Investor Presentation – A Growing and Profitable Specialty Insurer

Diversified

• US hybrid fronting platform participating in the admitted and non-admitted ('E&S') markets for 6 years

Specialty Platform

• Earnings supported by an attractive mix of underwriting income and recurring fee-based and investment income

• 10.2% Debt-to-capital1 below our internal target (20%) and capital in excess of regulatory requirements

Strong Balance Sheet

• Issuer rating of BBB (DBRS); Financial Strength ratings of A (low) (DBRS) and A- (AM Best) at operating subsidiaries

• 20% consolidated Operating ROE2 (ROE: 15%); 5-year average 83%3 combined ratio2 in Canada and 28% Q1 2024

and Profitability

Operating ROE (ROE: 29%); increasing profitability from US subsidiary reaching a 14% Q1 2024 Operating ROE (ROE: 4%)

• Conservative approach to reserving; consistent history of favourable prior year claims development in primary lines

• 5-year GPW4 CAGR of 68%3 (41%3 in Canada, 107%3 in US)

De-Risked Growth

• Growth supported by deepening distribution relationships in existing lines of business, expansion of primary lines to the US

Opportunities

and growth of our hybrid fronting model across North America

• Proven access to capital and reinsurance relationships to support growth

• Investment portfolio comprised primarily of cash (38%) and fixed income (49%)

Conservative Risk

• Conservative underwriting culture; limited retention in US and 5-year average loss ratio2 of 21%3 in Canada

• Disciplined reinsurance strategy; deep relationships with high-quality counterparties - 88% of reinsurance contract assets

Management

are with rated reinsurers, the remaining 12% from unrated reinsurers with appropriate collateral

• Strong enterprise risk management infrastructure in place

Experienced

• Management team with a diversity of skills, and strong relationships with regulators and distribution partners; senior

Management

management directly owns ~6% of shares outstanding

& Board of Directors

• Board of Directors comprised of seasoned executives with strong experience across financial services

Note: All figures in C$ million unless otherwise stated. 1 This is a supplementary financial measure. Refer to Q1 2024 MD&A, Section 10 for details. To access MD&A, see

Trisura's website or SEDAR+ at www.sedarplus.ca. 2 This is a non-IFRS financial ratio. Refer to Q1 2024 MD&A, Section 10 for details. 3 As of December 31st, 2023.

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4 This is a non-IFRS financial measure. Refer to Q1 2024 MD&A, Section 10 for details.

Note: All figures in C$ million unless otherwise stated.

1 This is a non-IFRS financial measure. Refer to Q1 2024 MD&A, Section 10 for details. 2 As at May 24th, 2024.

2

Trisura

TSX Financials

S&P/TSX

Consolidated LTM GPW

$153

38%

30%

Note: All figures in C$ million unless otherwise stated.

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1 Cumulative share price performance measured from close of business December 31st, 2017. 2 'Current' as at May 24th, 2024.

• Diversify earnings and demonstrate stable returns (underwriting with recurring fee and investment income)

• Demonstrate the value of specialty focus in primary lines through loss ratio outperformance

Profitability

• Drive stable fronting fees through diversified program book and prudent counterparty credit risk management

• Optimize risk-adjusted investment portfolio yield, improve diversification and maintain liquidity while enhancing

investment income

• Leverage fixed cost base and technology to gain scale, demonstrating sustainable mid-to-high teens ROE

• Expand North American insurance market share in niche lines through enhanced distribution and capacity relationships

Growth

• Expand proven platforms and expertise to new geographies (US Surety, US Corporate Insurance) and supplement

established practices in local markets

• Evaluate strategic partnerships and inorganic opportunities

• Maintain appropriate regulatory capital; improve ratings and size category

Risk & Capital

• Uphold risk management best-practices across the platform

Management

• Optimize retention and capital allocation

• Develop track record of execution and expand shareholder base

Capital Markets

• Enhance capital markets access through investor, banking, rating agency and other stakeholder communications

Note: All figures in C$ million unless otherwise stated.

1 Source: MSA Research, SNL Financial, A.M. Best. 2 Excludes premium written by Canadian entities outside of Canada. 'Specialty Market' in Canada

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includes Boiler & Machinery, Credit, Credit Protection, Fidelity, Hail, Legal Expense, Cyber Liability, Directors and Officers Liability, Excess Liability,

Source: Internal information, MSA Research

Note: All figures in C$ million unless otherwise stated.

