any person who will receive Exchange Notes in the Exchange Offer to distribute such Exchange Notes following completion of the Exchange Offer. We are not aware of any person that will participate in the Exchange Offer with a view to distribute the Exchange Notes.

Upon consummation of the Exchange Offer, any Initial Notes that are not tendered will remain outstanding and continue to accrue interest but, subject to certain limited exceptions, holders of Initial Notes who do not exchange their Initial Notes for Exchange Notes in the Exchange Offer will no longer be entitled to registration rights or the payment of additional interest. In addition, such holders will not be able to offer or sell their Initial Notes, unless such Initial Notes are subsequently registered under the Securities Act, except pursuant to an exemption from, or in a transaction not subject to, the Securities Act and applicable state securities laws. We will have no obligation to effect a subsequent registration of the Initial Notes.

Expiration Date; Extensions; Amendments; Termination

The Expiration Date shall be 5:00 p.m., New York City time, on , 2025, unless we, in our sole discretion, extend the Exchange Offer, in which case the Expiration Date shall be 5:00 p.m., New York City time, on the date to which the Exchange Offer is extended.

To extend the Expiration Date, we will notify the exchange agent of any extension by written notice and will notify the holders of Initial Notes by means of a press release or other public announcement prior to 9:00 a.m., New York City time, on the next business day after the Expiration Date. Such announcement will state that we are extending the Exchange Offer for a specified period of time.

We reserve the right:

·

to delay acceptance of any Initial Notes, to extend the Exchange Offer or to terminate the Exchange Offer and not permit acceptance of Initial Notes not previously accepted if any of the conditions set forth under "- Conditions" shall have occurred and shall not have been waived prior to the Expiration Date, by giving written notice of such delay, extension or termination to the exchange agent; or

·

to amend the terms of the Exchange Offer in any manner deemed by the Company or Allied World to be advantageous to the holders of the Initial Notes.

Any such delay in acceptance, extension, termination or amendment will be followed as promptly as practicable by written notice to the exchange agent. If the Exchange Offer is amended in a manner determined by the Company or Allied World to constitute a material change, we will promptly disclose such amendment in a manner reasonably calculated to inform the holders of the Initial Notes of such amendment and we will extend the Exchange Offer for a period of five to ten business days. In addition, if we amend or terminate the Exchange Offer, we will promptly file a post-effective amendment to the Registration Statement of which this prospectus forms a part. Without limiting the manner in which we may choose to make public the announcement of any delay, extension, amendment or termination of the Exchange Offer, we shall have no obligation to publish, advertise or otherwise communicate any such public announcement, other than by making a timely release to an appropriate news agency.

Absence of Dissenter's Rights of Appraisal

Holders of the Initial Notes do not have any dissenter's rights of appraisal in connection with the Exchange Offer.

Procedures for Tendering

To tender in the Exchange Offer, a holder must do either of the following:

·

properly complete, sign and date the letter of transmittal, including all other documents required by the letter of transmittal; have the signature on the letter of transmittal guaranteed if the letter of transmittal so requires; and deliver that letter of transmittal and other required documents to the exchange agent at the address listed in the letter of transmittal on or before the Expiration Date; or

·

if the Initial Notes are tendered under the book-entry transfer procedures described below, transmit to the exchange agent, on or before the Expiration Date, an agent's message.

In addition, one of the following must occur:

·

the exchange agent must receive certificates representing the holder's Initial Notes along with the letter of transmittal on or before the Expiration Date;

·

the exchange agent must receive a timely confirmation of book-entry transfer of the Initial Notes into the exchange agent's account at The Depository Trust Company ("DTC"), under the procedure for book-entry transfers described below along with a properly transmitted agent's message, on or before the Expiration Date; or

·

the holder must comply with the guaranteed delivery procedures described below.

The method of delivery of Initial Notes, letter of transmittal and all other required documents is at the election and risk of the holders. If such delivery is by mail, it is recommended that registered mail, properly insured, with retureceipt requested, be used. In all cases, sufficient time should be allowed to ensure timely delivery. No Initial Notes, letters of transmittal or other required documents should be sent to us. Delivery of all Initial Notes, if applicable, letters of transmittal and other documents must be made to the exchange agent before the Expiration Date at its address set forth in the letter of transmittal. Holders may also request their respective brokers, dealers, commercial banks, trust companies or nominees to effect such tender for such holders.

The tender by a holder of Initial Notes will constitute an agreement between such holder, the Company and Allied World in accordance with the terms and subject to the conditions set forth herein and in the applicable letter of transmittal. Any beneficial owner whose Initial Notes are registered in the name of a broker, dealer, commercial bank, trust company or other nominee and who wishes to tender should contact such registered holder promptly and instruct such registered holder to tender on its behalf.

Signatures on a letter of transmittal or a notice of withdrawal, as the case may be, must be guaranteed by any member firm of a registered national securities exchange or of the Financial Industry Regulatory Authority, Inc., a commercial bank or trust company having an office or correspondent in the United States or an "eligible guarantor" institution within the meaning of Rule 17Ad-15 under the Exchange Act or an eligible institution unless the Initial Notes tendered pursuant thereto are tendered (1) by a registered holder of Initial Notes who has not completed the box entitled "Special Issuance Instructions" or "Special Delivery Instructions" on the letter of transmittal, or (2) for the account of an eligible institution.

If a letter of transmittal is signed by trustees, executors, administrators, guardians, attorneys-in-fact, officers of corporations or others acting in a fiduciary or representative capacity, such person should so indicate when signing and, unless waived by us, evidence satisfactory to us of their authority to so act must be submitted with such letter of transmittal.

All questions as to the validity, form, eligibility, time of receipt and withdrawal of the tendered Initial Notes will be determined by us in our sole discretion, which determination will be final and binding, subject to the rights of the holders of the Initial Notes to challenge such determination in a court of competent jurisdiction. We reserve the absolute right to reject any and all Initial Notes not validly tendered or exchange any Initial Notes if such exchange would, in the opinion of counsel for the Company and Allied World, be unlawful. We also reserve the absolute right to waive any irregularities or conditions of tender as to particular Initial Notes. We will not waive any condition of the Exchange Offer with respect to an individual holder of Initial Notes unless we waive that condition for all holders of Initial Notes. Our interpretation of the terms and conditions of the Exchange Offer, including the instructions in the letter of transmittal, will be final and binding on all parties, subject to the rights of the holders of the Initial Notes to challenge such determination in a court of competent jurisdiction. Unless waived, any defects or irregularities in connection with tenders of Initial Notes must be cured within such time as we shall determine. None of the Company, Allied World, the exchange agent nor any other person shall be under any duty to give notification of defects or irregularities with respect to tenders of Initial Notes, nor shall any of them incur any liability for failure to give such notification. Tenders of Initial Notes will not be, or be deemed to have been, made until all irregularities have been cured or waived. Any Initial Note received by the exchange agent that is not validly tendered and as to which the defects or irregularities have not been cured or waived will be returned without cost to such holder by the exchange agent, unless otherwise provided in the letter of transmittal, promptly following the Expiration Date.

In addition, we reserve the right, in our sole discretion, subject to the provisions of the Indenture pursuant to which the Initial Notes were issued:

·

to purchase or make offers for any Initial Notes that remain outstanding subsequent to the Expiration Date or, as described under "- Conditions", to terminate the Exchange Offer;

·

to redeem Initial Notes as a whole, or in part, at any time and from time to time; and

·

to the extent permitted under applicable law, to purchase Initial Notes in the open market, in privately negotiated transactions or otherwise.

The terms of any such purchases or offers could differ from the terms of the Exchange Offer.

Each broker-dealer that receives Exchange Notes for its own account in exchange for Initial Notes where such Initial Notes were acquired by such broker-dealer as a result of market-making or other trading activities, must acknowledge that it will deliver a prospectus meeting the requirements of the Securities Act and that it has not entered into any arrangement or understanding with the Company or Allied World, or an affiliate of the Company or Allied World, to distribute the Exchange Notes in connection with any resale of such Exchange Notes.

Acceptance of Initial Notes for Exchange; Delivery of Exchange Notes

Upon satisfaction or waiver of all of the conditions to the Exchange Offer, all Initial Notes that are validly tendered will be accepted promptly after the Expiration Date and the Exchange Notes will be issued promptly after acceptance of the Initial Notes. See "- Conditions". For purposes of the Exchange Offer, Initial Notes shall be deemed to have been accepted as validly tendered for exchange when, as and if we have given written notice thereof to the exchange agent.

For each Initial Note accepted for exchange, the holder of such Initial Note will receive an Exchange Note having a principal amount equal to that of the surrendered Initial Note.

In all cases, issuance of Exchange Notes for Initial Notes that are accepted for exchange pursuant to the Exchange Offer will be made only after timely receipt by the exchange agent of:

·

certificates representing the Initial Notes or a timely book-entry confirmation of such Initial Notes into the exchange agent's account at DTC; and

·

a properly completed and duly executed letter of transmittal and all other required documents or a properly completed agent's message.

If any tendered Initial Notes are not accepted for any reason described in the terms and conditions of the Exchange Offer, such unaccepted or such non-exchanged Initial Notes will be returned promptly without expense to the tendering holder thereof (if in certificated form) or credited to an account maintained with DTC after the expiration or termination of the Exchange Offer.

Book-Entry Transfer

The exchange agent has established accounts with respect to the Initial Notes at DTC for purposes of the Exchange Offer. Any financial institution that is a participant in DTC's systems may make book-entry delivery of Initial Notes by causing DTC to transfer such Initial Notes into the exchange agent's account at DTC in accordance with DTC's procedures for transfer. However, although delivery of Initial Notes may be effected through book-entry transfer at DTC, the exchange agent must receive a properly completed and duly executed letter of transmittal with any required signature guarantees and all other required documents at its address listed in the letter of transmittal, or an agent's message instead of a letter of transmittal, on or before the Expiration Date, or if the holder complies with the guaranteed delivery procedures described below within the time period provided under those procedures.

Exchanging Book-Entry Notes

DTC has confirmed that any financial institution that is a participant in DTC may utilize DTC's Automated Tender Offer Program ("ATOP") procedures to tender Initial Notes.

Any participant in DTC may make book-entry delivery of Initial Notes by causing DTC to transfer such Initial Notes into the exchange agent's account in accordance with DTC's ATOP procedures for transfer. However, the exchange for the Initial Notes so tendered will only be made after a book-entry confirmation of the book-entry transfer of Initial Notes into the exchange agent's account and timely receipt by the exchange agent of an agent's message and any other documents required by the letter of transmittal. The term "agent's message" means a message, transmitted by DTC and received by the exchange agent and forming part of a book-entry confirmation, which states that DTC has received an express acknowledgment from a participant tendering Initial Notes that are the subject of such book-entry confirmation, that such participant has received and agrees to be bound by the terms of the letter of transmittal and that the Company may enforce such agreement against such participant.

Guaranteed Delivery Procedures

If the procedures for book-entry transfer cannot be completed on a timely basis, a tender may be effected if:

·

the tender is made through an eligible institution;

·

prior to the Expiration Date, the exchange agent receives by mail or hand delivery from such eligible institution a properly completed and duly executed letter of transmittal and notice of guaranteed delivery, substantially in the form provided by us, which:

(1)

sets forth the name and address of the holder of Initial Notes and identifies the Initial Notes tendered, including the principal amount of such Initial Notes;

(2)

states that the tender is being made thereby; and

(3)

guarantees that within three business days after the Expiration Date, the letter of transmittal and any other documents required by the letter of transmittal and certificates representing the Initial Notes in proper form for transfer, or a book-entry confirmation, will be deposited by the eligible institution with the exchange agent; and

·

a properly completed and executed letter of transmittal and any other documents required by the letter of transmittal as well as certificates representing all tendered Initial Notes in proper form for transfer, or a book-entry confirmation and agent's message, are received by the exchange agent within three business days after the Expiration Date.

Withdrawal of Tenders

Tenders of Initial Notes may be withdrawn at any time prior to the Expiration Date.

For a withdrawal to be effective, a written notice of withdrawal must be received by the exchange agent prior to the Expiration Date at the address set forth in the letter of transmittal. Any such notice of withdrawal must:

·

specify the name of the person having tendered the Initial Notes to be withdrawn;

·

identify the Initial Notes to be withdrawn, including the principal amount of such Initial Notes;

·

in the case of Initial Notes tendered by book-entry transfer, specify the number of the account at DTC from which the Initial Notes were tendered and specify the name and number of the account at DTC to be credited with the withdrawn Initial Notes and otherwise comply with the procedures of such facility;

·

contain a statement that such holder is withdrawing its election to have such Initial Notes exchanged;

·

be signed by the holder in the same manner as the original signature on the letter of transmittal by which such Initial Notes were tendered including any required signature guarantees, or be accompanied by documents of transfer to have the trustee with respect to the Initial Notes register the transfer of the Initial Notes in the name of the person withdrawing the tender; and

·

if certificates for Initial Notes have been transmitted, specify the name in which such Initial Notes are registered, if different from the person who tendered such Initial Notes.

All questions as to the validity, form, eligibility and time of receipt of such notice will be determined by us, which determination shall be final and binding on all parties, subject to the rights of the holders of the Initial Notes to challenge such determination in a court of competent jurisdiction. Any Initial Notes so withdrawn will be deemed not to have been validly tendered for exchange for purposes of the Exchange Offer. Tenders of Initial Notes will not be, or be deemed to have been, made if withdrawn. Any Initial Notes which have been tendered for exchange but which are not exchanged for any reason will be returned to the tendering holder thereof without cost to such holder, in the case of physically tendered Initial Notes, or credited to an account maintained with DTC for the Initial Notes promptly after withdrawal, rejection of tender or termination of the Exchange Offer. Properly withdrawn Initial Notes may be retendered by following one of the procedures described under "- Procedures for Tendering" and "- Book-Entry Transfer" above at any time prior to the Expiration Date.

Conditions

Notwithstanding any other provisions of the Exchange Offer, or any extension of the Exchange Offer, we will not be required to accept for exchange, or to exchange any Exchange Notes for, any Initial Notes and we may terminate the Exchange Offer or, at our option, modify, extend or otherwise amend the Exchange Offer, if any of the following conditions are not satisfied on or prior to the Expiration Date:

·

no action or event shall have occurred, no action shall have been taken, and no statute, rule, regulation, judgment, order, stay, decree or injunction shall have been issued, promulgated, enacted, entered, enforced or deemed to be applicable to the Exchange Offer or the exchange of Initial Notes for Exchange Notes under the Exchange Offer by or before any court or governmental regulatory or administrative agency, authority, instrumentality or tribunal, including, without limitation, taxing authorities, that either:

(1)

challenges the making of the Exchange Offer or prohibits, prevents, or materially restricts or delays consummation of, or might otherwise adversely affects in any material manner, the Exchange Offer or the exchange of Initial Notes for Exchange Notes under the Exchange Offer; or

(2)

materially adversely affects our (or our subsidiaries') business, condition (financial or otherwise), income, operations, properties, assets, liabilities or prospects or materially impairs the contemplated benefits to us of the Exchange Offer or the exchange of Initial Notes for Exchange Notes under the Exchange Offer as described in this prospectus;

·

nothing has occurred or may occur that would prohibit, prevent, or materially restrict or delay, the Exchange Offer or materially impair our ability to realize the anticipated benefits of the Exchange Offer, as described in this prospectus;

·

there shall not have occurred: (a) any general suspension of or limitation on trading in securities in Canadian or United States securities or financial markets, whether or not mandatory, (b) any material adverse change in the prices of the Initial Notes that are the subject of the Exchange Offer, (c) a material impairment in the general trading market for debt securities, (d) a declaration of a banking moratorium or any suspension of payments in respect of banks by federal or state authorities in Canada or the United States, whether or not mandatory, (e) a commencement of a war, armed hostilities, a terrorist act or other national or international calamity relating to Canada or the United States, (f) any material limitation by any governmental authority on the extension of credit by banks or other lending institutions in Canada or the United States, (g) any material adverse change in the securities or financial markets in Canada or the United States generally, or (h) in the case of any of the foregoing existing at the time of the commencement of the Exchange Offer, a material acceleration or worsening thereof; and

·

The Bank of New York Mellon, as trustee for the Initial Notes, shall have not been directed by any holders of Initial Notes to object in any respect to, nor take any action that could, in our reasonable judgment, adversely affect the consummation of the Exchange Offer or the exchange of Initial Notes for Exchange Notes under the Exchange Offer, nor shall the trustee have taken any action that challenges the validity or effectiveness of the procedures used by us in making the Exchange Offer or the exchange of Initial Notes for Exchange Notes under the Exchange Offer.

The foregoing conditions are for our sole benefit and may be asserted by us, regardless of the circumstances giving rise to any such condition, or may be waived by us, in whole or in part, at any time and from time to time in our reasonable discretion. All such conditions must be satisfied or waived by us, as applicable, at or before the expiration of the Exchange Offer.

If any of the foregoing conditions are not satisfied, we may, at any time on or prior to the Expiration Date:

·

terminate the Exchange Offer and promptly retuall tendered Initial Notes to the respective tendering holders;

·

modify, extend or otherwise amend the Exchange Offer and retain all tendered Initial Notes until the Expiration Date, as extended, subject, however, to the withdrawal rights of holders; or

·

waive the unsatisfied conditions with respect to the Exchange Offer and accept all Initial Notes that have been tendered and not previously validly withdrawn.

We will not accept for exchange any Initial Notes tendered, and no Exchange Notes will be issued in exchange for any such Initial Notes, in respect of the Exchange Offer, if at such time any SEC stop order shall be threatened or in effect with respect to the Registration Statement or the qualification of the Indenture under the Trust Indenture Act of 1939, as amended. The Company is required to use its commercially reasonable efforts to obtain the withdrawal of any SEC order suspending the effectiveness of the Registration Statement at the earliest practicable date.

Exchange Agent

The Bank of New York Mellon has been appointed as exchange agent for the Exchange Offer. Questions and requests for assistance and requests for additional copies of this prospectus, or of the letter of transmittal, should be directed to the exchange agent as provided in the letter of transmittal.

Fees and Expenses

The expenses of soliciting tenders pursuant to the Exchange Offer will be borne by us. The principal solicitation for tenders pursuant to the Exchange Offer is being made by mail; however, additional solicitations may be made by telephone, telecopy or in person by the Company's officers and regular employees.

We will not make any payments to brokers, dealers or other persons soliciting acceptances of the Exchange Offer. We will, however, pay the exchange agent reasonable and customary fees for its services and will reimburse the exchange agent for its reasonable out-of-pocket expenses in connection therewith. We may also pay brokerage houses and other custodians, nominees and fiduciaries the reasonable out-of-pocket expenses incurred by them in forwarding copies of the prospectus and related documents to the beneficial owners of the Initial Notes, and in handling or forwarding tenders for exchange.

The expenses to be incurred by us in connection with the Exchange Offer will be paid by us, including fees and expenses of the exchange agent and trustees for the Initial Notes and the Exchange Notes and accounting, legal, printing and related fees and expenses relating to the Exchange Offer.

We will pay all transfer taxes, if any, applicable to the exchange of Initial Notes pursuant to the Exchange Offer. If, however, Exchange Notes or Initial Notes for principal amounts not tendered or accepted for exchange are to be registered or issued in the name of any person other than the registered holder of the Initial Notes tendered, or if tendered Initial Notes are registered in the name of any person other than the person signing the letter of transmittal, or if a transfer tax is imposed for any reason other than the exchange of Initial Notes pursuant to the Exchange Offer, then the amount of any such transfer taxes imposed on the registered holder or any other persons will be payable by the tendering holder. If satisfactory evidence of payment of such taxes or exemption therefrom is not submitted with the letter of transmittal, the amount of such transfer taxes will be billed directly to such tendering holder.

Consequences of Failure to Exchange

Holders of Initial Notes who do not exchange their Initial Notes for Exchange Notes pursuant to the Exchange Offer will continue to be subject to the restrictions on transfer of such Initial Notes as set forth in the legend thereon as a consequence of the issuance of the Initial Notes pursuant to exemptions from, or in transactions not subject to, the registration requirements of the Securities Act and applicable state securities laws. The Company does not currently anticipate that it will register under the Securities Act the Initial Notes that are not tendered and accepted for purchase in the Exchange Offer, and the Company is not obligated to do so under the terms of the Registration Rights Agreement once the Exchange Offer is completed. To the extent that Initial Notes are tendered and accepted in the Exchange Offer, the trading market for any untendered and tendered but unaccepted Initial Notes could be adversely affected.

INSURANCE REGULATORY MATTERS

We are subject to regulation under the insurance laws of the various jurisdictions in which our operating insurance subsidiaries are domiciled or conduct business.

The following is a summary of the principal insurance regulatory considerations in the United States, Canada, Bermuda and the United Kingdom, being the jurisdictions in which we conduct the majority of our business.

United States

General

Our U.S. operating insurance subsidiaries are subject to extensive regulation throughout the United States. Although there is limited federal regulation of the insurance business in the United States, each state has a comprehensive system for regulating insurers operating in that state. The laws of the various states establish supervisory agencies with broad authority to regulate, among other things, licenses to transact business, premium rates, trade practices, market conduct, agent licensing, policy forms, underwriting and claims practices, insurance policy termination, reserve adequacy, permissible investments, governance and insurer solvency. States also regulate investment activities on the basis of quality, distribution and other quantitative criteria. Further, most states compel participation in and regulate composition of various shared market or residual market mechanisms. States have also enacted legislation that regulates insurance holding company systems, including acquisitions, dividends, the terms of affiliate transactions and other related matters. Our U.S. operating insurance subsidiaries are domiciled in Arkansas, California, Connecticut, Delaware, New Hampshire, New Jersey and New York.

Insurance companies are also affected by a variety of state and federal legislative and regulatory measures and judicial decisions that define the scope of the risks and benefits for which insurance is sought and provided. These include redefinitions of risk exposure in such areas as product liability, environmental damage and workers' compensation. In addition, individual state insurance departments may limit premium rates for some classes of insureds and prevent the insurance companies from charging rates adequate to reflect the level of risk assumed by the insurer for those classes. Such developments may result in adverse effects on the profitability of various lines of insurance. In some cases, these adverse effects on profitability can be minimized, when possible, through the repricing of coverages if permitted by applicable regulations, or the limitation or cessation of the affected business, which may be restricted by state law.

