# EDGAR Filing Document

**Accession Number:** 0001267395
**File Stem:** 0001267395-25-000049
**Filing Date:** 2025-8
**Character Count:** 220408
**Document Hash:** f329d77ffe721e7f8465b1d7bc050d37
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001267395-25-000049.hdr.sgml**: 20250807

**ACCESSION NUMBER**: 0001267395-25-000049

**CONFORMED SUBMISSION TYPE**: 6-K

**PUBLIC DOCUMENT COUNT**: 6

**CONFORMED PERIOD OF REPORT**: 20250630

**FILED AS OF DATE**: 20250807

**DATE AS OF CHANGE**: 20250807

**FILER**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** ASPEN INSURANCE HOLDINGS LTD
- **CENTRAL INDEX KEY:** 0001267395
- **STANDARD INDUSTRIAL CLASSIFICATION:** FIRE, MARINE & CASUALTY INSURANCE [6331]
- **ORGANIZATION NAME:** 02 Finance
- **EIN:** 000000000
- **STATE OF INCORPORATION:** D0
- **FISCAL YEAR END:** 1231

**FILING VALUES:**
- **FORM TYPE:** 6-K
- **SEC ACT:** 1934 Act
- **SEC FILE NUMBER:** 001-31909
- **FILM NUMBER:** 251194727

**BUSINESS ADDRESS:**
- **STREET 1:** 141 FRONT STREET
- **CITY:** HAMILTON
- **STATE:** D0
- **ZIP:** HM 19
- **BUSINESS PHONE:** 1 441 297 9301

**MAIL ADDRESS:**
- **STREET 1:** 141 FRONT STREET
- **CITY:** HAMILTON
- **STATE:** D0
- **ZIP:** HM 19

**UNITED STATES**

**SECURITIES AND EXCHANGE COMMISSION**

**Washington, D.C. 20549**

**Form 6-K**

**REPORT OF FOREIGN PRIVATE ISSUER PURSUANT TO RULE 13a-16 OR 15d-16 UNDER THE SECURITIES EXCHANGE ACT OF 1934**

For the month of August 2025

Commission File Number: 001-31909

**ASPEN INSURANCE HOLDINGS LIMITED**

(Translation of registrant's name into English)

**141 Front Street**

**Hamilton HM 19**

**Bermuda**

(Address of principal executive office)

Indicate by check mark whether the registrant files or will file annual reports under cover of Form 20-F or Form 40-F.

Form 20-F 🗷 Form 40-F ◻

------

On August 7, 2025, Aspen Insurance Holdings Limited (the "Company" or "Aspen") issued a press release announcing its financial results for the three and six months ended June 30, 2025, as well as the availability of its corresponding financial supplement.

The press release, furnished as Exhibit 99.1, and financial supplement, furnished as Exhibit 99.2, are incorporated by reference as part of this Form 6-K.

The information included in this Form 6-K, including the information set forth in Exhibit 99.1 and Exhibit 99.2, shall not be deemed "filed" for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the "Exchange Act"), or incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as shall be expressly set forth by specific reference in such filing.

**<u>EXHIBIT INDEX</u>**

**<u>Exhibit</u>**

&nbsp;&nbsp;&nbsp;&nbsp;99.1&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;<u>[Press Release, dated](a991-ahlq225pr.htm)[August 7](a991-ahlq225pr.htm)[, 2025](a991-ahlq225pr.htm)</u>

&nbsp;&nbsp;&nbsp;&nbsp;99.2&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;<u>[Fin](a992-ahlq225fs.htm)[anc](a992-ahlq225fs.htm)[ial Supplement, for the](a992-ahlq225fs.htm)[th](a992-ahlq225fs.htm)[ree and six months ended June 30, 2025](a992-ahlq225fs.htm)</u>

------

**SIGNATURES**

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned, thereunto duly authorized.

---

| | | |
|:---|:---|:---|
| | **ASPEN INSURANCE HOLDINGS LIMITED** | **ASPEN INSURANCE HOLDINGS LIMITED** |
| Dated: August 7, 2025 | By: | /s/ Mark Pickering |
|  | Name: | Mark Pickering |
|  | Title: | Chief Financial Officer |

---

## Exhibit 99.1

**Exhibit 99.1**

![aspenblackandwhitelogo.jpg](aspenblackandwhitelogo.jpg)

PRESS RELEASE

**Aspen Reports Second Quarter Net Income Available to Ordinary Shareholders of $36 million, or $0.39 per Diluted Ordinary Share and Operating Income of $111 million, or $1.22 per Diluted Ordinary Share** 

**For the three months ended June 30, 2025, Aspen reports:** 

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**• Improvement of 3.6 percentage points in the combined ratio of 85.1% compared to June 30, 2024, resulting in underwriting income of $100 million**

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**• Adjusted underwriting income of $106 million\*\* with an adjusted combined ratio of 84.3%\*\***

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**• Aspen Capital Markets fee income of $53 million**\*, **growth of 53.5% compared to June 30, 2024**

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**• Annualized operating return on average equity of 17.2%\*\***

**For the six months ended June 30, 2025, Aspen reports:** 

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**• Net income available to ordinary shareholders of $55 million, or $0.61 per diluted ordinary share and operating income of $161 million or $1.77 per diluted ordinary share**

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**• Underwriting income of $128 million, with a combined ratio of 90.8%**

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**• Adjusted underwriting income of $142 million\*\* and adjusted combined ratio of 89.7%\*\*** 

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**• Book value per ordinary share of $28.81 as at June 30, 2025, an increase of $5.51, or 23.6%, compared to June 30, 2024** 

**Hamilton, Bermuda, August 7, 2025** - Aspen Insurance Holdings Limited (NYSE: AHL) ("Aspen," the "Company," "we," or "us") today reported results for the three and six months ended June 30, 2025.

**Mark Cloutier, Executive Chairman and Group Chief Executive Officer, commented:** "Aspen delivered a strong performance for the second quarter, with both of our earnings engines contributing to growth in our operating income and an improvement in our adjusted combined ratio in the context of evolving market dynamics.

These results – our first quarter since our IPO – continue to demonstrate the strength and consistency of Aspen's performance which, alongside lower earnings volatility and an improved capital position, were recognized by S&P in May this year with an upgrade of our ratings outlook to Positive from Stable.

Aspen's nimble yet disciplined approach and multi-platform capabilities allow us to deliver much-needed solutions for our customers and trading partners while maintaining a profitable and well-balanced portfolio across market cycles. Looking forward, we remain confident that we have the business mix, risk appetite, market standing and culture to achieve sustainable growth and deliver shareholder value as a top quartile specialty (re)insurer across market cycles."

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

\*\* Non-GAAP financial measures are used throughout this release, such as operating income, annualized operating return on average equity, underwriting income, 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.

------

**Christian Dunleavy, Group President, said**: "Aspen's strong underwriting performance across both insurance and reinsurance in the second quarter is a testament to our continued focus on building a well-balanced portfolio, our disciplined risk selection, and our ability to allocate risk across platforms in competitive market conditions. Fee income from Aspen Capital Markets delivered strong growth through the last quarter, providing underwriting expertise to third-party capital investors while also enabling Aspen to further manage net exposures and volatility within our portfolio.

We remain on track to deliver mid-teens operating return on equity and will continue to focus on deploying our specialty expertise, further deepening our customer and trade relationships, growing Aspen Capital Markets, and investing in the technology and tools that will make us even better risk allocators. By concentrating our efforts on total value creation and sustainable profitability, we are confident that Aspen has the resilience, strategy and positioning to succeed across market cycles."

------

**Consolidated Highlights for the Three and Six Months Ended June 30, 2025**

---

| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
| | **Three Months Ended June 30,** | **Three Months Ended June 30,** | **Three Months Ended June 30,** | **Six Months Ended June 30,** | **Six Months Ended June 30,** | **Six Months Ended June 30,** |
| | **2025** | **2024** | **Change** | **2025** | **2024** | **Change** |
| | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** |
| Gross written premiums | $**1238.9** | $1250.4 | (0.9)% | $**2526.1** | $2481.8 | 1.8% |
| Net written premiums | $**715.5** | $811.1 | (11.8)% | $**1467.2** | $1552.0 | (5.5)% |
| Net earned premiums | $**674.9** | $705.4 | (4.3)% | $**1377.6** | $1371.1 | 0.5% |
| Underwriting income <sup>(1)</sup> | $**100.4** | $80.3 | 25.0% | $**127.6** | $169.8 | (24.9)% |
| Adjusted underwriting income <sup>(1)</sup> | $**105.9** | $93.9 | 12.8% | $**142.1** | $184.8 | (23.1)% |
| Net investment income | $**80.5** | $82.5 |  | $**156.4** | $159.3 |  |
| Net realized and unrealized investment (losses) | **(9.3)** | (26.1) |  | **(9.6)** | (27.1) |  |
| Interest expense | **(8.9)** | (14.0) |  | **(18.0)** | (30.1) |  |
| Corporate and other expenses | **(25.4)** | (39.0) |  | **(50.8)** | (64.7) |  |
| Non-operating expenses | **(47.3)** | (5.5) |  | **(55.6)** | (11.7) |  |
| Net realized and unrealized foreign exchange (losses)/gains | **(31.9)** | 1.9 |  | **(44.8)** | 11.0 |  |
| Income tax expense | **(11.6)** | (11.1) |  | **(21.9)** | (25.7) |  |
| Net income | $**46.5** | $69.0 |  | $**83.3** | $180.8 |  |
| Net income available to ordinary shareholders | $**35.5** | $55.3 |  | $**55.4** | $153.5 |  |
| Loss ratio | **56.2%** | 59.6% |  | **60.6%** | 58.7% |  |
| Expense ratio | **28.9%** | 29.1% |  | **30.2%** | 28.9% |  |
| Combined ratio | **85.1%** | 88.7% |  | **90.8%** | 87.6% |  |
| Adjusted combined ratio <sup>(1)</sup> | **84.3%** | 86.7% |  | **89.7%** | 86.5% |  |
| Operating income <sup>(1)</sup> | $**110.9** | $97.6 |  | $**161.3** | $201.0 |  |
| Annualized net income available to ordinary shareholders on average equity | **5.6%** | 10.3% |  | **4.4%** | 14.2% |  |
| Annualized operating return on average equity <sup>(1)</sup> | **17.2%** | 18.1% |  | **12.8%** | 18.7% |  |
| Net income available to ordinary shareholders per diluted ordinary share | $**0.39** | $0.61 |  | $**0.61** | $1.69 |  |
| Operating income per diluted ordinary share | $**1.22** | $1.07 |  | $**1.77** | $2.21 |  |

---

<sup>(1)</sup> Underwriting income, adjusted underwriting income, adjusted combined ratio, operating income and annualized operating return on average equity are non-GAAP financial measures as defined in SEC Regulation G. The reconciliations to the most comparable U.S. GAAP financial measures and 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 as a reduction to our reinsurance costs, and offers third-party investors access to Aspen's specialty insurance and reinsurance portfolios.***

*Consolidated Highlights for the Three Months Ended June 30, 2025*

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;*•* The Group continues to deliver strong underwriting performance, achieving a net combined ratio of 85.1% and underwriting income of $100 million. On an adjusted basis, underwriting income was $106 million, with an adjusted combined ratio of 84.3%.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Gross written premiums decreased by $12 million compared to June 30, 2024, mainly driven by Property lines within our Reinsurance Segment, which have seen property rate decreases, reductions in some line sizes and non-renewals of certain business that did not meet our risk appetite given the current market conditions.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Adjusted combined ratio improved by 2.4 percentage points compared to June 30, 2024, mainly due to benign catastrophe experience in the quarter compared to the Dubai and German floods in the comparative period.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Operating income of $111 million in the quarter, or $1.22 per diluted ordinary share, resulting in an annualized operating return on average equity of 17.2%.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Non-operating expenses of $47 million included a one-off charge of $39 million in relation to replacement share awards that were granted in substitution for legacy share options previously granted to certain employees upon the successful completion of the initial public offering ("IPO").

*Consolidated Highlights for the Six Months Ended June 30, 2025*

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Net income available to ordinary shareholders was $55 million or $0.61 per diluted ordinary share and operating income of $161 million or $1.77 per diluted ordinary share.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Adjusted underwriting income of $142 million was $43 million adverse to the same period in the prior year, primarily due to increased catastrophe losses from the California Wildfires in the first quarter.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Gross written premiums increased by $44 million compared to June 30, 2024, primarily driven by growth in the Insurance Segment, across our existing cross-class partnerships within Financial and Professional Lines. This has been partially offset by reductions in certain Property lines within the Reinsurance Segment due to rate decreases in the current market which do not meet our profitability expectations.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Third-party capital supporting Aspen Capital Markets grew to $2.4 billion, expanding our capacity and generating $99 million of fee income, an increase of 45.0% compared to June 30, 2024.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Net realized and unrealized foreign exchange gains/(losses) across net income and other comprehensive income totaled $7 million. Net income included a loss of $45 million, while other comprehensive income included a gain of $52 million, mainly for foreign exchange gains related to investments classified as available for sale and our foreign exchange cash flow hedges.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• As of June 30, 2025, we had approximately $295 million (December 31, 2024: $379 million) of remaining limit available on our LPT contract, representing 25% of our 2019 and prior accident year outstanding reserves. This contract provides protection against deterioration on these accident years, significantly limiting Aspen's exposure to the risk of unfavorable development from these accident years, and strengthens our balance sheet.

------

**Insurance Segment**

**Operating Highlights for the Three and Six Months Ended June 30, 2025**

---

| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
| | **Three Months Ended June 30,** | **Three Months Ended June 30,** | **Three Months Ended June 30,** | **Six Months Ended June 30,** | **Six Months Ended June 30,** | **Six Months Ended June 30,** |
| | **2025** | **2024** | **Change** | **2025** | **2024** | **Change** |
| | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** |
| **Underwriting Revenues** |  |  |  |  |  |  |
| Gross written premiums | $**693.5** | $684.2 | 1.4% | $**1380.0** | $1301.2 | 6.1% |
| Net written premiums | $**390.4** | $425.3 | (8.2)% | $**768.3** | $763.7 | 0.6% |
| Net earned premiums | $**395.8** | $378.3 | 4.6% | $**799.5** | $739.3 | 8.1% |
| **Underwriting Expenses** |  |  |  |  |  |  |
| Current accident year net losses and loss expenses  | $**(224.8)** | $(229.6) |  | $**(453.5)** | $(451.7) |  |
| Catastrophe losses | **(11.3)** | (5.0) |  | **(28.3)** | (16.6) |  |
| Prior year reserve development, post LPT years | **0.5** | 3.5 |  | **2.4** | 3.5 |  |
| Adjusted losses and loss adjustment expenses <sup>(1)</sup> | **(235.6)** | (231.1) |  | **(479.4)** | (464.8) |  |
| Impact of the LPT <sup>(2)</sup> | **(3.7)** | (0.1) |  | **(7.8)** | 4.5 |  |
| **Losses and loss adjustment expenses** | **(239.3)** | (231.2) |  | **(487.2)** | (460.3) |  |
| Acquisition costs | **(45.2)** | (48.2) |  | **(95.3)** | (83.9) |  |
| General and administrative expenses | **(67.1)** | (63.4) |  | **(141.6)** | (125.6) |  |
| **Underwriting income** <sup>(1)</sup> | $**44.2** | $35.5 | $8.7 | $**75.4** | $69.5 | $5.9 |
| Adjusted underwriting income <sup>(1)</sup> | $**47.9** | $35.6 |  | $**83.2** | $65.0 |  |
| **Ratios** |  |  |  |  |  |  |
| Current accident year loss ratio, excluding catastrophe losses | **56.8%** | 60.7% |  | **56.7%** | 61.2% |  |
| Current accident year catastrophe loss ratio | **2.9** | 1.3 |  | **3.5** | 2.2 |  |
| Current accident year loss ratio | **59.7** | 62.0 |  | **60.2** | 63.4 |  |
| Prior year reserve development ratio, post LPT years | **(0.2)** | (0.9) |  | **(0.3)** | (0.5) |  |
| Adjusted loss ratio <sup>(1)</sup> | **59.5** | 61.1 |  | **59.9** | 62.9 |  |
| Impact of the LPT <sup>(2)</sup> | **1.0** |  |  | **1.0** | (0.6) |  |
| **Loss ratio** | **60.5** | 61.1 |  | **60.9** | 62.3 |  |
| Acquisition cost ratio | **11.4** | 12.7 |  | **11.9** | 11.3 |  |
| General and administrative expense ratio | **17.0** | 16.8 |  | **17.7** | 17.0 |  |
| **Combined ratio** | **88.9%** | 90.6% |  | **90.5%** | 90.6% |  |
| Adjusted combined ratio <sup>(1)</sup> | **87.9%** | 90.6% |  | **89.5%** | 91.2% |  |

---

(1) Adjusted losses and loss adjustment expenses, underwriting income, adjusted underwriting income, 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 five portfolios of business: First Party Insurance, Specialty Insurance, Casualty and Liability Insurance, Financial and Professional Lines Insurance and Other Insurance.***

*Insurance Segment Highlights for the Three Months Ended June 30, 2025*

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Underwriting income was $44 million with a combined ratio of 88.9%, a 1.7 percentage point improvement from the same period in prior year. Adjusted underwriting income was $48 million with an adjusted combined ratio of 87.9%.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Gross written premiums were $9 million higher than the prior year period, mainly driven by growth in Financial and Professional Lines Insurance and Other Insurance, as a result of increased participation and growth within our program partners. This is partly offset by decreases in Casualty and Liability Insurance and First Party Insurance.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Adjusted loss ratio of 59.5% improved by 1.6 percentage points compared to June 30, 2024 with current accident year ex-catastrophe performance improving 3.9 percentage points primarily driven by lower loss activity in Financial and Professional Lines Insurance.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Acquisition expense ratio of 11.4% has improved by 1.3 percentage points compared to June 30, 2024. This is driven by business mix and increased cessions to Aspen Capital Markets structures which generated higher ceded commissions.

*Insurance Segment Highlights for the Six Months Ended June 30, 2025*

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Underwriting income was $75 million with a combined ratio of 90.5%, a 0.1 percentage point improvement from prior year period. Adjusted underwriting income was $83 million with an adjusted combined ratio of 89.5%.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Gross written premiums increased by $79 million compared to the same period in prior year. This is mainly attributable to growth in existing program partnerships, partially offset by changing market conditions within the U.S. property market.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Adjusted loss ratio of 59.9% improved by 3.0 percentage points compared to June 30, 2024. The current accident year ex-catastrophe loss ratio improved 4.5 percentage points driven by lower loss activity in Financial and Professional Lines Insurance. This is partially offset by an increase in catastrophe losses of 1.3 percentage points, mainly driven by losses on the California Wildfires in the first quarter.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• The expense ratio of 29.6%, which includes the acquisition cost ratio and general and administrative expense ratio, deteriorated by 1.3 percentage points. This is due to a change in business mix which attracts a higher acquisition expense along with a higher expense base due to investment in operational excellence enhancements.

------

**Reinsurance Segment**

**Operating Highlights for the Three and Six Months Ended June 30, 2025**

---

| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
| | **Three Months Ended June 30,** | **Three Months Ended June 30,** | **Three Months Ended June 30,** | **Six Months Ended June 30,** | **Six Months Ended June 30,** | **Six Months Ended June 30,** |
| | **2025** | **2024** | **Change** | **2025** | **2024** | **Change** |
| | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** |
| **Underwriting Revenues** |  |  |  |  |  |  |
| Gross written premiums | $**545.4** | $566.2 | (3.7)% | $**1146.1** | $1180.6 | (2.9)% |
| Net written premiums | $**325.1** | $385.8 | (15.7)% | $**698.9** | $788.3 | (11.3)% |
| Net earned premiums | $**279.1** | $327.1 | (14.7)% | $**578.1** | $631.8 | (8.5)% |
| **Underwriting Expenses** |  |  |  |  |  |  |
| Current accident year net losses and loss expenses | $**(135.4)** | $(136.0) |  | $**(270.6)** | $(264.6) |  |
| Catastrophe losses | **(12.3)** | (43.2) |  | **(86.7)** | (64.0) |  |
| Prior year reserve development, post LPT years | **9.7** | 3.7 |  | **16.8** | 3.7 |  |
| Adjusted losses and loss adjustment expenses <sup>(1)</sup> | **(138.0)** | (175.5) |  | **(340.5)** | (324.9) |  |
| Impact of the LPT <sup>(2)</sup> | **(1.8)** | (13.5) |  | **(6.7)** | (19.5) |  |
| **Losses and loss adjustment expenses** | **(139.8)** | (189.0) |  | **(347.2)** | (344.4) |  |
| Acquisition costs | **(44.8)** | (57.4) |  | **(90.4)** | (114.6) |  |
| General and administrative expenses | **(38.3)** | (35.9) |  | **(88.3)** | (72.5) |  |
| **Underwriting income** <sup>(1)</sup> | $**56.2** | $44.8 | $11.4 | $**52.2** | $100.3 | $(48.1) |
| Adjusted underwriting income <sup>(1)</sup> | $**58.0** | $58.3 |  | $**58.9** | $119.8 |  |
| **Ratios** |  |  |  |  |  |  |
| Current accident year loss ratio, excluding catastrophe losses | **48.5%** | 41.6% |  | **46.8%** | 41.9% |  |
| Current accident year catastrophe loss ratio | **4.4** | 13.2 |  | **15.0** | 10.1 |  |
| Current accident year loss ratio | **52.9** | 54.8 |  | **61.8** | 52.0 |  |
| Prior year reserve development ratio, post LPT years | **(3.5)** | (1.1) |  | **(2.9)** | (0.6) |  |
| Adjusted loss ratio <sup>(1)</sup> | **49.4** | 53.7 |  | **58.9** | 51.4 |  |
| Impact of the LPT <sup>(2)</sup> | **0.7** | 4.1 |  | **1.2** | 3.1 |  |
| **Loss ratio** | **50.1** | 57.8 |  | **60.1** | 54.5 |  |
| Acquisition cost ratio | **16.1** | 17.5 |  | **15.6** | 18.1 |  |
| General and administrative expense ratio | **13.7** | 11.0 |  | **15.3** | 11.5 |  |
| **Combined ratio** | **79.9%** | 86.3% |  | **91.0%** | 84.1% |  |
| Adjusted combined ratio <sup>(1)</sup> | **79.2%** | 82.2% |  | **89.8%** | 81.0% |  |

---

(1) Adjusted losses and loss adjustment expenses, underwriting income, adjusted underwriting income, 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 Reinsurance, Other Property Reinsurance, Casualty Reinsurance and Specialty Reinsurance. 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.*** 

*Reinsurance Segment Highlights for the Three Months Ended June 30, 2025*

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Underwriting income was $56 million with a combined ratio of 79.9%. Adjusted underwriting income was $58 million with an adjusted combined ratio of 79.2%.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Gross written premiums of $545 million decreased by $21 million compared to the same period in the prior year. This is mainly driven by a reduction in Property lines where we choose to be selective on businesses we underwrite given the current market conditions, partially offset by business growth in U.S. Casualty.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Loss ratio of 50.1% improved by 7.7 percentage points compared to June 30, 2024, mainly due to benign catastrophe experience in the quarter compared to Dubai and German floods in the prior year period.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• The expense ratio of 29.8%, which includes the acquisition cost ratio and general and administrative expense ratio, deteriorated by 1.3 percentage points from the prior year period. This is driven by a higher expense base due to investment in operational excellence enhancements, partially offset by increased cessions to Aspen Capital Markets structures which generated higher ceded commissions.

