Full Year 2023 Earnings Press Release

Exhibit 99.1

PRESS RELEASE

Aspen Reports Results for the Three and Twelve Months Ended December 31, 2023

Net Income Available to Ordinary Shareholders of $216 million and Operating Income of $98 million for the Three Months Ended Net Income Available to Ordinary Shareholders of $485 million and Operating Income of $368 million for theTwelve Months Ended

Operating Retuon Average Equity of 20.2% and Adjusted Combined Ratio of 86.4%for theTwelve Months Ended

Hamilton, Bermuda, April 1, 2024- Aspen Insurance Holdings Limited ("Aspen") today reported results for thethree and twelvemonths ended December 31, 2023.

Mark Cloutier, Executive Chairman and Group Chief Executive Officer, commented:"We are pleased to report an excellent set of results for 2023. Aspen's continued focus on underwriting discipline and operating excellence resulted in our adjusted combined ratio improving to 86.4%*, our net income available to ordinary shareholders increasing to$485 millionand an annualized operating retuon average equity of 20.2%*, all significant improvements over the prior year.

In addition to improved underwriting performance, investment income of $276 million represents a 47% increase year over year. For the full year 2023, Aspen Capital Markets generated $136 million** in total fee income from capital sourced across multiple lines and classes in both our insurance and reinsurance segments.

It is pleasing to note the quality of earnings we are now generating, with meaningful contributions from each of our core earning engines, underwriting, investments and capital markets fees. We believe we have reached a state where we are able to sustain strong ROEs across cycles through the very healthy mix in the sources of our earnings.

The combination of our "One Aspen Approach", balance sheet strength, and capital markets capabilities, positions us with a distinct advantage in the specialty (re)insurance sector, with the scale being an important source of capacity to our customers while still maintaining the ability to be nimble, decisive, and opportunistic in response to changes in trading conditions and market opportunities.

In a year that again saw our sector challenged by climate, geopolitical events, and socio-economic challenges, this fourth consecutive year of improved results gives us confidence we have the talent, strategy, platforms, and brand to continue to perform at the top of our class, delivering strong returns for our shareholders through changing market cycles and across a wide range of industry loss event scenarios."

* Non-GAAP financial measures are used throughout this release, such as operating income, operating retuon average equity, adjusted underwriting income and adjusted combined ratio. These are non-GAAP financial measures as defined in SEC Regulation G. For additional information and reconciliation of non-GAAP financial measures, refer to the end of this press release. Refer to "Cautionary Statement Regarding Forward-Looking Statements" at the end of this press release.

** Reflected in our underwriting result as a reduction to acquisition costs.

Consolidated Highlights for the Three and Twelve Months Ended December 31, 2023

Three Months Ended December 31,2023

Twelve Months Ended December 31,2022

Change

2023

2022

Change

Gross written premiums Net written premiums Net earned premiums Underwriting income(1)Adjusted underwriting income(1)

$ $ $ $ $

859.7

$ $ $ $ $

876.9

(2.0)%$

3,967.6$ 4,338.7 (8.6)%

667.1

678.4

(1.7)%$

2,614.5$ 2,688.7 (2.8)%

Net realized and unrealized investment (losses)/gains Interest expense

(14.1)

(20.1)

(55.2)(43.7)

Corporate and other expenses Non-operating expenses

(24.3)

(31.2)

(35.1)(36.0)

Net realized and unrealized foreign exchange (losses) Income tax benefit

173.5

88.9

132.178.1

Net income available to ordinary shareholders

$ $

215.6

$ $

152.6

• $ 484.8$ 6.5

Loss ratio

Expense ratio Combined ratio

60.8 % 28.6 89.4 % 84.3 %

53.9 % 30.8 84.7 % 82.9 %

59.4 % 28.1 87.5 % 86.4 %

62.5 % 30.5 93.0 % 92.4 %

Operating income(1)

Annualized operating retuon average equity(1)

$

97.6 20.0 % 12.2 %

$

115.6 31.2 %

$

367.6 20.2 % 5.7 %

$

202.3 11.9 %

(1)Underwriting income, adjusted underwriting income, operating income, annualized operating retuon average equity, adjusted combined ratio and annualized total investment retuare non-GAAP financial measures as defined in SEC Regulation G. The reconciliations to the most comparable U.S. GAAP financial measures and a discussion of the rationale for the presentation of these items is provided later in this press release.