Most states have insurance laws requiring that for certain lines of property and casualty insurance rate schedules, policy or coverage forms, and other information be filed with each such state's regulatory authority. In many cases, such rates and/or policy forms must be approved prior to use. A few states have considered or enacted limitations on the ability of insurers to share data used to compile rates. Such limitations have had, and are expected to have, no significant impact on us.

Insurance companies are required to file detailed annual and quarterly financial reports with the state insurance regulators in each of the states in which they do business, and their business and accounts are subject to examination by such regulators at any time. In addition, these insurance regulators periodically examine each insurer's financial condition, adherence to statutory accounting practices, and compliance with insurance department rules and regulations, including market conduct and claims practices.

Insurance Regulation Concerning Change or Acquisition of Control

The insurance codes in our operating insurance subsidiaries' respective domiciliary states each contain similar provisions (subject to certain variations) to the effect that the acquisition of "control" of a domestic insurer or of any person that directly or indirectly controls a domestic insurer cannot be consummated without the prior approval of the domiciliary insurance regulator. In general, a presumption of "control" arises from the direct or indirect ownership, control, possession with the power to vote or possession of proxies with respect to 10% or more of the outstanding voting securities of a domestic insurer or of a person that controls a domestic insurer. A person seeking to acquire control, directly or indirectly, of a domestic insurance company or of any person controlling a domestic insurance company generally must file with the relevant insurance regulatory authority a statement relating to the acquisition of control containing certain information regarding the proposed acquisition and acquiring party required by statute and regulations, provide a copy of such statement to the domestic insurer and obtain the prior approval of such regulatory authority for the acquisition. In addition, certain state insurance laws contain provisions that require pre-acquisition notification to the state insurance regulator of a change of control of a non-domestic insurance company licensed in that state. Such pre-acquisition notification statutes authorize certain remedies, including the issuance of cease-and-desist orders with respect to the non-domestic licensed insurer and its affiliates doing business in the state if certain conditions exist, such as undue market concentration. Additionally, in most states, the insurance regulator is authorized to deny an application to acquire control of a domestic insurer if the acquisition of control of the domestic insurer would substantially lessen competition in insurance in the state or tend to create a monopoly.

These laws regulating change of control may discourage potential acquisition proposals and may delay, deter or prevent a change of control of Fairfax, including through transactions and in particular unsolicited transactions, that some or all of our shareholders might consider to be desirable.

Regulation of Dividends and Other Payments

The Company is a legal entity separate and distinct from its subsidiaries. As a holding company with no other business operations, the Company's primary sources of cash to meet its obligations, including principal and interest payments with respect to indebtedness and preferred share dividend payments, are available dividends and other statutorily permitted payments, such as tax allocation payments and management and other fees, from our operating insurance subsidiaries. Our operating insurance subsidiaries are subject to various statutory and regulatory restrictions in their respective states of domicile that limit the amount of dividends or distributions an insurance company may pay to its shareholders without prior regulatory approval. Ordinary dividends, for which no regulatory approval is generally required, are limited to amounts determined by formula, which varies by state. The formula typically is based on the level of statutory surplus at the end of the prior year, as well as on some measure of statutory earnings for the prior year, in relation to total dividends paid during the prior 12 months. In addition, dividends generally may be paid only out of "earned surplus" as defined by each state. In every case, capital and surplus subsequent to the payment of any dividends must be reasonable in relation to an insurance company's outstanding liabilities and must be adequate to meet its financial needs. For these purposes, both surplus and earnings are determined in accordance with Statutory Accounting Principles (SAP), which differs in certain respects from IFRS Accounting Standards and U.S. generally accepted accounting principles.

No assurance can be given that some or all of our operating insurance subsidiaries' domiciliary states will not adopt statutory provisions more restrictive than those currently in effect.

If insurance regulators determine that payment of a dividend or any other payments to an affiliate (such as payments under a tax-sharing agreement or payments for employee or other services) would, because of the financial condition of the paying insurance company or otherwise, result in such insurance company being in a hazardous financial condition or would otherwise be prohibited by applicable law, the regulators may prohibit such payments that would otherwise be permitted without prior approval.

Statutory Surplus, Risk-Based Capital and Group Capital

An insurance regulator may limit or prohibit the writing of new business by an insurance company within its jurisdiction when, in the regulator's judgment, the insurance company is not maintaining adequate statutory capital and surplus. We do not currently anticipate that any regulator would limit the amount of new business that our operating insurance subsidiaries may write given their current levels of statutory capital and surplus.

In order to enhance the regulation of insurer solvency, the National Association of Insurance Commissioners ("NAIC") established risk based capital ("RBC") requirements for property and casualty insurance companies. These RBC requirements, which have been adopted in all of the states in which our operating insurance subsidiaries are domiciled, are designed to assess capital adequacy and raise the level of protection that statutory surplus provides for policyholder obligations. The NAIC RBC model law provides that, for property and casualty insurers, the RBC formula will take into account: (i) underwriting risk; (ii) asset risk; (iii) credit risk; and (iv) all other business risks and such other relevant risks as are set forth in the NAIC's Property/Casualty RBC Instructions. The RBC formula provides a mechanism for the calculation of an insurance company's Authorized Control Level ("ACL") RBC amount by the application of RBC risk factors to individual items reported on an insurer's statutory financial statements. The NAIC continuously evaluates these factors to identify and address emerging risks. Changes to risk factors or to statutory accounting can affect insurers by changing their ACL RBC.

The NAIC RBC model law stipulates four levels of regulatory action depending on how an insurer's statutory surplus compares to its RBC. The initial level, the "Company Action Level," requires the insurance company to submit a plan of corrective action to the relevant insurance commissioner if its surplus falls below 200% of the ACL amount (or below 300% of the ACL amount, when a "trend test" is triggered under the NAIC's Property/Casualty RBC Instructions). The next level, the "Regulatory Action Level," requires the company to submit a plan of corrective action and also allows the regulator to perform an examination of the company's business and operations and issue a corrective order if the surplus falls below 150% of the ACL amount (or other triggering events specified in the RBC model law occur). The third level, the ACL, permits the regulator to place the company under regulatory control, including rehabilitation or liquidation, if its surplus falls below 100% of that amount (or other triggering events specified in the RBC model law occur). The final action level, the "Mandatory Control Level," requires the insurance commissioner to place the company under regulatory control if its surplus falls below 70% of the ACL amount.

In addition, the NAIC has developed a group capital calculation tool using an RBC aggregation methodology. The group capital calculation is designed to assist state insurance regulators in understanding the financial condition of non-insurance entities that are part of an insurance holding company system and the degree to which insurance companies are supporting those non-insurance entities. In 2020, the NAIC adopted amendments to the Model Insurance Holding Company System Regulatory Act and the Insurance Holding Company System Model Regulation that implement the group capital calculation by requiring the ultimate controlling person of an insurer subject to registration to file the group capital calculation with its lead state regulator. The first annual group capital calculation filing was due in Delaware, our lead state, by June 1, 2023.

In 2019, the International Association of Insurance Supervisors ("IAIS") adopted the Common Framework for Supervision of Internationally Active Insurance Groups ("ComFrame") to establish minimum standards for the supervision of internationally active insurance groups ("IAIGs"). IAIS members (including supervisors of various Fairfax insurance subsidiaries) have committed to implementing ComFrame and the IAIS is expected to assess each IAIS member's compliance with ComFrame requirements going forward. Fairfax has been designated as an IAIG with the Delaware Insurance Commissioner as its group-wide supervisor.

ComFrame includes an Insurance Capital Standard ("ICS"), a risk-based, group-wide capital standard for IAIGs. Effective as of January 1, 2025, IAIS members are required to implement ICS as a group-wide prescribed capital requirement for IAIGs or a group-wide capital requirement that provides comparable outcomes to ICS. The IAIS has determined that the aggregation methodology used in the NAIC's group capital calculation provides comparable outcomes to the ICS. The impact of ICS and the group capital calculation on the Company are uncertain; however, they may result in an increase in the level of capital and liquidity required by insurance holding companies.

NAIC IRIS Ratios

The NAIC has developed a set of financial relationships or "tests" called the Insurance Regulatory Information System ("IRIS") that was designed to facilitate early identification of companies that may warrant special attention by insurance regulatory authorities. IRIS identifies 13 industry ratios (referred to as "IRIS ratios") and specifies "usual ranges" for each ratio. An IRIS ratio that falls outside the usual range is not necessarily considered adverse. An insurance company may fall out of the usual range for one or more ratios because of specific transactions that are in themselves immaterial or eliminated at the consolidated level. Generally, an insurance company may become subject to increased regulatory scrutiny if it falls outside the usual ranges on multiple ratios.

Investment Regulation

Our operating subsidiaries are subject to state laws and regulations that require diversification of investment portfolios and that limit the amount of investments in certain investment categories. Failure to comply with these laws and regulations may cause non-conforming investments to be treated as non-admitted assets for purposes of measuring statutory surplus and, in some instances, would require divestiture. As of the date of this prospectus, we believe our investments comply with such laws and regulations in all material respects.

Credit for Reinsurance and Licensing

A primary insurer ordinarily will enter into a reinsurance agreement only if it can obtain credit for the reinsurance ceded on its U.S. statutory financial statements. In general, credit for reinsurance is allowed in the following circumstances: (1) if the reinsurer is licensed in the state in which the primary insurer is domiciled; (2) if the reinsurer is an "accredited" or otherwise approved reinsurer in the state in which the primary insurer is domiciled; (3) in some instances, if the reinsurer (a) is domiciled in a state that is deemed to have substantially similar credit for reinsurance standards as the state in which the primary insurer is domiciled and (b) meets certain financial requirements; or (4) if none of the above apply, to the extent that the reinsurance obligations of the reinsurer are collateralized appropriately, typically through the posting of a letter of credit for the benefit of the primary insurer, the deposit of assets into a trust fund established for the benefit of the primary insurer, or by the primary insurer retaining as collateral for the reinsurer's obligations, assets that would otherwise be transferred by the primary insurer to the reinsurer as consideration for the reinsurance. With respect to reinsurance collateral requirements, states have adopted provisions of the NAIC Credit for Reinsurance Model Law and Regulation that allow full credit to U.S. ceding insurers for reinsurance ceded to qualified reinsurers (called "certified reinsurers" or "Reciprocal Jurisdiction Reinsurers") that do not otherwise satisfy the state's credit for reinsurance requirements based upon less than 100% collateralization. Under those provisions, collateral requirements may be reduced or eliminated for reinsurers meeting certain criteria as to financial strength and reliability that are domiciled in "qualified" or "reciprocal" jurisdictions. The NAIC reports that all 50 states have adopted the provisions of the NAIC Credit for Reinsurance Model Law and Regulation that provide for these reduced or eliminated reinsurance collateral requirements.

While the elimination or reduction of regulatory requirements for collateral for reinsurance ceded to Reciprocal Jurisdiction Reinsurers or certified reinsurers does not prevent our operating entities in the United States from continuing to request collateral, it is unclear how much collateral our U.S. operating entities will be able to obtain from these reinsurers going forward. In addition, it is unclear whether these changes will affect the competitive position of any of our U.S. and non-U.S. reinsurance subsidiaries.

Guaranty Funds

Virtually all U.S. states have separate insurance guaranty fund laws requiring property and casualty insurance companies licensed to do business in their respective jurisdictions to be members of their guaranty associations. These associations are organized to pay covered claims (as defined and limited by the various guaranty association statutes) under insurance policies issued by insolvent insurance companies. These associations generally levy assessments (up to prescribed limits) on all member insurers in a particular state on the basis of the proportionate share of the premiums written by member insurers in the covered lines of business in that state. Maximum assessments permitted by law in any one year generally vary between 1% and 2% of annual premiums written in the covered lines by a member in that state. Some states permit or require member insurers to recover assessments paid through surcharges on policyholders or through full or partial premium tax offsets, while other states permit recovery of assessments through the rate filing process.

Our policy is to accrue for insolvencies when the loss is probable and the assessment amount can be reasonably estimated. In the case of most insurance insolvencies, our ability to reasonably estimate the insolvent insurer's liabilities or develop a meaningful range of the insolvent insurer's liabilities is significantly impaired by inadequate financial data with respect to the estate of the insolvent company as supplied by the guaranty funds. Although the amounts of any future assessments by guaranty funds cannot be predicted with certainty, we believe that future guaranty association assessments for known insurer insolvencies will not have a material adverse effect on our results of operations or financial condition.

Shared Markets

As a condition of their licenses to do business, some of our operating insurance subsidiaries are required to participate in mandatory property and casualty shared market mechanisms, residual markets or pooling arrangements, which provide various types of insurance coverage to individuals or other entities that are otherwise unable to purchase such coverage in the commercial insurance marketplace. Our U.S. operating insurance subsidiaries' participation in such shared markets or pooling mechanisms is generally proportionate to the amount of each of our operating insurance subsidiaries' direct premiums written for the type of coverage written by the specific pooling mechanism or residual market mechanism in the applicable state.

Many states have laws that establish second-injury funds to provide compensation to injured employees for aggravation of a prior condition or injury. Generally, insurers writing workers' compensation in those states that have second-injury funds are subject to the laws creating the funds, including the various funding mechanisms that those states have adopted to fund the second-injury funds, including premium surcharges that effectively pass the cost of the fund on to policyholders.

Certain of our operating insurance subsidiaries participate in the Florida Hurricane Catastrophe Fund, a state mandated catastrophe reinsurance fund. Business insurance is also subject to pooled insurance on a small scale for commercial properties insured through the various Fair Access to Insurance Requirements Plans that exist in most states.

The amount of future losses or assessments from the shared and residual market mechanisms and pooling arrangements described above cannot be predicted with certainty. The underwriting results of these pools traditionally have been unprofitable. Although it is possible that future losses or assessments from such mechanisms and pooling arrangements could have a material adverse effect on our results of operations, we do not expect future losses or assessments from the shared and residual market mechanisms and pooling arrangements to have a material adverse effect on our liquidity or capital resources.

Insolvency of Insurers

Insolvency proceedings for U.S. insurance companies, including reinsurers, are generally conducted pursuant to state insurance law. In the event one of our U.S. operating insurance subsidiaries becomes insolvent or otherwise is found by its domiciliary regulator to be in a hazardous financial condition as provided under applicable state insurance law, insolvency proceedings, up to and including rehabilitation, conservation and liquidation, would be initiated by the insurance regulator of the state in which the subsidiary is domiciled, which would serve as the domestic receiver of its properties, assets and business. Insurance regulators located in other states in which we conduct business may have jurisdiction over assets or properties located in such states under certain circumstances. In an insolvency proceeding, policyholders' claims would have priority over investors' claims.

Privacy Regulation

We are subject to a number of U.S. federal and state laws and regulations that require financial institutions and other businesses to protect the confidentiality of individuals' personal information. The Gramm-Leach-Bliley Act and regulations promulgated thereunder govethe privacy of consumer financial information. The regulations set standards for the protection of, and limit disclosure by, financial institutions of "nonpublic personal information" about individuals who obtain financial products or services for personal, family or household purposes. A variety of state privacy statutes and regulations also govethe privacy of information about consumers and require notification to state authorities and individuals if certain personally identifiable information is subject to unauthorized access or disclosure. States, like New York State under its Stop Hacks and Improve Electronic Data Security Act of 2019, as amended (the "SHIELD Act"), have also begun to expand upon the definition of personal information that requires protection and notification in cases of a breach, to include biometric information, genetic information and email addresses with their corresponding passwords or security questions and answers. In June 2018, the State of California enacted the California Consumer Privacy Act of 2018 ("CCPA"), which went into effect on January 1, 2020 and (subject to certain exemptions) requires companies that process information that can be tied to identifiable California residents to make new disclosures to California residents about their data collection, use and sharing practices, and provides certain new rights, including allowing individuals to opt out of certain data sharing with third parties. The statute also created a new cause of action where an individual's personal information is subject to a data breach due to a business's failure to implement and maintain reasonable security practices. Additionally, California voters approved the California Privacy Rights Act of 2020 ("CPRA") as part of the November 2020 ballot. The CPRA substantially amends the CCPA, and it became fully effective on January 1, 2023. The CPRA provides for additional consumer privacy rights and additional regulatory obligations over certain data. It also created a new privacy focused California regulatory agency with enforcement authority, the California Privacy Protection Agency ("CPPA"). CPPA regulations that implement the CPRA became effective on March 29, 2023 and are enforceable.

A number of other states have also passed enhanced privacy laws that recently went into effect or will go into effect in the near future. While these states' laws provide consumer privacy rights and protections similar to those in the CCPA and CPRA, they exempt financial institutions and data subject to the Gramm-Leach-Bliley Act from their requirements.

In addition, states without comprehensive privacy laws, like New York, continue to signal their willingness to enforce privacy on consumer protection grounds, especially over website cookies and other web tracking technologies, based on existing consumer protection laws. Finally, there are several legislative proposals pending before the U.S. Congress and various state legislative bodies concerning privacy. Privacy regulation is an evolving area of state and federal regulation, which requires us to continue to monitor developments.

Cybersecurity

In 2017, the NAIC adopted an Insurance Data Security Model Law (#668-1) that establishes minimum cybersecurity requirements applicable to licensed insurance companies and licensed insurance intermediaries. Among other requirements, the Insurance Data Security Model Law requires licensees to maintain an information security program based on a cybersecurity risk assessment, establish a written incident response plan, provide an annual certification of compliance to state insurance regulators, and investigate and notify state insurance regulators regarding cybersecurity events. As of March 4, 2025, the NAIC reports that 26 states have adopted a version of the Insurance Data Security Model Law or portions thereof and adopting legislation was pending in three states. The New York Department of Financial Services already has a similar cybersecurity regulation in effect and adopted a number of substantial amendments to the regulation in November 2023 that further heighten its cybersecurity requirements, including with respect to governance, incident response and reporting, and implementing certain security controls. Most of the new requirements are now in effect, with the final remaining requirements set to take effect on or before November 1, 2025. Separately, Massachusetts also has regulations in place that require businesses to maintain a cybersecurity program that meets certain minimum requirements. See also "Risk Factors - Risk Factors Relating to Our Business - A disruption of our information technology systems could significantly affect our business".

In March 2022, the US government passed the Cyber Incident Reporting for Critical Infrastructure Act of 2022 ("CIRCIA"), which will require companies deemed to be part of U.S. critical infrastructure to report any "substantial" cybersecurity incidents to the Cybersecurity and Infrastructure Security Agency ("CISA") of the US Department of Homeland Security within 72 hours and ransomware payments within 24 hours. On April 4, 2024, CISA published proposed regulations, defining the scope of application and details around these reporting obligations. The proposed regulations would apply to any entity operating in one of the 16 critical infrastructure sectors (including the financial services sector) as designated by the President that either (i) exceeds the industry specific small business size standard defined under the Small Business Administration's small business size regulations (the "size-based criterion"), or (ii) falls within one or more specific critical infrastructure sectors or subsectors, including the "financial services sector" (the "sector-based criterion"). CISA currently considers the insurance business to be included in "financial services" for purposes of designated critical infrastructure and Fairfax and/or certain insurance subsidiaries thereof may become subject to CIRCIA requirements - including reporting requirements.

For reporting purposes, the proposed regulations define a substantial cyber incident to include: (i) incidents that lead to the substantial loss of confidentiality, integrity, or availability of systems; (ii) serious impact on the safety and resiliency of operational systems and processes; (iii) disrupt the ability to engage in business operations or deliver services; or (iv) any unauthorized access to systems or nonpublic information that is facilitated or caused by a compromise of a third-party data hosting provider (e.g., cloud provider) or a supply chain compromise. The proposed regulations also establish record retention requirements for background material supporting the filing of the report. The proposed regulations would also give CISA power to subpoena companies it believes are not reporting a substantial cybersecurity incident or ransomware. If CISA believes a company is not appropriately responding to a subpoena, it could refer the matter to the Department of Justice. CIRCIA requires that the final rules be published within 18 months of being proposed, meaning the rules must be finalized on or before October 4, 2025.

Regulation of Holding Company Systems

While insurance in the United States is regulated primarily on a legal-entity basis, the NAIC has increased its focus on risks presented by an insurer's holding company system. In 2010, the NAIC adopted revisions to the Model Insurance Holding Company System Regulatory Act and the Insurance Holding Company System Model Regulation (together, the "Revised Model Holding Company Act and Regulation") that include, among other amendments, a requirement for the ultimate controlling person of every insurer to file an enterprise risk report annually. "Enterprise risk" is defined as any activity, circumstance, event or series of events involving one or more affiliates of an insurer that, if not remedied promptly, is likely to have a material adverse effect upon the financial condition or liquidity of the insurer or its insurance holding company system as a whole. The Revised Model Holding Company Act and Regulation have been substantively adopted in each of our operating insurance subsidiaries' domiciliary states.

In 2012, the NAIC adopted the Risk Management and Own Risk and Solvency Assessment ("ORSA") Model Act, which has been substantively adopted in each of our operating insurance subsidiaries' domiciliary states. The ORSA Model Act requires insurers or their insurance group to conduct an ORSA consistent with a process comparable to the NAIC ORSA Guidance Manual no less than annually and at any time when there are significant changes to the risk profile of the insurer or the insurance group of which the insurer is a member. An ORSA is a confidential internal assessment, appropriate to the nature, scale and complexity of an insurer or insurance group, conducted by that insurer or insurance group of the material and relevant risks associated with the insurer or insurance group's current business plan, and the sufficiency of capital resources to support those risks. The assessments must be documented in an annual summary report, a copy of which must be submitted to state insurance regulators as required under the applicable laws of each state.

Corporate Governance Annual Disclosure Model Act

The NAIC has adopted the Corporate Governance Annual Disclosure Model Act ("CGAD"). CGAD requires an annual filing by an insurer or insurance group that provides a detailed report on corporate governance structure and policies and procedures. Fairfax submits CGAD filings on behalf of all of its U.S. operating insurance subsidiaries to the Delaware Department of Insurance.