*Reinsurance Segment Highlights for the Six Months Ended June 30, 2025*

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Underwriting income was $52 million with a combined ratio of 91.0%. Adjusted underwriting income was $59 million with an adjusted combined ratio of 89.8%.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Gross written premiums of $1,146 million decreased by $35 million compared to the same period in the prior year, driven by a reduction in Property lines due to property rate decreases in the current market, and as we remain selective on writing business which does not meet our profitability expectations, partially offset by business growth in U.S. Casualty.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Loss ratio of 60.1% deteriorated by 5.6 percentage points compared to June 30, 2024, mainly due to current accident year losses driven by rate reductions and mix of business along with catastrophe losses from the California Wildfires.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Acquisition cost ratio improved by 2.5 percentage points from the prior year period, driven by higher ceding commissions resulting from increased cessions from Casualty lines to our Aspen Capital Market partners.

------

**Investment Performance**

---

| | | | | |
|:---|:---|:---|:---|:---|
| | **Three Months Ended June 30,** | **Three Months Ended June 30,** | **Six Months Ended June 30,** | **Six Months Ended June 30,** |
| | &nbsp;&nbsp;&nbsp;**2025** | **2024** | &nbsp;&nbsp;**2025** | **2024** |
| | **($ in millions)** | **($ in millions)** | **($ in millions)** | **($ in millions)** |
| Net investment income | $**80.5** | $82.5 | $**156.4** | $159.3 |
| Net realized and unrealized investment (losses) recognized in net income <sup>(1)</sup>  | **(9.3)** | (26.1) | **(9.6)** | (27.1) |
| Change in unrealized gains/(losses) on available for sale investments (before tax) <sup>(2)</sup> | **61.8** | 9.6 | **131.6** | (17.1) |
| **Total return on investments** | $**133.0** | $66.0 | $**278.4** | $115.1 |
| **Average cash and investments** <sup>(3)</sup> | $**7877.8** | $7423.9 | $**7789.7** | $7399.1 |
| **Total return on average cash and investments, pre-tax** <sup>(4)</sup> | **1.7%** | 0.9% | **3.6%** | 1.6% |

---

---

| | | |
|:---|:---|:---|
| **Fixed Income Portfolio Characteristics** | **As at June 30, 2025** | **As at December 31, 2024** |
| Book yield | 4.4% | 4.2% |
| Average duration | 3.2 years | 2.9 years |
| Average credit rating | A+ | AA- |

---

<sup>(1)</sup> Includes net unrealized gains of $20.3 million and $24.2 million for the three and six months ended June 30, 2025, respectively (three and six months ended June 30, 2024 — gains of $3.1 million and $6.8 million, respectively).

<sup>(2)</sup> The tax impact of the change in unrealized gains/(losses) on available for sale investments was an expense of $12.6 million and $27.0 million for the three and six months ended June 30, 2025, respectively (three and six months ended June 30, 2024 — expense of $0.6 million and a benefit of $2.0 million, respectively).

<sup>(3)</sup> Average cash and investments are calculated by taking the average of the opening period and closing period balances for total investments plus cash and cash equivalents.

<sup>(4)</sup> Total return on average cash and investments, pre-tax represents total pre-tax return/(loss) on investments as a percentage of average cash and investments.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• For the three and six months ended June 30, 2025, the Company reported net investment income of $81 million and $156 million, respectively, compared to $83 million and $159 million for the same periods in 2024. The slight year-over-year decrease in both periods primarily reflects lower returns from our Real Estate fund investments.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Net realized and unrealized investment (losses) recognized in net income totaled $9 million and $10 million for the three and six months ended June 30, 2025, respectively, due to realized losses as a result of portfolio rotations, partially offset by unrealized gains on Trading assets and unrealized gains due to favorable foreign currency exchange rate movements in the quarter.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• The unrealized gains on available for sale investments of $62 million and $132 million for the three and six months ended June 30, 2025 were due to a combination of reductions in U.S. Treasury yields and active rotations of the portfolio.

------

---

| | |
|:---|:---|
| **Shareholders' Equity** | **Six Months Ended June 30, 2025** |
| | **($ in millions)** |
| Shareholders' equity as at December 31, 2024 | $**3371.9** |
| Net income for the period | **83.3** |
| Dividends on preference shares | **(23.5)** |
| Other comprehensive income | **156.4** |
| Redemption of preference shares | **(275.0)** |
| Share-based compensation | **32.6** |
| Shareholders' equity as at June 30, 2025 | $**3345.7** |

---

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Total shareholders' equity was $3,346 million as of June 30, 2025, compared with $3,372 million as of December 31, 2024. We continued to generate shareholder value during the six months ended June 30, 2025, with net income of $83 million and other comprehensive income of $156 million, primarily due to valuation and foreign exchange changes related to investments classified as available for sale.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• On January 1, 2025, the Company redeemed all of its issued and outstanding AHL PRC Preference Shares for an aggregate amount of $275 million.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• During the period the Company distributed preference share dividends of $24 million. Additionally, upon the successful completion of the IPO, the Company granted replacement awards in substitution for legacy share options previously granted to certain employees and introduced a 2025 Equity and Incentive plan, as a result issuing additional share-based compensation net of tax of $33 million.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Our shareholders' equity, excluding accumulated other comprehensive loss of $234 million and Preference Shares, net of issuance costs, with a total value of $700 million, was $2,880 million as of June 30, 2025 (December 31, 2024: $2,792 million).

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• During the three months ended June 30, 2025, the Company issued $300 million of Senior Notes at a coupon rate of 5.75%. The net proceeds were used to pay down the $300 million term loan.

**Book Value per Share**

---

| | | | |
|:---|:---|:---|:---|
| (in US$ millions except for per share amounts and percentages) | **As at June 30, 2025** | As at March 31, 2025 | As at June 30, 2024 |
| Book value per ordinary share | $**28.81** | $27.42 | $23.30 |
| Book value per diluted ordinary share | $**28.78** | $27.42 | $23.30 |
| Book value per ordinary share, ex AOCI | $**31.35** | $30.95 | $27.90 |
| Book value per diluted ordinary share, ex AOCI | $**31.32** | $30.95 | $27.90 |

---

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;• Book value per diluted ordinary share was $28.78 as at June 30, 2025, an increase of $1.36, or 4.9%, compared to March 31, 2025, driven by net income available to ordinary shareholders and other comprehensive gains.

------

**Earnings conference call and webcast**

**Aspen will host a conference call to discuss the results at 8:00am (Eastern Time) on Friday, August 8, 2025.**

**To participate in the August 8 conference call by phone**

Please call to register at least 10 minutes before the conference call begins by dialing:

1-800-715-9871 (North America toll-free) or

1-646-307-1963 (international)

Conference ID 8404542

**To download the material**s

The earnings press release is available on the Investors section of Aspen's website at <u>www.aspen.co</u>, along with a copy of the corresponding financial supplement, which includes additional information on Aspen's financial performance.

**To listen later**

A replay of the call will be available approximately two hours after the call concludes and will be available until August 22, 2025. The replay can be accessed through the Investors section of the Company's website, or by dialing:

1-800-770-2030 (US toll free) or

1-609-800-9909 (international)

Conference ID 8404542

The webcast will be archived in the Investor section of Aspen's website.

**For further information please contact**

Mariza Costa, Head of Investor Relations

<u>Mariza.Costa@Aspen.co</u>

+1 201 539 2668

Jo Scott, Group Head of Corporate Communications

<u>Jo.Scott@Aspen.co</u>

+44 20 3900 5744

------

**Aspen Insurance Holdings Limited**

**Summary condensed consolidated balance sheet (unaudited)**

$ in millions

---

| | | |
|:---|:---|:---|
| | **As at June 30, 2025** | As at December 31, 2024 |
| ASSETS |  |  |
| Total investments | $**6984.6** | $6741.5 |
| Cash and cash equivalents | **939.0** | 914.2 |
| Reinsurance recoverables <sup>(1)</sup> | **5376.1** | 5073.7 |
| Premiums receivable | **1921.8** | 1617.0 |
| Other assets | **1190.5** | 1402.1 |
| Total assets | $**16412.0** | $15748.5 |
| LIABILITIES |  |  |
| Losses and loss adjustment expenses reserves | $**8632.2** | $8122.6 |
| Unearned premiums | **2933.0** | 2645.8 |
| Other payables | **1204.7** | 1308.2 |
| Long-term debt | **296.4** | 300.0 |
| Total liabilities | $**13066.3** | $12376.6 |
| SHAREHOLDERS' EQUITY |  |  |
| Ordinary shares | $**0.1** | $0.1 |
| Preference shares | **699.9** | 970.5 |
| Additional paid-in capital | **794.3** | 761.7 |
| Retained earnings | **2085.1** | 2029.7 |
| Accumulated other comprehensive loss, net of tax | **(233.7)** | (390.1) |
| Total shareholders' equity | **3345.7** | 3371.9 |
| Total liabilities and shareholders' equity | $**16412.0** | $15748.5 |

---

(1) Included within reinsurance recoverables is $1.2 billion (December 31, 2024 — $1.2 billion) recoverable from Enstar under the LPT.

------

**Aspen Insurance Holdings Limited**

**Summary consolidated statement of income (unaudited)**

$ in millions, except ratios

---

| | | | | |
|:---|:---|:---|:---|:---|
| | **Three Months Ended June 30,** | **Three Months Ended June 30,** | **Six Months Ended June 30,** | **Six Months Ended June 30,** |
| | **2025** | **2024** | **2025** | **2024** |
| UNDERWRITING REVENUES |  |  |  |  |
| Gross written premiums | $**1238.9** | $1250.4 | $**2526.1** | $2481.8 |
| Premiums ceded | **(523.4)** | (439.3) | **(1058.9)** | (929.8) |
| Net written premiums | **715.5** | 811.1 | **1467.2** | 1552.0 |
| Change in unearned premiums | **(40.6)** | (105.7) | **(89.6)** | (180.9) |
| Net earned premiums | **674.9** | 705.4 | **1377.6** | 1371.1 |
| UNDERWRITING EXPENSES |  |  |  |  |
| Losses and loss adjustment expenses | **(379.1)** | (420.2) | **(834.4)** | (804.7) |
| Acquisition costs | **(90.0)** | (105.6) | **(185.7)** | (198.5) |
| General and administrative expenses | **(105.4)** | (99.3) | **(229.9)** | (198.1) |
| Total underwriting expenses | **(574.5)** | (625.1) | **(1250.0)** | (1201.3) |
| Underwriting income | **100.4** | 80.3 | **127.6** | 169.8 |
| Net investment income | **80.5** | 82.5 | **156.4** | 159.3 |
| Interest expense <sup>(1)</sup> | **(8.9)** | (14.0) | **(18.0)** | (30.1) |
| Corporate and other expenses | **(25.4)** | (39.0) | **(50.8)** | (64.7) |
| Non-operating expenses <sup>(2)</sup> | **(47.3)** | (5.5) | **(55.6)** | (11.7) |
| Net realized and unrealized foreign exchange (losses)/gains <sup>(3)</sup> | **(31.9)** | 1.9 | **(44.8)** | 11.0 |
| Net realized and unrealized investment (losses) | **(9.3)** | (26.1) | **(9.6)** | (27.1) |
| INCOME BEFORE TAX | **58.1** | 80.1 | **105.2** | 206.5 |
| Income tax expense | **(11.6)** | (11.1) | **(21.9)** | (25.7) |
| NET INCOME | **46.5** | 69.0 | **83.3** | 180.8 |
| Dividends paid on preference shares | **(11.0)** | (13.7) | **(23.5)** | (27.3) |
| Preference share redemption costs | **—** |  | **(4.4)** |  |
| Net income available to Aspen Insurance Holdings Limited's ordinary shareholders | $**35.5** | $55.3 | $**55.4** | $153.5 |
| Loss ratio | **56.2%** | 59.6% | **60.6%** | 58.7% |
| &nbsp;&nbsp;&nbsp;&nbsp;Acquisition cost ratio | **13.3%** | 15.0% | **13.5%** | 14.5% |
| &nbsp;&nbsp;&nbsp;&nbsp;General and administrative expense ratio | **15.6%** | 14.1% | **16.7%** | 14.4% |
| Expense ratio | **28.9%** | 29.1% | **30.2%** | 28.9% |
| Combined ratio | **85.1%** | 88.7% | **90.8%** | 87.6% |
| Adjusted combined ratio <sup>(4)</sup> | **84.3%** | 86.7% | **89.7%** | 86.5% |

---

(1) Interest expense includes interest on funds withheld balances related to the LPT contract.

(2) Non-operating expenses in the three and six months ended June 30, 2025 and June 30, 2024 includes expenses in relation to replacement awards granted on the successful completion of the IPO, certain consulting fees, non-recurring transformation activities, and other non-recurring costs.

(3) Includes the net realized and unrealized gains/(losses) from foreign exchange contracts.

(4) Adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract. Adjusted combined ratio represents the performance of our business for accident years 2020 onwards, which we believe is useful to management and investors because it reflects the underlying underwriting performance of the ongoing portfolio.

------

**Aspen Insurance Holdings Limited**

**Summary consolidated segment information (unaudited)**

$ in millions, except ratios

---

| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
| | **Three Months Ended June 30, 2025** | **Three Months Ended June 30, 2025** | **Three Months Ended June 30, 2025** | **Three Months Ended June 30, 2024** | **Three Months Ended June 30, 2024** | **Three Months Ended June 30, 2024** |
| | **Insurance** | **Reinsurance** | **Total** | **Insurance** | **Reinsurance** | **Total** |
| Gross written premiums | $**693.5** | $**545.4** | $**1238.9** | $684.2 | $566.2 | $1250.4 |
| Net written premiums | **390.4** | **325.1** | **715.5** | 425.3 | 385.8 | 811.1 |
| Gross earned premiums | **672.7** | **443.5** | **1116.2** | 620.9 | 434.3 | 1055.2 |
| Net earned premiums | **395.8** | **279.1** | **674.9** | 378.3 | 327.1 | 705.4 |
| Losses and loss adjustment expenses | **(239.3)** | **(139.8)** | **(379.1)** | (231.2) | (189.0) | (420.2) |
| Acquisition costs | **(45.2)** | **(44.8)** | **(90.0)** | (48.2) | (57.4) | (105.6) |
| General and administrative expenses | **(67.1)** | **(38.3)** | **(105.4)** | (63.4) | (35.9) | (99.3) |
| Underwriting income | $**44.2** | $**56.2** | $**100.4** | $35.5 | $44.8 | $80.3 |
| Net investment income |  |  | **80.5** |  |  | 82.5 |
| Net realized and unrealized investment (losses) | Net realized and unrealized investment (losses) | Net realized and unrealized investment (losses) | **(9.3)** |  |  | (26.1) |
| Corporate and other expenses |  |  | **(25.4)** |  |  | (39.0) |
| Non-operating expenses <sup>(1)</sup> | Non-operating expenses <sup>(1)</sup> |  | **(47.3)** |  |  | (5.5) |
| Interest expense <sup>(2)</sup> |  |  | **(8.9)** |  |  | (14.0) |
| Net realized and unrealized foreign exchange (losses)/gains <sup>(3)</sup> | Net realized and unrealized foreign exchange (losses)/gains <sup>(3)</sup> | Net realized and unrealized foreign exchange (losses)/gains <sup>(3)</sup> | **(31.9)** |  |  | 1.9 |
| Income before tax  |  |  | **58.1** |  |  | 80.1 |
| Income tax expense |  |  | **(11.6)** |  |  | (11.1) |
| **Net income** |  |  | $**46.5** |  |  | $69.0 |
| **Ratios** |  |  |  |  |  |  |
| Loss ratio | **60.5%** | **50.1%** | **56.2%** | 61.1% | 57.8% | 59.6% |
| &nbsp;&nbsp;&nbsp;&nbsp;Acquisition cost ratio | **11.4%** | **16.1%** | **13.3%** | 12.7% | 17.5% | 15.0% |
| &nbsp;&nbsp;&nbsp;&nbsp;General and administrative expense ratio | **17.0%** | **13.7%** | **15.6%** | 16.8% | 11.0% | 14.1% |
| Expense ratio | **28.4%** | **29.8%** | **28.9%** | 29.5% | 28.5% | 29.1% |
| Combined ratio  | **88.9%** | **79.9%** | **85.1%** | 90.6% | 86.3% | 88.7% |
| Adjusted combined ratio <sup>(4)</sup> | **87.9%** | **79.2%** | **84.3%** | 90.6% | 82.2% | 86.7% |

---

(1) Non-operating expenses in the three months ended June 30, 2025 and June 30, 2024 includes expenses in relation to replacement awards granted on the successful completion of the IPO, certain consulting fees, non-recurring transformation activities, and other non-recurring costs.

(2) Interest expense includes interest on funds withheld balances related to the LPT contract.

(3) Includes the net realized and unrealized gains/(losses) from foreign exchange contracts.

(4) Adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract. Adjusted combined ratio represents the performance of our business for accident years 2020 onwards, which we believe is useful to management and investors because it reflects the underlying underwriting performance of the ongoing portfolio.

------

**Aspen Insurance Holdings Limited**

**Summary consolidated segment information (unaudited)**

$ in millions, except ratios

---

| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
| | **Six Months Ended June 30, 2025** | **Six Months Ended June 30, 2025** | **Six Months Ended June 30, 2025** | **Six Months Ended June 30, 2024** | **Six Months Ended June 30, 2024** | **Six Months Ended June 30, 2024** |
| | **Insurance** | **Reinsurance** | **Total** | **Insurance** | **Reinsurance** | **Total** |
| Gross written premiums | $**1380.0** | $**1146.1** | $**2526.1** | $1301.2 | $1180.6 | $2481.8 |
| Net written premiums | **768.3** | **698.9** | **1467.2** | 763.7 | 788.3 | 1552.0 |
| Gross earned premiums | **1348.3** | **888.4** | **2236.7** | 1223.7 | 848.5 | 2072.2 |
| Net earned premiums | **799.5** | **578.1** | **1377.6** | 739.3 | 631.8 | 1371.1 |
| Losses and loss adjustment expenses | **(487.2)** | **(347.2)** | **(834.4)** | (460.3) | (344.4) | (804.7) |
| Acquisition costs | **(95.3)** | **(90.4)** | **(185.7)** | (83.9) | (114.6) | (198.5) |
| General and administrative expenses | **(141.6)** | **(88.3)** | **(229.9)** | (125.6) | (72.5) | (198.1) |
| Underwriting income | $**75.4** | $**52.2** | $**127.6** | $69.5 | $100.3 | $169.8 |
| Net investment income |  |  | **156.4** |  |  | 159.3 |
| Net realized and unrealized investment (losses) | Net realized and unrealized investment (losses) | Net realized and unrealized investment (losses) | **(9.6)** |  |  | (27.1) |
| Corporate and other expenses |  |  | **(50.8)** |  |  | (64.7) |
| Non-operating expenses <sup>(1)</sup> | Non-operating expenses <sup>(1)</sup> |  | **(55.6)** |  |  | (11.7) |
| Interest expense <sup>(2)</sup> |  |  | **(18.0)** |  |  | (30.1) |
| Net realized and unrealized foreign exchange (losses)/gains <sup>(3)</sup> | Net realized and unrealized foreign exchange (losses)/gains <sup>(3)</sup> | Net realized and unrealized foreign exchange (losses)/gains <sup>(3)</sup> | **(44.8)** |  |  | 11.0 |
| Income before tax  |  |  | **105.2** |  |  | 206.5 |
| Income tax expense |  |  | **(21.9)** |  |  | (25.7) |
| **Net income** |  |  | $**83.3** |  |  | $180.8 |
| **Ratios** |  |  |  |  |  |  |
| Loss ratio | **60.9%** | **60.1%** | **60.6%** | 62.3% | 54.5% | 58.7% |
| &nbsp;&nbsp;&nbsp;&nbsp;Acquisition cost ratio | **11.9%** | **15.6%** | **13.5%** | 11.3% | 18.1% | 14.5% |
| &nbsp;&nbsp;&nbsp;&nbsp;General and administrative expense ratio | **17.7%** | **15.3%** | **16.7%** | 17.0% | 11.5% | 14.4% |
| Expense ratio | **29.6%** | **30.9%** | **30.2%** | 28.3% | 29.6% | 28.9% |
| Combined ratio  | **90.5%** | **91.0%** | **90.8%** | 90.6% | 84.1% | 87.6% |
| Adjusted combined ratio <sup>(4)</sup> | **89.5%** | **89.8%** | **89.7%** | 91.2% | 81.0% | 86.5% |

---

(1) Non-operating expenses in the six months ended June 30, 2025 and June 30, 2024 includes expenses in relation to replacement awards granted on the successful completion of the IPO, certain consulting fees, non-recurring transformation activities, and other non-recurring costs.

(2) Interest expense includes interest on funds withheld balances related to the LPT contract.

(3) Includes the net realized and unrealized gains/(losses) from foreign exchange contracts.

(4) Adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract. Adjusted combined ratio represents the performance of our business for accident years 2020 onwards, which we believe is useful to management and investors because it reflects the underlying underwriting performance of the ongoing portfolio.