Aspen Group Consolidated Results

Aspen is a specialty (re)insurer focused on generating consistent returns for our shareholders. Our 'One Aspen' approach is designed to provide bespoke solutions to complex issues by bringing together our expertise spanning different lines of business, segments and platforms, enabling us to develop enhanced and differentiated offerings to our distribution partners and customers. We are organized across two segments: Insurance and Reinsurance. We adopt a dynamic capital allocation approach, utilizing our platforms across the U.S., U.K., Lloyd's and Bermuda to match risk with the most appropriate source of capital. In addition, through our Aspen Capital Markets team, Aspen generates fee income, which benefits our underwriting results, by offering investors access to Aspen's specialty insurance and reinsurance portfolios.

Significant improvement in underwriting and investment performance drove the improvement in our results.

Consolidated Highlights for the Three Months Ended December 31, 2023

• • Continued to see consistently strong results achieving a net combined ratio of 89.4% and an underwriting income of $71 million. On an adjusted basis, underwriting income was $105 million, with an adjusted combined ratio of 84.3%.

• • Operating income of $98 million in the quarter, resulting in an annualized operating retuon average equity of 20.0%.

• • Overall gross written premiums were broadly in line with the prior year. Active management of the portfolio in response to market conditions resulted in reductions in financial and professional insurance lines, offset by targeted growth in property and casualty lines.

• • On December 27, 2023, the Government of Bermuda enacted the Corporate Income Tax Act 2023 (the "CIT Act"), which will apply a 15% corporate income tax to certain Bermuda businesses in fiscal years beginning on or after January 1, 2025. The CIT Act includes a provision referred to as the economic transition adjustment, which is intended to provide a fair and equitable transition into the new tax regime and has resulted in the recognition of a deferred tax benefit of $201 million in the fourth quarter of 2023. The prior year benefited from the recognition of deferred tax benefit of $94 million in relation to our U.S. operating subsidiaries due to the reversal of a valuation allowance.

Consolidated Highlights for the Twelve Months Ended December 31, 2023

• • Net income available to ordinary shareholders increased significantly to $485 million. Operating income increased to $368 million. Aspen achieved an annualized operating retuon average equity of 20.2%.

• • The underwriting result improved by $136 million to $327 million (5.5 percentage point improvement in the combined ratio to 87.5%) The increase was driven by significantly lower current year catastrophe losses ($187 million), and an improvement in net acquisition costs ($52 million) and net operating expense ($32 million). Adjusted underwriting income increased to $355 million (6.0 percentage point improvement in the adjusted combined ratio to 86.4%).

• •Continued growth in capital sourced by Aspen Capital Markets to $1.7 billion resulted in a 30% increase in fee income to $136 million.

• • Investment income improved by $88 million largely as a result of the higher interest rate environment and reinvestment of maturing assets into higher yielding core fixed income assets.

• • Corporate and other expenses increased by $30 million due to higher letter of credit fees, higher professional services fees and IT costs.

• • Interest expense increased by $12 million in the period, due to higher interest costs on the funds withheld account on the Loss Portfolio Transfer contract with an affiliate of Enstar Group Limited ("Enstar") ("LPT" or the "LPT contract").

• • Tax benefit increased by $54 million to $132 million in the period primarily driven by the net deferred tax benefit for Bermuda discussed above, partially offset by increased income tax expense in the Company's other operating jurisdictions as a result of higher taxable income. Tax benefit in 2022 benefited from the reversal of brought forward valuation allowance for deferred tax assets in the U.S. operating subsidiaries.

• • As of December 31, 2023, we had $420 million of remaining limit available on our LPT contract covering 2019 and prior accident years.

Insurance Segment

Operating highlights for the Three and Twelve Months Ended December 31, 2023

Three Months Ended December 31,

Twelve Months Ended December 31,2023

2022

Change

2023

2022

Change

($ in millions, except for percentages)

($ in millions, except for percentages)

Underwriting RevenuesGross written premiums Net written premiums Net earned premiumsUnderwriting Expenses

Current accident year net losses and loss expenses Catastrophe losses

$ $ $ $

581.9 371.0 376.4

209.4

$ $ $ $

625.2 390.7 359.0

(6.9)%$(5.0)%$4.8 %$

2,446.6 1,483.9 1,460.0

• $ 2,531.7

• $ 1,469.6

• $ 1,436.9

  (3.4)% 1.0 % 1.6 %

  198.2

  $

  833.5

• $ 761.1

Prior year reserve development, post LPT years Adjusted losses and loss adjustment expenses(1)Impact of the LPT(2)

11.5

4.7

26.637.6

25.0

(1.8)

48.749.3

Total net losses and loss expensesAcquisition costs

45.0

38.4

171.6179.4

Underwriting income(1)

$ $

19.5 44.5

$ $

52.6 50.8

$

(33.1)