Terrorism Risk Insurance Act

The Terrorism Risk Insurance Act of 2002, as amended ("TRIA"), established a program under which the U.S. federal government will share with the insurance industry the risk of loss from certain acts of terrorism certified as such by the Secretary of the Treasury. The program was most recently extended in 2019 through December 31, 2027. Under the current program (i) the threshold for the program to go into effect (the triggering event) is $200 million in insured losses, (ii) the insurer deductible is 20% of the insurer's affiliated group's direct earned premium for the prior year from qualified property and casualty insurance lines, and (iii) the amount that insurers must cover as a whole through co-payments and deductibles, which is known in the industry as the aggregate retention, is $37.5 billion. TRIA is applicable to almost all commercial lines of property and casualty insurance, but excludes commercial auto, burglary and theft, surety, professional liability and farm owners' multi-peril insurance. Insurers with direct commercial property and casualty insurance exposure in the United States are required to participate in the program and make available coverage for certified acts of terrorism. Federal participation will be triggered when the Secretary of the Treasury certifies an act of terrorism.

While the provisions of TRIA and the purchase of certain terrorism reinsurance coverage mitigate our exposure in the event of a large-scale terrorist attack, the risk of severe losses to us from acts of terrorism remains because our effective deductible is significant, certain lines that we write are not covered by TRIA and there is no certainty that future acts of terrorism will be certified as such by the Secretary of the Treasury. There is also no certainty that the program will be extended beyond December 31, 2027, or, if it is extended, that the program will provide coverage in the same amounts and on the same terms. Moreover, regardless of TRIA, some state insurance regulators do not permit terrorism exclusions for various coverages or causes of loss. Accordingly, we continue to carefully monitor our concentrations of risk.

Possible Legislative, Regulatory and Policy Changes

In recent years, the insurance industry has been subject to increased scrutiny by legislators, regulators and policymakers. As noted above, the NAIC and a number of state legislatures have considered or adopted legislative proposals that alter and, in many cases, increase the authority of state regulators to regulate insurance companies and holding company systems. Additional regulations or new requirements may emerge from activities of various regulatory and policymaking bodies, including the Federal Reserve Board, the Federal Insurance Office, the Financial Stability Oversight Council, the U.S. Department of the Treasury, the Executive Office of the President and the NAIC. We cannot predict whether any specific state or federal measures will be adopted to change the nature or scope of the regulation of insurance or what effect any such measures would have on Fairfax and its U.S. operating insurance subsidiaries.

Finally, the ongoing investigations and scrutiny of insurance industry business practices, discussed above, may result in new laws or regulations at the state or federal level. See "Risk Factors - Risk Factors Relating to Our Business - Certain business practices of the insurance industry have been the subject of negative publicity and investigations by government authorities and the subject of class action litigation".

It is not possible to predict the outcome of any of the foregoing legislative, administrative or congressional activities or the potential effects thereof on us.

Canada

General

Each of our Canadian insurance subsidiaries is federally incorporated under the Insurance Companies Act ("ICA") and is licensed under insurance legislation in each of the provinces and territories in which it operates.

The ICA and provincial legislation require the filing by our Canadian insurance subsidiaries of annual and other reports on their financial condition and results. The ICA imposes restrictions on transactions with related parties and sets forth requirements governing reserves for actuarial liabilities and the safekeeping of assets and other matters. The ICA is administered, and the activities of our insurance subsidiaries are supervised, by the Office of the Superintendent of Financial Institutions ("OSFI"). OSFI conducts examinations to ensure compliance with the ICA and to confirm the financial condition of the companies.

Investment Powers

Under the ICA, the directors of a federally incorporated insurance company must establish and the insurance company must adhere to investment and lending policies, standards and procedures that a reasonable and prudent person would apply to a portfolio of investments and loans to avoid undue risk of loss and obtain a reasonable return, subject to certain overall limitations on the amount it may invest in certain classes of investments, such as commercial loans, real estate and equities. Additional restrictions (and in some cases, the need for regulatory approvals) limit the nature of an insurance company's investments.

Capital Requirements

Property and casualty insurers are required to meet a Minimum Capital Test ("MCT") that assesses the insurer's capital available to capital required. Federally regulated property and casualty insurers, including our Canadian insurance subsidiaries, must maintain available capital equal to at least the minimum capital requirement. OSFI expects insurers to establish a target capital level above the minimum requirement, and to maintain ongoing capital, at no less than the supervisory target of 150% of the MCT amount. OSFI expects federally regulated property and casualty insurers to establish an internal target capital ratio, and maintain ongoing capital, above the supervisory target. OSFI may, however, on a case-by-case basis, establish in consultation with an insurer an alternate supervisory target based upon the company's risk profile. The ICA requires property and casualty insurance companies to maintain adequate levels of capital and adequate and appropriate liquidity. The MCT calculates the required capital by reference to, and varying with, the risk characteristics of each category of on and off-balance sheet assets held by the company, the company's policy liabilities and reinsurance receivable and recoverable. This MCT calculation typically requires the application of quantitative factors to assets, as well as to certain off-balance sheet items, based on a number of prescribed risk components. The calculation of policy liabilities takes into account the risk associated with variations in claims, provisions, possible inadequacy of provisions for unearned premiums, possible inadequacy of provisions for premium deficiencies, and the occurrence of catastrophes. The calculation of reinsurance receivable and recoverable includes the risk of default for recoverables from reinsurers arising from both credit and actuarial risk.

Restrictions on Dividends and Capital Transactions

The ICA prohibits the declaration by the directors of a federally incorporated insurance company, or the payment by the insurance company, of any dividend on shares of an insurance company if there are reasonable grounds to believe the company is, or the payment of the dividend would cause the company to be, in contravention of applicable capital and liquidity requirements. The ICA also requires the directors of an insurance company to notify the Superintendent of Financial Institutions of the declaration of a dividend at least 15 days prior to the date fixed for its payment. Similarly, the ICA prohibits the purchase for cancellation of any shares issued by an insurance company or the redemption of any redeemable shares or other similar capital transactions, if there are reasonable grounds for believing that the company is, or the payment would cause the company to be, in contravention of its applicable capital and liquidity requirements. These latter transactions would also require the prior approval of the Superintendent of Financial Institutions.

Constraints on Shares

The ICA contains certain restrictions on the purchase or other acquisition, issue, transfer and voting of any shares of an insurance company. Pursuant to these restrictions, no person is permitted to acquire shares of any of our Canadian insurance subsidiaries, or to acquire control of a company which holds such an interest, if the acquisition would cause the person to have a "significant interest," or increase an existing "significant interest," in any class of shares of the insurance company, unless the prior approval of the Minister of Finance (Canada) is obtained. In addition, no insurance company is permitted to record any transfer or issue of its shares if the transfer or issue would cause the person to have a significant interest, or increase an existing significant interest, in the insurance company and such interest or increase has not been approved by the Minister of Finance (Canada). No person who has a significant interest in such a company may exercise any voting rights attached to the shares held by such person, or entities controlled by that person, unless the prior approval of the Minister of Finance (Canada) is obtained. In certain cases, if a person contravenes any of these restrictions, the Minister of Finance (Canada) may, by order, direct that person to dispose of all or any portion of those shares. For these purposes, a person has a significant interest in a class of shares of an insurance company where the aggregate of any shares of that class beneficially owned by that person, or an entity controlled by that person and by any person associated or acting jointly or in concert with that person, exceeds 10% of all outstanding shares of that class of shares of the company.

Provincial and Territorial Insurance Regulation

Each of our insurance subsidiaries is subject to provincial and territorial regulation and supervision in each of the provinces and territories of Canada in which it carries on business. Provincial insurance regulations deal primarily with the form and content of insurance contracts, the sale and marketing of insurance products, including licensing and supervision of insurance distributors, and the settlement of insurance claims. In the provinces of Alberta, Ontario, New Brunswick, Newfoundland and Labrador, Nova Scotia and Prince Edward Island premium rates for automobile insurance are regulated by public authorities. They require insurers to submit proposed rates to a regulatory body and have them approved before use. While Québec has a public auto insurance system for its base coverage, rates for excess insurance must be approved by the provincial insurance regulator. The approval process may also involve a hearing. Under provincial regulation, insurance contracts are deemed automatically to include certain terms that cannot be changed without the approval of the relevant regulatory authority, as well as certain terms that cannot be changed without statutory or regulatory amendment.

Property and Casualty Insurance Compensation Corporation ("PACICC")

PACICC was formed to respond to claims by Canadian policyholders and refund certain premiums paid in advance, within limits, in the event of the insolvency of their insurance company. The Canadian property and casualty insurance industry elects the directors of PACICC. PACICC is funded by its member insurance companies, including our Canadian property and casualty insurance subsidiaries.

United Kingdom

General

Fairfax is subject to regulation and supervision by the Prudential Regulation Authority ("PRA") and the Financial Conduct Authority ("FCA") in relation to the carrying on by certain of our operating subsidiaries of regulated activities in the United Kingdom. Fairfax is also subject to regulatory standards set by Lloyd's of London ("Lloyd's") by way of our operations in the Lloyd's market.

Our U.K. operating subsidiaries include:

·

the following Lloyd's managing agents: (a) Brit Syndicates Limited, which is the managing agent of Syndicates 2987 and 2988; (b) Newline Underwriting Management Limited, which is the managing agent of Syndicate 1218; and (c) Allied World Managing Agency Limited, which is the managing agent of Syndicate 2232; and

·

the U.K. branch of Allied World Assurance Company (Europe) dac, an Irish insurance company ("AWAC Europe U.K. Branch").

This section is principally focused on the application of the U.K. regulatory framework to the Lloyd's managing agents referenced above (but a number of the requirements also apply to AWAC Europe U.K. Branch, including, for example, the FCA's conduct of business requirements).

U.K. Regulatory Framework

Dual-regulation by PRA and FCA

The PRA and the FCA are the regulators for persons authorized under the Financial Services and Markets Act 2000 ("FSMA") to undertake regulated activities in the financial services sector in the United Kingdom. The PRA oversees and is responsible for the micro-prudential regulation of banks, insurers and some large investment firms (the Financial Policy Committee, a sub-committee of the Bank of England, is responsible for macro-prudential regulation in the United Kingdom). The FCA is responsible for conduct of business regulation and market regulation for all authorized firms, and the prudential regulation of firms not authorized by the PRA.

Each of the Lloyd's managing agents referred to above and AWAC Europe U.K. Branch is authorized and regulated by the PRA, as well as having its conduct of business regulated by the FCA, and is, therefore, considered a dual-regulated firm. The PRA and the FCA have extensive powers to supervise and intervene in the affairs of regulated firms, for example, if they consider it appropriate in order to protect policyholders against the risk that the firm may be unable to meet its liabilities as they fall due, that the Threshold Conditions (as defined below) may not be met, that the firm or its parent has failed to comply with obligations under the relevant legislation or rules, that the firm has furnished them with misleading or inaccurate information or that there has been substantial departure from any proposal or forecast submitted to the relevant regulator.

The PRA and the FCA also have the power to take a range of disciplinary and enforcement actions in relation to a breach by a firm of FSMA or the rules made under FSMA as set out in the PRA Rulebook and other guidance and supervisory statements that the PRA may publish from time to time (the "PRA Rulebook") and in the FCA Handbook of Rules and Guidance (the "FCA Handbook"), respectively. Such disciplinary and enforcement actions may include private censure, public censure, restitution, fines or sanctions and the award of compensation. The PRA (or, where relevant, the FCA) may also cancel or vary (including by imposing limitations on) a Part 4A Permission (described in greater detail below) of a firm.

Lloyd's of London

The Society of Lloyd's is itself authorized by the PRA and regulated by the PRA and the FCA, and its senior personnel are required to be approved by the regulators. Lloyd's regulated activities include arranging deals in contracts of insurance written at Lloyd's ("the basic market activity"), arranging deals in participations in Lloyd's syndicates ("the secondary market activity") and carrying out any activity in connection with, or for the purposes of, these two activities (article 14 of the Financial Services Act 2012 (Transitional Provisions) (Permission and Approval) Order 2013).

The Council of Lloyd's ("Council") is the governing body of the Lloyd's market, and under the Lloyd's Act 1982 (the "1982 Act"), it is responsible for the market's management and supervision. Under the 1982 Act, the Council has the power to regulate and direct the business of the market, and to make by-laws. Lloyd's market rules are set out in the by-laws, and in other guidance, codes of conduct, bulletins and principles issued by the Council or under its authority, although regulation of the Lloyd's market is under the ultimate direction of the PRA and the FCA.

Lloyd's does not carry on insurance activity itself, but regulates its members doing so. Members of Lloyd's form and underwrite all insurance business via syndicates which consist of one or more such members. Lloyd's supervises its own members (including in relation to setting the amount of capital required to be provided by each member to support its underwriting liabilities) under the direction of the PRA and the FCA. Members are not required to be authorized under FSMA, but must abide by the Lloyd's rules, which means that the PRA and the FCA indirectly regulate members (given that Lloyd's itself is a dual-regulated firm). Under sections 316 and 318 of FSMA, the PRA and the FCA can give directions to Lloyd's or its members in order to advance one or more of their statutory objectives, for example by imposing particular rules on members. Lloyd's has a memorandum of understanding with the PRA and the FCA to assist with cooperation in supervision and enforcement.

As regards to prudential requirements, the rules in the Solvency II UK Firms section of the PRA Rulebook apply to Lloyd's and its managing agents as a whole with some modifications (see "Prudential and Capital Requirements" below).

Syndicates are managed by managing agents who are authorized by the PRA and regulated by the PRA and the FCA.

Regulation of Lloyd's Managing Agents

Part 4A Permissions

Under section 19 of FSMA, it is unlawful to carry on the regulated business of being a Lloyd's managing agent in the United Kingdom without permission to do so from the PRA under Part 4A of FSMA ("Part 4A Permission"). A Lloyd's managing agent will hold permissions for managing the underwriting capacity of a Lloyd's syndicate as a managing agent at Lloyd's, and usually also for insurance distribution activities such as dealing in investments as agent, arranging, advising on investments, and assisting in the administration and performance of contracts of insurance. Each of the above managing agents holds permission for managing the underwriting capacity of a Lloyd's syndicate and one or more of the insurance distribution activities.

At the point of authorization (on the granting of Part 4A Permissions) and at all times thereafter, managing agents must meet specified threshold conditions which are set out in Schedule 6 of FSMA ("Threshold Conditions").

The PRA and the FCA each have their own sets of Threshold Conditions and, as dual-regulated firms, the managing agents must comply with both. The Threshold Conditions relate to matters including the adequacy of the firm's financial and other resources and whether a firm is a fit and proper person to conduct its regulated activities, having regard to all the circumstances (including whether the firm's affairs are conducted soundly and prudently).

When granted, a Part 4A Permission will specify: (i) a description of the activities the managing agent can carry on, including any limitations on the scope of the permission; (ii) the specified investments to which the permission relates; and (iii) requirements imposed in relation to the permission to require the managing agent to take, or to refrain from taking, specified action. These requirements may relate to a range of matters, including the scope of a managing agent's business, capital, liquidity and interactions with affiliates. Once authorized, in addition to continuing to meet the Threshold Conditions, managing agents must comply with the requirements of the PRA Rulebook and the FCA Handbook that apply to them.

Additionally, a managing agent needs the permission of Lloyd's to manage a syndicate.

A managing agent must also obtain prior approval from the PRA or the FCA (depending on the function in question) for any individual who carries on one or more specified "controlled functions," such as executive or non-executive directors and persons responsible for risk management, internal audit or compliance. The controlled functions of managing agents specified by the PRA and the FCA are known as senior management functions ("SMFs"). The relevant regulator will only approve an individual if it is satisfied that such individual is "fit and proper" to perform the SMF in question, including by reference to the person's honesty, integrity and reputation, competence and capability for the roles that the person is to assume in the firm and his or her financial soundness. The PRA and/or the FCA's assessment of fitness and propriety often includes an interview of the candidate to perform a SMF.

The managing agents must carry out ongoing assessments of fitness and propriety in relation to all SMF holders. Individuals in SMFs are subject to a duty of responsibility in accordance with FSMA and can be held accountable if they fail to take "reasonable steps" to prevent regulatory breaches. Each SMF holder will have a statement of responsibilities showing what they are responsible for within the business. These responsibilities will be set out alongside reporting lines in a "Responsibilities Map" which is available to the regulators.

Individuals who do not hold SMFs but whose role means that they have the potential to cause harm to either the relevant managing agent or its customers must be certified by the managing agent in question as fit and proper to perform their role. Such roles are "Certification Functions" and include those functions that are considered to be Key Functions under the Solvency II Directive (as implemented into law in the United Kingdom).

All staff in each of the managing agents, save for those who are in roles such as catering or security (where they cannot pose a risk to the business or its customers), must comply with individual conduct rules. SMF holders must comply with additional conduct rules relating to regulatory objectives.

Prudential and Capital Requirements

As noted above, we principally operate in the United Kingdom through the Lloyd's market. Lloyd's capital structure, often referred to as the "chain of security", is intended to provide a high degree of security for policyholders. There are three parts to the "chain of security":

(i)

Syndicate level assets: The insurance premiums that are collected by members and held in a premium trust fund for the benefit of policyholders whose contracts are underwritten by the syndicate. These monies are the first resource used for paying claims made by the members' policyholders from that syndicate.

(ii)

Funds at Lloyd's: Each member must provide capital to support its underwriting at Lloyd's. This capital is held in trust as a buffer to back up each member's underwriting liabilities in each syndicate in which it is a member. The amount of capital to be provided by each member is determined by reference to the rules on the Solvency Capital Requirement ("SCR") contained in the Solvency II UK Firms section of the PRA Rulebook, which apply to Lloyd's and to its managing agents. Lloyd's requires managing agents to determine the SCR on an ultimate basis ("uSCR") for each syndicate they manage (described in greater detail below). Lloyd's then applies an "Economic Capital Uplift" to each uSCR and the resulting figure is used to calculate each member's capital resources requirement in proportion to its share of each syndicate of which it is a member. Details of how a member's capital requirement is calculated are set out in the Lloyd's Membership & Underwriting Conditions and Requirements: Funds at Lloyd's.

(iii)

Mutual assets (Central Fund and callable layer): Members make annual contributions to the Central Fund which can be used to pay out in relation to the claims against any member who fails to meet its insurance liabilities in full. In addition, this is supplemented by a "callable layer" of up to 5% of members' overall premium limits which Lloyd's can call upon to meet claims.

When calibrating the SCR, Lloyd's is required to include, in addition to the risks impacting its members, all quantifiable risks to which Lloyd's itself is exposed, including risks to its central assets and central liabilities. Lloyd's and its managing agents must also comply with requirements to conduct own risk and solvency assessments and to report, as set out in, respectively, the Conditions Governing Business and the Reporting parts of the Solvency II UK Firms section of the PRA Rulebook.

As dual-regulated firms in their own right, managing agents are under an obligation to manage the syndicate assets and the insurance business carried on by members of the syndicate in accordance with the Solvency II UK Firms section of the PRA Rulebook. This requires managing agents to ensure that the financial resources for each syndicate they manage and the capital resources at syndicate level are adequate, and that they establish and maintain systems and controls for the management of prudential, credit, market, operational and insurance risks for each syndicate.

Managing agents must calculate capital resources at syndicate level under the rules in the Solvency II UK Firms section of the PRA Rulebook and, in particular, must calculate an SCR for each syndicate (which captures the risks that will emerge over the next 12 months) and a uSCR (to capture potential adverse developments which may arise until all liabilities have been paid). The SCR and uSCR take into account the risks, controls and financial resources available to each syndicate, and are notified to Lloyd's periodically.

Managing agents are also subject to their own regulatory capital requirements, comprising both a minimum qualifying capital requirement and minimum net asset requirement.

Conduct of Business

The FCA's conduct of business requirements for managing agents can be found in the Insurance: Conduct of Business Sourcebook of the FCA Handbook ("ICOBS"). These rules regulate the day-to-day conduct of business standards to be observed by managing agents involved in insurance distribution activities and/or the activity of managing the underwriting capacity of a Lloyd's syndicate (these are supplemented by Lloyd's own rules, including certain principles in respect of customer outcomes). Although the scope and range of obligations imposed by the ICOBS rules vary according to the scope of the firm's business and the nature of its clients, generally the rules include the need to provide clients with information about the firm, meet certain standards of product disclosure, ensure that promotional materials are clear, fair and not misleading, assess suitability when advising on certain products, manage conflicts of interest, report appropriately to clients and provide certain protections in relation to client assets. The rules in ICOBS were amended with effect from October 1, 2018 to implement Directive 2016/97/EU (the "Insurance Distribution Directive"). The key changes brought about by the Insurance Distribution Directive included the introduction of: (i) an overarching requirement to act in a customer's best interest; (ii) additional requirements to ensure that individuals who sell insurance are fit and proper (including new continuing professional development standards); (iii) a requirement for distributors to have in place product governance processes to ensure that policies are designed for their target audience; and (iv) information disclosure requirements providing for the delivery of simple, standardized policy summary documentation to retail customers. In addition, the Insurance Distribution Directive removed introducing as a regulated activity.

In July 2022, the FCA published policy statement "PS 22/9: A New Consumer Duty," setting out a new consumer duty which is intended to: (a) have a significant impact on how firms (including insurers and insurance intermediaries) interact with retail customers; and (b) set higher expectations for the standard of care firms give to such customers over the lifecycle of their products. The consumer duty is consistent with the FCA's continuing focus on outcomes for consumers (e.g., that they are sold products that provide valuable benefits at an appropriate price, that they receive the service and support promised or to be reasonably expected and that there are no barriers to them cancelling or deciding not to renew). Firms need to be able to demonstrate how their business models, the actions they take and their culture are focused on delivering good customer outcomes. The FCA believes that an outcome focused approach will also have benefits for firms as it will give them 'greater flexibility to adapt and innovate.' Firms have been required to apply the consumer duty to: (a) new and existing products and services that are open to sale (or renewal), since July 31, 2023; and (b) products and services held in closed books, since July 31, 2024.

Customer Complaints and Compensation

Lloyd's itself and managing agents are under the compulsory jurisdiction of the Financial Ombudsman Service ("FOS") which has been set up under FSMA. Authorized firms must have appropriate complaints handling procedures but, where these are exhausted, the FOS provides for dispute resolution in respect of complaints brought by eligible complainants.