------

**About Aspen Insurance Holdings Limited ("Aspen" or the "Company")**

Aspen provides insurance and reinsurance coverage to clients in various domestic and global markets through wholly-owned operating subsidiaries in Bermuda, the United States and the United Kingdom, as well as its branch operations in Canada, Singapore and Switzerland. For more information about Aspen, please visit <u>www.aspen.co</u>. Please refer to the "Financials – Annual Reports" section of Aspen's investor website for a copy of our most recent Annual Report on Form 20-F.

**Cautionary Statement Regarding Forward-Looking Statements** 

This press release or any other written or oral statements made by or on behalf of the Company may contain written "forward-looking statements" within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended, that are made pursuant to the "safe harbor" provisions of The Private Securities Litigation Reform Act of 1995. Forward-looking statements include all statements that do not relate solely to historical or current facts. In particular, statements that use the words such as "expect," "intend," "plan," "believe," "aim," "project," "anticipate," "seek," "will," "likely," "assume," "estimate," "may," "continue," "guidance," "objective," "outlook," "trends," "future," "could," "would," "should," "target," "predict," "potential," "on track" or their negatives or variations and similar terminology and words of similar import generally involve forward-looking statements.

All forward-looking statements rely on a number of assumptions, estimates and data concerning future results and events and that are subject to a number of uncertainties, assumptions and other factors, many of which are outside Aspen's control that could cause actual results to differ materially from such forward-looking statements. Accordingly, there are important factors that could cause our actual results to differ materially from those anticipated in the forward-looking statements, including uncertainties not currently known to us or that we currently deem to be immaterial may also materially and adversely affect us in the future. These important risks include, but are not limited to, the following: the occurrence of natural disasters, severe weather events and other catastrophe events, as well as outbreaks of pandemic or contagious diseases; unanticipated losses from war, terrorism and political unrest, cyber attacks, government action that is hostile to commercial interests and from sovereign, sub-sovereign and corporate defaults; global climate change, as well as increasing laws, regulation and litigation in the area of climate change; cyclical changes in the reinsurance and insurance industries; reinsurers not reimbursing us for claims on a timely basis, or at all, or associated coverage disputes; the reliance on the assessment and pricing of individual risks by third parties; the failure of any risk management and loss limitation methods we employ; if actual claims exceed our loss reserves; economic or social inflation; interest rate, credit, and real estate related risks within our investment portfolio; the failure of policyholders, brokers or other intermediaries or reinsurers to honor their payment obligations; competition and consolidation in the (re)insurance industry; the Company's ability to maintain its financial strength ratings; the Company's reliance on a small number of brokers; political, regulatory, governmental and industry initiatives and the inability of third parties with whom we do business to appropriately manage their risks; if our internal controls over financial reporting have gaps or other deficiencies; management turnover or our inability to attract and retain senior staff, including our executive officers, senior underwriters or other members of our senior management team; our ability to rely on exemptions from certain of the New York Stock Exchange corporate governance standards as a result of our foreign private issuer and "controlled company" status; a failure in our data security and/or technology systems or infrastructure or those of third parties, including those caused by security breaches or cyber-attacks or through the incorporation of artificial intelligence; the impact of compliance obligations with applicable laws, rules and regulations related to being a public company; and many other factors. For a detailed description of these uncertainties and other factors that could impact the forward-looking statements in this press release and other communications issued by or on behalf of Aspen, please see the "Risk Factors" section in Aspen's Annual Report on Form 20-F for the twelve months ended December 31, 2024, as filed with the SEC, which should be deemed incorporated herein.

The inclusion of forward-looking statements in this press release or any other communication should not be considered as a representation by Aspen that current plans or expectations will be achieved. Aspen undertakes no obligation to publicly update or revise any forward-looking statement, whether as a result of new information, future developments or otherwise, except as required by law.

**Basis of Preparation**

Aspen has prepared the financial information contained within this financial results press release in accordance with the principles of U.S. Generally Accepted Accounting Principles ("GAAP").

------

**Non-GAAP Financial Measures**

In presenting Aspen's results, management has included and discussed certain measurements that are considered "non-GAAP financial measures" under SEC rules and regulations. Management believes that these non-GAAP financial measures, which may be defined differently by other companies, help explain and enhance the understanding of Aspen's results of operations and aligns with how management view internal financial performance. However, these measures should not be viewed as a substitute for those determined in accordance with GAAP.

**Operating income** is a non-GAAP financial measure. Operating income is an internal performance measure used by Aspen in the management of its operations and represents after-tax operating results. Operating income includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to economically match the loss recoveries under the LPT contract with the underlying loss development of the assumed net loss reserves for the subject business of 2019 and prior accident years. Operating income also excludes certain costs related to the LPT contract with a subsidiary of Enstar Group Limited, net foreign exchange gains or losses, including net realized and unrealized gains and losses from foreign exchange contracts, net realized and unrealized gains or losses on investments, non-operating expenses and income, and preference share redemption costs. Non-operating expenses include expenses incurred in connection with non-recurring projects, such as consulting fees and other non-recurring transformation program costs, and are included within general, administrative and corporate expenses in the consolidated statement of operations. The non-operating income tax (benefit)/expense is calculated on the above items by applying the Company's effective current tax rate for each of the Company's material tax jurisdictions to the relevant income/expense for those same jurisdictions. The non-operating income tax (benefit)/expense is included within income tax benefit/(expense) in the consolidated statement of operations.

Aspen excludes these items above from its calculation of operating income because management believes they are not reflective of underlying performance or the amount of these gains or losses is heavily influenced by, and fluctuates according to, prevailing investment market and interest rate movements. Aspen believes these amounts are either largely independent of its business and underwriting process, not aligned with the economics of transactions undertaken, or including them would distort the analysis of trends in its operations. In addition to presenting net income determined in accordance with GAAP, Aspen believes that showing operating income enables users of its financial information to analyze Aspen's results of operations in a manner consistent with how management analyzes Aspen's underlying business performance. Operating income should not be viewed as a substitute for GAAP net income.

---

| | | | | |
|:---|:---|:---|:---|:---|
| **Operating Income Reconciliation** | **Three Months Ended** | **Three Months Ended** | **Six Months Ended** | **Six Months Ended** |
| **(in $ millions)** | **June 30, 2025** | **June 30, 2024** | **June 30, 2025** | **June 30, 2024** |
| Net income available to Aspen Insurance Holdings Limited's ordinary shareholders | $**35.5** | $55.3 | $**55.4** | $153.5 |
| Add/(deduct) items before tax |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Net foreign exchange losses/(gains) | **31.9** | (1.9) | **44.8** | (11.0) |
| &nbsp;&nbsp;&nbsp;&nbsp;Net realized and unrealized investment losses | **9.3** | 26.1 | **9.6** | 27.1 |
| &nbsp;&nbsp;&nbsp;&nbsp;Non-operating expenses | **47.3** | 5.5 | **55.6** | 11.7 |
| &nbsp;&nbsp;&nbsp;&nbsp;Impact of the LPT | **5.6** | 13.5 | **14.6** | 15.0 |
| &nbsp;&nbsp;&nbsp;&nbsp;Variable interest on the LPT funds withheld | **2.5** | 5.2 | **5.4** | 11.5 |
| &nbsp;&nbsp;&nbsp;&nbsp;Non-operating income tax benefit | **(21.2)** | (6.1) | **(28.5)** | (6.8) |
| &nbsp;&nbsp;&nbsp;&nbsp;Preference share redemption costs |  |  | **4.4** |  |
| Operating income | $**110.9** | $97.6 | $**161.3** | $201.0 |

---

------

**Underwriting result or income/loss** is a non-GAAP financial measure. Income or loss for each of the business segments is measured by underwriting income or loss. Underwriting income or loss is the excess of net earned premiums over the underwriting expenses. Underwriting expenses are the sum of losses and loss adjustment expenses, acquisition costs and general and administrative expenses. Underwriting income or loss provides a basis for management to evaluate the segment's underwriting performance.

**Adjusted underwriting income or loss** is a non-GAAP financial measure. It is the underwriting income or loss adjusted for the change in deferred gain on retroactive reinsurance contracts in order to economically match the loss recoveries under the LPT with the underlying loss development of the assumed net loss reserves for the subject business of 2019 and prior accident years. Adjusted underwriting income or loss represents the performance of our business for accident years 2020 onwards, which management believes reflects the underlying underwriting performance of the ongoing portfolio.

**Average equity,** a non-GAAP financial measure, is used in calculating ordinary shareholders return on average equity. Average equity is calculated by taking the arithmetic average of total shareholders' equity on a quarterly basis for the stated periods excluding the average value of preference shares less issue expenses.

**Loss ratio** is the sum of current year net losses, catastrophe losses, prior year reserve strengthening/(releases), and the impact of the LPT as a percentage of net earned premiums.

**Adjusted loss ratio** is a non-GAAP financial measure. It is the sum of current accident year net losses and loss expenses, catastrophe losses and prior year reserve strengthening/(releases) post-LPT years, as a percentage of net earned premiums. Adjusted loss ratio excludes the change in the deferred gain on retroactive reinsurance contracts and represents the performance of our business for accident years 2020 onwards, which management believes reflects the underlying underwriting performance of the ongoing business.

**Combined ratio** is the sum of the loss ratio and the expense ratio. The loss ratio is calculated by dividing losses and loss adjustment expenses by net earned premiums. The expense ratio is calculated by dividing the sum of acquisition costs and general and administrative expenses, by net earned premiums.

**Adjusted combined ratio** is a non-GAAP financial measure. It is the sum of the adjusted loss ratio and the expense ratio. The adjusted loss ratio is calculated by dividing the adjusted losses and loss adjustment expenses by net earned premiums. The expense ratio is calculated by dividing the sum of acquisition costs and general and administrative expenses, by net earned premium.

------

---

| | | | | |
|:---|:---|:---|:---|:---|
| **Underwriting Income, Adjusted Underwriting Income and Adjusted Combined Ratio** | **Three Months Ended June 30,** | **Three Months Ended June 30,** | **Six Months Ended June 30,** | **Six Months Ended June 30,** |
| (in $ millions except where stated) | **2025** | **2024** | **2025** | **2024** |
| **Net earned premium** | $**674.9** | $705.4 | $**1377.6** | $1371.1 |
| Current accident year net losses and loss expenses | **(360.2)** | (365.6) | **(724.1)** | (716.3) |
| Catastrophe losses | **(23.6)** | (48.2) | **(115.0)** | (80.6) |
| Prior year reserve development, post LPT years | **10.2** | 7.2 | **19.2** | 7.2 |
| Adjusted losses and loss adjustment expenses | **(373.6)** | (406.6) | **(819.9)** | (789.7) |
| Impact of the LPT <sup>(1)</sup> | **(5.5)** | (13.6) | **(14.5)** | (15.0) |
| **Losses and loss adjustment expenses** | **(379.1)** | (420.2) | **(834.4)** | (804.7) |
| Acquisition costs | **(90.0)** | (105.6) | **(185.7)** | (198.5) |
| General and administrative expenses | **(105.4)** | (99.3) | **(229.9)** | (198.1) |
| **Underwriting expenses** | $**(574.5)** | $(625.1) | $**(1250.0)** | $(1201.3) |
| **Underwriting income** | $**100.4** | $80.3 | $**127.6** | $169.8 |
| **Combined ratio** | **85.1%** | 88.7% | **90.8%** | 87.6% |
| Adjusted underwriting income | $**105.9** | $93.9 | $**142.1** | $184.8 |
| Adjusted combined ratio | **84.3%** | 86.7% | **89.7%** | 86.5% |
| Adjusted loss ratio | **55.4%** | **57.6%** | **59.5%** | **57.6%** |

---

(1) 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.

**Operating return on average equity ("Operating ROE")** is calculated by taking the operating income divided by average equity. Aspen presents Operating ROE as a measure that is commonly recognized as a standard of performance by investors, analysts, rating agencies and other users of its financial information. Operating return on average equity for the three and six months ended June 30, 2025 and 2024 has been annualized.

---

| | | | | |
|:---|:---|:---|:---|:---|
| | **Three Months Ended June 30,** | **Three Months Ended June 30,** | **Six Months Ended June 30,** | **Six Months Ended June 30,** |
| (in $ millions except where stated) | **2025** | **2024** | **2025** | **2024** |
| Total shareholders' equity | $**3345.7** | $2870.1 | $**3345.7** | $2870.1 |
| Preference shares less issue expenses | **(699.9)** | (753.5) | **(699.9)** | (753.5) |
| Average adjustment | **(77.6)** | 39.0 | **(133.2)** | 38.8 |
| &nbsp;&nbsp;&nbsp;Average equity | $**2568.2** | $2155.6 | $**2512.6** | $2155.4 |
| Net Income available to ordinary shareholders | $**35.5** | $55.3 | $**55.4** | $153.5 |
| Operating income | $**110.9** | $97.6 | $**161.3** | $201.0 |
| Annualized net income available to ordinary shareholders on average equity | **5.6%** | 10.3% | **4.4%** | 14.2% |
| Annualized operating return on average equity | **17.2%** | 18.1% | **12.8%** | 18.7% |

---

------

**Basic Earnings per Ordinary Share** is calculated by dividing net income available to ordinary shareholders by the weighted average number of ordinary shares outstanding during the period. **Diluted Earnings per Ordinary Share** illustrates the effect on basic earnings per share of dilutive securities and is calculated using the treasury stock method.

**Basic Operating Earnings per Share and Diluted Operating Earnings per Share** are non-GAAP financial measures. Basic operating earnings per share and diluted operating earnings per share are calculated by dividing operating income by the basic or diluted weighted average number of shares outstanding for the period.

---

| | | | | |
|:---|:---|:---|:---|:---|
| | **Three Months Ended June 30,** | **Three Months Ended June 30,** | **Six Months Ended June 30,** | **Six Months Ended June 30,** |
| | **2025** | **2024** | **2025** | **2024** |
| Basic earnings per ordinary share |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Net income available to ordinary shareholders | $**0.39** | $0.61 | $**0.61** | $1.69 |
| &nbsp;&nbsp;&nbsp;&nbsp;Operating income | $**1.22** | $1.07 | $**1.77** | $2.21 |
| Diluted earnings per ordinary share |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Net income available to ordinary shareholders | $**0.39** | $0.61 | $**0.61** | $1.69 |
| &nbsp;&nbsp;&nbsp;&nbsp;Operating income | $**1.22** | $1.07 | $**1.77** | $2.21 |
| Weighted average number of ordinary shares outstanding (in millions) | **90.977** | 90.833 | **90.906** | 90.833 |
| Weighted average number of ordinary shares outstanding and dilutive potential ordinary shares (in millions) | **91.042** | 90.833 | **90.938** | 90.833 |
| The dilutive effect of options has been calculated using the treasury stock method. The treasury stock method assumes that the proceeds received from the exercise of options will be used to purchase the Company's ordinary shares at the average market price during the period of calculation. | The dilutive effect of options has been calculated using the treasury stock method. The treasury stock method assumes that the proceeds received from the exercise of options will be used to purchase the Company's ordinary shares at the average market price during the period of calculation. | The dilutive effect of options has been calculated using the treasury stock method. The treasury stock method assumes that the proceeds received from the exercise of options will be used to purchase the Company's ordinary shares at the average market price during the period of calculation. | The dilutive effect of options has been calculated using the treasury stock method. The treasury stock method assumes that the proceeds received from the exercise of options will be used to purchase the Company's ordinary shares at the average market price during the period of calculation. | The dilutive effect of options has been calculated using the treasury stock method. The treasury stock method assumes that the proceeds received from the exercise of options will be used to purchase the Company's ordinary shares at the average market price during the period of calculation. |

---

------

**Book value per ordinary share ("BVPS")** is calculated by adjusting shareholders' equity by removing the impact of Preference Shares as at period end, and dividing it by the number of outstanding ordinary shares at the end of the period.

**Book value per ordinary share ex AOCI** is a non-GAAP financial measure. It is book value per ordinary share adjusted to remove the impact of accumulated other comprehensive income ("AOCI").

**Diluted Book Value per Ordinary Share** illustrates the effect on basic book value per share of dilutive securities and is calculated using the treasury stock method.

---

| | | | |
|:---|:---|:---|:---|
| (in US$ millions except for per share amounts) | **As at June 30, 2025** | As at March 31, 2025 | As at June 30, 2024 |
| Total shareholders' equity | $**3345.7** | $3190.5 | $2870.1 |
| Less: preference shares | **(699.9)** | (699.9) | (753.5) |
| Ordinary shareholders' equity | **2645.8** | 2490.6 | 2116.6 |
| Less: AOCI | **233.7** | 320.8 | 417.2 |
| Ordinary shareholders' equity, ex AOCI | $**2879.5** | $2811.4 | $2533.8 |
| Ordinary shares outstanding (in millions) as at period end | **91.838** | 90.833 | 90.833 |
| Diluted shares outstanding (in millions) as at period end | **91.948** | 90.833 | 90.833 |
| Book value per ordinary share | $**28.81** | $27.42 | $23.30 |
| Book value per diluted ordinary share | $**28.78** | $27.42 | $23.30 |
| Book value per ordinary share, ex AOCI | $**31.35** | $30.95 | $27.90 |
| Book value per diluted ordinary share, ex AOCI | $**31.32** | $30.95 | $27.90 |

---

## Exhibit 99.2

**Exhibit 99.2**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

---

| | | |
|:---|:---|:---|
| ![aspen_primaryxlogoxblackxca.jpg](aspen_primaryxlogoxblackxca.jpg) |  |  |
| ![aspen_primaryxlogoxblackxca.jpg](aspen_primaryxlogoxblackxca.jpg) | FINANCIAL SUPPLEMENT |  |
| ![aspen_primaryxlogoxblackxca.jpg](aspen_primaryxlogoxblackxca.jpg) | As of June 30, 2025 |  |
| ![aspen_primaryxlogoxblackxca.jpg](aspen_primaryxlogoxblackxca.jpg) |  |  |
| ![aspen_primaryxlogoxblackxca.jpg](aspen_primaryxlogoxblackxca.jpg) |  | Aspen Insurance Holdings Limited |
| ![aspen_primaryxlogoxblackxca.jpg](aspen_primaryxlogoxblackxca.jpg) |  |  |
| ![aspen_primaryxlogoxblackxca.jpg](aspen_primaryxlogoxblackxca.jpg) | This financial supplement is for information purposes only. All financial information contained herein is unaudited. This financial supplement is not being filed with the U.S Securities and Exchange Commission ("SEC"). It should be read in conjunction with documents filed by Aspen Insurance Holdings Limited with the SEC, including its Annual Report on Form 20-F. Please refer to the Company's website at www.aspen.co for further information about Aspen.<br>**<u>Investor Contact:</u>**<br>**Aspen Insurance Holdings Limited**<br>Mariza Costa, Head of Investor Relations<br><u>Mariza.Costa@Aspen.co</u><br>+1 201 539 2668<br>Jo Scott, Group Head of Corporate Communications<br><u>Jo.Scott@Aspen.co</u><br>+44 20 7184 8000 |  |
| ![aspen_primaryxlogoxblackxca.jpg](aspen_primaryxlogoxblackxca.jpg) | This financial supplement is for information purposes only. All financial information contained herein is unaudited. This financial supplement is not being filed with the U.S Securities and Exchange Commission ("SEC"). It should be read in conjunction with documents filed by Aspen Insurance Holdings Limited with the SEC, including its Annual Report on Form 20-F. Please refer to the Company's website at www.aspen.co for further information about Aspen.<br>**<u>Investor Contact:</u>**<br>**Aspen Insurance Holdings Limited**<br>Mariza Costa, Head of Investor Relations<br><u>Mariza.Costa@Aspen.co</u><br>+1 201 539 2668<br>Jo Scott, Group Head of Corporate Communications<br><u>Jo.Scott@Aspen.co</u><br>+44 20 7184 8000 |  |
| This financial supplement is for information purposes only. All financial information contained herein is unaudited. This financial supplement is not being filed with the U.S Securities and Exchange Commission ("SEC"). It should be read in conjunction with documents filed by Aspen Insurance Holdings Limited with the SEC, including its Annual Report on Form 20-F. Please refer to the Company's website at www.aspen.co for further information about Aspen.<br>**<u>Investor Contact:</u>**<br>**Aspen Insurance Holdings Limited**<br>Mariza Costa, Head of Investor Relations<br><u>Mariza.Costa@Aspen.co</u><br>+1 201 539 2668<br>Jo Scott, Group Head of Corporate Communications<br><u>Jo.Scott@Aspen.co</u><br>+44 20 7184 8000 |  |  |
| This financial supplement is for information purposes only. All financial information contained herein is unaudited. This financial supplement is not being filed with the U.S Securities and Exchange Commission ("SEC"). It should be read in conjunction with documents filed by Aspen Insurance Holdings Limited with the SEC, including its Annual Report on Form 20-F. Please refer to the Company's website at www.aspen.co for further information about Aspen.<br>**<u>Investor Contact:</u>**<br>**Aspen Insurance Holdings Limited**<br>Mariza Costa, Head of Investor Relations<br><u>Mariza.Costa@Aspen.co</u><br>+1 201 539 2668<br>Jo Scott, Group Head of Corporate Communications<br><u>Jo.Scott@Aspen.co</u><br>+44 20 7184 8000 |  |  |
| This financial supplement is for information purposes only. All financial information contained herein is unaudited. This financial supplement is not being filed with the U.S Securities and Exchange Commission ("SEC"). It should be read in conjunction with documents filed by Aspen Insurance Holdings Limited with the SEC, including its Annual Report on Form 20-F. Please refer to the Company's website at www.aspen.co for further information about Aspen.<br>**<u>Investor Contact:</u>**<br>**Aspen Insurance Holdings Limited**<br>Mariza Costa, Head of Investor Relations<br><u>Mariza.Costa@Aspen.co</u><br>+1 201 539 2668<br>Jo Scott, Group Head of Corporate Communications<br><u>Jo.Scott@Aspen.co</u><br>+44 20 7184 8000 |  |  |
| This financial supplement is for information purposes only. All financial information contained herein is unaudited. This financial supplement is not being filed with the U.S Securities and Exchange Commission ("SEC"). It should be read in conjunction with documents filed by Aspen Insurance Holdings Limited with the SEC, including its Annual Report on Form 20-F. Please refer to the Company's website at www.aspen.co for further information about Aspen.<br>**<u>Investor Contact:</u>**<br>**Aspen Insurance Holdings Limited**<br>Mariza Costa, Head of Investor Relations<br><u>Mariza.Costa@Aspen.co</u><br>+1 201 539 2668<br>Jo Scott, Group Head of Corporate Communications<br><u>Jo.Scott@Aspen.co</u><br>+44 20 7184 8000 |  |  |
|  | This financial supplement is for information purposes only. All financial information contained herein is unaudited. This financial supplement is not being filed with the U.S Securities and Exchange Commission ("SEC"). It should be read in conjunction with documents filed by Aspen Insurance Holdings Limited with the SEC, including its Annual Report on Form 20-F. Please refer to the Company's website at www.aspen.co for further information about Aspen.<br>**<u>Investor Contact:</u>**<br>**Aspen Insurance Holdings Limited**<br>Mariza Costa, Head of Investor Relations<br><u>Mariza.Costa@Aspen.co</u><br>+1 201 539 2668<br>Jo Scott, Group Head of Corporate Communications<br><u>Jo.Scott@Aspen.co</u><br>+44 20 7184 8000 |  |
|  | This financial supplement is for information purposes only. All financial information contained herein is unaudited. This financial supplement is not being filed with the U.S Securities and Exchange Commission ("SEC"). It should be read in conjunction with documents filed by Aspen Insurance Holdings Limited with the SEC, including its Annual Report on Form 20-F. Please refer to the Company's website at www.aspen.co for further information about Aspen.<br>**<u>Investor Contact:</u>**<br>**Aspen Insurance Holdings Limited**<br>Mariza Costa, Head of Investor Relations<br><u>Mariza.Costa@Aspen.co</u><br>+1 201 539 2668<br>Jo Scott, Group Head of Corporate Communications<br><u>Jo.Scott@Aspen.co</u><br>+44 20 7184 8000 |  |