$ $

112.6 161.3

$ $

103.8 153.1

$

8.8

Ratios

Current accident year loss ratio, excluding catastrophe losses Catastrophe losses

• 55.6 %

• 55.2 %

0.1

0.1

57.1 % 2.3

53.0 % 4.3

Current accident year loss ratio

55.7

55.3

59.457.3

Prior year reserve development ratio, post LPT years Adjusted loss ratio(1)

58.8

56.6

61.260.0

Loss ratioAcquisition cost ratio

65.4

56.1

64.563.3

General and administrative expense ratio

17.5

18.6

16.017.0

Adjusted combined ratio(1)

88.2 %

85.8 %

92.3 % 89.0 %

92.8 % 89.3 %

(1)Adjusted losses and loss adjustment expenses, underwriting income, adjusted underwriting income/(loss), adjusted loss ratio and adjusted combined ratio are non-GAAP financial measures as defined in SEC Regulation G. The reconciliations to the most comparable U.S. GAAP financial measures are shown above and a discussion of the rationale for the presentation of these items is provided later in this press release.

(2)Impact of the LPT includes the impact of prior year development on 2019 and prior accident years, net of the change in the deferred gain recognized in relation to retroactive reinsurance contracts as per accounting requirements for retroactive reinsurance under U.S. GAAP.

Insurance Segment Results

Aspen Insurance operates on a global and regional product basis, delivers service excellence from underwriting through to claims, thereby transforming risk for our customers into opportunities. Aspen Insurance focuses on market segments with high barriers to entry that require bespoke underwriting expertise and customized solutions to address client needs. Aspen Insurance has long-standing partnerships with brokers and other distribution partners, and our responsiveness and innovative mindset make us an ideal partner to deliver effective risk management solutions. Aspen Insurance is organized into four portfolios of business: Financial and Professional Lines; Casualty and Liability Lines, First Party Lines and Specialty Lines.

During 2023, Aspen Insurance has continued its focus on disciplined underwriting and operational efficiency in response to evolving market conditions.

Insurance Segment Highlights for the Three Months Ended December 31, 2023

• • Underwriting result of $20 million and combined ratio of 94.9%. Adjusted underwriting income of $45 million with an adjusted combined ratio of 88.2%.

• • Reduction in underwriting income is primarily driven by a $25 million expense in relation to the LPT, which includes the impact of adverse prior year development on 2019 and prior accident years, net of the change in the deferred gain recognized in relation to retroactive reinsurance contracts.

• • Prior year adverse reserve development of $12 million on post LPT years was primarily driven by adverse development in U.S. primary casualty lines as a result of strengthening of reserving assumptions due to emerging development patterns and to account for greater uncertainty around social inflation.

• • Active management of the portfolio resulted in the exit of certain programs that did not meet our pricing expectations and the deteriorating pricing environment for Directors & Officers and Mergers & Acquisitions business contributed to a decrease in gross written premiums of $43 million or (7)%. This was partially offset by new construction policies in casualty lines and rate increases achieved on our renewal portfolio.

Insurance Segment Highlights for the Twelve Months Ended December 31, 2023

• • Delivered increased underwriting income to $113 million and combined ratio of 92.3%. On an adjusted basis, underwriting income increased to $161 million with an adjusted combined ratio of 89.0%.

• • Our strategy to reduce property exposure in our insurance segment helped to limit the impact of industry catastrophe events during 2023, contributing to a reduction in the CAT loss ratio by 2.0 percentage points compared with prior year, which was also impacted by Hurricane Ian. This has been offset by increased provisions in our current accident year ex-CAT loss ratios to proactively recognize the potential impact of higher economic uncertainty and economic and social inflation, the impact of business mix changes and an increase in estimated claims handling costs.

• • Prior year adverse reserve development of $27 million on post LPT years is primarily driven by adverse development in U.S. primary casualty and U.S. management liability lines as a result of strengthening of reserving assumptions due to emerging development patterns and to account for greater uncertainty around social inflation.

• • Increased cessions to Aspen Capital Markets resulted in increased fee income which, combined with the exit of certain U.S. programs which had higher acquisition cost ratios, contributed to a 0.7 percentage point reduction in the insurance segment's acquisition cost ratio.