The FOS is available to eligible complainants in addition to their right to bring a claim in the courts. If the FOS determines a dispute in favor of a complainant, it has the power to order a firm to pay compensation for any loss or damage it caused to the complainant, or to direct a firm to take such steps in relation to the complainant as the FOS considers just and appropriate, irrespective of whether a similar award could be made by a court. The FOS is mainly funded by levies and case fees payable by firms falling within the jurisdiction of the FOS.

The Financial Services Compensation Scheme ("FSCS") is established under FSMA and may provide compensation to certain categories of customers who suffer losses as a consequence of the inability of a regulated firm to meet its liabilities arising from claims made in connection with regulated activities. The FSCS is funded by means of levies on all of its participating financial services firms, including Lloyd's.

Money Laundering and Other Financial Crime

All FSMA authorized firms are required to undertake certain administrative procedures and checks, which are designed to prevent money laundering. The FCA Handbook contains rules which require firms to establish and maintain effective systems and controls for countering the risk that the firm might be used to further financial crime. For these purposes, financial crime includes any offence involving fraud or dishonesty, misconduct in, or misuse of information relating to, a financial market or handling the proceeds of crime, as well as bribery and corruption offences. One of the FCA's statutory objectives is to protect and enhance the integrity of the U.K. financial system which includes, among other things, reducing the opportunity for the U.K. financial system to be used for purposes connected with financial crime.

Qualifying Parent Undertaking

The PRA and the FCA have the power, in certain circumstances, to give directions to certain "qualifying parent undertakings" of U.K. authorized firms even where those parent undertakings are not themselves regulated, provided that the parent undertaking is incorporated in the United Kingdom or has a place of business in the United Kingdom. This power of direction allows the PRA or the FCA to direct the parent to take or refrain from taking specified action or to remedy past actions in prescribed circumstances.

Change of Control of Authorized Firms

Under section 178 of FSMA, if a person intends to acquire or increase "control" over a PRA-authorized firm (including a Lloyd's managing agent), it must first notify and get prior approval from the PRA before becoming a "controller" or increasing its level of control above certain thresholds. A person must also notify the PRA when the transaction that results in this acquisition or increase of control takes place.

A proposed "controller" for the purposes of the change of control regime is any natural or legal person (whether alone or "acting in concert" with other persons) who decides to acquire or increase, directly or indirectly, his, her or its control over a U.K. authorized firm.

"Control" over a PRA authorized firm is acquired if the acquirer:

·

holds 10% or more of the shares or voting rights in that company or in its (direct or indirect) parent undertaking; or

·

is able to exercise significant influence over the management of the firm by virtue of the acquirer's shares or voting power in the company or its (direct or indirect) parent undertaking.

Increases of control of a PRA authorized firm require the consent of the PRA where they reach the thresholds of 20%, 30% and 50% of the shares or voting power in the firm or its parent. Reducing or proposing to reduce control below the relevant threshold also gives rise to an obligation to notify the PRA.

Breach of the notification and approval regime is a criminal offence.

The approval of Lloyd's is also required in relation to the change of control of a Lloyd's managing agent or member. Broadly, Lloyd's applies the same tests in relation to control as are set out in FSMA and, in practice, where the application relates to a managing agent, coordinates its approval process with that of the PRA.

The same approval process applies in respect of FCA authorized firms. However, for FCA authorized firms that are non-Directive firms (e.g., non-MiFID firms, general insurance intermediaries, full permission consumer credit firms and home finance providers), the FSMA (Controllers) (Exemption) Order 2009 provides that there is only one threshold and control band of 20% or more.

Financial Services and Markets Act 2023

The Financial Services and Markets Act 2023 (the "2023 Act") received Royal Assent on June 29, 2023 (although certain provisions have yet to come into force).

The 2023 Act permits the revocation of all retained European Union law relating to financial services, including the Solvency II Directive and the Insurance Distribution Directive, although such revocation will only take effect once regulators have drafted and consulted on replacement rules and are ready to enforce them.

Other changes implemented by the 2023 Act include:

(i)

a new statutory objective for the PRA and FCA requiring them to act in a way which facilitates the long-term growth and international competitiveness of the U.K. economy; and

(ii)

a requirement for the regulators to consider the sustainable growth in the U.K. economy in the medium or long term in a manner consistent with the United Kingdom's net zero emissions commitments.

In parallel with the 2023 Act, HM Treasury and the PRA consulted on proposed reforms to the Solvency II Directive regime in April 2022, June 2023 and September 2023 and such reforms have now been fully implemented. These reforms include a reduction in the risk margin required to be held by insurers and a reduction in the reporting and administrative burdens to which U.K. insurers were previously subject. Of particular note to Fairfax's business is the removal of the requirements for U.K. branches of foreign insurers (such as AWAC Europe U.K. Branch) to calculate branch capital requirements and to hold local assets to cover them.

Additional proposed regulatory developments that may impact Fairfax include:

(i)

changes to operational resilience requirements. Operational resilience is a key focus area for regulators in the United Kingdom and in Europe. In the United Kingdom, the FCA and the PRA published final rules and policy on operational resilience in 2022 requiring firms to perform mapping and testing in relation to their operational resilience. In Europe, the Digital Operational Resilience Act came into force on January 17, 2025; and

(ii)

a focus on the commercial insurance market. On July 29, 2024, the FCA issued a discussion paper (DP24/1: Regulation of Commercial and Bespoke Insurance) which set out proposals focused on attempting to ensure an appropriate balance between consumer protection and competitiveness in the commercial insurance market.

Other Relevant Issues for the Insurance Sector in the United Kingdom

Passporting

Firms authorized in a European Economic Area ("EEA") state to carry on activities regulated under one of the relevant directives emanating from the European Union (the "Single Market directives") are entitled to carry on those regulated activities in any other EEA state without needing to become directly authorized by the regulator of the host EEA state. This is known as "passporting" and can involve either the setting up of an establishment in the host EEA state or the provision of cross-border services. The Solvency II Directive is, for example, a Single Market directive. Whilst the United Kingdom was part of the EEA, Brit Syndicates Limited had permission from the PRA to exercise passporting rights out of the United Kingdom and into other EEA states.

The United Kingdom left the European Union at 23:00 (Greenwich Mean Time) on January 31, 2020. Prior to this date, the European Union (Withdrawal Agreement) Act 2020 (the "Withdrawal Act") entered into law in the United Kingdom on January 23, 2020. The Withdrawal Act provided for an "implementation period," during which time existing arrangements between the United Kingdom and European Union would continue to apply, until December 31, 2020 (and, during that period, U.K. firms were able to continue to benefit from their passporting permissions). Following December 31, 2020, U.K. firms are no longer able to exercise passporting rights. To enable clients with EEA business to continue to access the Lloyd's market, Lloyd's has established a subsidiary in Belgium, Lloyd's Insurance Company S.A. ("Lloyd's Europe"), which is authorized by the National Bank of Belgium ("NBB"), regulated by the NBB and the Financial Services and Markets Authority in Belgium and benefits from passporting permissions in all EEA states. Lloyd's Europe can accept risks and issue policies via Lloyd's Europe registered brokers, service companies and coverholders. All Lloyd's Europe policies are then 100% reinsured back to Lloyd's syndicates (each risk bound by Lloyd's Europe is allocated to a relevant syndicate), meaning that clients will benefit from Lloyd's chain of security (as described above). This structure enables the members of Syndicate 2987, Syndicate 2988, Syndicate 1218 and Syndicate 2232 to continue to have an interest in EEA business (albeit as reinsurers rather than direct insurers). For completeness, we note that all of Lloyd's historic general insurance EEA business was transferred from Lloyd's to Lloyd's Europe with effect from December 30, 2020 pursuant to Part VII of FSMA (including any EEA business of the members of Syndicate 2987, Syndicate 2988, Syndicate 1218 and Syndicate 2232 - such business was subsequently 100% reinsured by the members of the relevant syndicate).

With regard to EEA firms (such as AWAC Europe U.K. Branch) carrying on business in the United Kingdom, HM Treasury legislated for a temporary permissions regime ("TPR") that took effect from the end of the implementation period referred to above. The aim of the TPR was to allow firms that wished to continue carrying on business in the United Kingdom in the longer term to operate in the United Kingdom for a limited period after the passporting regime ended while they sought full authorization from U.K. regulators. Under the TPR, a firm that was previously authorized to carry on regulated activities in the United Kingdom on a freedom of establishment or freedom of services basis was able to obtain a deemed permission to carry on those activities for a maximum of three years from the end of the implementation period, subject to HM Treasury's power to extend the duration of the regime by increments of 12 months. AWAC Europe U.K. Branch previously benefited from the TPR but exited the TPR, on July 13, 2023 upon receiving authorization for its U.K. branch to become a U.K. branch of an international insurer.

Ogden Tables

Our insurance business in the United Kingdom includes insurance of liability for personal injury. Where a personal injury claim is determined or settled with a lump sum payment, the payment is calculated in accordance with the "Ogden Tables". The Ogden Tables contain a discount rate that is set by the U.K. government and is applied when calculating the present value of loss of earnings for claims settlement purposes. A change in the discount rate used in the Ogden Tables impacts all relevant claims settled after that date, regardless of whether the insurance to which the claim relates was priced on that basis or not (or occurred after that date or not). A reduction in the Ogden discount rate increases lump sum payments to personal injury claimants, and in consequence the amount of reserves required to be held by insurers in relation to outstanding claims. The U.K. Government recently announced that the Ogden discount rate would be aligned in England and Wales, Scotland and NortheIreland to 0.5%.

Data protection

The United Kingdom and the European Union are subject to data protection laws, which regulate the obtaining and use of personal data relating to living individuals. As a result of leaving the European Union, the key data protection laws of the United Kingdom are the U.K. General Data Protection Regulation ("UK GDPR"), supplemented by the Data Protection Act 2018. The UK GDPR currently aligns with the European Union's GDPR ("EU GDPR"), which applies across the EEA (also supplemented by national data protection laws), which has applied since May 25, 2018. The UK GDPR or EU GDPR (as applicable) applies to everyone working in Fairfax's businesses in the EEA and the United Kingdom, as well as Fairfax's businesses outside the EEA or the United Kingdom that provide services to or monitor individuals (including customers) in the EEA or the United Kingdom (as applicable) as a result of the extraterritorial application of these laws. The UK GDPR and/or EU GDPR require, among other things, businesses to: (a) process personal data fairly, lawfully and transparently, for specified and legitimate purposes and in accordance with data minimization; (b) store personal data no longer than needed; (c) adequately protect personal data; and (d) demonstrate compliance. Businesses are also required to perform data protection impact assessments on a mandatory basis when undertaking high risk data processing activities, and to respond to requests to exercise rights granted to individuals in respect of their personal data including to allow individuals to request access to their data, the erasure/correction of their data and data portability (in some cases subject to certain restrictions).

The UK GDPR and EU GDPR prohibit companies from transferring personal data from inside the EEA or the United Kingdom to countries that are outside the EEA or the United Kingdom that are not considered to provide "adequate" protections to personal data unless an export solution is in place or a derogation is used. Countries considered to be "adequate" are Andorra, Argentina, Canada (commercial organizations only), Faroe Islands, Guernsey, Isle of Man, Israel, Japan (private-sector organizations only), Jersey, New Zealand, the Republic of Korea, Switzerland, the United States (only commercial organizations participating in the EU-US Data Privacy Framework ("DPF") and Uruguay. The United Kingdom is also considered "adequate" under the EU GDPR in respect of transfers from the EEA, and the EEA is considered "adequate" under the UK GDPR in respect of transfers from the United Kingdom.

In July 2020, a European Court of Justice decision ("Schrems II") invalidated one of the primary methods for transferring personal data to the United States at the time (Privacy Shield) and placed additional conditions on the use of the main alternative export solution, the Standard Contractual Clauses (the "SCCs") (which could also be relied upon for transfers of personal data subject to the UK GDPR, if used alongside an addendum approved by the U.K. Information Commissioner's Office). On July 10, 2023, the European Commission also adopted an "adequacy decision" in relation to the DPF, which enables the transfer of personal data from the EEA to DPF-certified U.S. organizations without using the SCCs or other export mechanisms and replaces the transfer mechanism from the European Union to companies in the United States that was invalidated by the Schrems II decision. Transfers can also be made from the United Kingdom to DPF-certified US organizations without using the SCCs or other export mechanisms, provided that the U.S. organization has certified to the "UK Extension" of the DPF.

National data protection authorities have increased enforcement powers under the EU GDPR and UK GDPR (which provide for maximum fines for non-compliance of the higher of €20 million/£17.5 million and four per cent of an organization's worldwide turnover). In recent years, enforcement has been particularly focused on issues such as inadequate security resulting in personal data breaches, the sending of unsolicited marketing communications (especially in the United Kingdom), and the retention of data for excessive periods of time. Alongside the EU GDPR and UK GDPR, the rules surrounding the sending of electronic marketing communications are governed by the -e-Privacy Directive, which has been implemented at a local level across each EU Member State and in the United Kingdom as the Privacy and Electronic Communications Regulations (commonly known as PECR).

The concept of accountability is at the heart of the data protection regime, meaning that companies need to be able to demonstrate that they have implemented a compliance program that reflects and enables them to meet the legal requirements for processing of personal data in the EEA and/or the United Kingdom. On October 23, 2024, the Labour Government introduced the Data (Use and Access) Bill, a successor to the previous government's Data Protection and Digital Information Bill (which did not pass) which set out proposed amendments to the UK GDPR. These include amendments to the rules on automated decision making, introducing the concept of recognized "legitimate interests" and amendments to the purpose limitation and export rules. The proposed Bill is currently working its way through the legislative process. It remains to be seen if such reforms could potentially challenge the United Kingdom's "adequacy" designation and make it more difficult for companies to transfer personal data from the EEA to the United Kingdom.

Regulators are also increasingly focused on artificial intelligence ("AI"). In the United Kingdom, this focus is currently on the ways in which risks associated with the deployment of AI can be assessed in the context of existing laws, including the UK GDPR and requirements around treating customers fairly, with a clear focus on conducting risk assessments on the use of AI. In the EU, alongside a focus on assessment and compliance with existing laws, further laws are also now in force - most notably, the EU AI Act which applies from February 2, 2025. The current and emerging regulatory regimes will require increased assessments of AI solutions and failure to comply with relevant requirements in relation to the deployment of AI may result in regulatory fines, damages claims and reputational damage.

Business interruption test case

Our insurance business in the United Kingdom includes insurance of business interruption risks. In May 2020, the FCA announced its intention to bring a test case in the High Court of England and Wales to seek legal clarity about the meaning and effect of selected business interruption insurance policy wordings in the context of COVID-19 claims. The FCA provided a representative sample of business interruption policies to the High Court and asked it to determine whether on the basis of certain agreed and assumed facts: (a) the policies provide cover in principle; and (b) the policyholders of the policies can establish the necessary causal link (as a matter of the application of the law and the wording of the policies) between the assumed losses sustained by policyholders and any relevant peril, event or circumstance that is covered by relevant terms in the policies. The hearing took place in late July 2020 and judgment was handed down at first instance on September 15, 2020 (FCA v Arch Insurance (UK) Ltd and others [2020] EWHC 244).

In January 2021, the U.K. Supreme Court handed down judgment on appeal which was 'leapfrogged' from the decision of the High Court (FCA v Arch Insurance (UK) Ltd and others [2021] UKSC 1). The judgment is legally binding on the insurers that were parties to the case in respect of interpreting the business interruption policy wordings considered. The decision provides persuasive guidance for the interpretation of similar policy wordings and claims that can be taken into account by the court, the FOS and the FCA. The FCA has also introduced new guidance setting out its expectation that insurers should apply the judgment in assessing or reassessing all outstanding or rejected claims and complaints that may be affected by the test case (except those that have been referred to the FOS). The FCA has estimated that the judgment affects around 370,000 policyholders who are able to recover losses relating to business interruption due to COVID-19, but the implications of the decision go beyond the pandemic and will impact other business interruption claims. The judgment has changed the law in respect of various terms applied in business interruption policies such as trends clauses with the effect that higher settlement figures should be anticipated.

Bermuda

General

Our Bermuda licensed insurers and reinsurers are subject to the Insurance Act 1978 of Bermuda and the applicable rules and regulations promulgated thereunder, each as amended (the "Bermuda Insurance Act"). The Bermuda Insurance Act imposes solvency and liquidity standards as well as auditing and reporting requirements on Bermuda insurers and reinsurers. It also empowers the Bermuda Monetary Authority ("BMA") to supervise, investigate and intervene in the affairs of these entities. There are a number of remedial actions available to the BMA in order to protect the public interest if the BMA determines that a Bermuda insurer or reinsurer may become insolvent or that a breach of the Bermuda Insurance Act or of any of the conditions of registration on a Bermuda insurer or reinsurer has occurred or is about to occur.

Our material Bermuda (re)insurer is registered as a Class 4 (re)insurer under the Bermuda Insurance Act.

In addition to maintaining a principal office in Bermuda and appointing specified officers, the summary below comprises the material aspects of the insurance regulatory framework in Bermuda applicable to Class 4 (re)insurers under the Bermuda Insurance Act with which our material Bermuda (re)insurer must comply.

Solvency and Capital Standards

The Bermuda Insurance Act provides that the value of the statutory assets of a (re)insurer must exceed the value of its statutory liabilities by an amount greater than its prescribed minimum solvency margin ("MSM"). The MSM that must be maintained by a Class 4 (re)insurer is the greater of:

(i)

$100,000,000;

(ii)

50% of net premiums written (with a credit of reinsurance ceded not exceeding 25% of gross premiums);

(iii)

15% of net losses and loss expense reserves; or

(iv)

25% of the (re)insurer's enhanced capital requirement.

Class 4 (re)insurers are also required to maintain available statutory economic capital and surplus equal to or in excess of their "enhanced capital requirement" ("ECR") as determined by the BMA under the Bermuda Solvency Capital Requirement model (the "BSCR model"). The BSCR model is a risk-based capital model that establishes an enhanced capital requirement and total capital level by taking into account risk characteristics specific to an insurer's or reinsurer's business. The BMA also has established a target capital level ("TCL") equal to 120% of the (re)insurer's ECR. The TCL serves as an early warning tool for the BMA and failure to maintain statutory capital at least equal to the TCL will likely result in increased regulatory oversight.

Liquidity

The Bermuda Insurance Act also prescribes a minimum liquidity ratio ("MLR") for Class 4 (re)insurers. A Class 4 (re)insurer is required to maintain the value of its relevant assets at not less than 75% of its relevant liabilities. Relevant assets include cash and time deposits, quoted investments, unquoted bonds and debentures, first liens on real estate, investment income due and accrued, accounts and premiums receivable, reinsurance balances receivable, funds held by ceding reinsurers and any other assets which the BMA, on application in any particular case made to it with reasons, accepts in that case.

There are certain categories of assets which, unless specifically permitted by the BMA, do not automatically qualify as relevant assets, such as unquoted equity securities, investments in and advances to affiliates and real estate, and collateral loans.

The relevant liabilities are total general business insurance reserves and total other liabilities less deferred income taxes and letters of credit, guarantees and other instruments.

Eligible Capital

Our material Bermuda (re)insurer is required to disclose the makeup of its capital under a "three-tiered capital system". Under this system, capital instruments are classified as either "basic" or "ancillary" capital, and are further classified into one of three tiers based on "loss absorbency" characteristics, as prescribed in the Insurance (Eligible Capital) Rules 2012, as amended (the "Eligible Capital Rules"). Highest quality capital is classified as Tier 1 Capital; lesser quality capital is classified as either Tier 2 Capital or Tier 3 Capital. Under this regime, up to certain specified percentages of Tier 1, Tier 2 and Tier 3 Capital (as specified in the Eligible Capital Rules) may be used to support a Class 4 (re)insurer's MSM, ECR and TCL.

Restrictions on Dividends and Distributions

As a Class 4 (re)insurer, our material Bermuda (re)insurer is prohibited from declaring or paying dividends if it is, or if the declaration or payment of such dividend would cause it to be, in breach of its MSM, MLR or ECR. Moreover, where a Class 4 (re)insurer fails to meet its MSM or MLR on the last day of any financial year, it will be prohibited from declaring or paying any dividends during the next financial year without the approval of the BMA.

In addition, as a Class 4 (re)insurer, our material Bermuda (re)insurer is prohibited from declaring or paying in any financial year dividends of more than 25% of its total statutory capital and surplus (as shown in its previous financial year's statutory balance sheet) unless it files (at least seven days before payment of such dividends) an affidavit with the BMA stating that it will continue to meet its MSM and MLR.

Additionally, under the Companies Act 1981 of Bermuda (the "Bermuda Companies Act"), no Bermuda company may declare or pay a dividend, or make a distribution out of contributed surplus, if there are reasonable grounds for believing that: (a) the company is, or would after the payment, be, unable to pay its liabilities as they become due, or (b) the realizable value of its assets would thereby be less than its liabilities.

Reduction of Capital

No Class 4 (re)insurer may reduce its total statutory capital by 15% or more, as set out in its previous year's financial statements, unless it has received the prior approval of the BMA. Total statutory capital consists of the insurer's paid-in share capital, its contributed surplus (sometimes called additional paid-in capital) and any other fixed capital designated by the BMA as statutory capital (such as letters of credit).

A Class 4 (re)insurer seeking to reduce its statutory capital by 15% or more, as set out in its previous year's financial statements, is also required to submit an affidavit to the BMA stating that the proposed reduction will not cause the insurer to fail its relevant margins and such other information as the BMA may require.

Insurance Code of Conduct

Our material Bermuda (re)insurer must comply with the BMA's Insurance Code of Conduct (the "Bermuda Insurance Code"), which prescribes the duties, standards, procedures and sound business principles with which all companies registered under the Bermuda Insurance Act must comply.

Failure to comply with the requirements of the Bermuda Insurance Code will be taken into account by the BMA in determining whether an insurer is conducting its business in a sound and prudent manner as prescribed by the Bermuda Insurance Act and may result in the BMA exercising its powers of intervention and investigation (see below) and will be a factor in calculating the operational risk charge under the insurer's BSCR or approved internal model.