---

**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**

------

---

| | | |
|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Table Of Contents |  |
|  |  | **Page** |
| <u>[Basis of Presentation](#if179e4f5187f483da88a856a99fd78a2_7)</u> | <u>[Basis of Presentation](#if179e4f5187f483da88a856a99fd78a2_7)</u> | <u>[1](#if179e4f5187f483da88a856a99fd78a2_7)</u> |
| <u>[Cautionary Statement Regarding Forward-Looking Statements](#if179e4f5187f483da88a856a99fd78a2_10)</u> | <u>[Cautionary Statement Regarding Forward-Looking Statements](#if179e4f5187f483da88a856a99fd78a2_10)</u> | <u>[2](#if179e4f5187f483da88a856a99fd78a2_10)</u> |
| <u>[Financial Highlights](#if179e4f5187f483da88a856a99fd78a2_13)</u> | <u>[Financial Highlights](#if179e4f5187f483da88a856a99fd78a2_13)</u> | <u>[3](#if179e4f5187f483da88a856a99fd78a2_13)</u> |
| <u>[Consolidated Statements of Operations - Quarterly Results](#if179e4f5187f483da88a856a99fd78a2_16)</u> | <u>[Consolidated Statements of Operations - Quarterly Results](#if179e4f5187f483da88a856a99fd78a2_16)</u> | <u>[4](#if179e4f5187f483da88a856a99fd78a2_16)</u> |
| <u>[Consolidated Statements of Operations - Year to Date Results](#if179e4f5187f483da88a856a99fd78a2_19)</u> | <u>[Consolidated Statements of Operations - Year to Date Results](#if179e4f5187f483da88a856a99fd78a2_19)</u> | <u>[5](#if179e4f5187f483da88a856a99fd78a2_19)</u> |
| <u>[Condensed](#if179e4f5187f483da88a856a99fd78a2_25)[Consolidated Balance Sheets](#if179e4f5187f483da88a856a99fd78a2_25)</u> | <u>[Condensed](#if179e4f5187f483da88a856a99fd78a2_25)[Consolidated Balance Sheets](#if179e4f5187f483da88a856a99fd78a2_25)</u> | <u>[6](#if179e4f5187f483da88a856a99fd78a2_25)</u> |
| <u>[Earnings Per Ordinary Share](#if179e4f5187f483da88a856a99fd78a2_79)</u> | <u>[Earnings Per Ordinary Share](#if179e4f5187f483da88a856a99fd78a2_79)</u> | <u>[7](#if179e4f5187f483da88a856a99fd78a2_79)</u> |
| <u>Book Value Per Ordinary Share</u> | <u>Book Value Per Ordinary Share</u> | <u>[8](#if179e4f5187f483da88a856a99fd78a2_28)</u> |
| <u>[Return on Average Equity](#if179e4f5187f483da88a856a99fd78a2_31)</u> | <u>[Return on Average Equity](#if179e4f5187f483da88a856a99fd78a2_31)</u> | <u>[9](#if179e4f5187f483da88a856a99fd78a2_31)</u> |
| <u>[Consolidated Underwriting Results by Operating Segment](#if179e4f5187f483da88a856a99fd78a2_34)</u> | <u>[Consolidated Underwriting Results by Operating Segment](#if179e4f5187f483da88a856a99fd78a2_34)</u> | <u>[10](#if179e4f5187f483da88a856a99fd78a2_34)-[11](#if179e4f5187f483da88a856a99fd78a2_37)</u>  |
| <u>[Operating Segment - Quarterly Results](#if179e4f5187f483da88a856a99fd78a2_43)</u> | <u>[Operating Segment - Quarterly Results](#if179e4f5187f483da88a856a99fd78a2_43)</u> | <u>[12](#if179e4f5187f483da88a856a99fd78a2_43)[-](#if179e4f5187f483da88a856a99fd78a2_43)[13](#if179e4f5187f483da88a856a99fd78a2_40)</u> |
| <u>[Aspen Capital Markets](#if179e4f5187f483da88a856a99fd78a2_46)</u> | <u>[Aspen Capital Markets](#if179e4f5187f483da88a856a99fd78a2_46)</u> | <u>[14](#if179e4f5187f483da88a856a99fd78a2_46)</u> |
| <u>[Written and Earned Premiums by Segment and Lines of Business](#if179e4f5187f483da88a856a99fd78a2_49)</u> | <u>[Written and Earned Premiums by Segment and Lines of Business](#if179e4f5187f483da88a856a99fd78a2_49)</u> | <u>[15](#if179e4f5187f483da88a856a99fd78a2_49)[-](#if179e4f5187f483da88a856a99fd78a2_49)[16](#if179e4f5187f483da88a856a99fd78a2_52)</u> |
| <u>[Consolidated Statements of Changes in Shareholders' Equity](#if179e4f5187f483da88a856a99fd78a2_55)</u> | <u>[Consolidated Statements of Changes in Shareholders' Equity](#if179e4f5187f483da88a856a99fd78a2_55)</u> | <u>[17](#if179e4f5187f483da88a856a99fd78a2_55)</u> |
| <u>[Consolidated Statements of Comprehensive Income](#if179e4f5187f483da88a856a99fd78a2_58)</u> | <u>[Consolidated Statements of Comprehensive Income](#if179e4f5187f483da88a856a99fd78a2_58)</u> | <u>[18](#if179e4f5187f483da88a856a99fd78a2_58)</u> |
| <u>Condensed [Consolidated Statements of Cash Flows](#if179e4f5187f483da88a856a99fd78a2_61)</u> | <u>Condensed [Consolidated Statements of Cash Flows](#if179e4f5187f483da88a856a99fd78a2_61)</u> | <u>[19](#if179e4f5187f483da88a856a99fd78a2_61)</u> |
| <u>[Reserves for Losses and Loss Adjustment Expenses](#if179e4f5187f483da88a856a99fd78a2_64)</u> | <u>[Reserves for Losses and Loss Adjustment Expenses](#if179e4f5187f483da88a856a99fd78a2_64)</u> | <u>[20](#if179e4f5187f483da88a856a99fd78a2_64)</u> |
| <u>[Prior Year Reserve](#if179e4f5187f483da88a856a99fd78a2_70)Movements</u> | <u>[Prior Year Reserve](#if179e4f5187f483da88a856a99fd78a2_70)Movements</u> | <u>[21](#if179e4f5187f483da88a856a99fd78a2_70)</u> |
| <u>[Consolidated Investment Portfolio](#if179e4f5187f483da88a856a99fd78a2_73)</u> | <u>[Consolidated Investment Portfolio](#if179e4f5187f483da88a856a99fd78a2_73)</u> | <u>[22](#if179e4f5187f483da88a856a99fd78a2_73)</u> |
| <u>[Investment Analysis](#if179e4f5187f483da88a856a99fd78a2_76)</u> | <u>[Investment Analysis](#if179e4f5187f483da88a856a99fd78a2_76)</u> | <u>[23](#if179e4f5187f483da88a856a99fd78a2_76)</u> |
| <u>[Operating Income Reconciliation](#if179e4f5187f483da88a856a99fd78a2_82)</u> | <u>[Operating Income Reconciliation](#if179e4f5187f483da88a856a99fd78a2_82)</u> | <u>[24](#if179e4f5187f483da88a856a99fd78a2_82)</u> |
| <u>[Non-GAAP Financial Measures](#if179e4f5187f483da88a856a99fd78a2_997)</u> | <u>[Non-GAAP Financial Measures](#if179e4f5187f483da88a856a99fd78a2_997)</u> | <u>[25](#if179e4f5187f483da88a856a99fd78a2_997)-26</u> |
| <u>Derivatives</u> | <u>Derivatives</u> | <u>[27](#if179e4f5187f483da88a856a99fd78a2_88)</u> |

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| | |
|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Basis of Presentation |
| **Definitions and presentations**: All financial information contained herein is unaudited. Unless otherwise noted, all data is in U.S. dollar millions, except for per share amounts, percentages and ratio information. | **Definitions and presentations**: All financial information contained herein is unaudited. Unless otherwise noted, all data is in U.S. dollar millions, except for per share amounts, percentages and ratio information. |
| In presenting Aspen's results, management has included and discussed certain "non-GAAP financial measures". Management believes that these non-GAAP measures, which may be defined differently by other companies within or outside of the re/insurance industry, help explain and enhance Aspen's results of operations in a manner that allows for a more complete understanding of the underlying trends in Aspen's business and aligns with how management view internal financial performance. However, these measures should not be viewed as a substitute for those determined in accordance with GAAP. The reconciliation of such non-GAAP financial measures to their respective most directly comparable GAAP financial measures is included in this financial supplement. Investors are cautioned not to place undue reliance on these non-GAAP measures in assessing the Company's overall financial performance. | In presenting Aspen's results, management has included and discussed certain "non-GAAP financial measures". Management believes that these non-GAAP measures, which may be defined differently by other companies within or outside of the re/insurance industry, help explain and enhance Aspen's results of operations in a manner that allows for a more complete understanding of the underlying trends in Aspen's business and aligns with how management view internal financial performance. However, these measures should not be viewed as a substitute for those determined in accordance with GAAP. The reconciliation of such non-GAAP financial measures to their respective most directly comparable GAAP financial measures is included in this financial supplement. Investors are cautioned not to place undue reliance on these non-GAAP measures in assessing the Company's overall financial performance. |
| **Operating income** (a non-GAAP financial measure): Operating income is an internal performance measure used by Aspen in the management of its operations and represents after-tax operating results. Operating income includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to economically match the loss recoveries under the loss portfolio transfer ("LPT") contract with the underlying loss development of the assumed net loss reserves for the subject business of 2019 and prior accident years. Operating income also excludes certain costs related to the LPT contract with a subsidiary of Enstar Group Limited, net foreign exchange gains or losses, including net realized and unrealized gains and losses from foreign exchange contracts, net realized and unrealized gains or losses on investments, non-operating expenses and income, and preference share redemption costs. Non-operating expenses include expenses incurred in connection with non-recurring projects, such as consulting fees and other non-recurring transformation program costs, and are included within general, administrative and corporate expenses in the consolidated statement of operations. The non-operating income tax (benefit)/expense is calculated on the above items by applying the Company's effective current tax rate for each of the Company's material tax jurisdictions to the relevant income/expense for those same jurisdictions. The non-operating income tax (benefit)/expense is included within income tax benefit/(expense) in the consolidated statement of operations. | **Operating income** (a non-GAAP financial measure): Operating income is an internal performance measure used by Aspen in the management of its operations and represents after-tax operating results. Operating income includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to economically match the loss recoveries under the loss portfolio transfer ("LPT") contract with the underlying loss development of the assumed net loss reserves for the subject business of 2019 and prior accident years. Operating income also excludes certain costs related to the LPT contract with a subsidiary of Enstar Group Limited, net foreign exchange gains or losses, including net realized and unrealized gains and losses from foreign exchange contracts, net realized and unrealized gains or losses on investments, non-operating expenses and income, and preference share redemption costs. Non-operating expenses include expenses incurred in connection with non-recurring projects, such as consulting fees and other non-recurring transformation program costs, and are included within general, administrative and corporate expenses in the consolidated statement of operations. The non-operating income tax (benefit)/expense is calculated on the above items by applying the Company's effective current tax rate for each of the Company's material tax jurisdictions to the relevant income/expense for those same jurisdictions. The non-operating income tax (benefit)/expense is included within income tax benefit/(expense) in the consolidated statement of operations. |
| Aspen excludes these items above from its calculation of operating income because management believes they are not reflective of underlying performance or the amount of these gains or losses is heavily influenced by, and fluctuates according to, prevailing investment market and interest rate movements. Aspen believes these amounts are largely independent of its business and underwriting process, not aligned with the economics of transactions undertaken, or including them would distort the analysis of trends in its operations. In addition to presenting net income determined in accordance with GAAP, Aspen believes that showing operating income enables users of its financial information to analyze Aspen's results of operations in a manner similar to how management analyzes Aspen's underlying business performance. Operating income should not be viewed as a substitute for GAAP net income. Please see page 24 for a reconciliation of net income to operating income. | Aspen excludes these items above from its calculation of operating income because management believes they are not reflective of underlying performance or the amount of these gains or losses is heavily influenced by, and fluctuates according to, prevailing investment market and interest rate movements. Aspen believes these amounts are largely independent of its business and underwriting process, not aligned with the economics of transactions undertaken, or including them would distort the analysis of trends in its operations. In addition to presenting net income determined in accordance with GAAP, Aspen believes that showing operating income enables users of its financial information to analyze Aspen's results of operations in a manner similar to how management analyzes Aspen's underlying business performance. Operating income should not be viewed as a substitute for GAAP net income. Please see page 24 for a reconciliation of net income to operating income. |
| **Average equity** (a non-GAAP financial measure): Average equity is used in calculating ordinary shareholders return on average equity. Average equity is calculated by taking the arithmetic average of total shareholders' equity on a quarterly basis for the stated periods excluding the average value of preference shares less issue expenses. | **Average equity** (a non-GAAP financial measure): Average equity is used in calculating ordinary shareholders return on average equity. Average equity is calculated by taking the arithmetic average of total shareholders' equity on a quarterly basis for the stated periods excluding the average value of preference shares less issue expenses. |
| **Annualized operating return on average equity ("Operating ROE")** (a non-GAAP financial measure): Operating ROE is calculated by dividing operating income by average equity, both of which are defined above. Aspen presents Operating ROE as a measure that is commonly recognized as a standard of performance by investors, analysts, rating agencies and other users of its financial information. See page 24 for a reconciliation of operating income to net income and page 9 for a reconciliation of average shareholders' equity to average ordinary shareholders' equity. | **Annualized operating return on average equity ("Operating ROE")** (a non-GAAP financial measure): Operating ROE is calculated by dividing operating income by average equity, both of which are defined above. Aspen presents Operating ROE as a measure that is commonly recognized as a standard of performance by investors, analysts, rating agencies and other users of its financial information. See page 24 for a reconciliation of operating income to net income and page 9 for a reconciliation of average shareholders' equity to average ordinary shareholders' equity. |
| **Book value per ordinary share ("BVPS")** is calculated by adjusting shareholders' equity by removing the impact of Preference Shares as at period end, and dividing it by the number of outstanding ordinary shares at the end of the period. **Book value per ordinary share ex AOCI** is a non-GAAP financial measure. It is book value per ordinary share adjusted to remove the impact of accumulated other comprehensive income ("AOCI"). **Diluted Book Value per Ordinary Share** illustrates the effect on basic book value per share of dilutive securities and is calculated using the treasury stock method. | **Book value per ordinary share ("BVPS")** is calculated by adjusting shareholders' equity by removing the impact of Preference Shares as at period end, and dividing it by the number of outstanding ordinary shares at the end of the period. **Book value per ordinary share ex AOCI** is a non-GAAP financial measure. It is book value per ordinary share adjusted to remove the impact of accumulated other comprehensive income ("AOCI"). **Diluted Book Value per Ordinary Share** illustrates the effect on basic book value per share of dilutive securities and is calculated using the treasury stock method. |
| **Basic Earnings per Ordinary Share** is calculated by dividing net income available to ordinary shareholders by the weighted average number of ordinary shares outstanding during the period. **Diluted Earnings per Ordinary Share** illustrates the effect on basic earnings per share of dilutive securities and is calculated using the treasury stock method. <br>**Basic Operating Earnings per Share and Diluted Operating Earnings per Share** are non-GAAP financial measures. Basic operating earnings per share and diluted operating earnings per share are calculated by dividing operating income by the basic or diluted weighted average number of shares outstanding for the period. | **Basic Earnings per Ordinary Share** is calculated by dividing net income available to ordinary shareholders by the weighted average number of ordinary shares outstanding during the period. **Diluted Earnings per Ordinary Share** illustrates the effect on basic earnings per share of dilutive securities and is calculated using the treasury stock method. <br>**Basic Operating Earnings per Share and Diluted Operating Earnings per Share** are non-GAAP financial measures. Basic operating earnings per share and diluted operating earnings per share are calculated by dividing operating income by the basic or diluted weighted average number of shares outstanding for the period. |
| **Underwriting income or loss** (a non-GAAP financial measure): Income or loss for each of the business segments is measured by underwriting income or loss. Underwriting income or loss is the excess of net earned premiums over the sum of losses and loss adjustment expenses, acquisition costs and general and administrative expenses. Underwriting income or loss provides a basis for management to evaluate the segment's underwriting performance. See pages 10-11 for a reconciliation of underwriting income or loss. **Adjusted underwriting income or loss** includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to economically match the loss recoveries under the LPT contract with the underlying loss development of the assumed net loss reserves for the subject business of 2019 and prior accident years. See pages 25-26 for a reconciliation of adjusted underwriting income or loss. | **Underwriting income or loss** (a non-GAAP financial measure): Income or loss for each of the business segments is measured by underwriting income or loss. Underwriting income or loss is the excess of net earned premiums over the sum of losses and loss adjustment expenses, acquisition costs and general and administrative expenses. Underwriting income or loss provides a basis for management to evaluate the segment's underwriting performance. See pages 10-11 for a reconciliation of underwriting income or loss. **Adjusted underwriting income or loss** includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to economically match the loss recoveries under the LPT contract with the underlying loss development of the assumed net loss reserves for the subject business of 2019 and prior accident years. See pages 25-26 for a reconciliation of adjusted underwriting income or loss. |
| **Catastrophe losses:** Aspen has defined catastrophe losses in the three and six months ended June 30, 2025 and June 30, 2024 as losses primarily associated with natural disasters and extreme weather-related events, and can include pandemics and other events depending on their severity. | **Catastrophe losses:** Aspen has defined catastrophe losses in the three and six months ended June 30, 2025 and June 30, 2024 as losses primarily associated with natural disasters and extreme weather-related events, and can include pandemics and other events depending on their severity. |
| General Insurance: Along with most property and casualty insurance companies, Aspen uses the loss ratio, the expense ratio and the combined ratio as measures of underwriting performance. These ratios are relative measurements that describe, for every $100 of net premiums earned, the amount of losses and loss adjustment expenses, and the amount of other underwriting expenses that would be incurred. A combined ratio of less than 100 indicates underwriting income and a combined ratio of over 100 indicates an underwriting loss. Combined ratio is the sum of the loss ratio and the expense ratio. The loss ratio is calculated by dividing losses and loss adjustment expenses by net earned premiums. The expense ratio is calculated by dividing the sum of acquisition costs and general and administrative expenses, by net earned premiums. **Adjusted loss/combined ratio** includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract with the underlying loss development of the assumed net loss reserves for the subject business of 2019 and prior accident years. See pages 25-26 for a reconciliation of adjusted loss/combined ratio. | General Insurance: Along with most property and casualty insurance companies, Aspen uses the loss ratio, the expense ratio and the combined ratio as measures of underwriting performance. These ratios are relative measurements that describe, for every $100 of net premiums earned, the amount of losses and loss adjustment expenses, and the amount of other underwriting expenses that would be incurred. A combined ratio of less than 100 indicates underwriting income and a combined ratio of over 100 indicates an underwriting loss. Combined ratio is the sum of the loss ratio and the expense ratio. The loss ratio is calculated by dividing losses and loss adjustment expenses by net earned premiums. The expense ratio is calculated by dividing the sum of acquisition costs and general and administrative expenses, by net earned premiums. **Adjusted loss/combined ratio** includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract with the underlying loss development of the assumed net loss reserves for the subject business of 2019 and prior accident years. See pages 25-26 for a reconciliation of adjusted loss/combined ratio. |