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1

Fee income reflects fees for surety services. 2 Risk Solutions now segmented into Warranty and Fronting in Q1 2023. 3 As at December 31st, 2022.

4

Canadian Speciality includes D&O, E&O, Cyber, XS and Fidelity Markets.

Illustration of Hybrid Fronting Model

GPW and Fronting Fee Income2($ millions)

Premiums

Premiums

GPW

Fee Income Earned Premiums to Capital3

LTM Operating ROE

13.6% Op. ROE

(-1.0% ROE)

Claims

Claims

13.4% Op. ROE

$80

(-12.1% ROE)

Payment

Payment

$67

14.0%

11.7%

$43

13.6% Op. ROE 14.3% Op. ROE

(-16.0% ROE)

(4.1% ROE)

$24

$2,037

5.0%

$1,702

$22

$18

n/a

Distribution Partners

Capacity Providers

$8

$999

(Managing General

$1

$647

(Reinsurers)

$483

$501

Agents)

Fronting Fee

$264

(% of Ceded Premiums)

2018

2019

2020

2021

2022

2023

Q1/23

Q1/24

0.8x

2.4x

4.1x

4.7x

6.2x

6.7x

6.4x

6.2x

14

29

48

62

69

74

70

71

1 "Other" includes Allied Lines - Flood, Auto Physical Damage, Burglary and Theft, Boiler and Machinery, Dwelling Fire, Farmowners Multiple - Peril, Inland

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Marine, MonoLine Property, Prepaid Legal, Private Auto, Product Liability, and Surety. 2 Trisura US began writing business in February 2018. 3 This is a non-

IFRS financial ratio. Composition: annualized GPW / end of period capital. End of period capital includes 25 million USD surplus note in Trisura US.

Balance Sheet ($ millions)

Assets

Cash and Cash Equivalents

636.2

Investments

1,056.6

Other Assets

33.7

Reinsurance Contract Assets

1,947.3

Capital Assets and Intangible Assets

28.1

Deferred Tax Assets

34.9

Total Assets

3,736.8

Liabilities & Shareholders' Equity

Insurance Contract Liabilities

2,871.7

Other Liabilities

127.9

Loan Payable

75.0

Total Liabilities

3,074.6

Shareholders' Equity

662.2

Total Liabilities & Shareholders' Equity

3,736.8

Shares Outstanding (millions)

47.7

Book Value Per Share

13.89

Debt-to-Capital (20% Target)

10.2%

Segmented Book Value

Q1 2024 Reported

Trisura

Trisura

Corporate

Canada

US

and other

Total

Assets1

1,151.5

2,491.1

94.2

3,736.8

Liabilities1

817.9

2,201.3

55.4

3,074.6

Book Value1

333.7

289.8

38.7

662.2

Book Value Per Share

7.00

6.08

0.81

13.89

1 Individual segmented amounts are supplementary financial measures. The total amount is presented in the consolidated financial statements.

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Portfolio by Asset Class1

Fixed Income Portfolio by Term1,2,3

Common Shares and Other,

> 10 Years, 5%

Preferred Shares, 2%

Alternatives, 7%

4%

High Yield Bonds,

3%

<>1 Year,

19%

Cash & Short

5-10 Years,

Term Securities,

24%

38%

1-3 Years,

Investment Grade

25%

Bonds,

39%

3-5 Years,

27%

Government Bonds,

7%

Fixed Income Portfolio by Rating1,2,4

Portfolio by Industry1,2,5

High-Yield,

6%

AAA,

6%

AA,

Other

15%

22%

Financial

BBB,

Telecommunications

37%

35%

5%

Energy

A,

6%

38%

Government

Real Estate

12%

8%

Industrial

10%

1 Investment portfolio categorization as at March 31st, 2024. US and International portfolios converted to CAD at quarter-end exchange rate. 2 Cash

excluded from Rating, Term and Industry segmentation. 3 This is a supplementary financial measure. Composition: carrying value for each term, divided by

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total carrying value for fixed income investments. 4 This is a supplementary financial measure. Composition: carrying value for each credit rating, divided by