Cyber Code of Conduct

Our material Bermuda (re)insurer must comply with the Insurance Sector Operational Cyber Risk Management Code of Conduct (the "Cyber Risk Code"), which prescribes the duties, requirements, standards, procedures and principles with which all companies registered under the Bermuda Insurance Act must comply. The Cyber Risk Code is designed to promote the stable and secure management of information technology systems of regulated entities and requires that all regulated entities implement their own technology risk program, determine what their top risks are and develop an appropriate risk response. This requires, inter alia, all regulated entities to develop a cyber risk policy that is to be delivered pursuant to an operational cyber risk management program and appoint an appropriately qualified member of staff or outsourced resource to the role of Chief Information Security Officer. The role of the Chief Information Security Officer is to deliver the operational cyber risk management program.

It is expected that the cyber risk policy will be approved by the regulated entity's board of directors at least annually. The BMA will assess a regulated entity's compliance with the Cyber Risk Code in a proportionate manner relative to the nature, scale and complexity of its business. While it is acknowledged that some regulated entities will use a third party to provide technology services and that they may outsource their IT resources (for example, to an insurance manager where applicable), when so outsourced, the overall responsibility for the outsourced functions will remain with the regulated entity's board of directors. Failure to comply with the requirements of the Cyber Risk Code will be taken into account by the BMA in determining whether a regulated entity is conducting its business in a sound and prudent manner as prescribed by the Bermuda Insurance Act and may result in the BMA exercising its powers of intervention and investigation.

DESCRIPTION OF THE NOTES

As used under this heading "Description of the Notes", the terms "Fairfax" and the "Company" refer only to Fairfax Financial Holdings Limited, and not its subsidiaries, and the term "Allied World" refers to Allied World Assurance Company Holdings, Ltd. The Company issued the Initial Notes under an indenture, dated as of December 1, 1993, as supplemented and amended by the first supplemental indenture dated May 9, 2011 and the Third Supplemental Indenture (as amended, the "Base Indenture"), among the Company, The Bank of New York Mellon, as successor U.S. trustee (the "U.S. trustee" or the "trustee"), and Computershare Advantage Trust of Canada (formerly BNY Trust Company of Canada) (as successor trustee to CIBC Mellon Trust Company), as successor Canadian trustee (the "Canadian trustee" and, together with the U.S. Trustee, the "trustees") in a private transaction that was not subject to the registration requirements of the Securities Act. On July 19, 2024, the Company entered into the fourth supplemental indenture by and among the Company, Allied World, and the trustee (the "Fourth Supplemental Indenture") to add Allied World as a Co-Obligor (as defined herein) of the Initial Notes in accordance with the terms of the Initial Notes, and on March 14, 2025, the Company and Allied World entered into the fifth supplemental indenture by and among the Company, Allied World, and the trustee (the "Fifth Supplemental Indenture" and together with the Base Indenture and the Fourth Supplemental Indenture, the "Indenture") to amend the Base Indenture to comply with the Trust Indenture Act (as defined below) without regard to the exemption provided by Rule 4d-9 thereunder.

The Company and Allied World have agreed to offer to exchange the Initial Notes for a new issue of substantially identical debt securities (as previously defined as the Exchange Notes) registered under the Securities Act. The issuance of the Exchange Notes in the Exchange Offer (together with any Initial Notes that are not tendered and accepted for purchase) is limited to $600 million. The Exchange Notes, together with any Initial Notes that remain outstanding after the closing of the Exchange Offer, are referred to herein as the "Notes".

The Notes bear interest from the date of issuance at the rate of 6.100% per annum and will mature on March 15, 2055. Interest is payable in semi-annual installments in arrears on March 15 and September 15 each year (each, an "Interest Payment Date"), to the persons in whose names the Notes are registered at the close of business on the preceding September 1 and March 1, respectively (whether or not a business day) (the "Regular Record Date").

Interest is calculated on the basis of a 360-day year consisting of twelve 30-day months. Principal of and interest on the Notes is payable in such coin or currency of the United States as at the time of payment is legal tender for the payment of public and private debts.

If any Interest Payment Date, maturity date or redemption date of the Notes falls on a day that is not a business day, the required payment of principal, premium, if any, and interest will be made on the next succeeding business day as if made on the date that the payment was due and no interest will accrue on that payment for such period from and after that Interest Payment Date, maturity date or redemption date, as the case may be, to the date of that payment on the next succeeding business day. The term "business day" means any day, other than a Saturday or Sunday, which is not a day on which banking institutions in the City of New York are authorized or required by law or executive order to close.

The Notes are not redeemable at the option of the holder prior to maturity and are not subject to any sinking fund.

The Indenture is being qualified under the U.S. Trust Indenture Act of 1939, as amended (the "Trust Indenture Act"), a copy of which is filed as an exhibit to the registration statement to which this prospectus forms a part. References to accounting terms in the Indenture and in this summary, unless otherwise defined, have the meanings assigned to them in accordance with IFRS Accounting Standards.

The Indenture provides that, in addition to the Notes, securities of other series may be issued under the Indenture without limitation as to aggregate principal amount. The securities of other series may have such terms and provisions not inconsistent with the Indenture as the Company may determine from time to time. The securities of any series issued under the Indenture, including the Notes, are referred to as "securities".

General

The Notes are the Company's and Allied World's direct, unsecured obligations and rank equally and ratably with all of the Company's and Allied World's respective other unsecured and unsubordinated indebtedness from time to time outstanding. The Notes rank among themselves equally and ratably without preference or priority. The Notes would be structurally subordinated to all obligations of the Company's subsidiaries (other than Allied World) and Allied World's subsidiaries. The Notes would be effectively subordinated to any future secured indebtedness of the Company and Allied World, to the extent of the assets securing such indebtedness.

On July 19, 2024, the Company entered into the Fourth Supplemental Indenture to add Allied World as a Co-Obligor of the Initial Notes in accordance with the terms of the Initial Notes. Pursuant to the Fourth Supplemental Indenture, the Company remains a full and unconditional obligor under the Notes and is not relieved of any of its obligations or covenants under the Indenture or the Notes. The Fourth Supplemental Indenture also provides for the payment of Bermuda Additional Amounts (as defined below) by Allied World in the event of changes in law resulting in Bermuda Taxes (as defined below), as well as a corresponding option of Allied World to redeem the Notes in the event such Bermuda Additional Amounts become payable. See "- Optional Redemption - Redemption for Tax Reasons" and "- Optional Redemption -Payment of Additional Amounts" below.

As of December 31, 2024, the Company and Allied World had approximately $8.6 billion aggregate principal amount of total outstanding senior unsecured indebtedness, all of which would rank equally to the Notes. The Company's other subsidiaries had approximately $3.3 billion aggregate principal amount of total outstanding indebtedness, all of which would be structurally senior to the Notes.

The Indenture permits the Company and Allied World from time to time, without notice to or the consent of the holders of any series of securities issued under the Indenture, to create and issue further securities of the same series as the Notes, ranking pari passu with the Notes in all respects and having the same terms as the Notes (except for the issue date, issue price and initial Interest Payment Date following the issue date of such further Notes) and so that such further Notes shall be consolidated and form a single series with, and shall have the same terms as to status, redemption or otherwise as, the Notes that are currently issued and outstanding; provided that such further Notes will not be issued with the same CUSIP and/or ISIN numbers as the Notes unless such further notes are fungible with the Notes for U.S. federal income tax purposes.

The Notes are issued in minimum denominations of $2,000 and integral multiples of $1,000 in excess thereof.

The Indenture does not contain any provisions that would limit the Company's or Allied World's ability to incur indebtedness or that would afford holders of Notes protection in the event of a highly leveraged or similar transaction involving the Company or Allied World.

Optional Redemption

Prior to September 15, 2054 (the "Par Call Date"), the Company or Allied World may redeem the Notes at their option, in whole or in part, at any time and from time to time, at a redemption price (expressed as a percentage of principal amount and rounded to three decimal places) equal to the greater of:

(1)

(a) the sum of the present values of the remaining scheduled payments of principal and interest thereon discounted to the date fixed for redemption of the Notes (assuming the Notes matured on the Par Call Date) on a semi annual basis (assuming a 360-day year consisting of twelve 30-day months) at the Treasury Rate plus 30 basis points less (b) interest accrued to the date of redemption, and

(2)

100% of the principal amount of the Notes to be redeemed,

plus, in either case, accrued and unpaid interest to, but excluding, the redemption date. The Company or Allied World will pay any interest due on an Interest Payment Date that occurs on or prior to a redemption date to the registered holders of the Notes as of the close of business on the Regular Record Date immediately preceding that Interest Payment Date.

On or after the Par Call Date, the Company or Allied World may redeem the Notes, in whole or in part, at any time and from time to time, at a redemption price equal to 100% of the principal amount of the Notes being redeemed, plus accrued and unpaid interest thereon to, but excluding, the redemption date.

"Treasury Rate" means, with respect to any redemption date, the yield determined by the Company or Allied World in accordance with the following two paragraphs.

The Treasury Rate shall be determined by the Company or Allied World after 4:15 p.m., New York City time (or after such time as yields on U.S. government securities are posted daily by the Board of Governors of the Federal Reserve System), on the third business day preceding the redemption date based upon the yield or yields for the most recent day that appear after such time on such day in the most recent statistical release published by the Board of Governors of the Federal Reserve System designated as "Selected Interest Rates (Daily) - H.15" (or any successor designation or publication) ("H.15") under the caption "U.S. government securities - Treasury constant maturities - Nominal" (or any successor caption or heading) ("H.15 TCM"). In determining the Treasury Rate, the Company or Allied World shall select, as applicable: (1) the yield for the Treasury constant maturity on H.15 exactly equal to the period from the redemption date to the Par Call Date (the "Remaining Life"); or (2) if there is no such Treasury constant maturity on H.15 exactly equal to the Remaining Life, the two yields - one yield corresponding to the Treasury constant maturity on H.15 immediately shorter than and one yield corresponding to the Treasury constant maturity on H.15 immediately longer than the Remaining Life - and shall interpolate to the Par Call Date on a straight-line basis (using the actual number of days) using such yields and rounding the result to three decimal places; or (3) if there is no such Treasury constant maturity on H.15 shorter than or longer than the Remaining Life, the yield for the single Treasury constant maturity on H.15 closest to the Remaining Life. For purposes of this paragraph, the applicable Treasury constant maturity or maturities on H.15 shall be deemed to have a maturity date equal to the relevant number of months or years, as applicable, of such Treasury constant maturity from the redemption date.

If on the third business day preceding the redemption date H.15 TCM is no longer published, the Company or Allied World shall calculate the Treasury Rate based on the rate per annum equal to the semi-annual equivalent yield to maturity at 11:00 a.m., New York City time, on the second business day preceding such redemption date of the U.S. Treasury security maturing on, or with a maturity that is closest to, the Par Call Date, as applicable. If there is no U.S. Treasury security maturing on the Par Call Date but there are two or more U.S. Treasury securities with a maturity date equally distant from the Par Call Date, one with a maturity date preceding the Par Call Date and one with a maturity date following the Par Call Date, the Company or Allied World shall select the U.S. Treasury security with a maturity date preceding the Par Call Date. If there are two or more U.S. Treasury securities maturing on the Par Call Date or two or more U.S. Treasury securities meeting the criteria of the preceding sentence, the Company or Allied World shall select from among these two or more U.S. Treasury securities the U.S. Treasury security that is trading closest to par based upon the average of the bid and asked prices for such U.S. Treasury securities at 11:00 a.m., New York City time. In determining the Treasury Rate in accordance with the terms of this paragraph, the semi-annual yield to maturity of the applicable U.S. Treasury security shall be based upon the average of the bid and asked prices (expressed as a percentage of principal amount) at 11:00 a.m., New York City time, of such U.S. Treasury security, and rounded to three decimal places.

The Company's and Allied World's actions and determinations in determining the redemption price shall be conclusive and binding for all purposes, absent manifest error.

Notice of any redemption will be mailed or electronically delivered (or otherwise transmitted in accordance with the depositary's procedures) at least 10 days but not more than 60 days before the redemption date to each holder of Notes to be redeemed. See "- Selection and Notice of Redemption" below.

The Notes are also subject to redemption prior to maturity if certain changes in Canadian or Bermuda tax law occur. If such changes occur, the Notes may be redeemed at a redemption price of 100% of their principal amount, plus any interest accrued but not paid to but excluding the redemption date and any additional amounts due and payable on the Notes up to but excluding the redemption date. See "- Redemption for Tax Reasons".

Payment of Additional Amounts

All payments made by the Company under or with respect to the Notes will be made free and clear of, and without withholding or deduction for or on account of, any present or future tax, duty, levy, impost, assessment or other governmental charge imposed or levied by or on behalf of the Government of Canada or of any province or territory thereof or by any authority or agency therein or thereof having power to tax (hereinafter "Taxes"), unless the Company is required to withhold or deduct Taxes by law or by the interpretation or administration thereof. If the Company is so required to withhold or deduct any amount for or on account of Taxes from any payment made under or with respect to the Notes, the Company will pay as interest such additional amounts ("Additional Amounts") as may be necessary so that the net amount received by each holder of such Notes or the beneficial owner thereof (including Additional Amounts) after such withholding or deduction will not be less than the amount such holder or beneficial owner would have received if such Taxes had not been withheld or deducted; provided that no Additional Amounts will be payable with respect to: (a) any payment made to a holder of the Notes or beneficial owner who is liable for such Taxes in respect of such Notes (i) by reason of such holder or beneficial owner, or any other person entitled to payments on the Notes, being a person with which the Company does not deal at arm's length (within the meaning of the Income Tax Act (Canada) (the "Canadian Tax Act")), (ii) by reason of such holder or beneficial owner being a "specified shareholder" of the Company or not dealing at arm's length with a "specified shareholder" of the Company (as defined in subsection 18(5) of the Canadian Tax Act), (iii) by reason of such holder or beneficial owner being a "specified entity" as defined in revised proposals to amend the Canadian Tax Act on November 28, 2023, with respect to "hybrid mismatch arrangements" (which were enacted on June 20, 2024), (iv) by reason of the existence of any present or former connection between such holder or beneficial owner (or between a fiduciary, settlor, beneficiary, member or shareholder of, or possessor of power over, such holder or beneficial owner, if such holder or beneficial owner is an estate, trust, partnership, limited liability company or corporation) and Canada or any province or territory thereof or therein or agency thereof or therein other than the mere acquisition, holding, use or ownership or deemed holding, use or ownership, or receiving payments or enforcing any rights in respect of such Notes as a non-resident or deemed non-resident of Canada or any province or territory thereof or therein or agency thereof or therein, or (v) by reason of such holder or beneficial owner's failure to comply with any certification, identification, documentation or other reporting requirements if compliance is required by law, regulation, administrative practice or an applicable treaty as a pre-condition to exemption from, or a reduction in the rate of deduction or withholding of, such Taxes, in each case, to the extent such holder or beneficial holder is legally entitled to such exemption or reduction; (b) any estate, inheritance, gift, sales, transfer, excise or personal property tax or any similar Taxes; (c) any Notes presented for payment more than 15 days after the date on which such payment or such Notes became due and payable or the date on which payment thereof is duly provided for, whichever is later (except to the extent that the holder would have been entitled to such Additional Amounts had the Notes been presented on the last day of such 15-day period); (d) any withholding or deduction imposed on a payment to a holder or beneficial owner pursuant to Sections 1471 to 1474 of the U.S. Internal Revenue Code of 1986, as amended (the "Code") or any successor version thereof, any agreements entered into pursuant to current Section 1471(b)(1) of the Code, and any fiscal or regulatory legislation, rules or official guidance, adopted pursuant to any intergovernmental agreement among governmental authorities entered into in connection with the implementation of the foregoing, and including for greater certainty, Part XVIII and Part XIX of the Canadian Tax Act ("FATCA"), or any Taxes or penalties that arise from the holder or beneficial owner's failure to properly comply with its obligations with respect to FATCA or the Canada United States Enhanced Tax Information Exchange Agreement Implementation Act; (e) any Taxes which are payable otherwise than by withholding or deduction from any payment made under or with respect to the Notes; or (f) any combination of the foregoing clauses (a) to (e); nor will such Additional Amounts be paid with respect to any payment on any Note to a holder or beneficial owner who is a fiduciary or partnership or, other than the sole beneficial owner of such Note, to the extent that a beneficiary or settlor with respect to such fiduciary, or a member of such partnership or a beneficial owner thereof would not have been entitled to receive a payment of such Additional Amounts had such beneficiary, settlor, member or beneficial owner received directly its beneficial or distributive share of such payment (collectively, "Excluded Taxes"). The Company will also (a) make such withholding or deduction and (b) remit the full amount deducted or withheld to the relevant authority in accordance with applicable law. Upon the written request of the trustee or a holder of Notes, the Company will furnish, as soon as reasonably practicable, to the trustee or such holder of Notes, as applicable, certified copies of tax receipts evidencing such payment by the Company. The Company will indemnify and hold harmless each holder of Notes and any beneficial owner thereof and, upon written request of any such holder or beneficial owner, reimburse such holder or beneficial owner for the amount of (i) any such Taxes (other than Excluded Taxes) so levied or imposed and paid by such holder or beneficial owner as a result of any failure of the Company to withhold, deduct or remit to the relevant tax authority, on a timely basis, the full amounts required under applicable law and (ii) any such Taxes (other than Excluded Taxes) so levied or imposed with respect to any reimbursement under the foregoing clause (i), so that the net amount received by such holder or beneficial owner after such reimbursement would not be less than the net amount such holder or beneficial owner would have received if such Taxes (other than Excluded Taxes) on such reimbursement had not been imposed.

All payments made by Allied World on the Notes will be made free and clear of, and without withholding or deduction for or on account of, any present or future tax, duty, levy, impost, assessment or other governmental charge imposed or levied by or on behalf of the Government of Bermuda or by any authority or agency therein or thereof having power to tax (hereinafter "Bermuda Taxes"), unless Allied World is required to withhold or deduct Bermuda Taxes by law or by the interpretation or administration thereof. If Allied World is so required to withhold or deduct any amount for or on account of Bermuda Taxes from any payment made under or with respect to the Notes, Allied World will pay as interest such additional amounts ("Bermuda Additional Amounts") as may be necessary so that the net amount received by each holder or the beneficial owner thereof (including Bermuda Additional Amounts) after such withholding or deduction will not be less than the amount such holder or beneficial owner would have received if such Bermuda Taxes had not been withheld or deducted; provided that no Bermuda Additional Amounts shall be payable with respect to: (a) any Bermuda Tax which would not have been imposed but for the fact that such holder or beneficial owner (i) was a resident, domiciliary or national of, or engaged in business or maintained a permanent establishment or was physically present in, Bermuda or any political subdivision thereof or otherwise had some connection with Bermuda other than by reason of the mere ownership of, or receipt of payment under, this Note, (ii) presented this Note for payment in Bermuda or any political subdivision thereof, unless this Note could not have been presented for payment elsewhere, or (iii) presented this Note for payment more than 15 days after the date on which such payment or this Note became due and payable or the date on which payment thereof is duly provided for, whichever is later (except to the extent that the holder of such Note would have been entitled to such Bermuda Additional Amounts had this Note been presented on the last day of such 15-day period); (b) any estate, inheritance, gift, sales, transfer, excise or personal property tax or any similar Bermuda Taxes; (c) any tax by reason of such holder or beneficial owner's failure to comply with any certification, identification, documentation or other reporting requirements if compliance is required by law, regulation, administrative practice or an applicable treaty as a pre-condition to exemption from, or a reduction in the rate of deduction or withholding of, such Bermuda Taxes to the extent such holder or beneficial owner is legally entitled to such exemption or reduction; (d) any withholding or deduction imposed on a payment to a holder or beneficial owner pursuant to Sections 1471 to 1474 of the Code, or any successor version thereof, any agreements entered into pursuant to current Section 1471(b)(1) of the Code, and any fiscal or regulatory legislation, rules or official guidance, adopted pursuant to any intergovernmental agreement among governmental authorities entered into in connection with the implementation of the foregoing, or any Bermuda Taxes or penalties that arise from the holder or beneficial owner's failure to properly comply with its obligations with respect to FATCA; (e) any Bermuda Taxes which are payable otherwise than by withholding or deduction from any payment made under or with respect to the Notes; or (f) any combination of the foregoing clauses (a) to (e); nor shall such Bermuda Additional Amounts be paid with respect to any payment on any Notes to a holder or beneficial owner who is a fiduciary or partnership or, other than the sole beneficial owner of the Notes, to the extent that a beneficiary or settlor with respect to such fiduciary, or a member of such partnership or a beneficial owner thereof would not have been entitled to receive a payment of such Bermuda Additional Amounts had such beneficiary, settlor, member or beneficial owner received directly its beneficial or distributive share of such payment (collectively, "Excluded Bermuda Taxes"). Allied World shall also (a) make such withholding or deduction and (b) remit the full amount deducted or withheld to the relevant authority in accordance with applicable law. Upon the written request of the trustee or a holder of the Notes, Allied World will furnish, as soon as reasonably practicable, to the trustee or such holder, as applicable, certified copies of tax receipts evidencing such payment by Allied World. Allied World shall indemnify and hold harmless each holder of the Notes and any beneficial owner thereof and, upon written request of any such holder or beneficial owner, reimburse such holder or beneficial owner for the amount of (i) any such Bermuda Taxes (other than Excluded Bermuda Taxes) so levied or imposed and paid by such Note holder or beneficial owner as a result of any failure of Allied World to withhold, deduct or remit to the relevant tax authority, on a timely basis, the full amounts required under applicable law and (ii) any such Bermuda Taxes (other than Excluded Bermuda Taxes) so levied or imposed with respect to any reimbursement under the foregoing clause (i), so that the net amount received by such holder or beneficial owner after such reimbursement would not be less than the net amount such holder or beneficial owner would have received if such Bermuda Taxes (other than Excluded Bermuda Taxes) on such reimbursement had not been imposed.

Whenever in the Indenture there is mentioned, in any context, the payment of principal (and premium, if any), redemption price, interest or any other amount payable under or with respect to the Notes, such mention shall be deemed to include mention of the payment of Additional Amounts and Bermuda Additional Amounts to the extent that, in such context, Additional Amounts and Bermuda Additional Amounts are, were or would be payable in respect thereof.