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| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Cautionary Statement Regarding Forward-Looking Statements |
| This report contains forward-looking statements within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended, that are made pursuant to the "safe harbor" provisions of The Private Securities Litigation Reform Act of 1995. Forward-looking statements include all statements that do not relate solely to historical or current facts. In particular, statements that use the words such as "expect," "intend," "plan," "believe," "aim," "project," "anticipate," "seek," "will," "likely," "assume," "estimate," "may," "continue," "guidance," "objective," "outlook," "trends," "future," "could," "would," "should," "target," "predict," "potential," "on track" or their negatives or variations and similar terminology and words of similar import generally involve forward-looking statements.<br>All forward-looking statements rely on a number of assumptions, estimates and data concerning future results and events and that are subject to a number of uncertainties, assumptions and other factors, many of which are outside Aspen's control that could cause actual results to differ materially from such forward-looking statements. Accordingly, there are important factors that could cause our actual results to differ materially from those anticipated in the forward-looking statements, including uncertainties not currently known to us or that we currently deem to be immaterial may also materially and adversely affect us in the future. These important risks include, but are not limited to, the following: the occurrence of natural disasters, severe weather events and other catastrophe events, as well as outbreaks of pandemic or contagious diseases; unanticipated losses from war, terrorism and political unrest, cyber attacks, government action that is hostile to commercial interests and from sovereign, sub-sovereign and corporate defaults; global climate change, as well as increasing laws, regulation and litigation in the area of climate change; cyclical changes in the reinsurance and insurance industries; reinsurers not reimbursing us for claims on a timely basis, or at all, or associated coverage disputes; the reliance on the assessment and pricing of individual risks by third parties; the failure of any risk management and loss limitation methods we employ; if actual claims exceed our loss reserves; economic or social inflation; interest rate, credit, and real estate related risks within our investment portfolio; the failure of policyholders, brokers or other intermediaries or reinsurers to honor their payment obligations; competition and consolidation in the (re)insurance industry; the Company's ability to maintain its financial strength ratings; the Company's reliance on a small number of brokers; political, regulatory, governmental and industry initiatives and the inability of third parties with whom we do business to appropriately manage their risks; if our internal controls over financial reporting have gaps or other deficiencies; management turnover or our inability to attract and retain senior staff, including our executive officers, senior underwriters or other members of our senior management team; our ability to rely on exemptions from certain of the New York Stock Exchange corporate governance standards as a result of our foreign private issuer and "controlled company" status; a failure in our data security and/or technology systems or infrastructure or those of third parties, including those caused by security breaches or cyber-attacks or through the incorporation of artificial intelligence; the impact of compliance obligations with applicable laws, rules and regulations related to being a public company; and many other factors. For a detailed description of these uncertainties and other factors that could impact the forward-looking statements in this press release and other communications issued by or on behalf of Aspen, please see the "Risk Factors" section in Aspen's Annual Report on Form 20-F for the twelve months ended December 31, 2024, as filed with the SEC, which should be deemed incorporated herein.<br>The inclusion of forward-looking statements in this report should not be considered as a representation by us that current plans or expectations will be achieved. Aspen undertakes no obligation to publicly update or revise any forward-looking statement, whether as a result of new information, future developments or otherwise, except as required by law. | This report contains forward-looking statements within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended, that are made pursuant to the "safe harbor" provisions of The Private Securities Litigation Reform Act of 1995. Forward-looking statements include all statements that do not relate solely to historical or current facts. In particular, statements that use the words such as "expect," "intend," "plan," "believe," "aim," "project," "anticipate," "seek," "will," "likely," "assume," "estimate," "may," "continue," "guidance," "objective," "outlook," "trends," "future," "could," "would," "should," "target," "predict," "potential," "on track" or their negatives or variations and similar terminology and words of similar import generally involve forward-looking statements.<br>All forward-looking statements rely on a number of assumptions, estimates and data concerning future results and events and that are subject to a number of uncertainties, assumptions and other factors, many of which are outside Aspen's control that could cause actual results to differ materially from such forward-looking statements. Accordingly, there are important factors that could cause our actual results to differ materially from those anticipated in the forward-looking statements, including uncertainties not currently known to us or that we currently deem to be immaterial may also materially and adversely affect us in the future. These important risks include, but are not limited to, the following: the occurrence of natural disasters, severe weather events and other catastrophe events, as well as outbreaks of pandemic or contagious diseases; unanticipated losses from war, terrorism and political unrest, cyber attacks, government action that is hostile to commercial interests and from sovereign, sub-sovereign and corporate defaults; global climate change, as well as increasing laws, regulation and litigation in the area of climate change; cyclical changes in the reinsurance and insurance industries; reinsurers not reimbursing us for claims on a timely basis, or at all, or associated coverage disputes; the reliance on the assessment and pricing of individual risks by third parties; the failure of any risk management and loss limitation methods we employ; if actual claims exceed our loss reserves; economic or social inflation; interest rate, credit, and real estate related risks within our investment portfolio; the failure of policyholders, brokers or other intermediaries or reinsurers to honor their payment obligations; competition and consolidation in the (re)insurance industry; the Company's ability to maintain its financial strength ratings; the Company's reliance on a small number of brokers; political, regulatory, governmental and industry initiatives and the inability of third parties with whom we do business to appropriately manage their risks; if our internal controls over financial reporting have gaps or other deficiencies; management turnover or our inability to attract and retain senior staff, including our executive officers, senior underwriters or other members of our senior management team; our ability to rely on exemptions from certain of the New York Stock Exchange corporate governance standards as a result of our foreign private issuer and "controlled company" status; a failure in our data security and/or technology systems or infrastructure or those of third parties, including those caused by security breaches or cyber-attacks or through the incorporation of artificial intelligence; the impact of compliance obligations with applicable laws, rules and regulations related to being a public company; and many other factors. For a detailed description of these uncertainties and other factors that could impact the forward-looking statements in this press release and other communications issued by or on behalf of Aspen, please see the "Risk Factors" section in Aspen's Annual Report on Form 20-F for the twelve months ended December 31, 2024, as filed with the SEC, which should be deemed incorporated herein.<br>The inclusion of forward-looking statements in this report should not be considered as a representation by us that current plans or expectations will be achieved. Aspen undertakes no obligation to publicly update or revise any forward-looking statement, whether as a result of new information, future developments or otherwise, except as required by law. |

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|:---|:---|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Financial Highlights | Financial Highlights | Financial Highlights | Financial Highlights | Financial Highlights | Financial Highlights |  |
|  |  | **Three Months Ended June 30,** | **Three Months Ended June 30,** | **Three Months Ended June 30,** | **Six Months Ended June 30,** | **Six Months Ended June 30,** | **Six Months Ended June 30,** |
| **(in US$ millions except for percentages, share and per share amounts)** | **(in US$ millions except for percentages, share and per share amounts)** | **2025** | **2024** | **Change** | **2025** | **2024** | **Change** |
| Gross written premiums | Gross written premiums | $**1238.9** | $1250.4 | (0.9)% | $**2526.1** | $2481.8 | 1.8% |
| Net written premiums | Net written premiums | $**715.5** | $811.1 | (11.8)% | $**1467.2** | $1552 | (5.5)% |
| Net earned premiums | Net earned premiums | $**674.9** | $705.4 | (4.3)% | $**1377.6** | $1371.1 | 0.5% |
| Net income | Net income | $**46.5** | $69 | (32.6)% | $**83.3** | $180.8 | (53.9)% |
| Operating income | Operating income | $**110.9** | $97.6 | 13.6% | $**161.3** | $201 | (19.8)% |
| Net investment income | Net investment income | $**80.5** | $82.5 | (2.4)% | $**156.4** | $159.3 | (1.8)% |
| Underwriting income | Underwriting income | $**100.4** | $80.3 | 25.0% | $**127.6** | $169.8 | (24.9)% |
| Adjusted underwriting income <sup>(1)</sup> | Adjusted underwriting income <sup>(1)</sup> | $**105.9** | $93.9 | 12.8% | $**142.1** | $184.8 | (23.1)% |
| Aspen Capital Markets fee income | Aspen Capital Markets fee income | $**53.4** | $34.8 | 53.5% | $**99.0** | $68.3 | 45.0% |
| ***Underwriting Ratios*** | ***Underwriting Ratios*** |  |  |  |  |  |  |
| Loss ratio | Loss ratio | **56.2%** | 59.6% |  | **60.6%** | 58.7% |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Acquisition cost ratio | &nbsp;&nbsp;&nbsp;&nbsp;Acquisition cost ratio | **13.3%** | 15.0% |  | **13.5%** | 14.5% |  |
| &nbsp;&nbsp;&nbsp;&nbsp;General, administrative and corporate expense ratio | &nbsp;&nbsp;&nbsp;&nbsp;General, administrative and corporate expense ratio | **15.6%** | 14.1% |  | **16.7%** | 14.4% |  |
| Expense ratio | Expense ratio | **28.9%** | 29.1% |  | **30.2%** | 28.9% |  |
| Combined ratio | Combined ratio | **85.1%** | 88.7% |  | **90.8%** | 87.6% |  |
| Adjusted combined ratio <sup>(1)</sup> | Adjusted combined ratio <sup>(1)</sup> | **84.3%** | 86.7% |  | **89.7%** | 86.5% |  |
| ***Shareholders' Return Metrics*** | ***Shareholders' Return Metrics*** |  |  |  |  |  |  |
| Shareholders' equity, excluding preference shares | Shareholders' equity, excluding preference shares | $**2645.8** | $2116.6 | 25.0% | $**2645.8** | $2116.6 | 25.0% |
| Shareholders' equity, excluding AOCI and preference shares <sup>(2)</sup> | Shareholders' equity, excluding AOCI and preference shares <sup>(2)</sup> | $**2879.5** | $2533.8 | 13.6% | $**2879.5** | $2533.8 | 13.6% |
| Annualized operating income return on average equity | Annualized operating income return on average equity | **17.2%** | 18.1% |  | **12.8%** | 18.7% |  |
| ***Earnings Per Share*** | ***Earnings Per Share*** |  |  |  |  |  |  |
| Basic earnings per share | Basic earnings per share |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp; Net income available to ordinary shareholders | &nbsp;&nbsp;&nbsp; Net income available to ordinary shareholders | $**0.39** | $0.61 | (35.9)% | $**0.61** | $1.69 | (63.9)% |
| &nbsp;&nbsp;&nbsp; Operating income | &nbsp;&nbsp;&nbsp; Operating income | $**1.22** | $1.07 | 13.5% | $**1.77** | $2.21 | (20.0)% |
| Diluted earnings per share | Diluted earnings per share |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Net income available to ordinary shareholders | &nbsp;&nbsp;&nbsp;&nbsp;Net income available to ordinary shareholders | $**0.39** | $0.61 | (35.9)% | $**0.61** | $1.69 | (63.9)% |
| &nbsp;&nbsp;&nbsp;&nbsp;Operating income | &nbsp;&nbsp;&nbsp;&nbsp;Operating income | $**1.22** | $1.07 | 13.5% | $**1.77** | $2.21 | (20.0)% |
| ***Book Value Per Share*** | ***Book Value Per Share*** |  |  |  |  |  |  |
| Book value per ordinary share | Book value per ordinary share | $**28.81** | $23.30 | 23.6% | $**28.81** | $23.30 | 23.6% |
| Book value per diluted ordinary share | Book value per diluted ordinary share | $**28.78** | $23.30 | 23.5% | $**28.78** | $23.30 | 23.5% |
| Book value per ordinary share, ex AOCI | Book value per ordinary share, ex AOCI | $**31.35** | $27.90 | 12.4% | $**31.35** | $27.90 | 12.4% |
| Book value per diluted ordinary share, ex AOCI | Book value per diluted ordinary share, ex AOCI | $**31.32** | $27.90 | 12.3% | $**31.32** | $27.90 | 12.3% |
| See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. See page 14 for more details regarding Aspen Capital Markets. | See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. See page 14 for more details regarding Aspen Capital Markets. | See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. See page 14 for more details regarding Aspen Capital Markets. | See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. See page 14 for more details regarding Aspen Capital Markets. | See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. See page 14 for more details regarding Aspen Capital Markets. | See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. See page 14 for more details regarding Aspen Capital Markets. | See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. See page 14 for more details regarding Aspen Capital Markets. | See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. See page 14 for more details regarding Aspen Capital Markets. |
| (1) Adjusted underwriting income and adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract.  | (1) Adjusted underwriting income and adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract.  | (1) Adjusted underwriting income and adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract.  | (1) Adjusted underwriting income and adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract.  | (1) Adjusted underwriting income and adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract.  | (1) Adjusted underwriting income and adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract.  | (1) Adjusted underwriting income and adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract.  | (1) Adjusted underwriting income and adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract.  |
| (2) Accumulated other comprehensive income "AOCI". | (2) Accumulated other comprehensive income "AOCI". | (2) Accumulated other comprehensive income "AOCI". | (2) Accumulated other comprehensive income "AOCI". | (2) Accumulated other comprehensive income "AOCI". | (2) Accumulated other comprehensive income "AOCI". | (2) Accumulated other comprehensive income "AOCI". |  |

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3&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

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| | | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Consolidated Statements of Operations - Quarterly Results | Consolidated Statements of Operations - Quarterly Results | Consolidated Statements of Operations - Quarterly Results | Consolidated Statements of Operations - Quarterly Results | Consolidated Statements of Operations - Quarterly Results | Consolidated Statements of Operations - Quarterly Results |  |
| **(in US$ millions except for percentages)** | **(in US$ millions except for percentages)** | **Q2 2025** | **Q1 2025** | **Q4 2024** | **Q3 2024** | **Q2 2024** | **Q1 2024** |
| UNDERWRITING REVENUES | UNDERWRITING REVENUES |  |  |  |  |  |  |
| Gross written premiums | Gross written premiums | $**1238.9** | $1287.2 | $1010.7 | $1116.8 | $1250.4 | $1231.4 |
| Premiums ceded | Premiums ceded | **(523.4)** | (535.5) | (293.7) | (443.2) | (439.3) | (490.5) |
| Net written premiums | Net written premiums | **715.5** | 751.7 | 717.0 | 673.6 | 811.1 | 740.9 |
| Change in unearned premiums | Change in unearned premiums | **(40.6)** | (49.0) | 103.3 | 24.7 | (105.7) | (75.2) |
| Net earned premiums | Net earned premiums | **674.9** | 702.7 | 820.3 | 698.3 | 705.4 | 665.7 |
| UNDERWRITING EXPENSES | UNDERWRITING EXPENSES |  |  |  |  |  |  |
| Losses and loss adjustment expenses | Losses and loss adjustment expenses | **(379.1)** | (455.3) | (438.9) | (474.2) | (420.2) | (384.5) |
| Acquisition costs | Acquisition costs | **(90.0)** | (95.7) | (130.0) | (91.7) | (105.6) | (92.9) |
| General and administrative expenses | General and administrative expenses | **(105.4)** | (124.5) | (108.4) | (99.4) | (99.3) | (98.8) |
| Total underwriting expenses | Total underwriting expenses | **(574.5)** | (675.5) | (677.3) | (665.3) | (625.1) | (576.2) |
| Underwriting income | Underwriting income | **100.4** | 27.2 | 143.0 | 33.0 | 80.3 | 89.5 |
| Net investment income | Net investment income | **80.5** | 75.9 | 79.1 | 79.6 | 82.5 | 76.8 |
| Interest expense <sup>(1)</sup> | Interest expense <sup>(1)</sup> | **(8.9)** | (9.1) | (11.1) | (20.9) | (14.0) | (16.1) |
| Corporate and other expenses | Corporate and other expenses | **(25.4)** | (25.4) | (14.0) | (18.6) | (39.0) | (25.7) |
| Non-operating expenses <sup>(2)</sup> | Non-operating expenses <sup>(2)</sup> | **(47.3)** | (8.3) | (10.6) | (7.6) | (5.5) | (6.2) |
| Net realized and unrealized foreign exchange (losses)/gains <sup>(3)</sup> | Net realized and unrealized foreign exchange (losses)/gains <sup>(3)</sup> | **(31.9)** | (12.9) | 36.6 | (8.5) | 1.9 | 9.1 |
| Net realized and unrealized investment (losses)/gains | Net realized and unrealized investment (losses)/gains | **(9.3)** | (0.3) | (28.5) | 6.1 | (26.1) | (1.0) |
| INCOME BEFORE INCOME TAX | INCOME BEFORE INCOME TAX | **58.1** | 47.1 | 194.5 | 63.1 | 80.1 | 126.4 |
| Income tax (expense)/benefit | Income tax (expense)/benefit | **(11.6)** | (10.3) | 54.1 | (6.4) | (11.1) | (14.6) |
| NET INCOME AFTER TAX, attributable to Aspen Insurance Holdings Limited | NET INCOME AFTER TAX, attributable to Aspen Insurance Holdings Limited | **46.5** | 36.8 | 248.6 | 56.7 | 69.0 | 111.8 |
| Dividends paid on preference shares | Dividends paid on preference shares | **(11.0)** | (12.5) | (13.8) | (13.8) | (13.7) | (13.6) |
| Preference share redemption costs | Preference share redemption costs | **—** | (4.4) |  |  |  |  |
| Income available to Aspen Insurance Holdings Limited's ordinary shareholders | Income available to Aspen Insurance Holdings Limited's ordinary shareholders | $**35.5** | $19.9 | $234.8 | $42.9 | $55.3 | $98.2 |
| Loss ratio | Loss ratio | **56.2%** | 64.8% | 53.5% | 67.9% | 59.6% | 57.8% |
| &nbsp;&nbsp;&nbsp;&nbsp;Acquisition cost ratio | &nbsp;&nbsp;&nbsp;&nbsp;Acquisition cost ratio | **13.3%** | 13.6% | 15.8% | 13.1% | 15.0% | 14.0% |
| &nbsp;&nbsp;&nbsp;&nbsp;General and administrative expense ratio | &nbsp;&nbsp;&nbsp;&nbsp;General and administrative expense ratio | **15.6%** | 17.7% | 13.2% | 14.2% | 14.1% | 14.8% |
| Expense ratio | Expense ratio | **28.9%** | 31.3% | 29.0% | 27.3% | 29.1% | 28.8% |
| Combined ratio | Combined ratio | **85.1%** | 96.1% | 82.5% | 95.2% | 88.7% | 86.6% |
| Adjusted combined ratio <sup>(4)</sup> | Adjusted combined ratio <sup>(4)</sup> | **84.3%** | 94.8% | 83.4% | 91.5% | 86.7% | 86.3% |
| See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. | See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. | See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. | See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. | See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. | See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. | See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. | See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. |

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(1) Interest expense includes interest on funds withheld related to the LPT contract.

(2) Non-operating expenses in Q2 2025 includes expenses in relation to replacement awards granted on the successful completion of the IPO, certain consulting fees, non-recurring transformation activities, and other non-recurring costs.

(3) Includes the net realized and unrealized (losses)/gains from foreign exchange contracts.

(4) Adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract. Adjusted combined ratio represents the performance of our business for accident years 2020 onwards, which we believe is useful to management and investors because it reflects the underlying underwriting performance of the ongoing portfolio.

4&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

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| | | | |
|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Consolidated Statements of Operations - Year To Date Results | Consolidated Statements of Operations - Year To Date Results |  |
| **(in US$ millions except for percentages)** | **(in US$ millions except for percentages)** | **Six Months Ended June 30,** | **Six Months Ended June 30,** |
|  |  | **2025** | **2024** |
| UNDERWRITING REVENUES | UNDERWRITING REVENUES |  |  |
| Gross written premiums | Gross written premiums | $**2526.1** | $2481.8 |
| Premiums ceded | Premiums ceded | **(1058.9)** | (929.8) |
| Net written premiums | Net written premiums | **1467.2** | 1552.0 |
| Change in unearned premiums | Change in unearned premiums | **(89.6)** | (180.9) |
| Net earned premiums | Net earned premiums | **1377.6** | 1371.1 |
| UNDERWRITING EXPENSES | UNDERWRITING EXPENSES |  |  |
| Losses and loss adjustment expenses | Losses and loss adjustment expenses | **(834.4)** | (804.7) |
| Acquisition costs | Acquisition costs | **(185.7)** | (198.5) |
| General and administrative expenses | General and administrative expenses | **(229.9)** | (198.1) |
| Total underwriting expenses | Total underwriting expenses | **(1250.0)** | (1201.3) |
| Underwriting income | Underwriting income | **127.6** | 169.8 |
| Net investment income | Net investment income | **156.4** | 159.3 |
| Interest expense <sup>(1)</sup> | Interest expense <sup>(1)</sup> | **(18.0)** | (30.1) |
| Corporate and other expenses | Corporate and other expenses | **(50.8)** | (64.7) |
| Non-operating expenses <sup>(2)</sup> | Non-operating expenses <sup>(2)</sup> | **(55.6)** | (11.7) |
| Net realized and unrealized foreign exchange (losses)/gains <sup>(3)</sup> | Net realized and unrealized foreign exchange (losses)/gains <sup>(3)</sup> | **(44.8)** | 11.0 |
| Net realized and unrealized investment (losses) | Net realized and unrealized investment (losses) | **(9.6)** | (27.1) |
| INCOME BEFORE INCOME TAX  | INCOME BEFORE INCOME TAX  | **105.2** | 206.5 |
| Income tax expense | Income tax expense | **(21.9)** | (25.7) |
| NET INCOME AFTER TAX, attributable to Aspen Insurance Holdings Limited | NET INCOME AFTER TAX, attributable to Aspen Insurance Holdings Limited | **83.3** | 180.8 |
| Dividends paid on preference shares | Dividends paid on preference shares | **(23.5)** | (27.3) |
| Preference share redemption costs | Preference share redemption costs | **(4.4)** |  |
| Income available to Aspen Insurance Holdings Limited's ordinary shareholders | Income available to Aspen Insurance Holdings Limited's ordinary shareholders | $**55.4** | $153.5 |
| Loss ratio | Loss ratio | **60.6%** | 58.7% |
| Acquisition cost ratio | Acquisition cost ratio | **13.5%** | 14.5% |
| General and administrative expense ratio | General and administrative expense ratio | **16.7%** | 14.4% |
| Expense ratio | Expense ratio | **30.2%** | 28.9% |
| Combined ratio | Combined ratio | **90.8%** | 87.6% |
| Adjusted combined ratio <sup>(4)</sup> | Adjusted combined ratio <sup>(4)</sup> | **89.7%** | 86.5% |
| See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. | See pages 9-11 and 24-26 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. |  |  |

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(1) Interest expense includes interest on deferred premium payments for the LPT contract.

(2) Non-operating expenses in the six months ended June 30, 2025 includes expenses in relation to replacement awards granted on the successful completion of the IPO, certain consulting fees, non-recurring transformation activities, and other non-recurring costs.

(3) Includes the net realized and unrealized gains/(losses) from foreign exchange contracts.

(4) Adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract. Adjusted combined ratio represents the performance of our business for accident years 2020 onwards, which we believe is useful to management and investors because it reflects the underlying underwriting performance of the ongoing portfolio.