Reinsurance Segment

Operating highlights for the Three and Twelve Months Ended December 31, 2023

Three Months Ended December 31,

Twelve Months Ended December 31,2023

2022

Change

2023

2022

Change

($ in millions, except for percentages)

($ in millions, except for percentages)

1,098.0$ 1,426.4 (23.0)%Underwriting RevenuesGross written premiums Net written premiums Net earned premiumsUnderwriting Expenses

Current accident year net losses and loss expenses Catastrophe losses

$ $ $ $

277.8 231.8 290.7

134.6

$ $ $ $

251.7 215.1 319.4

10.4 %$7.8 %$(9.0)%$

1,521.0$ 1,807.0 (15.8)%

1,154.5$ 1,251.8 (7.8)%

151.9

$

538.6

$ 584.0

10.8

28.2

Prior year reserve development, post LPT years Adjusted losses and loss adjustment expenses(1)Impact of the LPT(2)

4.5

(30.2)

87.0245.15.7(24.6)

149.9

149.9

9.3

14.2

631.3 (20.2)

804.5 (34.2)

Total net losses and loss expensesAcquisition costs

48.0

67.4

208.6252.4

Underwriting income(1)

$ $

51.0 60.3

$ $

51.3 65.5

$

(0.3)

$ $

214.2 194.0

$ $

86.6 52.4

$

127.6

Ratios

Current accident year loss ratio, excluding catastrophe losses Catastrophe losses

46.3 %

47.6 %

46.7 %

46.6 %

3.7

8.8

7.5

19.6

Current accident year loss ratio

50.0

56.4

54.2

66.2

Prior year reserve development ratio, post LPT years Adjusted loss ratio(1)

1.5

(9.4)

0.5

(2.0)

51.6

46.9

54.7

64.2

Loss ratioAcquisition cost ratio

54.8

51.4

52.961.5

General and administrative expense ratio

11.2

11.5

10.411.4

Adjusted combined ratio(1)

79.3 %

79.5 %

81.4 % 83.2 %

93.1 % 95.8 %

(1)Adjusted losses and loss adjustment expenses, underwriting income, adjusted underwriting income/(loss), adjusted loss ratio and adjusted combined ratio are non-GAAP financial measures as defined in SEC Regulation G. The reconciliations to the most comparable U.S. GAAP financial measures are shown above and a discussion of the rationale for the presentation of these items is provided later in this press release.

(2)Impact of the LPT includes the impact of prior year development on 2019 and prior accident years, net of the change in the deferred gain recognized in relation to retroactive reinsurance contracts as per accounting requirements for retroactive reinsurance under U.S. GAAP.

Reinsurance Segment Results

Aspen Reinsurance offers a full suite of products organized around core products in Property, Catastrophe, Other Property Reinsurance, Casualty and Specialty. Through our highly experienced underwriting teams which are supported by claims, modelling and actuarial functions, we have developed longstanding relationships with our clients and brokers. We also provide innovative solutions to risk including utilizing Aspen Capital Markets to access additional third-party capital.

During 2023, Aspen Reinsurance has continued to focus on disciplined underwriting, reducing and repositioning our property catastrophe exposures.

Reinsurance Segment Highlights for the Three Months Ended December 31, 2023

• • Underwriting income of $51 million, combined ratio of 82.5%. Adjusted underwriting income of $60 million, adjusted combined ratio of 79.3%.

• • Gross written premiums were $26 million higher than the prior year despite exiting aviation, space & bloodstock, reflecting continuous underwriting discipline to focus on portfolio optimization and sustainable growth.

• • Acquisition cost ratio improved 4.6 percentage points as a result of higher ACM management fees of $11 million and the impact of business mix.

• • Adjusted loss ratio of 51.6 percentage points is a 4.7 percentage points reduction from the prior period. This is driven by a 6.4 percentage point improvement in the current year loss ratio (improvement of 5.1 percentage points on the catastrophe loss ratio) partially offset by adverse development on post LPT prior years. Prior year strengthening in the period was driven by development on credit and surety of $7 million and Covid related losses of $4 million. The favorable prior years reserve development in 2022 related to large reserve releases on Property-exposed classes.

Reinsurance Segment Highlights for the Twelve Months Ended December 31, 2023

• • Delivered strong growth in underwriting income to $214 million and a combined ratio of 81.4%. Adjusted underwriting income was $194 million with an adjusted combined ratio of 83.2%.

• • The main driver of improved performance is an 8.6 percentage points improvement in the loss ratio, driven by a 12.1 percentage point improvement in the catastrophe loss ratio as a result of initiatives to reduce exposure and volatility and lower number of large industry losses impacting reinsurance programs. Prior year reserve strengthening of $6 million on post LPT years is driven by adverse development in non-CAT Property reinsurance. Prior year included releases of $25 million primarily in relation to property exposed reinsurance lines.

• • The acquisition cost ratio improved by 0.7 percentage points due to changes in business mix, additional fees earned from increased cessions to ACM, partially offset by an increase in profit commissions in certain lines due to favorable loss performance.