Redemption for Tax Reasons

In the event that the Company has become or would become obligated to pay, on the next date on which any amount would be payable under or with respect to the Notes, any Additional Amounts as a result of a change in the laws (including any regulations promulgated thereunder) or treaties of Canada (or any political subdivision or taxing authority thereof or therein), or any change in any official position regarding the application or interpretation of such laws, regulations or treaties, which change is announced and becomes effective on or after the date of issuance of the Notes, then the Company may at any time at the Company's option redeem the Notes, in whole, but not in part, at a redemption price equal to 100% of their principal amount, plus any interest accrued but not paid to but excluding the redemption date and any Additional Amounts due and payable on the Notes up to, but excluding, the redemption date.

If the Company exercises its option to redeem the Notes pursuant to the preceding paragraph, the Company will deliver to the trustee a certificate signed by an authorized officer stating that the Company is entitled to redeem the Notes to the effect that the circumstances described above exist.

In the event that Allied World has become or would become obligated to pay, on the next date on which any amount would be payable under or with respect to the Notes, any Bermuda Additional Amounts as a result of a change in the laws (including any regulations promulgated thereunder) or treaties of Bermuda (or any political subdivision or taxing authority thereof or therein), or any change in any official position regarding the application or interpretation or enforcement of such laws, regulations or treaties of Bermuda (including a holding by a court of competent jurisdiction or by a taxing authority), which change is announced and becomes effective on or after July 19, 2024, then Allied World may, at any time at Allied World's option, redeem the Notes, in whole, but not in part, at a redemption price equal to 100% of their principal amount, plus any interest accrued but not paid up to, but excluding, the redemption date and any Bermuda Additional Amounts due and payable on the Notes up to, but excluding, the redemption date.

If Allied World exercises its option to redeem the Notes, pursuant to the preceding paragraph, Allied World will deliver to the trustee a certificate signed by an authorized officer stating that Allied World is entitled to redeem the Notes to the effect that the circumstances described above exist.

Selection and Notice of Redemption

In the case of a partial redemption, selection of Notes held in the form of definitive certificates for redemption will be made pro rata, by lot or by such other method as the trustee deems appropriate. For so long as the Notes are held by DTC (or another depositary), the selection of partially redeemed Notes and the redemption of the Notes shall be conducted in accordance with the policies and procedures of the depositary. No Notes of a principal amount of $2,000 or less will be redeemed in part. If any Note is to be redeemed in part only, the notice of redemption that relates to such Note will state the portion of the principal amount of the Note to be redeemed. In respect of Notes held in the form of definitive certificates, a new definitive certificate representing Notes in a principal amount equal to the unredeemed portion of such Note will be issued in the name of the holder of such Note upon surrender of the original Note in the form of a definitive certificate for cancellation.

Notice of redemption of Notes held in the form of Definitive Certificates (as defined below) will be mailed by first-class mail at least 10 days but not more than 60 days before the redemption date to each holder of Notes to be redeemed at its registered address. Notice of redemption of Notes held in the form of global certificates will be given to DTC in accordance with its applicable procedures at least 10 days but not more than 60 days before the redemption date. The notice of redemption may be subject to one or more conditions precedent as set forth in such notice.

Unless the Company and Allied World default in payment of the redemption price, on and after the applicable redemption date, interest will cease to accrue on the Notes or portions thereof called for redemption.

Certain Covenants

Limitation on Liens on Capital Stock of Restricted Subsidiaries. Until the Amendment Date (as defined below), the Indenture provides that the Company and Allied World may not, and may not permit any subsidiary to, create, assume, incur or suffer to exist any lien, other than a purchase money lien, upon any capital stock, whether owned on the date of the Indenture or thereafter acquired, of any restricted subsidiary, to secure any obligation (other than the securities issued under the Indenture) of the Company, Allied World, any subsidiary or any other person, without in any such case making effective provision whereby all of the outstanding securities issued under the Indenture shall be directly secured equally and ratably with such obligation; provided, however, that this restriction will not apply to (i) liens on the capital stock of any restricted subsidiary securing obligations outstanding from time to time under any bank credit facility, provided that the principal amount of all such obligations secured by liens on the capital stock of any restricted subsidiary, at the time of each incurrence of any portion of any such obligation, does not exceed 15% of the sum of (A) the Company's consolidated shareholders' equity at the end of the Company's most recently completed fiscal quarter immediately preceding such incurrence for which financial statements are, or are required to be, available and (B) the aggregate principal amount of all obligations which are outstanding under any bank credit facility immediately after giving effect to such incurrence and which are secured by liens on the capital stock of a restricted subsidiary, and (ii) liens securing obligations from the Company to any wholly-owned restricted subsidiary or from any wholly-owned restricted subsidiary to the Company or any other wholly-owned restricted subsidiary. This provision will not restrict any other property of the Company or that of its subsidiaries (other than Allied World).

The Indenture defines "lien" as any mortgage, pledge, hypothecation, lien, encumbrance, charge or security interest of any kind; "obligation" as indebtedness for money borrowed or indebtedness evidenced by a bond, note, debenture or other evidence of indebtedness; "purchase money lien" as (i) any mortgage, pledge, hypothecation, lien, encumbrance, charge or security interest of any kind upon any capital stock of any restricted subsidiary acquired after the date of the Indenture if such purchase money lien is for the purpose of financing, and does not exceed, the cost to the Company, or any subsidiary of acquiring the capital stock of such restricted subsidiary and such financing is effected concurrently with, or within six months after, the date of such acquisition, and (ii) any extension, renewal or refinancing of any purchase money lien so long as the principal amount of obligations secured thereby shall not exceed the original principal amount of obligations so secured at the time of such extension, renewal or refinancing; "restricted subsidiary" as any subsidiary that is a licensed insurance company, other than any licensed insurance company that the Company's board of directors, in good faith, determines is not, individually or together with any other licensed insurance company as to which a similar determination has been made, material to the Company and its subsidiaries, considered as a whole; and "subsidiary" as a corporation or business trust, a majority of the outstanding voting stock of which is owned, directly or indirectly, by the Company or one or more other subsidiaries, or by the Company and one or more other subsidiaries. As of the date hereof, each of the Company's licensed insurance company subsidiaries is a restricted subsidiary.

Amalgamation, Consolidation, Merger, Conveyance, Transfer or Lease. The Indenture provides that the Company and/or Allied World shall not amalgamate or consolidate with or merge into any other corporation or convey, transfer or lease its properties and assets substantially as an entirety to any other person, unless, (i) the corporation formed by such consolidation or amalgamation or into which the Company and/or Allied World merged or the person which shall have acquired or leased such properties or assets (if other than the Company and/or Allied World) shall be a corporation, partnership, company or trust organized and validly existing under the laws of Canada or any province thereof or the United States, any state thereof or the District of Columbia, and shall expressly assume by supplemental Indenture the Company and/or Allied World (as applicable) obligation for the due and punctual payment of the principal of (and premium, if any, on) and interest on all the outstanding securities issued under the Indenture, all other amounts payable by the Company and/or Allied World (as applicable) pursuant to the Indenture and the performance and observance of every covenant of the Indenture on the Company or Allied World's part to be performed or observed, (ii) immediately after giving effect to such transaction, no event of default or event that after notice or passage of time or both would be an event of default shall have occurred and be continuing and (iii) the Company or Allied World (as applicable) has delivered to the trustee an officers' certificate and an opinion of counsel, each stating that such amalgamation, consolidation, merger, conveyance, transfer or lease, and supplemental Indenture (if any), complies with this covenant and that all conditions precedent provided for in the Indenture relating to such transaction have been complied with.

Available Information. So long as the Notes are "restricted securities" within the meaning of Rule 144 under the U.S. Securities Act ("Rule 144"), both the Company and Allied World are not subject to the reporting requirements of the Exchange Act, the Company and Allied World will furnish to any holder of Notes, or to any prospective purchaser designated by such a holder, upon the request of the holder, the business and financial information concerning the Company and Allied World called for under paragraph (d)(4) of Rule 144A.

Waiver of Certain Covenants. The Company and/or Allied World may elect in any particular instance to not comply with any term, provision or condition of the covenants described above under "- Certain Covenants - Limitation on Liens on Capital Stock of Restricted Subsidiaries" and "- Certain Covenants - Available Information" if the holders of at least a majority in principal amount of all outstanding Notes issued under the Indenture and then outstanding waive compliance in such instance with such term, provision or condition.

Third Supplemental Indenture. On February 26, 2021, the Company entered into the Third Supplemental Indenture to eliminate or amend certain restrictive covenants of the Company. The Third Supplemental Indenture provides that the covenant described under "- Certain Covenants - Limitation on Liens on Capital Stock of Restricted Subsidiaries" will be automatically eliminated or amended effective as of the first date on which there are no securities outstanding of any series created pursuant to the Indenture prior to February 26, 2021. The Third Supplemental Indenture also provides that if the Company grants any security interest to any collateral agent or trustee pursuant to such covenant in connection with any series created after the date of the Third Supplemental Indenture, such security interest shall be automatically released on the Amendment Date and any such collateral agent or trustee shall be authorized to take such further actions as the Company may reasonably request to give effect to such release.

Events of Default

The following constitute events of default with respect to the Notes under the Indenture: (a) a default for 30 days in the payment of any interest on any Note; (b) a default in the payment of the principal of (or premium, if any, on) any Note when due; (c) a default in the performance, or breach, of any other covenant or warranty in the Indenture (other than a covenant or warranty included in the Indenture solely for the benefit of one or more series of securities other than the Notes) which default or breach continues for a period of 60 days after notice; (d) a default in the payment, at the stated maturity, of any outstanding indebtedness for money borrowed by the Company or Allied World in excess of $100,000,000 and continuing after any applicable grace period, which default shall not have been cured or waived, or the acceleration of indebtedness for money borrowed by the Company or Allied World outstanding under or evidenced by any single Indenture or instrument in excess of $100,000,000, if such indebtedness has not been discharged, or such acceleration has not been rescinded or annulled, within 10 days after written notice has been given by the trustee, or the holders of at least 25% in principal amount of the outstanding Notes, as provided in the Indenture; and (e) certain events of bankruptcy, insolvency or reorganization.

If an event of default relating to a default in payment of principal of (or premium, if any, on) or interest on the Notes, or to a default in the performance, or breach, of any other covenant or warranty of the Company or Allied World applicable to the Notes but not applicable to all outstanding securities issued under the Indenture, or to a default in the payment, at stated maturity, of, or to the acceleration of, any indebtedness for money borrowed shall have occurred and be continuing, the trustee or the holders of not less than 25% in principal amount of the Notes then outstanding may then declare the principal of all Notes to be due and payable immediately. If an event of default relating to a default in the performance, or breach, of any other covenant or warranty in the Indenture applicable to all securities issued thereunder and then outstanding shall have occurred and be continuing, the trustee or the holders of not less than 25% in principal amount of all securities issued under the Indenture and then outstanding (treated as one class) may declare the principal amount of all the securities then outstanding to be due and payable immediately. If an event of default described in clause (e) above shall occur, other than with respect to one of the Company's or Allied World's subsidiaries, the principal amount of all the securities will automatically, and without any action by the trustee or any holder, become immediately due and payable. In each case, the holders of a majority in principal amount of the outstanding Notes may under certain circumstances rescind and annul such declaration by written notice to the Company, Allied World and the trustee. In the event of a declaration of acceleration because an event of default specified in clause (d) above has occurred and is continuing, such declaration of acceleration shall be automatically annulled if the indebtedness which is the subject of such event of default has been discharged or the holders thereof have rescinded their declaration of acceleration in respect of such indebtedness, and written notice of such discharge or rescission is given to the trustee by the Company, Allied World and countersigned by the holders of such indebtedness or their representative, within 30 days after such declaration of acceleration in respect of the Notes, and no other event of default has occurred during such 30-day period which has not been cured or waived during such period.

The holders of not less than a majority in principal amount of the outstanding Notes, in the case of an event of default applicable to such series but not to all outstanding securities, or a majority in principal amount of the outstanding securities of all series, in the case of an event of default applicable to all outstanding securities, may waive any past default and its consequences, except a default in respect of the payment of the principal of (or premium, if any, on) or interest on any security or in respect of a covenant or provision of the Indenture which cannot be modified or amended without the consent of the holder of each outstanding security affected thereby.

The Indenture provides that the trustee shall be under no obligation to exercise any of the rights or powers vested in it by the Indenture at the request or direction of holders of securities unless such holders shall have offered to the trustee reasonable funding, security and indemnity against the costs, expenses and liabilities which might be incurred by the trustee in compliance with such request or direction. Subject to such provisions for the indemnification of the trustee, the holders of not less than a majority in principal amount of the securities of any series (with respect to any remedy, trust or power relating to any default in payment of principal (or premium, if any, on) or interest on the securities of such series or any default in the performance or breach of any other covenant or warranty of the Company or Allied World applicable to the securities of such series but not applicable to all outstanding securities issued under the Indenture) or the holders of not less than a majority in principal amount of all securities issued under the Indenture and then outstanding (treated as one class) (with respect to any other remedy, trust or power) shall have the right to direct the time, method and place of conducting any proceeding for any remedy available to the trustee, or exercising any trust or power conferred on the trustee, with respect to such securities.

Co-Obligors and/or Guarantors

When authorized by a resolution of the Company's and Allied World's board of directors and without the consent of any holders of the Notes, the Company, Allied World and the trustees may enter into a supplemental indenture to the Indenture in respect of the Notes (but not with respect to any other series of outstanding securities), in accordance with the terms of the Indenture, for the purpose of adding one or more of the Company's or Allied World's subsidiaries as an additional co-obligor (whether as an additional issuer or a guarantor) of the Notes and the Indenture (each, a "Co-Obligor"); provided that any such Co-Obligor shall be organized or formed under the laws of (1) any state of the United States or the District of Columbia, (2) Canada or any province or territory thereof, (3) the United Kingdom, (4) Bermuda, (5) Barbados or (6) any country that is a member of the European Union. Any such supplemental indenture entered into for the purpose of adding a Co-Obligor formed under any jurisdiction other than a state of the United States (each, a "Non-U.S. Co-Obligor") shall include a provision for (i) the payment of additional amounts in the form substantially similar to that described in "- Optional Redemption - Payment of Additional Amounts" above, with such modifications as the Company, Allied World and such Non-U.S. Co-Obligor reasonably determine are customary and appropriate for U.S. and Canadian bondholders to address then-applicable (or potentially applicable future) taxes, duties, levies, imposts, assessments or other governmental charges imposed or levied by or on behalf of the applicable governmental authority in respect of payments made by such Non-U.S. Co-Obligor under or with respect to the Notes, including any exceptions thereto as the Company, Allied World and such Non-U.S. Co-Obligor shall reasonably determine would be customary and appropriate for U.S. and Canadian noteholders and (ii) the right of the Company, Allied World or the Co-Obligor to redeem the Notes at 100% of the aggregate principal amount thereof plus accrued interest thereon in the event that additional amounts become payable by a Non-U.S. Co-Obligor in respect of the Notes as a result of any change in law or official position regarding the application or interpretation of any law that is announced or becomes effective after the date of such supplemental indenture.

Any such Co-Obligor shall be jointly and severally liable with the Company and Allied World to pay the principal, premium, if any, and interest on the Notes and all other amounts payable by the Company or Allied World under the Indenture. The Company and Allied World will only add a Co-Obligor if the Company and Allied World determine that adding a Co-Obligor would (i) not result in a deemed sale or exchange of the Notes by any holder for U.S. federal income tax purposes under applicable then existing Treasury Regulations promulgated under the Code or a disposition of the Notes by any holder for Canadian federal income tax purposes and (ii) not adversely affect the interests of the holders of any outstanding series of securities under the Indenture in any material respect.

Pursuant to the terms of the Fourth Supplemental Indenture, Allied World was added as a Co-Obligor of the Initial Notes in accordance with the terms of the Initial Notes. Upon completion of the Exchange Offer, the Exchange Notes will include Allied World as a Co-Obligor as of the issue date of such Exchange Notes, and the Company will remain a full and unconditional Co-Obligor in respect of the Exchange Notes for all purposes under the Indenture.

Discharge, Defeasance and Covenant Defeasance

The Company and/or Allied World may discharge certain obligations to holders of Notes that have not already been delivered to the trustee for cancellation and that have either become due and payable or are by their terms due and payable within one year by irrevocably depositing with the trustee trust funds in an amount sufficient to pay at maturity the principal of and interest on the Notes.

The Company and/or Allied World may, at their option, and at any time, elect to have its obligations discharged with respect to all outstanding Notes. This is referred to as "defeasance". Such defeasance means that the Company and/or Allied World shall be deemed to have paid and discharged the entire indebtedness represented by the outstanding Notes and to have satisfied its other obligations with respect to the Notes under the Indenture, except for (i) the rights of the holders of outstanding Notes to receive, solely from the trust fund described below, payments in respect of the principal of (and premium, if any) and interest on such Notes when such payments are due, (ii) the Company and/or Allied World's obligations with respect to the Notes relating to the issuance of temporary Notes, the registration, transfer and exchange of Notes, the replacement of mutilated, destroyed, lost or stolen Notes, the maintenance of an office or agency for payment of the Notes, and the holding of money for security payments in trust and statements as to compliance with the Indenture, (iii) the rights, powers, trusts, duties and immunities of the trustees under the Indenture and (iv) the defeasance provisions of the Indenture. In addition, the Company and Allied World may, at their option and at any time, elect to be released from its obligations with respect to certain of the covenants under the Indenture (including those described under "- Certain Covenants - Limitation on Liens on Capital Stock of Restricted Subsidiaries"), referred to as "covenant defeasance", and any omission to comply with such obligations shall not constitute a default or an event of default with respect to the Notes.

In order to exercise either defeasance or covenant defeasance with respect to the Notes, (i) the Company and/or Allied World must irrevocably deposit with the trustee, in trust, for the benefit of the holders of the Notes, cash in U.S. dollars, certain U.S. government obligations, or a combination thereof, in such amounts as will be sufficient, in the opinion of a nationally recognized firm of independent public accountants, to pay the principal of and interest on the outstanding Notes on the stated maturity (or redemption date, if applicable) of such principal or installment of interest; (ii) in the case of defeasance, the Company and/or Allied World shall have delivered to the trustees an opinion of counsel in the United States stating that (x) they have received from, or there has been published by, the Internal Revenue Service a ruling or (y) since June 18, 2024 (the date of the offering memorandum for the Initial Notes), there has been a change in the applicable U.S. federal income tax law, in either case to the effect that, and based thereon such opinion of counsel shall confirm that, the holders of the outstanding Notes will not recognize income, gain or loss for U.S. federal income tax purposes as a result of such defeasance and will be subject to U.S. federal income tax on the same amounts, in the same manner and at the same times as would have been the case if such defeasance had not occurred; (iii) in the case of covenant defeasance, the Company and/or Allied World shall have delivered to the trustees an opinion of counsel in the United States to the effect that the holders of the outstanding Notes will not recognize income, gain or loss for U.S. federal income tax purposes as a result of such covenant defeasance and will be subject to U.S. federal income tax on the same amounts, in the same manner and at the same times as would have been the case if such covenant defeasance had not occurred; and (iv) the Company and/or Allied World must comply with certain other conditions.

Modification

The Indenture provides that the Company, Allied World and the trustees may enter into supplemental indentures without the consent of the holders of the Notes or the holders of the securities of any other series to: (a) evidence the succession of another person to the Company and the obligations assumed by such successor under the Indenture; (b) add to the Company's and Allied World's covenants for the benefit of the holders of the securities of any series or to surrender any right or power conferred upon the Company or Allied World by the Indenture; (c) add events of default for the benefit of the holders of the securities of any series; (d) change or eliminate any provisions of the Indenture, provided that any such change or elimination shall become effective only when there is no security issued under the Indenture then outstanding of any series created prior thereto which is entitled to the benefit of such provision; (e) secure any series of securities; (f) establish the form and terms of any series of securities permitted to be issued under the Indenture; (g) evidence the acceptance of appointment by a successor trustee under the Indenture and provide for or facilitate the administration of one or more trusts under the Indenture by one or more trustees; (h) cure any ambiguity, correct or supplement any inconsistency or make any other modification, provided that such action does not adversely affect the interests of the holders of outstanding securities of any series in any material respect; and (i) supplement any of the provisions of the Indenture to the extent necessary to permit or facilitate the defeasance or discharge of any series of securities, provided such action does not adversely affect the interests of the holders of securities of any series in any material respect.

The Indenture also contains provisions permitting the Company, Allied World and the trustees, with the consent of the holders of not less than a majority in principal amount of all securities issued under the Indenture then outstanding and affected (treated as one class), to add any provisions to, change in any manner or eliminate any of the provisions of, the Indenture or modify in any manner the rights of the holders of securities under the Indenture; provided that the Company, Allied World and the trustees may not, without the consent of the holder of each outstanding security affected thereby, among other things: (a) change the stated maturity of the principal of or any installment of interest on any security, (b) reduce the principal amount of or the rate of interest on, or premium payable upon the redemption of, any such security, (c) reduce the amount of the principal of an original issue discount security that would be due and payable upon a declaration of acceleration of the maturity thereof, (d) adversely affect any right of repayment at the option of the holder of any security, (e) change the place or currency of payment of principal of, or any premium or interest on, any such security, (f) impair the right to institute suit for the enforcement of any such payment on any security when due, (g) reduce the percentage in principal amount of securities of any series whose consent is necessary to modify or amend the Indenture or to waive compliance with certain provisions of the Indenture or certain defaults and their consequences or (h) modify the foregoing requirements, except to increase any percentage or to provide that certain provisions of the Indenture cannot be modified or waived without the consent of the holder of each outstanding security affected thereby.

Enforceability of Judgments

Fairfax

Since some of the Company's assets are in Canada, any judgment obtained outside of Canada against the Company, including any judgment with respect to the payment of principal or interest on the Notes may not be collectible outside of Canada.