5&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

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| | | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Condensed Consolidated Balance Sheets | Condensed Consolidated Balance Sheets | Condensed Consolidated Balance Sheets | Condensed Consolidated Balance Sheets | Condensed Consolidated Balance Sheets |  |  |
| **(in US$ millions except for per share amounts)** | **(in US$ millions except for per share amounts)** | **June 30, <br>2025** | **March 31, <br>2025** | **December 31, <br>2024** | **September 30, <br>2024** | **June 30, <br>2024** | **March 31, <br>2024** |
|  |  | **June 30, <br>2025** | **March 31, <br>2025** | **December 31, <br>2024** | **September 30, <br>2024** | **June 30, <br>2024** | **March 31, <br>2024** |
| ASSETS | ASSETS |  |  |  |  |  |  |
| Investments | Investments | $**6984.6** | $6986.8 | $6741.5 | $6487.1 | $6436.4 | $6746.8 |
| Cash and cash equivalents | Cash and cash equivalents | **939.0** | 845.2 | 914.2 | 1244.9 | 921.2 | 743.4 |
| Unpaid losses recoverable from reinsurers <sup>(1)</sup> | Unpaid losses recoverable from reinsurers <sup>(1)</sup> | **4273.9** | 4228.4 | 4172.0 | 4431.3 | 4275.3 | 4389.5 |
| Ceded unearned premiums | Ceded unearned premiums | **1102.2** | 1019.0 | 901.7 | 1001.0 | 962.1 | 872.9 |
| Underwriting premiums receivable | Underwriting premiums receivable | **1921.8** | 1728.3 | 1617.0 | 1819.1 | 1838.4 | 1667.0 |
| Deferred acquisition costs | Deferred acquisition costs | **364.7** | 350.8 | 322.1 | 361.0 | 340.9 | 331.3 |
| Derivative assets | Derivative assets | **28.1** | 19.2 | 17.0 | 26.0 | 5.6 | 3.4 |
| Deferred tax assets | Deferred tax assets | **369.5** | 384.9 | 397.9 | 304.4 | 310.0 | 311.2 |
| Other assets | Other assets | **408.3** | 380.4 | 645.2 | 407.8 | 380.0 | 360.7 |
| Intangible assets and goodwill | Intangible assets and goodwill | **19.9** | 19.9 | 19.9 | 21.7 | 21.7 | 21.7 |
| &nbsp;&nbsp;&nbsp;&nbsp;Total assets | &nbsp;&nbsp;&nbsp;&nbsp;Total assets | $**16412.0** | $15962.9 | $15748.5 | $16104.3 | $15491.6 | $15447.9 |
| LIABILITIES | LIABILITIES |  |  |  |  |  |  |
| Reserves for losses and loss adjustment expenses | Reserves for losses and loss adjustment expenses | $**8632.2** | $8448.9 | $8122.6 | $8201.3 | $7833.0 | $7796.0 |
| Unearned premiums | Unearned premiums | **2933.0** | 2812.0 | 2645.8 | 2849.8 | 2834.6 | 2640.5 |
| Reinsurance premiums | Reinsurance premiums | **856.4** | 858.6 | 901.1 | 1309.7 | 1310.4 | 1390.4 |
| Other payables | Other payables | **325.9** | 348.9 | 357.6 | 412.6 | 332.0 | 352.8 |
| Derivative liabilities | Derivative liabilities | **22.4** | 4.0 | 49.5 | 7.7 | 11.5 | 20.2 |
| Long-term debt <sup>(4)</sup> | Long-term debt <sup>(4)</sup> | **296.4** | 300.0 | 300.0 | 300.0 | 300.0 | 300.0 |
| &nbsp;&nbsp;&nbsp;&nbsp;Total liabilities | &nbsp;&nbsp;&nbsp;&nbsp;Total liabilities | **13066.3** | 12772.4 | 12376.6 | 13081.1 | 12621.5 | 12499.9 |
| SHAREHOLDERS' EQUITY | SHAREHOLDERS' EQUITY |  |  |  |  |  |  |
| Ordinary shares | Ordinary shares | **0.1** | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 |
| Preference shares <sup>(2) (3)</sup> | Preference shares <sup>(2) (3)</sup> | **699.9** | 699.9 | 970.5 | 753.5 | 753.5 | 753.5 |
| Additional paid-in capital | Additional paid-in capital | **794.3** | 761.7 | 761.7 | 761.7 | 761.7 | 761.7 |
| Retained earnings <sup>(3)</sup> | Retained earnings <sup>(3)</sup> | **2085.1** | 2049.6 | 2029.7 | 1794.9 | 1772.0 | 1866.7 |
| Accumulated other comprehensive loss, net of taxes | Accumulated other comprehensive loss, net of taxes | **(233.7)** | (320.8) | (390.1) | (287.0) | (417.2) | (434.0) |
| &nbsp;&nbsp;&nbsp;&nbsp;Total shareholders' equity | &nbsp;&nbsp;&nbsp;&nbsp;Total shareholders' equity | **3345.7** | 3190.5 | 3371.9 | 3023.2 | 2870.1 | 2948.0 |
| &nbsp;&nbsp;&nbsp;&nbsp;Total liabilities and shareholders' equity | &nbsp;&nbsp;&nbsp;&nbsp;Total liabilities and shareholders' equity | $**16412.0** | $15962.9 | $15748.5 | $16104.3 | $15491.6 | $15447.9 |

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(1) Unpaid losses recoverable from reinsurers includes ceded reserves on the LPT of $1.2 billion for Q2 2025, $1.2 billion for Q1 2025, $1.2 billion for Q4 2024, $1.4 billion for Q3 2024, $1.4 billion for Q2 2024 and $1.5 billion for Q1 2024.

(2) Includes preference shares with a total value as measured by their liquidation preferences of $725 million less issue expenses of $25.1 million as at Q2 2025 and Q1 2025, $1,000 million less issue expenses of $29.5 million as at Q4 2024, and $775 million less issue expenses of $21.5 million as at Q3 2024 and prior periods shown above.

(3) On January 1, 2025, the Company redeemed its 5.950% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares (the "AHL PRC Shares"), representing an aggregate amount of $275 million, plus a reclassification of $4.4 million, between retained earnings and preference shares which represents the difference between the capital raised upon issuance, net of issuance costs and the final redemption cost.

(4) During Q2 2025, the Company issued $300 million of Senior Notes at a coupon rate of 5.75%. The proceeds were used to pay down the $300 million term loan.

6&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

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| | | | | | |
|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Earnings Per Ordinary Share | Earnings Per Ordinary Share | Earnings Per Ordinary Share | Earnings Per Ordinary Share |  |
|  |  | **Three Months Ended** | **Three Months Ended** | **Six Months Ended** | **Six Months Ended** |
| **(in US$ millions except for number of shares and per share amounts)** | **(in US$ millions except for number of shares and per share amounts)** | **June 30, 2025** | **June 30, 2024** | **June 30, 2025** | **June 30, 2024** |
| Basic earnings per ordinary share | Basic earnings per ordinary share |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Net income available to ordinary shareholders | &nbsp;&nbsp;&nbsp;&nbsp;Net income available to ordinary shareholders | $**0.39** | $0.61 | $**0.61** | $1.69 |
| &nbsp;&nbsp;&nbsp;&nbsp;Operating income | &nbsp;&nbsp;&nbsp;&nbsp;Operating income | $**1.22** | $1.07 | $**1.77** | $2.21 |
| Diluted earnings per ordinary share | Diluted earnings per ordinary share |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Net income available to ordinary shareholders | &nbsp;&nbsp;&nbsp;&nbsp;Net income available to ordinary shareholders | $**0.39** | $0.61 | $**0.61** | $1.69 |
| &nbsp;&nbsp;&nbsp;&nbsp;Operating income | &nbsp;&nbsp;&nbsp;&nbsp;Operating income | $**1.22** | $1.07 | $**1.77** | $2.21 |
| Weighted average number of ordinary shares outstanding (in millions) | Weighted average number of ordinary shares outstanding (in millions) | **90.977** | 90.833 | **90.906** | 90.833 |
| Weighted average number of ordinary shares outstanding and dilutive potential ordinary shares (in millions) | Weighted average number of ordinary shares outstanding and dilutive potential ordinary shares (in millions) | **91.042** | 90.833 | **90.938** | 90.833 |
| The dilutive effect of options has been calculated using the treasury stock method. The treasury stock method assumes that the proceeds received from the exercise of options will be used to purchase the Company's ordinary shares at the average market price during the period of calculation. | The dilutive effect of options has been calculated using the treasury stock method. The treasury stock method assumes that the proceeds received from the exercise of options will be used to purchase the Company's ordinary shares at the average market price during the period of calculation. | The dilutive effect of options has been calculated using the treasury stock method. The treasury stock method assumes that the proceeds received from the exercise of options will be used to purchase the Company's ordinary shares at the average market price during the period of calculation. | The dilutive effect of options has been calculated using the treasury stock method. The treasury stock method assumes that the proceeds received from the exercise of options will be used to purchase the Company's ordinary shares at the average market price during the period of calculation. | The dilutive effect of options has been calculated using the treasury stock method. The treasury stock method assumes that the proceeds received from the exercise of options will be used to purchase the Company's ordinary shares at the average market price during the period of calculation. | The dilutive effect of options has been calculated using the treasury stock method. The treasury stock method assumes that the proceeds received from the exercise of options will be used to purchase the Company's ordinary shares at the average market price during the period of calculation. |

---

7&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

---

| | | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Book Value Per Ordinary Share | Book Value Per Ordinary Share | Book Value Per Ordinary Share | Book Value Per Ordinary Share | Book Value Per Ordinary Share |  |  |
| **(in US$ millions except for per share amounts and percentages)** | **(in US$ millions except for per share amounts and percentages)** | **June 30, <br>2025** | **March 31, 2025** | **December 31, <br>2024** | **September 30, 2024** | **June 30, <br>2024** | **March 31, <br>2024** |
| Total shareholders' equity | Total shareholders' equity | $**3345.7** | $3190.5 | $3371.9 | $3023.2 | $2870.1 | $2948.0 |
| Less: preference shares <sup>(1)</sup> | Less: preference shares <sup>(1)</sup> | **(699.9)** | (699.9) | (970.5) | (753.5) | (753.5) | (753.5) |
| Ordinary shareholders' equity | Ordinary shareholders' equity | $**2645.8** | $2490.6 | $2401.4 | $2269.7 | $2116.6 | $2194.5 |
| Less: AOCI | Less: AOCI | **233.7** | 320.8 | 390.1 | 287.0 | 417.2 | 434.0 |
| Ordinary shareholders' equity, ex AOCI | Ordinary shareholders' equity, ex AOCI | $**2879.5** | $2811.4 | $2791.5 | $2556.7 | $2533.8 | $2628.5 |
| Ordinary shares outstanding (in millions) as at period end | Ordinary shares outstanding (in millions) as at period end | **91.838** | 90.833 | 90.833 | 90.833 | 90.833 | 90.833 |
| Diluted shares outstanding (in millions) as at period end | Diluted shares outstanding (in millions) as at period end | **91.948** | 90.833 | 90.833 | 90.833 | 90.833 | 90.833 |
| Book value per ordinary share | Book value per ordinary share | $**28.81** | $27.42 | $26.44 | $24.99 | $23.30 | $24.16 |
| Book value per diluted ordinary share | Book value per diluted ordinary share | $**28.78** | $27.42 | $26.44 | $24.99 | $23.30 | $24.16 |
| Book value per ordinary share, ex AOCI | Book value per ordinary share, ex AOCI | $**31.35** | $30.95 | $30.73 | $28.15 | $27.90 | $28.94 |
| Book value per diluted ordinary share, ex AOCI | Book value per diluted ordinary share, ex AOCI | $**31.32** | $30.95 | $30.73 | $28.15 | $27.90 | $28.94 |

---

<sup>(1)</sup> Includes preference share with a total value as measured by their liquidation preferences of $725 million less issue expenses of $25.1 million as at Q2 2025 and Q1 2025, $1,000 million less issue expenses of $29.5 million as at Q4 2024, and $775 million less issue expenses of $21.5 million as at Q3 2024 and prior periods shown above.

8&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

---

| | | | | | |
|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Return On Average Equity | Return On Average Equity | Return On Average Equity | Return On Average Equity |  |
|  |  | **Three Months Ended** | **Three Months Ended** | **Six Months Ended** | **Six Months Ended** |
| **(in US$ millions except for percentages)** | **(in US$ millions except for percentages)** | **June 30, 2025** | **June 30, 2024** | **June 30, 2025** | **June 30, 2024** |
| Average shareholders' equity | Average shareholders' equity | $**3268.1** | $2909.1 | $**3302.7** | $2908.9 |
| Average preference shares <sup>(1)</sup> | Average preference shares <sup>(1)</sup> | **(699.9)** | (753.5) | **(790.1)** | (753.5) |
| Average ordinary shareholders' equity | Average ordinary shareholders' equity | $**2568.2** | $2155.6 | $**2512.6** | $2155.4 |
| Return on average equity: | Return on average equity: |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Net income available to ordinary shareholders | &nbsp;&nbsp;&nbsp;&nbsp;Net income available to ordinary shareholders | **1.4%** | 2.6% | **2.2%** | 7.1% |
| &nbsp;&nbsp;&nbsp;&nbsp;Operating income | &nbsp;&nbsp;&nbsp;&nbsp;Operating income | **4.3%** | 4.5% | **6.4%** | 9.3% |
| Annualized return on average equity: | Annualized return on average equity: |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Net income available to ordinary shareholders | &nbsp;&nbsp;&nbsp;&nbsp;Net income available to ordinary shareholders | **5.6%** | 10.3% | **4.4%** | 14.2% |
| &nbsp;&nbsp;&nbsp;&nbsp;Operating income | &nbsp;&nbsp;&nbsp;&nbsp;Operating income | **17.2%** | 18.1% | **12.8%** | 18.7% |

---

<sup>(1)</sup> Includes preference shares with a total value as measured by their liquidation preferences of $725 million less issue expenses of $25.1 million as at the current period, and $775 million less issue expenses of $21.5 million for the comparative periods shown above.

9&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

---

| | | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Consolidated Underwriting Results by Operating Segment | Consolidated Underwriting Results by Operating Segment | Consolidated Underwriting Results by Operating Segment | Consolidated Underwriting Results by Operating Segment | Consolidated Underwriting Results by Operating Segment | Consolidated Underwriting Results by Operating Segment |  |
|  |  | **Three Months Ended June 30, 2025** | **Three Months Ended June 30, 2025** | **Three Months Ended June 30, 2025** | **Three Months Ended June 30, 2024** | **Three Months Ended June 30, 2024** | **Three Months Ended June 30, 2024** |
| **(in US$ millions except for percentages)** | **(in US$ millions except for percentages)** | **Insurance** | **Reinsurance** | **Total** | **Insurance** | **Reinsurance** | **Total** |
| Gross written premiums | Gross written premiums | $**693.5** | $**545.4** | $**1238.9** | $684.2 | $566.2 | $1250.4 |
| Net written premiums | Net written premiums | **390.4** | **325.1** | **715.5** | 425.3 | 385.8 | 811.1 |
| Gross earned premiums | Gross earned premiums | **672.7** | **443.5** | **1116.2** | 620.9 | 434.3 | 1055.2 |
| Net earned premiums | Net earned premiums | **395.8** | **279.1** | **674.9** | 378.3 | 327.1 | 705.4 |
| Losses and loss adjustment expenses | Losses and loss adjustment expenses | **(239.3)** | **(139.8)** | **(379.1)** | (231.2) | (189.0) | (420.2) |
| Acquisition costs | Acquisition costs | **(45.2)** | **(44.8)** | **(90.0)** | (48.2) | (57.4) | (105.6) |
| General and administrative expenses | General and administrative expenses | **(67.1)** | **(38.3)** | **(105.4)** | (63.4) | (35.9) | (99.3) |
| Underwriting income | Underwriting income | $**44.2** | $**56.2** | $**100.4** | $35.5 | $44.8 | $80.3 |
| Net investment income | Net investment income |  |  | **80.5** |  |  | 82.5 |
| Net realized and unrealized investment (losses) | Net realized and unrealized investment (losses) |  |  | **(9.3)** |  |  | (26.1) |
| Corporate and other expenses | Corporate and other expenses |  |  | **(25.4)** |  |  | (39.0) |
| Non-operating expenses <sup>(1)</sup> | Non-operating expenses <sup>(1)</sup> |  |  | **(47.3)** |  |  | (5.5) |
| Interest expense <sup>(2)</sup> | Interest expense <sup>(2)</sup> |  |  | **(8.9)** |  |  | (14.0) |
| Net realized and unrealized foreign exchange (losses)/gains <sup>(3)</sup> | Net realized and unrealized foreign exchange (losses)/gains <sup>(3)</sup> |  |  | **(31.9)** |  |  | 1.9 |
| Income before income tax  | Income before income tax  |  |  | $**58.1** |  |  | $80.1 |
| Income tax expense | Income tax expense |  |  | **(11.6)** |  |  | (11.1) |
| **Net income** | **Net income** |  |  | $**46.5** |  |  | $69.0 |
| **Ratios** | **Ratios** |  |  |  |  |  |  |
| Current accident year loss ratio, excluding catastrophe losses | Current accident year loss ratio, excluding catastrophe losses | **56.8%** | **48.5%** | **53.4%** | 60.7% | 41.6% | 51.9% |
| Catastrophe losses | Catastrophe losses | **2.9%** | **4.4%** | **3.5%** | 1.3% | 13.2% | 6.8% |
| Current year loss ratio | Current year loss ratio | **59.7%** | **52.9%** | **56.9%** | 62.0% | 54.8% | 58.7% |
| Prior year reserve development, post LPT years | Prior year reserve development, post LPT years | **(0.2)%** | **(3.5)%** | **(1.5)%** | (0.9)% | (1.1)% | (1.1)% |
| Adjusted loss ratio | Adjusted loss ratio | **59.5%** | **49.4%** | **55.4%** | 61.1% | 53.7% | 57.6% |
| Impact of the LPT | Impact of the LPT | **1.0%** | **0.7%** | **0.8%** | —% | 4.1% | 2.0% |
| Loss ratio | Loss ratio | **60.5%** | **50.1%** | **56.2%** | 61.1% | 57.8% | 59.6% |
| Acquisition cost ratio | Acquisition cost ratio | **11.4%** | **16.1%** | **13.3%** | 12.7% | 17.5% | 15.0% |
| General and administrative expense ratio | General and administrative expense ratio | **17.0%** | **13.7%** | **15.6%** | 16.8% | 11.0% | 14.1% |
| Expense ratio | Expense ratio | **28.4%** | **29.8%** | **28.9%** | 29.5% | 28.5% | 29.1% |
| Combined ratio | Combined ratio | **88.9%** | **79.9%** | **85.1%** | 90.6% | 86.3% | 88.7% |
| Adjusted combined ratio <sup>(4)</sup> | Adjusted combined ratio <sup>(4)</sup> | **87.9%** | **79.2%** | **84.3%** | 90.6% | 82.2% | 86.7% |

---

(1) Non-operating expenses for the three months ended June 30, 2025 includes expenses in relation to replacement awards granted on the successful completion of the IPO, certain consulting fees, non-recurring transformation activities, and other non-recurring costs.

(2) Interest expense includes interest on deferred premium payments for the LPT contract.

(3) Includes the net realized and unrealized gains/(losses) from foreign exchange contracts.

(4) Adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract. Adjusted combined ratio represents the performance of our business for accident years 2020 onwards, which we believe is useful to management and investors because it reflects the underlying underwriting performance of the ongoing portfolio.

10&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

---

| | | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Consolidated Underwriting Results by Operating Segment | Consolidated Underwriting Results by Operating Segment | Consolidated Underwriting Results by Operating Segment | Consolidated Underwriting Results by Operating Segment | Consolidated Underwriting Results by Operating Segment | Consolidated Underwriting Results by Operating Segment |  |
|  |  | **Six Months Ended June 30, 2025** | **Six Months Ended June 30, 2025** | **Six Months Ended June 30, 2025** | **Six Months Ended June 30, 2024** | **Six Months Ended June 30, 2024** | **Six Months Ended June 30, 2024** |
| **(in US$ millions except for percentages)** | **(in US$ millions except for percentages)** | **Insurance** | **Reinsurance** | **Total** | **Insurance** | **Reinsurance** | **Total** |
| Gross written premiums | Gross written premiums | $**1380.0** | $**1146.1** | $**2526.1** | $1301.2 | $1180.6 | $2481.8 |
| Net written premiums | Net written premiums | **768.3** | **698.9** | **1467.2** | 763.7 | 788.3 | 1552.0 |
| Gross earned premiums | Gross earned premiums | **1348.3** | **888.4** | **2236.7** | 1223.7 | 848.5 | 2072.2 |
| Net earned premiums | Net earned premiums | **799.5** | **578.1** | **1377.6** | 739.3 | 631.8 | 1371.1 |
| Losses and loss adjustment expenses | Losses and loss adjustment expenses | **(487.2)** | **(347.2)** | **(834.4)** | (460.3) | (344.4) | (804.7) |
| Acquisition costs | Acquisition costs | **(95.3)** | **(90.4)** | **(185.7)** | (83.9) | (114.6) | (198.5) |
| General and administrative expenses | General and administrative expenses | **(141.6)** | **(88.3)** | **(229.9)** | (125.6) | (72.5) | (198.1) |
| Underwriting income | Underwriting income | $**75.4** | $**52.2** | $**127.6** | $69.5 | $100.3 | $169.8 |
| Net investment income | Net investment income |  |  | **156.4** |  |  | 159.3 |
| Net realized and unrealized investment (losses) | Net realized and unrealized investment (losses) |  |  | **(9.6)** |  |  | (27.1) |
| Corporate and other expenses | Corporate and other expenses |  |  | **(50.8)** |  |  | (64.7) |
| Non-operating expenses <sup>(1)</sup> | Non-operating expenses <sup>(1)</sup> |  |  | **(55.6)** |  |  | (11.7) |
| Interest expense <sup>(2)</sup> | Interest expense <sup>(2)</sup> |  |  | **(18.0)** |  |  | (30.1) |
| Net realized and unrealized foreign exchange (losses)/gains <sup>(3)</sup> | Net realized and unrealized foreign exchange (losses)/gains <sup>(3)</sup> |  |  | **(44.8)** |  |  | 11.0 |
| Income before income tax | Income before income tax |  |  | **105.2** |  |  | 206.5 |
| Income tax expense | Income tax expense |  |  | **(21.9)** |  |  | (25.7) |
| **Net income** | **Net income** |  |  | $**83.3** |  |  | $180.8 |
| **Ratios** | **Ratios** |  |  |  |  |  |  |
| Current accident year loss ratio, excluding catastrophe losses | Current accident year loss ratio, excluding catastrophe losses | **56.7%** | **46.8%** | **52.6%** | 61.2% | 41.9% | 52.2% |
| Catastrophe losses | Catastrophe losses | **3.5%** | **15.0%** | **8.3%** | 2.2% | 10.1% | 5.9% |
| Current year loss ratio | Current year loss ratio | **60.2%** | **61.8%** | **60.9%** | 63.4% | 52.0% | 58.1% |
| Prior year reserve development,post LPT years | Prior year reserve development,post LPT years | **(0.3)%** | **(2.9)%** | **(1.4)%** | (0.5)% | (0.6)% | (0.5)% |
| Adjusted loss ratio | Adjusted loss ratio | **59.9%** | **58.9%** | **59.5%** | 62.9% | 51.4% | 57.6% |
| Impact of the LPT | Impact of the LPT | **1.0%** | **1.2%** | **1.1%** | (0.6)% | 3.1% | 1.1% |
| Loss ratio | Loss ratio | **60.9%** | **60.1%** | **60.6%** | 62.3% | 54.5% | 58.7% |
| Acquisition cost ratio | Acquisition cost ratio | **11.9%** | **15.6%** | **13.5%** | 11.3% | 18.1% | 14.5% |
| General and administrative expense ratio | General and administrative expense ratio | **17.7%** | **15.3%** | **16.7%** | 17.0% | 11.5% | 14.4% |
| Expense ratio | Expense ratio | **29.6%** | **30.9%** | **30.2%** | 28.3% | 29.6% | 28.9% |
| Combined ratio | Combined ratio | **90.5%** | **91.0%** | **90.8%** | 90.6% | 84.1% | 87.6% |
| Adjusted combined ratio <sup>(4)</sup> | Adjusted combined ratio <sup>(4)</sup> | **89.5%** | **89.8%** | **89.7%** | 91.2% | 81.0% | 86.5% |

---

(1) Non-operating expenses in the six months ended June 30, 2025 includes expenses in relation to replacement awards granted on the successful completion of the IPO, certain consulting fees, non-recurring transformation activities, and other non-recurring costs.