• • Management's planned initiatives to reduce exposure as well as respond to concerns about market conditions in certain lines led to a decrease in gross written premiums of $286 million, primarily related to reductions in mortgage and property pro rata business as well as our previously announced exit from space, aviation, and bloodstock. These reductions were partially offset by strong rate increases during the year in continuing lines of business.

• • Net catastrophe exposure has been further reduced through increased cessions to Aspen Capital Markets on our property reinsurance lines, with premiums ceded to reinsurers as a percentage of gross written premiums in the period, increasing to 28% compared with 21% in the prior year.

• • Reduction in underwriting result driven by the impact of the LPT includes the impact of prior year development on 2019 and prior accident years, net of the change in the deferred gain recognized in relation to retroactive reinsurance contracts which is primarily driven by the LPT, totaling $20 million.

Investment Performance

Three Months Ended December 31, Twelve Months Ended December

31,2023

2022

2023

2022

(in $ millions, except percentages) (in $ millions, except percentages)

Net realized and unrealized (losses)/gains from trading portfolios recognized in net income(1)Change in unrealized gains/(losses) on available for sale investments (gross of tax)(2)

(1.7) 158.9

• 51.7$10.5 (87.5)

14.5(177.6)

126.2(391.7)

Total return/(loss) on investments

$

225.6

$

(25.3)

$

416.4

$

(381.2)

Average cash and investments

$

7,387.1

$

7,311.0

$

7,242.8

$

7,438.0

Book yield

Average duration Average credit rating

3.8 % 2.6 years

3.2 % 3.0 years

AA-

AA-

• (1)Includes net unrealized gains of $23.2 million for the quarter (2022 - $26.4 million), and $51.8 million gains for the twelve months ended December 31, 2023 (2022 - $116.5 million losses).

• (2)The tax impact of the change in unrealized gains/(losses) on available for sale investments was an expense of $18.8 million for the quarter (2022 - $5.6 million), and an expense of $20.6

million for the twelve months ended December 31, 2023 (2022 - benefit of $23.9 million).

• • Active repositioning of our investments to take advantage of higher interest rates resulted in an increase of 32% in our net investment income to $68 million in the quarter.

• • Net unrealized gains/(losses) on available for sale investments recognized as other comprehensive income was a gain of $159 million for the three months ended December 31, 2023. The change in net realized and unrealized investment gains and losses is a result of valuation changes, predominantly driven by the lower US Treasury yields in the quarter.

• • The total return, pre-tax, on Aspen's cash and investments was 12.2% in the quarter, compared to (1.4)% in the fourth quarter of 2022, and reflects the increase in net investment income and the impact of changes in net realized and unrealized gains and losses.

Shareholders' equity and debt

• •Total shareholders' equity was $2,909 million as of December 31, 2023, an increase of $551 million, compared with $2,358 million as of December 31, 2022. This is primarily due to net income of $535 million, partially offset by ordinary and preference dividends totaling $90 million and other comprehensive income of $106 million primarily in relation to valuation changes related to investments classified as available for sale.

• • On November 9, 2023, Aspen drew down on the $300 million term loan facility and the proceeds were used to redeem the $300 million 4.65% Senior Notes due November 15, 2023.

Earnings materials

The earnings press release for the three and twelve months ended December 31, 2023 will be published on Aspen's website atwww.aspen.co.

For further information please contact

Marc MacGillivray, Chief Accounting Officer[email protected]+44 20 7184 8455

Aspen Insurance Holdings Limited

Summary condensed consolidated balance sheet (unaudited)$ in millions

ASSETS

Total investments

As at December 31, 2023

As at December 31, 2022

$

6,412.4$1,028.1

6,085.8

Cash and cash equivalents Reinsurance recoverables Premiums receivable Other assets

959.2

5,311.35,635.0

870.0

815.5

LIABILITIES

Losses and loss adjustment expenses reserves Unearned premiums

Other payables Debt

Total liabilities

$

7,810.6$ 7,710.92,426.32,457.51,779.42,331.0

300.0

$

12,316.3

$

299.9 12,799.3

SHAREHOLDERS' EQUITY Ordinary shares Preference shares Additional paid-in capital Retained earnings

Accumulated other comprehensive loss, net of tax Total shareholders' equity

753.5753.5

1,793.5 (400.3)

1,349.0 (506.3)

2,908.52,358.0

10

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Aspen Insurance Holdings Ltd. published this content on 31 March 2024 and is solely responsible for the information contained therein. Distributed by Public, unedited and unaltered, on 01 April 2024 20:10:36 UTC.