The Company has been informed by counsel to the Company that a court of competent jurisdiction in the Province of Ontario (an "Ontario Court") would give a judgment based upon a final and conclusive in personam judgment of a court exercising jurisdiction in the Borough of New York, The City of New York, State of New York (a "New York Court") for a sum certain, obtained against the Company, with respect to a claim arising out of the Indenture (in respect of the Notes) or the Notes (a "New York Judgment"), without reconsideration of the merits, provided that (i) an action to enforce the New York Judgment must be commenced in the Ontario Court within any applicable limitation period; (ii) the Ontario Court has discretion to stay or decline to hear an action on the New York Judgment if the New York Judgment is under appeal or there is another subsisting judgment in any jurisdiction relating to the same cause of action; (iii) the Ontario Court will render judgment only in Canadian dollars; (iv) an action in the Ontario Court on the New York Judgment may be affected by bankruptcy, insolvency or other similar laws affecting the enforcement of creditors' rights generally; and (v) an action in the Ontario Court on the New York Judgment would be subject to the following defenses: (A) the New York Judgment was obtained by fraud or in a manner contrary to the principles of natural justice but the New York Judgment would not be contrary to natural justice by reason only that service of process was effected on the agent for service of process appointed by the Company pursuant to the Indenture; (B) the New York Judgment is for a claim which under the laws of the Province of Ontario and the federal laws of Canada applicable therein would be characterized as based on a foreign revenue, expropriatory, penal or other public law; (C) the New York Judgment is contrary to Ontario public policy, as such term is interpreted under the laws of the Province of Ontario and the federal laws of Canada applicable therein, or to an order made by the Attorney General of Canada under the Foreign Extraterritorial Measures Act (Canada) or by the Competition Tribunal under the Competition Act (Canada) in respect of certain judgments referred to in these statutes; and (D) the New York Judgment has been satisfied or is void under the laws of the State of New York. In the opinion of such counsel, there are currently no reasons under the law of Ontario for avoiding recognition of said judgments of New York Courts under the Indenture or on the Notes based upon public policy. The Company has been advised by such counsel that a monetary judgment of a U.S. court predicated solely upon civil liability provisions of U.S. federal securities laws would likely be enforceable in Canada if the U.S. court in which judgment was obtained had a basis for jurisdiction that was recognized by a Canadian court for such purposes. The Company has also been advised by its counsel, that it is less certain that an original action could be commenced in Canada on the basis of liability predicated solely upon such laws.

Allied World

Allied World is a Bermuda exempted company incorporated under the laws of Bermuda. A substantial portion of Allied World's assets are located outside of Canada and the United States and certain of the directors, as well as certain of the experts named in this prospectus, may be residents of jurisdictions outside of Canada and the United States. Allied World has appointed an agent for service of process in the United States. However, it may be difficult for investors to effect service within the United States or upon those directors and experts who are not residents of the United States, as applicable. Holders of Notes are advised that it may also not be possible for them to enforce judgments obtained in the United States against any person or company that is incorporated, continued or otherwise organized under the laws of a foreign jurisdiction or resides outside of the United States, even if the party has appointed an agent for service of process. Furthermore, it may be difficult to realize upon or enforce in the United States any judgment of a court in the United States against Allied World or the experts named in this prospectus since a substantial portion of Allied World's assets and the assets of such persons may be located outside of the United States. Allied World has been advised by counsel that there is no treaty in force between the United States and Bermuda providing for the reciprocal recognition and enforcement of judgments in civil and commercial matters. As a result, whether a U.S. judgment would be enforceable in Bermuda against Allied World or the experts named in this prospectus depends on whether the U.S. court that entered the judgment is recognized by a Bermuda court as having jurisdiction over Allied World or the experts named in this prospectus, as determined by reference to Bermuda conflict of law rules. The courts of Bermuda would likely give recognition to a valid, final and conclusive in personam judgment obtained in a U.S. court pursuant to which a debt or definitive sum of money is payable (other than a sum of money payable in respect of multiple damages, taxes or other charges of a like nature or in respect of a fine or other penalty) as long as: (i) the U.S. court issuing the judgment had proper jurisdiction over the parties subject to the judgment and had jurisdiction to give the judgment as a matter of Bermuda law; (ii) the U.S. court issuing the judgment did not contravene the rules of natural justice of Bermuda; (iii) the judgment was not obtained by fraud; (iv) the enforcement of the judgment would not be contrary to the public policy of Bermuda (this is likely to be the case if, for example, there is a Bermuda judgment which conflicts with the judgment of the foreign court in respect of which the enforcement is sought or if the judgment creditor has unsettled judgment debts in Bermuda); (v) there was due compliance with the correct procedures under the laws of Bermuda; and (vi) the application for recognition is brought within the relevant limitations period.

In addition to and irrespective of jurisdictional issues, Bermuda courts will not enforce a provision of U.S. federal securities laws that is either penal in nature or contrary to public policy. It is the advice of Allied World's Bermuda counsel that an action brought pursuant to a public or penal law, the purpose of which is the enforcement of a sanction, power or right at the instance of the state in its sovereign capacity, is unlikely to be enforced by a Bermuda court. Specified remedies available under the laws of U.S. jurisdictions, including specified remedies under U.S. federal securities laws, would not likely be available under Bermuda law or enforceable in a Bermuda court, as they may be contrary to Bermuda public policy. Further, no claim may be brought in Bermuda against Allied World or the experts named in this prospectus in the first instance for a violation of U.S. federal securities laws because these laws have no extraterritorial application under Bermuda law and do not have force of law in Bermuda.

Consent to Jurisdiction

Each of the Company and Allied World have irrevocably appointed Fairfax (US) Inc., 401 East Corporate Drive, Suite 200 Lewisville, TX 75057, as its authorized agent for service of process in any legal action or proceeding arising out of or relating to the Indenture and the Notes for actions brought under U.S. federal or state securities laws or for actions brought by either trustee or for any actions arising out of or related to the Indenture or the Notes in any New York Court, and has irrevocably submitted to the jurisdiction of the New York Courts for such purposes.

Governing Law

The Indenture and the Notes are governed by and shall be construed in accordance with the laws of the State of New York.

Trustees, Paying Agent and Securities Registrar

The Bank of New York Mellon of 240 Greenwich Street, Floor 7E, New York, New York, 10286, U.S.A. currently acts as U.S. trustee, paying agent and securities registrar for the Notes.

Computershare Advantage Trust of Canada (formerly BNY Trust Company of Canada) of 88A East Beaver Creek Rd., Richmond Hill, Ontario, Canada, L4B 4A8 currently acts as Canadian trustee for the Notes.

CERTAIN ERISA CONSIDERATIONS

General

The U.S. Employee Retirement Income Security Act of 1974, as amended ("ERISA"), imposes certain requirements on employee benefit plans subject to Title I of ERISA and on entities that are deemed to hold the assets of such plans ("ERISA Plans"), and on those persons who are fiduciaries with respect to ERISA Plans. Investments by ERISA Plans are subject to ERISA's general fiduciary requirements, including, but not limited to, the requirement of investment prudence and diversification and the requirement that an ERISA Plan's investments be made in accordance with the documents governing the plan.

Section 406 of ERISA and Section 4975 of the Code, prohibit certain transactions involving the assets of an ERISA Plan (as well as those plans that are not subject to ERISA, but are subject to Section 4975 of the Code, such as individual retirement accounts (together with ERISA Plans, "Plans")) and certain persons (referred to as "parties in interest" or "disqualified persons") having certain relationships to such Plans, unless a statutory or administrative exemption is applicable to the transaction. A party in interest or disqualified person who engages in a non-exempt prohibited transaction may be subject to excise taxes and other penalties and liabilities under ERISA and Section 4975 of the Code.

Any Plan fiduciary that proposes to cause a Plan to acquire the Exchange Notes should consult with its counsel regarding the applicability of the fiduciary responsibility and prohibited transaction provisions of ERISA and Section 4975 of the Code to such an investment, and to confirm that such purchase and holding will not constitute or result in a non-exempt prohibited transaction or any other violation of an applicable requirement of ERISA.

Non-U.S. plans, governmental plans and certain church plans, while not subject to the fiduciary responsibility provisions of ERISA or the prohibited transaction provisions of ERISA and Section 4975 of the Code, may nevertheless be subject to non-U.S. or U.S. federal, state, local or other laws or regulations that are substantially similar to the foregoing provisions of ERISA and the Code ("Similar Law"). Fiduciaries of any such plans (and entities in which such plans invest, as applicable) should consult with their counsel before purchasing Exchange Notes to determine the need for, and the availability, if necessary, of any exemptive relief under any applicable Similar Law.

Prohibited Transaction Exemptions

The fiduciary of a Plan that proposes to purchase and hold any Exchange Notes should consider, among other things, whether such purchase and holding may involve (i) the direct or indirect extension of credit to a party in interest or a disqualified person, (ii) the sale or exchange of any property between a Plan and a party in interest or a disqualified person, or (iii) the transfer to, or use by or for the benefit of, a party in interest or a disqualified person, of any Plan assets. Such parties in interest or disqualified persons could include, without limitation, the Company, the initial purchasers of the Initial Notes, the holders of senior notes of the Company, or any of their respective agents or affiliates. Depending on the satisfaction of certain conditions, which may include the identity of the Plan fiduciary making the decision to acquire or hold the Exchange Notes on behalf of a Plan, Section 408(b)(17) of ERISA or Prohibited Transaction Class Exemption ("PTCE") 84-14 (relating to transactions effected by a "qualified professional asset manager"), PTCE 90-1 (relating to investments by insurance company pooled separate accounts), PTCE 91-38 (relating to investments by bank collective investment funds), PTCE 95-60 (relating to investments by insurance company general accounts) or PTCE 96-23 (relating to transactions directed by an in-house asset manager) (collectively, the "Class Exemptions") could provide an exemption from the prohibited transaction provisions of ERISA and Section 4975 of the Code. However, there can be no assurance that any of these Class Exemptions or any other exemption will be available with respect to any particular transaction involving the Exchange Notes.

By its purchase of any Exchange Note, the purchaser thereof will be deemed to have represented and warranted that either:

(i)

no assets of a Plan or non-U.S., governmental or church plan subject to Similar Law have been used to acquire Exchange Note or an interest therein; or

(ii)

the purchase and holding of Exchange Note or an interest therein by such person do not and will not constitute or result in a non-exempt prohibited transaction under ERISA or Section 4975 of the Code or a violation of Similar Law.

Plan Assets Regulation

The U.S. Department of Labor has promulgated a regulation (as modified by Section 3(42) of ERISA, the "Plan Assets Regulation") describing what constitutes the assets of a Plan with respect to the Plan's investment in an entity for purposes of ERISA's fiduciary responsibility provisions and Section 4975 of the Code. Under the Plan Assets Regulation, if a Plan invests in an "equity interest" of an entity, then the Plan's assets will include both the equity interest and an undivided interest in each of the underlying assets of the entity, unless equity participation in the entity by Benefit Plan Investors (as defined below) is not "significant," as provided under the Plan Assets Regulation, or another exception under the Plan Assets Regulation applies. Under the Plan Assets Regulation, the term "equity interest" means any interest in an entity other than an instrument that is treated as indebtedness under applicable local law and which has no substantial equity features.

For purposes of the Plan Assets Regulation, equity participation in an entity by Benefit Plan Investors will not be significant if such investors hold, in the aggregate, less than 25% of the value of each class of equity in the entity, excluding equity interests held by persons (other than a Benefit Plan Investor) with discretionary authority or control over the assets of the entity or who provide investment advice for a fee (direct or indirect) with respect to such assets, and any affiliates thereof. For purposes of this 25% test, "Benefit Plan Investor" is as defined in the Plan Assets Regulation and includes (i) any "employee benefit plan" (as defined in Section 3(3) of ERISA) that is subject to Part 4 of Subtitle B of Title I of ERISA, (ii) any "plan" as defined in and subject to Section 4975 of the Code and (iii) any entity whose underlying assets are deemed to include plan assets by reason of an employee benefit plan's or other plan's investment in the entity or otherwise.

The Exchange Notes are not intended to be treated as equity interests in the Company for purposes of the Plan Assets Regulation. Notwithstanding the foregoing, in the event that the Exchange Notes are considered "equity interests" within the meaning of the Plan Asset Regulation, the Company will endeavor to prohibit ownership of the Exchange Notes by Benefit Plan Investors or otherwise limit ownership of the Exchange Notes by Benefit Plan Investors so that Benefit Plan Investors are deemed to own less than 25% of any class of equity in the Company, unless another exception under the Plan Assets Regulation applies. If Benefit Plan Investors are deemed to own 25% or more of any class of equity in the Company and another exception under the Plan Assets Regulation is not applicable, the Company is deemed to hold "plan assets" for purposes of ERISA and Section 4975 of the Code and transactions in which the Company may engage will be subject to ERISA's fiduciary obligations, as well as the prohibited transaction rules of ERISA and Section 4975 of the Code.

The foregoing discussion is general in nature. Due to the complexity of the applicable rules and penalties under ERISA, the Code and Similar Laws, each Plan fiduciary (and each fiduciary for non-U.S., governmental or church plans subject to Similar Law) should consult with its legal advisor concerning the potential consequences to the applicable Plan or plan under ERISA, Section 4975 of the Code or such Similar Laws of an investment in the Exchange Notes.

CERTAIN UNITED STATES FEDERAL INCOME TAX CONSIDERATIONS

The exchange of Initial Notes for Exchange Notes pursuant to the Exchange Offer will not be treated as a taxable transaction for U.S. federal income tax purposes because the terms of the Exchange Notes will not be considered to differ materially in kind or in extent from the terms of the Initial Notes. Rather, the Exchange Notes you receive will be treated as a continuation of your investment in the Initial Notes. As a result, you will not recognize gain or loss upon the exchange of your Initial Notes for Exchange Notes. In addition, your basis and holding period in the Exchange Notes will be the same as your basis and holding period in the Initial Notes exchanged therefor.

THE FOREGOING DISCUSSION OF U.S. FEDERAL INCOME TAX CONSEQUENCES DOES NOT CONSIDER THE FACTS AND CIRCUMSTANCES SPECIFIC TO ANY PARTICULAR HOLDER OF INITIAL NOTES. IF YOU ARE CONSIDERING EXCHANGING YOUR INITIAL NOTES FOR EXCHANGE NOTES, YOU SHOULD CONSULT YOUR TAX ADVISERS CONCERNING THE TAX CONSEQUENCES OF THE EXCHANGE UNDER U.S. FEDERAL, STATE, LOCAL AND FOREIGN LAWS.

CERTAIN BERMUDA CONSIDERATIONS

Tax

On December 27, 2023, Bermuda enacted the CIT Act. Entities subject to tax under the CIT Act are the Bermuda constituent entities of multi-national groups. A multi-national group is defined under the CIT Act as a group with entities in more than one jurisdiction with consolidated revenues of at least EUR750 million for two of the four previous fiscal years.

If Bermuda constituent entities of a multi-national group are subject to tax under the CIT Act, such tax is charged at a rate of 15% of the net taxable income of such constituent entities as determined in accordance with and subject to the adjustments set out in the CIT Act (including in respect of foreign tax credits applicable to the Bermuda constituent entities). Tax is chargeable under the CIT Act for tax years starting on or after January 1, 2025. In addition, the CIT Act includes transition rules including carryforward tax losses incurred in the five fiscal years preceding the effective date or increases in the tax basis of assets and liabilities.

The CIT Act also provides relief from double taxation via foreign tax credit based on the adjusted amount of foreign taxes accrued by the group. The CIT Act is designed as a covered tax for the purposes of the OECD's Global Case Anti-Erosion Rules ("GloBE Model Rules"), meaning the CIT Act does not presently apply an income-inclusion rule or under taxed profits rule in the same way as the GloBE Model Rules do.

Future developments and guidance under the GloBE Model Rules may impact Bermuda's implementation of its corporate tax regime, and any future changes to the Bermuda corporate income tax regime may impact our tax liability, financial condition and results of operations and could increase our administrative expenses.

The CIT Act does not impose any withholding tax, capital transfer tax, estate duty or inheritance and no such taxes are payable by us or our Holders of Notes (who are non-residents of Bermuda) in respect of the exchange of Initial Notes for Exchange Notes pursuant to the Exchange Offer. This discussion does not, however, apply to the taxation of persons ordinarily resident in Bermuda. Bermuda resident shareholders should consult their own tax advisors regarding possible Bermuda taxes with respect to the exchange of Initial Notes for Exchange Notes pursuant to the Exchange Offer.

Bermuda currently has no tax treaties in place with other countries in relation to double-taxation or for the withholding of tax for foreign tax authorities.

Economic Substance

Legislation enacted in Bermuda as to economic substance may affect our operations. Pursuant to the Economic Substance Act 2018 (as amended) of Bermuda (the "ES Act") that came into force on 1 January 2019, a registered entity other than an entity which is resident for tax purposes in certain jurisdictions outside Bermuda ("non-resident entity") that carries on as a business any one or more of the "relevant activities" referred to in the ES Act must comply with economic substance requirements. The ES Act may require in-scope Bermuda entities that are engaged in such "relevant activities" to be directed and managed in Bermuda, have an adequate level of qualified employees in Bermuda, incur an adequate level of annual expenditure in Bermuda, maintain physical offices and premises in Bermuda or perform core income-generating activities in Bermuda. The list of "relevant activities" includes carrying on any one or more of: banking, insurance, fund management, financing, leasing, headquarters, shipping, distribution and service centre, intellectual property and holding entities.

Privacy Regulation

Bermuda's principal data protection and privacy legislation is the Personal Information Protection Act 2016 ("PIPA"). On January 1, 2025, PIPA was fully implemented. PIPA applies to every organization (which includes any individual, entity or public authority) that uses personal information in Bermuda where that personal information is used by automated or other means which form, or are intended to form, part of a structured filing system. PIPA does not define privacy explicitly, but rather defines "personal information" and sets out privacy rules for institutions to follow for the collection, use, disclosure, maintenance, retention, security and disposal of personal information. For the purposes of PIPA, "personal information" means any information about an identified or identifiable individual (meaning a natural person), and "use" or "using" are very broadly defined and means carrying out any operation on personal information, including collecting, obtaining, recording, holding, storing, organizing, adapting, altering, retrieving, transferring, consulting, disclosing, disseminating or otherwise making available, combining, blocking, erasing or destroying it. Personal information used by an entity, such as in Bermuda would include (without limitation) information relating to policyholders, employees, consultants, service providers, officers, employees, consultants or any other third party of the insurer. Our Bermuda entities are subject to PIPA requirements.

Insolvency and Winding up

Bermuda's insolvency regime is generally premised upon the concept of pari passu distribution of assets amongst the unsecured creditors of the insolvent company, subject to the rights of secured creditors of that company to enforce their security interests. However, the Bermuda Insurance Act provides for the prior payment of policyholders' liabilities ahead of general unsecured creditors in the event of the liquidation or winding up of an insurer. The Bermuda Insurance Act provides, amongst other things that, subject to certain statutorily preferred debts, the insurance debts of an insurer must be paid in priority to all other unsecured debts of the insurer. Insurance debt is defined as a debt to which an insurer is or may become liable pursuant to an insurance contract excluding debts owed to an insurer under an insurance contract where the insurer is the person insured.

An insolvent Bermuda company may be the subject in Bermuda of winding up proceedings. In the context of insolvency, the other proceedings that may be used in Bermuda are a scheme of arrangement or receivership, but these are not exclusive to insolvency. There are two types of insolvent liquidations in Bermuda: voluntary and compulsory. The former is commenced by the company itself (which can be on a solvent or insolvent basis and will require a resolution of the members and, if the company is insolvent, a creditors' resolution), while the latter is commenced by way of a petition presented to the Supreme Court of Bermuda by either the Company or its creditors or contributories upon which the court is asked to make a winding-up order. There are a number of circumstances provided for in Section 161 of the Bermuda Companies Act in which a Bermuda company may be wound up by the court, the most common of which is when the company is unable to pay its debts.

Under Bermuda law, certain transactions may be set aside or otherwise be varied or amended by order of a Bermuda court when an insolvent Bermuda company goes into liquidation, including but not limited to transactions for fraudulent trading, fraudulent preference and/or a fraudulent conveyance (as such terms are understood under Bermuda law).

Set-off of debts is permissible upon the commencement of winding-up of an insolvent Bermuda company, but only in respect of mutual dealings subsisting at the commencement of winding-up. If there is a net balance after the set-off, such sums may be claimed in the liquidation.

There are no bankruptcy treaties in force under the laws of Bermuda.

CERTAIN CANADIAN FEDERAL INCOME TAX CONSIDERATIONS

The following is a summary of the principal Canadian federal income tax considerations under the Canadian Tax Act generally applicable to a holder of Initial Notes who acquires Exchange Notes, including entitlement to all payments thereunder, as a beneficial owner pursuant to the Exchange Offer and who, for purposes of the Canadian Tax Act, and at all relevant times, (i) is not, and is not deemed to be, resident in Canada, (ii) holds the Notes as capital property, (iii) deals at arm's length and is not affiliated with the Company, (iv) is neither a "specified shareholder" of the Company nor a person not dealing at arm's length with a "specified shareholder" of the Company as defined in subsection 18(5) of the Canadian Tax Act, (v) is not a "specified entity" as defined in Bill C-59 "An Act to implement certain provisions of the fall economic statement tabled in Parliament on November 21, 2023 and certain provisions of the budget tabled in Parliament on March 28, 2023" which have been enacted on June 20, 2024 with respect to "hybrid mismatch arrangements," (vi) deals at arm's length with any Canadian resident (or deemed Canadian resident) to whom the holder disposes of the Notes and (vii) does not use or hold, and is not deemed to use or hold, the Notes in a business carried on in Canada (a "Non Resident Holder"). Special rules, which are not discussed herein, may apply to a Non Resident Holder that holds the Notes in connection with carrying on an insurance business in Canada and elsewhere. This summary assumes that no interest paid on the Notes will be in respect of a debt or other obligation to pay an amount to a person with whom the Company does not deal at arm's length for purposes of the Canadian Tax Act.

The summary is based on the current provisions of the Canadian Tax Act, the regulations thereunder (the "Regulations") and an understanding of the current administrative policies and assessing practices published by the Canada Revenue Agency (the "CRA") and takes into account all specific proposals to amend the Canadian Tax Act and Regulations publicly announced by the Minister of Finance (Canada) prior to the date hereof. This summary does not take into account or anticipate any other changes in law, whether by judicial, governmental or legislative action or decisions, or any changes in the CRA's administrative policies and assessing practices, nor does it take into account provincial, territorial or foreign tax legislation or considerations which may differ significantly from those discussed herein.