(2) Interest expense includes interest on deferred premium payments for the LPT contract.

(3) Includes the net realized and unrealized gains/(losses) from foreign exchange contracts.

(4) Adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract. Adjusted combined ratio represents the performance of our business for accident years 2020 onwards, which we believe is useful to management and investors because it reflects the underlying underwriting performance of the ongoing portfolio.

11&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

---

| | | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Insurance Segment - Quarterly Results | Insurance Segment - Quarterly Results | Insurance Segment - Quarterly Results | Insurance Segment - Quarterly Results | Insurance Segment - Quarterly Results | Insurance Segment - Quarterly Results |  |
| **(in US$ millions except for percentages)** | **(in US$ millions except for percentages)** | **Q2 2025** | **Q1 2025** | **Q4 2024** | **Q3 2024** | **Q2 2024** | **Q1 2024** |
| Gross written premiums | Gross written premiums | $**693.5** | $686.5 | $721.7 | $700.6 | $684.2 | $617 |
| Net written premiums | Net written premiums | **390.4** | 377.9 | 493.3 | 409.9 | 425.3 | 338.4 |
| Gross earned premiums | Gross earned premiums | **672.7** | 675.6 | 689.5 | 652.5 | 620.9 | 602.8 |
| Net earned premiums | Net earned premiums | **395.8** | 403.7 | 439.9 | 404.8 | 378.3 | 361.0 |
| Net losses and loss adjustment expenses | Net losses and loss adjustment expenses | **(239.3)** | (247.9) | (250.6) | (265.6) | (231.2) | (229.1) |
| Amortization of deferred policy acquisition costs | Amortization of deferred policy acquisition costs | **(45.2)** | (50.1) | (61.5) | (47.8) | (48.2) | (35.7) |
| General and administrative expenses | General and administrative expenses | **(67.1)** | (74.5) | (80.4) | (58.2) | (63.4) | (62.2) |
| Underwriting income | Underwriting income | $**44.2** | $31.2 | $47.4 | $33.2 | $35.5 | $34.0 |
| **Ratios** | **Ratios** |  |  |  |  |  |  |
| Current accident year loss ratio, excluding catastrophe losses | Current accident year loss ratio, excluding catastrophe losses | **56.8%** | 56.7% | 55.4% | 56.7% | 60.7% | 61.6% |
| Catastrophe losses | Catastrophe losses | **2.9%** | 4.2% | 3.2% | 2.4% | 1.3% | 3.2% |
| Current accident year loss ratio | Current accident year loss ratio | **59.7%** | 60.9% | 58.6% | 59.1% | 62.0% | 64.8% |
| Prior year reserve development ratio, post LPT years | Prior year reserve development ratio, post LPT years | **(0.2)%** | (0.5)% | —% | 1.0% | (0.9)% | —% |
| Adjusted loss ratio | Adjusted loss ratio | **59.5%** | 60.4% | 58.6% | 60.1% | 61.1% | 64.8% |
| Impact of the LPT | Impact of the LPT | **1.0%** | 1.0% | (1.6)% | 5.5% | —% | (1.3)% |
| Loss ratio | Loss ratio | **60.5%** | 61.4% | 57.0% | 65.6% | 61.1% | 63.5% |
| Acquisition cost ratio | Acquisition cost ratio | **11.4%** | 12.4% | 14.0% | 11.8% | 12.7% | 9.9% |
| General and administrative expense ratio | General and administrative expense ratio | **17.0%** | 18.5% | 18.3% | 14.4% | 16.8% | 17.2% |
| Combined ratio | Combined ratio | **88.9%** | 92.3% | 89.3% | 91.8% | 90.6% | 90.6% |
| Adjusted combined ratio <sup>(1)</sup> | Adjusted combined ratio <sup>(1)</sup> | **87.9%** | 91.3% | 90.9% | 86.3% | 90.6% | 91.9% |

---

(1) Adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract. Adjusted combined ratio represents the performance of our business for accident years 2020 onwards, which we believe is useful to management and investors because it reflects the underlying underwriting performance of the ongoing portfolio.

12&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

---

| | | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Reinsurance Segment - Quarterly Results | Reinsurance Segment - Quarterly Results | Reinsurance Segment - Quarterly Results | Reinsurance Segment - Quarterly Results | Reinsurance Segment - Quarterly Results | Reinsurance Segment - Quarterly Results |  |
| **(in US$ millions except for percentages)** | **(in US$ millions except for percentages)** | **Q2 2025** | **Q1 2025** | **Q4 2024** | **Q3 2024** | **Q2 2024** | **Q1 2024** |
| Gross written premiums | Gross written premiums | $**545.4** | $600.7 | $289.0 | $416.2 | $566.2 | $614.4 |
| Net written premiums | Net written premiums | **325.1** | 373.8 | 223.7 | 263.7 | 385.8 | 402.5 |
| Gross earned premiums | Gross earned premiums | **443.5** | 444.9 | 523.9 | 449.7 | 434.3 | 414.2 |
| Net earned premiums | Net earned premiums | **279.1** | 299.0 | 380.4 | 293.5 | 327.1 | 304.7 |
| Net losses and loss adjustment expenses | Net losses and loss adjustment expenses | **(139.8)** | (207.4) | (188.3) | (208.6) | (189.0) | (155.4) |
| Amortization of deferred policy acquisition costs | Amortization of deferred policy acquisition costs | **(44.8)** | (45.6) | (68.5) | (43.9) | (57.4) | (57.2) |
| General and administrative expenses | General and administrative expenses | **(38.3)** | (50.0) | (28.0) | (41.2) | (35.9) | (36.6) |
| Underwriting income/(loss) | Underwriting income/(loss) | $**56.2** | $(4.0) | $95.6 | $(0.2) | $44.8 | $55.5 |
| **Ratios** | **Ratios** |  |  |  |  |  |  |
| Current accident year loss ratio, excluding catastrophe losses | Current accident year loss ratio, excluding catastrophe losses | **48.5%** | 45.3% | 38.9% | 53.8% | 41.6% | 42.2% |
| Catastrophe losses | Catastrophe losses | **4.4%** | 24.9% | 9.9% | 15.4% | 13.2% | 6.8% |
| Current accident year loss ratio | Current accident year loss ratio | **52.9%** | 70.2% | 48.8% | 69.2% | 54.8% | 49.0% |
| Prior year reserve development ratio, post LPT years | Prior year reserve development ratio, post LPT years | **(3.5)%** | (2.4)% | 0.5% | 0.3% | (1.1)% | —% |
| Adjusted loss ratio | Adjusted loss ratio | **49.4%** | 67.8% | 49.3% | 69.5% | 53.7% | 49.0% |
| Impact of the LPT | Impact of the LPT | **0.7%** | 1.6% | 0.2% | 1.6% | 4.1% | 2.0% |
| Loss ratio | Loss ratio | **50.1%** | 69.4% | 49.5% | 71.1% | 57.8% | 51.0% |
| Acquisition cost ratio | Acquisition cost ratio | **16.1%** | 15.3% | 18.0% | 15.0% | 17.5% | 18.8% |
| General and administrative expense ratio | General and administrative expense ratio | **13.7%** | 16.7% | 7.4% | 14.0% | 11.0% | 12.0% |
| Combined ratio | Combined ratio | **79.9%** | 101.4% | 74.9% | 100.1% | 86.3% | 81.8% |
| Adjusted combined ratio <sup>(1)</sup> | Adjusted combined ratio <sup>(1)</sup> | **79.2%** | 99.8% | 74.7% | 98.5% | 82.2% | 79.8% |

---

(1) Adjusted combined ratio includes an adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contract. Adjusted combined ratio represents the performance of our business for accident years 2020 onwards, which we believe is useful to management and investors because it reflects the underlying underwriting performance of the ongoing portfolio.

13&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

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| | | | |
|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Aspen Capital Markets | Aspen Capital Markets |  |
| Aspen Capital Markets sources capital and develops alternative reinsurance structures and products to leverage the Company's underwriting and analytical expertise and earns underwriting, management and performance fees for Aspen from other third party investors primarily through the placement and management of side cars, Insurance Linked Securities (ILS) funds and other offerings. The numbers in the table below are exclusive of co-investments made by the Company. | Aspen Capital Markets sources capital and develops alternative reinsurance structures and products to leverage the Company's underwriting and analytical expertise and earns underwriting, management and performance fees for Aspen from other third party investors primarily through the placement and management of side cars, Insurance Linked Securities (ILS) funds and other offerings. The numbers in the table below are exclusive of co-investments made by the Company. | Aspen Capital Markets sources capital and develops alternative reinsurance structures and products to leverage the Company's underwriting and analytical expertise and earns underwriting, management and performance fees for Aspen from other third party investors primarily through the placement and management of side cars, Insurance Linked Securities (ILS) funds and other offerings. The numbers in the table below are exclusive of co-investments made by the Company. | Aspen Capital Markets sources capital and develops alternative reinsurance structures and products to leverage the Company's underwriting and analytical expertise and earns underwriting, management and performance fees for Aspen from other third party investors primarily through the placement and management of side cars, Insurance Linked Securities (ILS) funds and other offerings. The numbers in the table below are exclusive of co-investments made by the Company. |
|  |  | **Six Months Ended June 30,** | **Six Months Ended June 30,** |
| **(in US$ millions)** | **(in US$ millions)** | **2025** | **2024** |
| Third Party Capital | Third Party Capital | $**2355.3** | $1855.4 |
| Earned Premium | Earned Premium | $**545.8** | $386.8 |
| Fee Income <sup>(1)</sup> | Fee Income <sup>(1)</sup> | $**99.0** | $68.3 |

---

(1) Fee income of $99.0 million and $68.3 million is included as an offset to acquisition expenses for the the six months ended June 30, 2025 and the the six months ended June 30, 2024, respectively.

14&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

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| | | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Written and Earned Premiums by Segment and Lines of Business | Written and Earned Premiums by Segment and Lines of Business | Written and Earned Premiums by Segment and Lines of Business | Written and Earned Premiums by Segment and Lines of Business | Written and Earned Premiums by Segment and Lines of Business | Written and Earned Premiums by Segment and Lines of Business |  |
| **(in US$ millions)** | **(in US$ millions)** |  |  |  |  |  |  |
| **<u>Gross Written Premiums</u>** | **<u>Gross Written Premiums</u>** | **Q2 2025** | **Q1 2025** | **Q4 2024** | **Q3 2024** | **Q2 2024** | **Q1 2024** |
| &nbsp;&nbsp;&nbsp;**<u>Insurance</u>** | &nbsp;&nbsp;&nbsp;**<u>Insurance</u>** |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;First Party Insurance | &nbsp;&nbsp;&nbsp;&nbsp;First Party Insurance | $**66.7** | $65.0 | $78.3 | $71.1 | $74.2 | $66.3 |
| &nbsp;&nbsp;&nbsp;&nbsp;Specialty Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Specialty Insurance | **122.7** | 116.5 | 127.4 | 120.3 | 127.8 | 106.2 |
| &nbsp;&nbsp;&nbsp;&nbsp;Casualty and Liability Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Casualty and Liability Insurance | **192.3** | 168.3 | 193.3 | 182.0 | 200.2 | 162.7 |
| &nbsp;&nbsp;&nbsp;&nbsp;Financial and Professional Lines Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Financial and Professional Lines Insurance | **258.0** | 290.2 | 290.6 | 285.6 | 243.1 | 234.2 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other Insurance <sup>(1)</sup> | &nbsp;&nbsp;&nbsp;&nbsp;Other Insurance <sup>(1)</sup> | **53.8** | 46.5 | 32.1 | 41.6 | 38.9 | 47.6 |
| &nbsp;&nbsp;&nbsp;**Total Insurance** | &nbsp;&nbsp;&nbsp;**Total Insurance** | $**693.5** | $686.5 | $721.7 | $700.6 | $684.2 | $617.0 |
| &nbsp;&nbsp;&nbsp;**<u>Reinsurance</u>** | &nbsp;&nbsp;&nbsp;**<u>Reinsurance</u>** |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Property Catastrophe Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Property Catastrophe Reinsurance | $**177.5** | $145.1 | $17.4 | $88.3 | $172.9 | $151.6 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other Property Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Other Property Reinsurance | **73.8** | 97.7 | 69.9 | 103.1 | 109.9 | 125.9 |
| &nbsp;&nbsp;&nbsp;&nbsp;Casualty Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Casualty Reinsurance | **219.2** | 258.2 | 161.5 | 171.9 | 201.1 | 228.8 |
| &nbsp;&nbsp;&nbsp;&nbsp;Specialty Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Specialty Reinsurance | **74.9** | 99.7 | 40.2 | 52.9 | 82.3 | 108.1 |
| &nbsp;&nbsp;&nbsp;**Total Reinsurance** | &nbsp;&nbsp;&nbsp;**Total Reinsurance** | $**545.4** | $600.7 | $289.0 | $416.2 | $566.2 | $614.4 |
| &nbsp;&nbsp;&nbsp;**Total Gross Written Premiums** | &nbsp;&nbsp;&nbsp;**Total Gross Written Premiums** | $**1238.9** | $1287.2 | $1010.7 | $1116.8 | $1250.4 | $1231.4 |
| **<u>Net Written Premiums</u>** | **<u>Net Written Premiums</u>** |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;**<u>Insurance</u>** | &nbsp;&nbsp;&nbsp;**<u>Insurance</u>** |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;First Party Insurance | &nbsp;&nbsp;&nbsp;&nbsp;First Party Insurance | $**49.6** | $43.0 | $73.3 | $65.7 | $56.8 | $33.2 |
| &nbsp;&nbsp;&nbsp;&nbsp;Specialty Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Specialty Insurance | **82.6** | 62.7 | 105.7 | 93.7 | 88.6 | 63.7 |
| &nbsp;&nbsp;&nbsp;&nbsp;Casualty and Liability Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Casualty and Liability Insurance | **101.4** | 88.4 | 121.7 | 64.7 | 115.2 | 95.0 |
| &nbsp;&nbsp;&nbsp;&nbsp;Financial and Professional Lines Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Financial and Professional Lines Insurance | **125.5** | 154.4 | 157.1 | 162.8 | 145.9 | 120.9 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other Insurance <sup>(1)</sup> | &nbsp;&nbsp;&nbsp;&nbsp;Other Insurance <sup>(1)</sup> | **31.3** | 29.4 | 35.5 | 23.0 | 18.8 | 25.6 |
| &nbsp;&nbsp;&nbsp;**Total Insurance** | &nbsp;&nbsp;&nbsp;**Total Insurance** | $**390.4** | $377.9 | $493.3 | $409.9 | $425.3 | $338.4 |
| &nbsp;&nbsp;&nbsp;**<u>Reinsurance</u>** | &nbsp;&nbsp;&nbsp;**<u>Reinsurance</u>** |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Property Catastrophe Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Property Catastrophe Reinsurance | $**58.0** | $48.5 | $12.0 | $18.5 | $69.2 | $43.8 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other Property Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Other Property Reinsurance | **62.6** | 81.9 | 66.5 | 92.1 | 106.7 | 109.8 |
| &nbsp;&nbsp;&nbsp;&nbsp;Casualty Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Casualty Reinsurance | **133.7** | 153.0 | 98.2 | 105.2 | 127.9 | 146.2 |
| &nbsp;&nbsp;&nbsp;&nbsp;Specialty Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Specialty Reinsurance | **70.8** | 90.4 | 47.0 | 47.9 | 82.0 | 102.7 |
| &nbsp;&nbsp;&nbsp;**Total Reinsurance** | &nbsp;&nbsp;&nbsp;**Total Reinsurance** | $**325.1** | $373.8 | $223.7 | $263.7 | $385.8 | $402.5 |
| &nbsp;&nbsp;&nbsp;**Total Net Written Premiums** | &nbsp;&nbsp;&nbsp;**Total Net Written Premiums** | $**715.5** | $751.7 | $717.0 | $673.6 | $811.1 | $740.9 |
| **<u>Net Earned Premiums</u>** | **<u>Net Earned Premiums</u>** |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;**<u>Insurance</u>** | &nbsp;&nbsp;&nbsp;**<u>Insurance</u>** |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;First Party Insurance | &nbsp;&nbsp;&nbsp;&nbsp;First Party Insurance | $**50.9** | $58.1 | $59.7 | $62.8 | $56.0 | $58.3 |
| &nbsp;&nbsp;&nbsp;&nbsp;Specialty Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Specialty Insurance | **83.3** | 83.7 | 89.2 | 85.9 | 78.4 | 79.8 |
| &nbsp;&nbsp;&nbsp;&nbsp;Casualty and Liability Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Casualty and Liability Insurance | **92.7** | 93.1 | 103.7 | 91.6 | 88.5 | 91.1 |
| &nbsp;&nbsp;&nbsp;&nbsp;Financial and Professional Lines Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Financial and Professional Lines Insurance | **139.9** | 149.7 | 150.3 | 149.1 | 143.0 | 125.0 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other Insurance <sup>(1)</sup> | &nbsp;&nbsp;&nbsp;&nbsp;Other Insurance <sup>(1)</sup> | **29.0** | 19.1 | 37.0 | 15.4 | 12.4 | 6.8 |
| &nbsp;&nbsp;&nbsp;**Total Insurance** | &nbsp;&nbsp;&nbsp;**Total Insurance** | $**395.8** | $403.7 | $439.9 | $404.8 | $378.3 | $361.0 |
| &nbsp;&nbsp;&nbsp;**<u>Reinsurance</u>** | &nbsp;&nbsp;&nbsp;**<u>Reinsurance</u>** |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Property Catastrophe Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Property Catastrophe Reinsurance | $**19.4** | $47.5 | $42.4 | $36.2 | $33.1 | $32.3 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other Property Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Other Property Reinsurance | **70.5** | 81.8 | 87.6 | 92.2 | 101.3 | 103.2 |
| &nbsp;&nbsp;&nbsp;&nbsp;Casualty Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Casualty Reinsurance | **130.6** | 116.2 | 115.9 | 116.0 | 117.3 | 107.5 |
| &nbsp;&nbsp;&nbsp;&nbsp;Specialty Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Specialty Reinsurance | **58.6** | 53.5 | 134.5 | 49.1 | 75.4 | 61.7 |
| &nbsp;&nbsp;&nbsp;**Total Reinsurance** | &nbsp;&nbsp;&nbsp;**Total Reinsurance** | $**279.1** | $299.0 | $380.4 | $293.5 | $327.1 | $304.7 |
| &nbsp;&nbsp;&nbsp;**Total Net Earned Premiums** | &nbsp;&nbsp;&nbsp;**Total Net Earned Premiums** | $**674.9** | $702.7 | $820.3 | $698.3 | $705.4 | $665.7 |

---

(1) Includes Aspen's share of written and earned premiums through Carbon Syndicate 4747 and its digital follow capacity through Ki's Lloyd's platform.