This summary is of a general nature only and is not intended to be, and should not be construed to be, legal or tax advice to any particular holder of the Notes. Holders of the Notes should consult their own tax advisors as to the tax consequences to them of acquiring, holding and disposing of the Notes in their particular circumstances, including the application and effect, if any, of the income and other tax laws of any province, territory, state or local tax authority or foreign jurisdiction.

For the purposes of the Canadian Tax Act, the exchange of the Initial Notes for the Exchange Notes pursuant to the Exchange Offer should not constitute a taxable transaction.

Amounts paid or credited, or deemed to be paid or credited, as, on account or in lieu of payment of, or in satisfaction of, the principal of the Exchange Notes or premium, discount or interest on the Exchange Notes by the Company to a Non Resident Holder, including in respect of a redemption of the Exchange Notes, will be exempt from Canadian withholding tax.

No other taxes on income (including taxable capital gains) will be payable under the Canadian Tax Act by a Non Resident Holder in respect of the ownership or disposition of the Exchange Notes.

PLAN OF DISTRIBUTION

The Company issued $600 million principal amount of Initial Notes on June 24, 2024 pursuant to a private offering that was underwritten by BofA Securities, Inc., J.P. Morgan Securities LLC, Citigroup Global Markets Inc. and BMO Capital Markets. On July 19, 2024, Allied World was added as a Co-Obligor of the Initial Notes in accordance with the terms of the Initial Notes, following which the Company remains a full and unconditional Co-Obligor in respect of the Notes for all purposes under the Indenture. If all the conditions of the Exchange Offer are satisfied, we will exchange all Initial Notes that are validly tendered and not validly withdrawn for an equal principal amount of Exchange Notes that have been registered under the Securities Act.

Any broker-dealer that resells or transfers Exchange Notes in the United States that were received by it for its own account pursuant to the Exchange Offer in exchange for Initial Notes acquired by such broker-dealer as a result of market-making or other trading activities and any broker or dealer that participates in a distribution of such Exchange Notes may be deemed to be an "underwriter" within the meaning of the Securities Act, and any profit of any such resale or transfer of Exchange Notes and any commissions or concessions received by any such persons may be deemed to be underwriting compensation under the Securities Act. Accordingly, each such broker-dealer must acknowledge that it will deliver, and must deliver, a prospectus meeting the requirements of the Securities Act in connection with any resale or transfer of such Exchange Notes in the United States. The letter of transmittal states that by acknowledging that it will deliver, and by delivering, such a prospectus, a broker-dealer will not be deemed to admit that it is an "underwriter" within the meaning of the Securities Act.

This prospectus, as it may be amended or supplemented from time to time, may be used by a broker-dealer in connection with resales or transfers in the United States of Exchange Notes received in exchange for Initial Notes where such Initial Notes were acquired as a result of market-making or other trading activities. We have agreed to make this prospectus, as amended or supplemented, available to any broker-dealer for use in connection with any such resale or transfer for a period ending on the earlier of (i) 180 days after the date on which the Registration Statement is declared effective by the SEC and (ii) the date on which participating broker-dealers are no longer required to deliver a prospectus in connection with market-making or other trading activities.

We will not receive any proceeds from any sale of Exchange Notes by broker-dealers. Exchange Notes received by broker-dealers for their own account pursuant to the Exchange Offer may be sold from time to time in one or more transactions in the over-the-counter market, in negotiated transactions, through the writing of options on the Exchange Notes or a combination of such methods of resale, at market prices prevailing at the time of resale, at prices related to such prevailing market prices or at negotiated prices. Any such resale may be made directly to purchasers or to or through brokers or dealers who may receive compensation in the form of commissions or concessions from any such broker-dealer and/or the purchasers of any of the Exchange Notes.

For a period of 180 days after the expiration of the Exchange Offer or, if shorter, for a period ending on the date on which a broker-dealer is no longer required to deliver a prospectus in connection with market-making or other trading activities, we will promptly send additional copies of this prospectus and any amendment or supplement to this prospectus to any broker-dealer that requests such documents in the letter of transmittal. We have agreed to (i) pay all expenses incident to the Exchange Offer, other than (a) commissions or concessions of any brokers or dealers, (b) in certain circumstances described under "The Exchange Offer - Terms of the Exchange Offer - Fees and Expenses", transfer taxes and (c) any other taxes you may incur; and (ii) indemnify the holders of the Initial Notes (including any broker-dealer) against certain liabilities, including liabilities under the Securities Act.

LEGAL MATTERS

Certain legal matters relating to the Exchange Notes offered by this prospectus will be passed upon on our behalf by Torys LLP, New York, New York, and Toronto, Canada, with respect to U.S. and Canadian law. Certain matters with respect to Bermuda law will be passed upon by Conyers Dill & Pearman Limited.

INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM

The consolidated financial statements of the Company as of and for the years ended December 31, 2024 and 2023 incorporated by reference in this prospectus, and the effectiveness of internal control over financial reporting as of December 31, 2024, have been audited by PricewaterhouseCoopers LLP, an independent registered public accounting firm, as stated in their report incorporated by reference herein.

PART II

INFORMATION NOT REQUIRED IN Prospectus

Item 20. Indemnification of Officers and Directors

Canada

The by-laws of the Company provide that, subject to the relevant provisions of the Canada Business Corporations Act, the Company shall indemnify a director or officer of the Company, a former director or officer of the Company, or another individual who acts or acted at the Company's request as a director or officer, or an individual acting in a similar capacity, of another entity, against all costs, charges and expenses, including an amount paid to settle an action or satisfy a judgment, reasonably incurred by the individual in respect of any civil, criminal, administrative, investigative or other proceeding in which the individual is involved because of that association with the Company or such other entity if (i) the individual acted honestly and in good faith with a view to the best interests of the Company or, as the case may be, to the best interests of the other entity for which the individual acted as a director or officer or in a similar capacity at the Company's request; and (ii) in the case of a criminal or administrative action or proceeding that is enforced by a monetary penalty, the individual has reasonable grounds for believing that the individual's conduct was lawful.

The Company also maintains insurance for the benefit of its directors and officers against liability in their respective capacities as directors and officers. The directors and officers are not required to pay any premium in respect of the insurance. The policy contains standard industry exclusions.

Bermuda

Section 98 of the Bermuda Companies Act provides generally that a Bermuda company may indemnify its directors, officers and auditors against any liability that by virtue of any rule of law would otherwise be imposed on them in respect of any negligence, default, breach of duty or breach of trust, except in cases where such liability arises from fraud or dishonesty of which such director, officer or auditor may be guilty in relation to the company. Section 98 further provides that a Bermuda company may indemnify its directors, officers and auditors against any liability incurred by them in defending any proceedings, whether civil or criminal, in which judgment is awarded in their favor or in which they are acquitted or granted relief by the Supreme Court of Bermuda pursuant to section 281 of the Bermuda Companies Act.

Allied World has adopted provisions in its bye-laws that provide that it shall indemnify its officers and directors in respect of their actions and omissions, except in respect of their fraud or dishonesty. Allied World's bye-laws provide that the shareholders waive all claims or rights of action that they might have, individually or in right of the company, against any of the company's directors or officers for any act or failure to act in the performance of such director's or officer's duties, except in respect of any fraud or dishonesty of such director or officer. Section 98A of the Bermuda Companies Act permits Allied World to purchase and maintain insurance for the benefit of any officer or director in respect of any loss or liability in respect of any negligence, default, breach of duty or breach of trust, whether or not we may otherwise indemnify such officer or director. Allied World has purchased and maintains a directors' and officers' liability policy for such a purpose.

Insofar as indemnification for liabilities arising under the Securities Act of 1933 may be permitted to directors, officers or persons controlling the Registrants pursuant to the foregoing provisions, the Registrants have been informed that in the opinion of the U.S. Securities and Exchange Commission such indemnification is against public policy as expressed in the Securities Act of 1933 and is therefore unenforceable.

Item 21.Exhibits and Financial Statement Schedules

The following documents are filed as exhibits hereto:

	Exhibit No.
	3.1		Articles of Incorporation of Fairfax Financial Holdings Limited (incorporated by reference to Exhibit 3.1 to Fairfax's Registration Statement on Form F-4, filed with the Commission on February 15, 2017)
	3.2		Certificate of Amendment of the Articles of Fairfax Financial Holdings Limited (incorporated by reference to Exhibit 99.1 to our Report on Form 6-K furnished to the SEC on April 30, 2018)
	3.3		By-Laws of Fairfax Financial Holdings Limited (incorporated by reference to Exhibit 3.2 to Fairfax's Registration Statement on Form F-4, filed with the Commission on February 15, 2017)
	3.4		Certificate of Continuance, Memorandum of Continuance, Certificate of Merger and Certificate of Incorporation on Change of Name of Allied World Assurance Company Holdings, Ltd.
	3.5		Amended and Restated Bye-laws of Allied World Assurance Company Holdings, Ltd.
	4.1		Indenture dated as of December 1, 1993, by and amongFairfax Financial Holdings Limited, Bank of Montreal Trust Company and the R-M Trust Company(the "Indenture") (incorporated by reference to Exhibit 7.1 to our Registration Statement on Form F-10 (File No. 333-228518) filed on November 21, 2018 (the "2018 Registration Statement"))
	4.2		First Supplemental Indenture to the Indenture dated as of May 9, 2011,by and amongFairfax Financial Holdings Limited, The Bank of New York Mellon and CIBC Mellon Trust Company (incorporated by reference to Exhibit 7.2 to the 2018 Registration Statement)
	4.3		Third Supplemental Indenture to the Indenture dated as of February 26, 2021, by and among Fairfax Financial Holdings Limited, The Bank of New York Mellon and BNY Trust Company of Canada (incorporated by reference to Exhibit 99.4 to our Report on Form 6-K, furnished to the SEC on March 1, 2021)
	4.4		Fourth Supplemental Indenture to the Indenture dated as of July 19, 2024, by and among Fairfax Financial Holdings Limited, Allied World Assurance Company Holdings, Ltd., The Bank of New York Mellon and BNY Trust Company of Canada (incorporated by reference to Exhibit 99.1 to our Report on Form 6-K, furnished to the SEC on July 19, 2024)
	4.5		Fifth Supplemental Indenture to the Indenture dated as of March 14, 2025, by and among Fairfax Financial Holdings Limited, Allied World Assurance Company Holdings, Ltd, The Bank of New York Mellon and Computershare Advantage Trust of Canada (formerly BNY Trust Company of Canada)
	4.6		Form of Exchange Note
	4.7		Registration Rights Agreement dated as of June 24, 2024, among Fairfax Financial Holdings Limited and the initial purchasers named therein (incorporated by reference to Exhibit 99.2 to our Report on Form 6-K, furnished to the SEC on June 24, 2024)
	5.1		Opinion of Torys LLP as to the validity of the Exchange Notes
	5.2		Opinion of Conyers Dill & Pearman Limited as to Bermuda law matters
	21.1		Subsidiaries of Fairfax Financial Holdings Limited and Allied World Assurance Company Holdings, Ltd (incorporated by reference to the section entitled "Intercorporate Relationships" on pages 3 to 5 of Exhibit 99.1 to the Company's Annual Report on Form 40-F, filed with the SEC on March 7, 2025)
	22.1		List of Subsidiary Obligors
	23.1		Consent of PricewaterhouseCoopers LLP
	23.2		Consent of Torys LLP (included in Exhibit 5.1)
	23.3		Consent of Conyers Dill & Pearman Limited (included in Exhibit 5.2)
	24.1		Powers of Attorney (included in the signature page to this Form F-4)
	25.1		Statement of Eligibility and Qualification of the U.S. trustee under the Trust Indenture Act of 1939 on Form T-1
	99.1		Form of Letter of Transmittal
	99.2		Form of Notice of Guaranteed Delivery
	99.3		Form of Letter to DTC Participants
	107		Filing Fee Table

Item 22. Undertakings

(a) Each of the undersigned F-4 Registrants hereby undertakes:

(1) To file, during any period in which offers or sales are being made, a post-effective amendment to this Registration Statement:

(i) To include any prospectus required by Section 10(a)(3) of the Securities Act;

(ii) To reflect in the prospectus any facts or events arising after the effective date of this Registration Statement (or the most recent post-effective amendment thereof) which, individually or in the aggregate, represent a fundamental change in the information set forth in this Registration Statement. Notwithstanding the foregoing, any increase or decrease in the volume of securities offered (if the total dollar value of securities offered would not exceed that which was registered) and any deviation from the low or high end of the estimated maximum offering range may be reflected in the form of prospectus filed with the Commission, pursuant to Rule 424(b) if, in the aggregate, the changes in volume and price represent no more than a 20% change in the maximum aggregate offering price set forth in the "Calculation of Registration Fee" table in the effective registration statement; and

(iii) To include any material information with respect to the plan of distribution not previously disclosed in this Registration Statement or any material change to such information in this Registration Statement.

(2) That, for the purpose of determining any liability under the Securities Act, each such post-effective amendment shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide offering thereof.

(3) To remove from registration by means of a post-effective amendment any of the securities being registered which remain unsold at the termination of the offering.

(4) To file a post-effective amendment to this Registration Statement to include any financial statements required by Item 8.A of Form 20-F at the start of any delayed offering or throughout a continuous offering. Financial statements and information otherwise required by Section 10(a)(3) of the Securities Act need not be furnished, provided that the registrant includes in the prospectus, by means of a post-effective amendment, financial statements required pursuant to this paragraph (a)(4) and other information necessary to ensure that all other information in the prospectus is at least as current as the date of those financial statements.

(5) That for the purpose of determining liability under the Securities Act to any purchaser, each prospectus filed pursuant to Rule 424(b) as part of a registration statement relating to an offering, other than registration statements relying on Rule 430B or other than prospectuses filed in reliance on Rule 430A, shall be deemed to be part of and included in the Registration Statement as of the date it is first used after effectiveness. Provided, however, that no statement made in a registration statement or prospectus that is part of the Registration Statement or made in a document incorporated or deemed incorporated by reference into the registration statement or prospectus that is part of the Registration Statement will, as to a purchaser with a time of contract of sale prior to such first use, supersede or modify any statement that was made in the registration statement or prospectus that was part of the Registration Statement or made in any such document immediately prior to such date of first use.

(6) That, for the purpose of determining liability of a F-4 Registrant under the Securities Act to any purchaser in the initial distribution of the securities: each undersigned F-4 Registrant undertakes that in a primary offering of securities of such undersigned F-4 Registrant pursuant to this Registration Statement, regardless of the underwriting method used to sell the securities to the purchaser, if the securities are offered or sold to such purchaser by means of any of the following communications, such undersigned F-4 Registrant will be a seller to the purchaser and will be considered to offer or sell such securities to such purchaser:

(i) Any preliminary prospectus or prospectus of the undersigned F-4 Registrant relating to the offering required to be filed pursuant to Rule 424;

(ii) Any free writing prospectus relating to the offering prepared by or on behalf of such undersigned F-4 Registrant or used or referred to by such undersigned F-4 Registrant;

(iii) The portion of any other free writing prospectus relating to the offering containing material information about such undersigned F-4 Registrant or its securities provided by or on behalf of such undersigned F-4 Registrant; and

(iv) Any other communication that is an offer in the offering made by such undersigned F-4 Registrant to the purchaser.

(b) Insofar as indemnification for liabilities arising under the Securities Act may be permitted to directors, officers and controlling persons of the F-4 Registrants pursuant to the foregoing provisions, or otherwise, such Registrants have been advised that, in the opinion of the Commission, such indemnification is against public policy as expressed in the Securities Act and is, therefore, unenforceable. In the event that a claim for indemnification against such liabilities (other than the payment by the F-4 Registrants of expenses incurred or paid by a director, officer or controlling person of the F-4 Registrants in the successful defense of any action, suit or proceeding) is asserted by such director, officer or controlling person in connection with the securities being registered, the F-4 Registrants will, unless in the opinion of their counsel the matter has been settled by controlling precedent, submit to a court of appropriate jurisdiction the question whether such indemnification by them is against public policy as expressed in the Securities Act and will be governed by the final adjudication of such issue.

(c) Each of the undersigned F-4 Registrants undertakes (i) to respond to requests for information that is incorporated by reference into the prospectus pursuant to Items 4, 10(b), 11, or 13 of this Form, within one business day of receipt of such request, and to send the incorporated documents by first class mail or other equally prompt means, and (ii) to arrange or provide for a facility in the United States for the purpose of responding to such requests. The undertaking in subparagraph (i) above includes information contained in documents filed subsequent to the effective date of the Registration Statement through the date of responding to the request.

(d) Each of the undersigned F-4 Registrants undertakes to supply by means of a post-effective amendment all information concerning a transaction, and the company being acquired involved therein, that was not the subject of and included in the Registration Statement when it became effective.

SIGNATURES

Pursuant to the requirements of the Securities Act of 1933, the registrant has duly caused this registration statement to be signed on its behalf by the undersigned, thereunto duly authorized, in the city of Toronto, country of Canada, on March 14, 2025.

	FAIRFAX FINANCIAL HOLDINGS LIMITED
	By:	/s/ Amy Sherk
		Name:	Amy Sherk
		Title:	Vice President and Chief Financial Officer

POWER OF ATTORNEY

KNOW ALL PERSONS BY THESE PRESENTS, that each person whose signature appears below hereby constitutes and appoints V. Prem Watsa, Amy Sherk and Derek Bulas as his or her true and lawful attorney-in-fact and agent, with full power of substitution and resubstitution, for him or her and in his or her name, place and stead, in any and all capacities, to sign any and all amendments (including post-effective amendments) to this Registration Statement and any Registration Statements filed by the registrant pursuant to Rule 462(b) of the Securities Act of 1933 relating thereto and to file the same, with all exhibits thereto, and other documents in connection therewith, with the U.S. Securities and Exchange Commission, granting to said attorney-in-fact and agent, with full power to act alone, full power and authority to do and perform each and every act and thing appropriate or necessary to be done in connection therewith, as fully to all intents and purposes as he or she might or could do in person, hereby ratifying and confirming all that said attorney-in-fact and agent, or his or her substitute, may lawfully do or cause to be done by virtue hereof.

Pursuant to the requirements of the Securities Act of 1933, as amended, this Registration Statement has been signed below by the following persons in the capacities set forth below on March 14, 2025.

/s/ V. Prem Watsa		/s/ Amy Sherk
Name: V. Prem Watsa		Name: Amy Sherk
Title: Chairman, Chief Executive Officer and Director (principal executive officer)		Title: Vice President and Chief Financial Officer (principal financial officer and principal accounting officer)
/s/ Robert J. Gunn		/s/ David L. Johnston
Name: Robert J. Gunn		Name: David L. Johnston
Title: Director		Title: Director
/s/ Karen L. Jurjevich		/s/ R. William McFarland
Name: Karen L. Jurjevich		Name: R. William McFarland
Title: Director		Title: Director
/s/ Christine N. McLean		/s/ Brian J. Porter
Name: Christine N. McLean		Name: Brian J. Porter
Title: Director		Title: Director
/s/ Timothy R. Price		/s/ Brandon W. Sweitzer
Name: Timothy R. Price		Name: Brandon W. Sweitzer
Title: Director		Title: Director
/s/ Lauren C. Templeton		/s/ Benjamin P. Watsa
Name: Lauren C. Templeton		Name: Benjamin P. Watsa
Title: Director		Title: Director
/s/ V. Prem Watsa		/s/ William C. Weldon
Name: V. Prem Watsa		Name: William C. Weldon
Title: Director		Title: Director

SIGNATURES

Pursuant to the requirements of the Securities Act of 1933, the registrant has duly caused this registration statement to be signed on its behalf by the undersigned, thereunto duly authorized, in Pembroke, Bermuda, on March 14, 2025.

	ALLIED WORLD ASSURANCE COMPANY HOLDINGS, LTD
	By:	/s/ Michael Cann
		Name:	Michael Cann
		Title:	Vice President, Bermuda Controller

POWER OF ATTORNEY

KNOW ALL PERSONS BY THESE PRESENTS, that each person whose signature appears below hereby constitutes and appoints V. Prem Watsa, Amy Sherk and Derek Bulas as his or her true and lawful attorney-in-fact and agent, with full power of substitution and resubstitution, for him or her and in his or her name, place and stead, in any and all capacities, to sign any and all amendments (including post-effective amendments) to this Registration Statement and any Registration Statements filed by the registrant pursuant to Rule 462(b) of the Securities Act of 1933 relating thereto and to file the same, with all exhibits thereto, and other documents in connection therewith, with the U.S. Securities and Exchange Commission, granting to said attorney-in-fact and agent, with full power to act alone, full power and authority to do and perform each and every act and thing appropriate or necessary to be done in connection therewith, as fully to all intents and purposes as he or she might or could do in person, hereby ratifying and confirming all that said attorney-in-fact and agent, or his or her substitute, may lawfully do or cause to be done by virtue hereof.

Pursuant to the requirements of the Securities Act of 1933, as amended, this Registration Statement has been signed below by the following persons in the capacities set forth below on March 14, 2025.

/s/ Louis Iglesias		/s/ Joseph Roesler
Name: Louis Iglesias		Name: Joseph Roesler
Title: President & Chief Executive Officer and Director (principal executive officer)		Title: Chief Financial Officer (principal financial officer and principal accounting officer)
/s/ Jean Cloutier		/s/ Graham Collis
Name: Jean Cloutier		Name: Graham Collis
Title: Director		Title: Director
/s/ Adrian Croft		/s/ Scott Hunter
Name: Adrian Croft		Name: Scott Hunter
Title: Director		Title: Director
/s/ Michael McCrimmon
Name: Michael McCrimmon
Title: Director

AUTHORIZED UNITED STATES REPRESENTATIVE

Pursuant to the requirements of Section 6(a) of the Securities Act, this Registration Statement on Form F-4 has been signed below by the undersigned, solely in its capacity as the registrants' duly authorized representative in the United States, on March 14, 2025.

	FAIRFAX (US) INC.
	By:	/s/ Sonja Lundy
		Name:	Sonja Lundy
		Title:	President

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Fairfax Financial Holdings Limited published this content on March 14, 2025, and is solely responsible for the information contained therein. Distributed by Public, unedited and unaltered, on March 14, 2025 at 21:15:42.440.