15&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

---

| | | | |
|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Written and Earned Premiums by Segment and Lines of Business | Written and Earned Premiums by Segment and Lines of Business |  |
| **(in US$ millions)** | **(in US$ millions)** | **Six Months Ended June 30,** | **Six Months Ended June 30,** |
| **<u>Gross Written Premiums</u>** | **<u>Gross Written Premiums</u>** | **2025** | **2024** |
| &nbsp;&nbsp;&nbsp;**<u>Insurance</u>** | &nbsp;&nbsp;&nbsp;**<u>Insurance</u>** |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;First Party Insurance | &nbsp;&nbsp;&nbsp;&nbsp;First Party Insurance | $**131.7** | $140.5 |
| &nbsp;&nbsp;&nbsp;&nbsp;Specialty Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Specialty Insurance | **239.2** | 234.0 |
| &nbsp;&nbsp;&nbsp;&nbsp;Casualty and Liability Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Casualty and Liability Insurance | **360.6** | 362.9 |
| &nbsp;&nbsp;&nbsp;&nbsp;Financial and Professional Lines Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Financial and Professional Lines Insurance | **548.2** | 477.3 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other Insurance <sup>(1)</sup> | &nbsp;&nbsp;&nbsp;&nbsp;Other Insurance <sup>(1)</sup> | **100.3** | 86.5 |
| &nbsp;&nbsp;&nbsp;**Total Insurance** | &nbsp;&nbsp;&nbsp;**Total Insurance** | $**1380.0** | $1301.2 |
| &nbsp;&nbsp;&nbsp;**<u>Reinsurance</u>** | &nbsp;&nbsp;&nbsp;**<u>Reinsurance</u>** |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Property Catastrophe Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Property Catastrophe Reinsurance | $**322.6** | $324.5 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other Property Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Other Property Reinsurance | **171.5** | 235.8 |
| &nbsp;&nbsp;&nbsp;&nbsp;Casualty Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Casualty Reinsurance | **477.4** | 429.9 |
| &nbsp;&nbsp;&nbsp;&nbsp;Specialty Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Specialty Reinsurance | **174.6** | 190.4 |
| &nbsp;&nbsp;&nbsp;**Total Reinsurance** | &nbsp;&nbsp;&nbsp;**Total Reinsurance** | $**1146.1** | $1180.6 |
| &nbsp;&nbsp;&nbsp;**Total Gross Written Premiums** | &nbsp;&nbsp;&nbsp;**Total Gross Written Premiums** | $**2526.1** | $2481.8 |
| **<u>Net Written Premiums</u>** | **<u>Net Written Premiums</u>** |  |  |
| &nbsp;&nbsp;&nbsp;**<u>Insurance</u>** | &nbsp;&nbsp;&nbsp;**<u>Insurance</u>** |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;First Party Insurance | &nbsp;&nbsp;&nbsp;&nbsp;First Party Insurance | $**92.6** | $90.0 |
| &nbsp;&nbsp;&nbsp;&nbsp;Specialty Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Specialty Insurance | **145.3** | 152.3 |
| &nbsp;&nbsp;&nbsp;&nbsp;Casualty and Liability Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Casualty and Liability Insurance | **189.8** | 210.2 |
| &nbsp;&nbsp;&nbsp;&nbsp;Financial and Professional Lines Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Financial and Professional Lines Insurance | **279.9** | 266.8 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other Insurance <sup>(1)</sup> | &nbsp;&nbsp;&nbsp;&nbsp;Other Insurance <sup>(1)</sup> | **60.7** | 44.4 |
| &nbsp;&nbsp;&nbsp;**Total Insurance** | &nbsp;&nbsp;&nbsp;**Total Insurance** | $**768.3** | $763.7 |
| &nbsp;&nbsp;&nbsp;**<u>Reinsurance</u>** | &nbsp;&nbsp;&nbsp;**<u>Reinsurance</u>** |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Property Catastrophe Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Property Catastrophe Reinsurance | $**106.5** | $113.0 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other Property Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Other Property Reinsurance | **144.5** | 216.5 |
| &nbsp;&nbsp;&nbsp;&nbsp;Casualty Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Casualty Reinsurance | **286.7** | 274.1 |
| &nbsp;&nbsp;&nbsp;&nbsp;Specialty Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Specialty Reinsurance | **161.2** | 184.7 |
| &nbsp;&nbsp;&nbsp;**Total Reinsurance** | &nbsp;&nbsp;&nbsp;**Total Reinsurance** | $**698.9** | $788.3 |
| &nbsp;&nbsp;&nbsp;**Total Net Written Premiums** | &nbsp;&nbsp;&nbsp;**Total Net Written Premiums** | $**1467.2** | $1552.0 |
| **<u>Net Earned Premiums</u>** | **<u>Net Earned Premiums</u>** |  |  |
| &nbsp;&nbsp;&nbsp;**<u>Insurance</u>** | &nbsp;&nbsp;&nbsp;**<u>Insurance</u>** |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;First Party Insurance | &nbsp;&nbsp;&nbsp;&nbsp;First Party Insurance | $**109.0** | $114.3 |
| &nbsp;&nbsp;&nbsp;&nbsp;Specialty Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Specialty Insurance | **167.0** | 158.2 |
| &nbsp;&nbsp;&nbsp;&nbsp;Casualty and Liability Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Casualty and Liability Insurance | **185.8** | 179.6 |
| &nbsp;&nbsp;&nbsp;&nbsp;Financial and Professional Lines Insurance | &nbsp;&nbsp;&nbsp;&nbsp;Financial and Professional Lines Insurance | **289.6** | 268.0 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other Insurance <sup>(1)</sup> | &nbsp;&nbsp;&nbsp;&nbsp;Other Insurance <sup>(1)</sup> | **48.1** | 19.2 |
| &nbsp;&nbsp;&nbsp;**Total Insurance** | &nbsp;&nbsp;&nbsp;**Total Insurance** | $**799.5** | $739.3 |
| &nbsp;&nbsp;&nbsp;**<u>Reinsurance</u>** | &nbsp;&nbsp;&nbsp;**<u>Reinsurance</u>** |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Property Catastrophe Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Property Catastrophe Reinsurance | $**66.9** | $65.4 |
| &nbsp;&nbsp;&nbsp;&nbsp;Other Property Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Other Property Reinsurance | **152.3** | 204.5 |
| &nbsp;&nbsp;&nbsp;&nbsp;Casualty Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Casualty Reinsurance | **246.8** | 224.8 |
| &nbsp;&nbsp;&nbsp;&nbsp;Specialty Reinsurance | &nbsp;&nbsp;&nbsp;&nbsp;Specialty Reinsurance | **112.1** | 137.1 |
| &nbsp;&nbsp;&nbsp;**Total Reinsurance** | &nbsp;&nbsp;&nbsp;**Total Reinsurance** | $**578.1** | $631.8 |
| &nbsp;&nbsp;&nbsp;**Total Net Earned Premiums** | &nbsp;&nbsp;&nbsp;**Total Net Earned Premiums** | $**1377.6** | $1371.1 |

---

(1) Includes Aspen's share of written and earned premiums through Carbon Syndicate 4747 and its digital follow capacity through Ki's Lloyd's platform.

16&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

---

| | | | |
|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Consolidated Statements of Changes in Shareholders' Equity | Consolidated Statements of Changes in Shareholders' Equity |  |
|  |  | **Six Months Ended June 30,** | **Six Months Ended June 30,** |
| **(in US$ millions)** | **(in US$ millions)** | **2025** | **2024** |
| Ordinary shares | Ordinary shares |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Beginning of period | &nbsp;&nbsp;&nbsp;&nbsp;Beginning of period | $**0.1** | $0.1 |
| &nbsp;&nbsp;&nbsp;&nbsp;End of period | &nbsp;&nbsp;&nbsp;&nbsp;End of period | **0.1** | 0.1 |
| Preference shares <sup>(1)</sup> | Preference shares <sup>(1)</sup> |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Beginning of period | &nbsp;&nbsp;&nbsp;&nbsp;Beginning of period | **970.5** | 753.5 |
| &nbsp;&nbsp;&nbsp;&nbsp;Preference shares redeemed | &nbsp;&nbsp;&nbsp;&nbsp;Preference shares redeemed | **(270.6)** |  |
| &nbsp;&nbsp;&nbsp;&nbsp;End of period | &nbsp;&nbsp;&nbsp;&nbsp;End of period | **699.9** | 753.5 |
| Additional paid-in capital | Additional paid-in capital |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Beginning of period - share premium | &nbsp;&nbsp;&nbsp;&nbsp;Beginning of period - share premium | **761.7** | 761.7 |
| &nbsp;&nbsp;&nbsp;&nbsp;Share-based compensation | &nbsp;&nbsp;&nbsp;&nbsp;Share-based compensation | **32.6** |  |
| &nbsp;&nbsp;&nbsp;&nbsp;End of period | &nbsp;&nbsp;&nbsp;&nbsp;End of period | **794.3** | 761.7 |
| Retained earnings  | Retained earnings  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Beginning of period | &nbsp;&nbsp;&nbsp;&nbsp;Beginning of period | **2029.7** | 1793.5 |
| &nbsp;&nbsp;&nbsp;&nbsp;Net income for the period | &nbsp;&nbsp;&nbsp;&nbsp;Net income for the period | **83.3** | 180.8 |
| &nbsp;&nbsp;&nbsp;&nbsp;Dividends paid on preference shares | &nbsp;&nbsp;&nbsp;&nbsp;Dividends paid on preference shares | **(23.5)** | (27.3) |
| &nbsp;&nbsp;&nbsp;&nbsp;Dividends paid on ordinary shares | &nbsp;&nbsp;&nbsp;&nbsp;Dividends paid on ordinary shares | **—** | (175.0) |
| &nbsp;&nbsp;&nbsp;&nbsp;Preference share redemption costs<sup>(1)</sup> | &nbsp;&nbsp;&nbsp;&nbsp;Preference share redemption costs<sup>(1)</sup> | **(4.4)** |  |
| &nbsp;&nbsp;&nbsp;&nbsp;End of period | &nbsp;&nbsp;&nbsp;&nbsp;End of period | **2085.1** | 1772.0 |
| Accumulated other comprehensive income: | Accumulated other comprehensive income: |  |  |
| Cumulative foreign currency translation adjustments, net of taxes: | Cumulative foreign currency translation adjustments, net of taxes: |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Beginning of period | &nbsp;&nbsp;&nbsp;&nbsp;Beginning of period | **(186.6)** | (172.5) |
| &nbsp;&nbsp;&nbsp;&nbsp;Change for the period | &nbsp;&nbsp;&nbsp;&nbsp;Change for the period | **43.5** | (1.6) |
| &nbsp;&nbsp;&nbsp;&nbsp;End of period | &nbsp;&nbsp;&nbsp;&nbsp;End of period | **(143.1)** | (174.1) |
| (Loss)/gain on derivatives: | (Loss)/gain on derivatives: |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Beginning of period | &nbsp;&nbsp;&nbsp;&nbsp;Beginning of period | **(5.3)** | (0.2) |
| &nbsp;&nbsp;&nbsp;&nbsp;Net change from current period hedged transactions | &nbsp;&nbsp;&nbsp;&nbsp;Net change from current period hedged transactions | **8.3** | (0.2) |
| &nbsp;&nbsp;&nbsp;&nbsp;End of period | &nbsp;&nbsp;&nbsp;&nbsp;End of period | **3.0** | (0.4) |
| Unrealized (depreciation)/appreciation on available for sale investments, net of taxes: | Unrealized (depreciation)/appreciation on available for sale investments, net of taxes: |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Beginning of period | &nbsp;&nbsp;&nbsp;&nbsp;Beginning of period | **(198.2)** | (227.6) |
| &nbsp;&nbsp;&nbsp;&nbsp;Change for the period | &nbsp;&nbsp;&nbsp;&nbsp;Change for the period | **104.6** | (15.1) |
| &nbsp;&nbsp;&nbsp;&nbsp;End of period | &nbsp;&nbsp;&nbsp;&nbsp;End of period | **(93.6)** | (242.7) |
| Total accumulated other comprehensive (loss) | Total accumulated other comprehensive (loss) | **(233.7)** | (417.2) |
| Total shareholders' equity | Total shareholders' equity | $**3345.7** | $2870.1 |

---

<sup>(1)</sup> On January 1, 2025, the Company redeemed its 5.950% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares (the "AHL PRC Shares"), representing an aggregate amount of $275 million, plus a reclassification of $4.4 million, between retained earnings and preference shares, which represents the difference between the capital raised upon issuance, net of issuance costs and the final redemption cost.

17&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

---

| | | | | | |
|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Consolidated Statements of Comprehensive Income | Consolidated Statements of Comprehensive Income | Consolidated Statements of Comprehensive Income | Consolidated Statements of Comprehensive Income |  |
|  |  | **Three Months Ended June 30,** | **Three Months Ended June 30,** | **Six Months Ended June 30,** | **Six Months Ended June 30,** |
| **(in US$ millions)** | **(in US$ millions)** | **2025** | **2024** | **2025** | **2024** |
| Net income | Net income | $**46.5** | $69.0 | $**83.3** | $180.8 |
| Other comprehensive income, net of taxes: | Other comprehensive income, net of taxes: |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Available for sale investments: | &nbsp;&nbsp;&nbsp;&nbsp;Available for sale investments: |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Reclassification adjustment for net realized losses included in net income | &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Reclassification adjustment for net realized losses included in net income | **23.8** | 19.5 | **26.5** | 23.0 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Change in net unrealized gains/(losses) on available for sale securities held | &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Change in net unrealized gains/(losses) on available for sale securities held | **25.4** | (10.5) | **78.1** | (38.1) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Net change from current period hedged transactions | &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Net change from current period hedged transactions | **4.1** | 0.3 | **8.3** | (0.2) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Change in foreign currency translation adjustment | &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Change in foreign currency translation adjustment | **33.8** | 7.5 | **43.5** | (1.6) |
| &nbsp;&nbsp;&nbsp;&nbsp;Other comprehensive income/(loss) | &nbsp;&nbsp;&nbsp;&nbsp;Other comprehensive income/(loss) | **87.1** | 16.8 | **156.4** | (16.9) |
| Comprehensive income | Comprehensive income | $**133.6** | $85.8 | $**239.7** | $163.9 |

---

18&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

---

| | | | | | |
|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Condensed Consolidated Statements of Cash Flows | Condensed Consolidated Statements of Cash Flows | Condensed Consolidated Statements of Cash Flows | Condensed Consolidated Statements of Cash Flows |  |
|  |  | **Three Months Ended June 30,** | **Three Months Ended June 30,** | **Six Months Ended June 30,** | **Six Months Ended June 30,** |
| **(in US$ millions)** | **(in US$ millions)** | **2025** | **2024** | **2025** | **2024** |
| Net cash from operating activities | Net cash from operating activities | $**22.9** | $74.5 | $**128.0** | $177.2 |
| Net cash from (used in) investing activities | Net cash from (used in) investing activities | **73.6** | 292.2 | **(92.3)** | (77.1) |
| Net cash (used in) financing activities | Net cash (used in) financing activities | **(14.6)** | (188.7) | **(27.1)** | (202.3) |
| Effect of exchange rate movements on cash and cash equivalents | Effect of exchange rate movements on cash and cash equivalents | **11.9** | (0.2) | **16.2** | (4.7) |
| Increase (Decrease) in cash and cash equivalents | Increase (Decrease) in cash and cash equivalents | **93.8** | 177.8 | **24.8** | (106.9) |
| Cash and cash equivalents at beginning of period | Cash and cash equivalents at beginning of period | **845.2** | 743.4 | **914.2** | 1028.1 |
| Cash and cash equivalents at end of period <sup>(1)</sup> | Cash and cash equivalents at end of period <sup>(1)</sup> | $**939.0** | $921.2 | $**939.0** | $921.2 |

---

<sup>(1)</sup> Cash and cash equivalents includes restricted cash for the the six months ended June 30, 2025 of $217.2 million (the the six months ended June 30, 2024 — $220.9 million) which are held in trusts.

19&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

---

| | | | | |
|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Reserves for Losses and Loss Adjustment Expenses | Reserves for Losses and Loss Adjustment Expenses | Reserves for Losses and Loss Adjustment Expenses | Reserves for Losses and Loss Adjustment Expenses |
| **(in US$ millions)** | **(in US$ millions)** | **For the Six Months Ended June 30, 2025** | **For the Six Months Ended June 30, 2024** | **For the Twelve Months Ended December 31, 2024** |
| Reserves for losses and loss adjustment expenses at the start of the period | Reserves for losses and loss adjustment expenses at the start of the period | $**8122.6** | $7810.6 | $7810.6 |
| Unpaid losses recoverable from reinsurers at the start of the period | Unpaid losses recoverable from reinsurers at the start of the period | **(4172.0)** | (4577.8) | (4577.8) |
| Net reserve for losses and loss adjustment expenses at the start of the period | Net reserve for losses and loss adjustment expenses at the start of the period | **3950.6** | 3232.8 | 3232.8 |
| Movement in net reserve for losses and loss adjustment expenses for claims incurred | Movement in net reserve for losses and loss adjustment expenses for claims incurred |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Current period | &nbsp;&nbsp;&nbsp;&nbsp;Current period | **839.1** | 796.9 | 1682.2 |
| &nbsp;&nbsp;&nbsp;&nbsp;Prior period reserve development <sup>(1)</sup> | &nbsp;&nbsp;&nbsp;&nbsp;Prior period reserve development <sup>(1)</sup> | **(4.7)** | 7.8 | 35.6 |
| &nbsp;&nbsp;&nbsp;&nbsp;Total incurred | &nbsp;&nbsp;&nbsp;&nbsp;Total incurred | **834.4** | 804.7 | 1717.8 |
| Net losses and loss adjustment expenses payments for claims incurred | Net losses and loss adjustment expenses payments for claims incurred | **(522.3)** | (453.1) | (941.5) |
| Foreign exchange losses/(gains) | Foreign exchange losses/(gains) | **95.6** | (26.7) | (58.5) |
| Net reserve for losses and loss adjustment expenses at the end of the period | Net reserve for losses and loss adjustment expenses at the end of the period | **4358.3** | 3557.7 | 3950.6 |
| Unpaid losses recoverable from reinsurers at the end of the period | Unpaid losses recoverable from reinsurers at the end of the period | **4273.9** | 4275.3 | 4172.0 |
| Reserves for losses and loss adjustment expenses at the end of the period | Reserves for losses and loss adjustment expenses at the end of the period | $**8632.2** | $7833.0 | $8122.6 |

---

<sup>(1)</sup> Prior period reserve development includes an increase adjustment for the change in deferred gain on retroactive reinsurance contracts in order to match the loss recoveries under the LPT contracts with the underlying loss development of the assumed net loss reserves for the subject business of 2019 and prior accident years of $14.5 million (June 30, 2024 — $15.0 million).

20&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

---

| | | | | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Prior Year Reserve Movements | Prior Year Reserve Movements | Prior Year Reserve Movements | Prior Year Reserve Movements | Prior Year Reserve Movements | Prior Year Reserve Movements | Prior Year Reserve Movements | Prior Year Reserve Movements |  |
| **(in US$ millions)** | **(in US$ millions)** | **Three Months Ended June 30, 2025** | **Three Months Ended June 30, 2025** | **Three Months Ended June 30, 2025** | **Three Months Ended June 30, 2025** | **Three Months Ended June 30, 2024** | **Three Months Ended June 30, 2024** | **Three Months Ended June 30, 2024** | **Three Months Ended June 30, 2024** |
|  |  | **Gross\*** | **Reinsurance Recoverables\*** | **Impact of LPT Deferred Gain\*** | **Net**  | **Gross\*** | **Reinsurance Recoverables\*** | **Impact of LPT Deferred Gain\*** | **Net** |
| Insurance | Insurance | $(11.5) | $12.0 | $(3.7) | $(3.2) | $2.6 | $0.9 | $(0.1) | $3.4 |
| Reinsurance | Reinsurance | 7.3 | 2.4 | (1.8) | 7.9 | 9.4 | (5.7) | (13.5) | (9.8) |
| (Adverse)/favorable movements in reserves for prior years during the period | (Adverse)/favorable movements in reserves for prior years during the period | $(4.2) | $14.4 | $(5.5) | $4.7 | $12.0 | $(4.8) | $(13.6) | $(6.4) |
|  |  | **Six Months Ended June 30, 2025** | **Six Months Ended June 30, 2025** | **Six Months Ended June 30, 2025** | **Six Months Ended June 30, 2025** | **Six Months Ended June 30, 2024** | **Six Months Ended June 30, 2024** | **Six Months Ended June 30, 2024** | **Six Months Ended June 30, 2024** |
|  |  | **Gross\*** | **Reinsurance Recoverables\*** | **Impact of LPT Deferred Gain\*** | **Net** | **Gross\*** | **Reinsurance Recoverables\*** | **Impact of LPT Deferred Gain\*** | **Net** |
| Insurance | Insurance | $(30.4) | $32.8 | $(7.8) | $(5.4) | $(5.1) | $8.6 | $4.5 | $8.0 |
| Reinsurance | Reinsurance | 21.8 | (5.0) | (6.7) | 10.1 | (6.1) | 9.8 | (19.5) | (15.8) |
| (Adverse)/favorable movements in reserves for prior years during the period | (Adverse)/favorable movements in reserves for prior years during the period | $(8.6) | $27.8 | $(14.5) | $4.7 | $(11.2) | $18.4 | $(15.0) | $(7.8) |

---

\*Gross and reinsurance recoverables represent the prior year reserve movements for accident years 2020 onwards, which which we believe reflects the underlying underwriting performance of the ongoing portfolio. The impact of LPT deferred gain reflects development in the 2019 and prior accident years net of the movement in the deferred gain on retroactive contracts.

21&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

---

| | | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Consolidated Investment Portfolio | Consolidated Investment Portfolio | Consolidated Investment Portfolio | Consolidated Investment Portfolio | Consolidated Investment Portfolio | Consolidated Investment Portfolio |  |
| **(in US$ millions)** | **(in US$ millions)** | **Fair Market Value** | **Fair Market Value** | **Fair Market Value** | **Fair Market Value** | **Fair Market Value** | **Fair Market Value** |
|  |  | **June 30, <br>2025** | **March 31, <br>2025** | **December 31, <br>2024** | **September 30, 2024** | **June 30,<br>2024** | **March 31,<br>2024** |
| **Fixed Income Securities - Available For Sale** | **Fixed Income Securities - Available For Sale** |  |  |  |  |  |  |
| U.S. government securities | U.S. government securities | $**1408.4** | $1407.2 | $1480.6 | $1326.4 | $1260.9 | $1252.2 |
| U.S. agency securities | U.S. agency securities | **7.4** | 7.4 | 7.2 | 7.4 | 7.2 | 7.2 |
| Municipal securities | Municipal securities | **113.9** | 116.1 | 82.3 | 79.4 | 78.2 | 105.0 |
| Corporate securities | Corporate securities | **2201.1** | 2161.8 | 1986.4 | 1964.2 | 1933.8 | 2039.4 |
| Non-U.S. government securities | Non-U.S. government securities | **342.2** | 296.9 | 246.8 | 272.9 | 264.1 | 277.2 |
| Non-U.S. government-backed corporate securities | Non-U.S. government-backed corporate securities | **126.1** | 130.2 | 131.3 | 144.2 | 136.6 | 129.1 |
| Asset - backed securities | Asset - backed securities | **382.6** | 341.3 | 234.5 | 200.1 | 154.9 | 141.1 |
| Mortgage-backed securities | Mortgage-backed securities | **564.6** | 627.2 | 523.1 | 561.2 | 548.4 | 553.2 |
| **Total fixed income securities - Available for sale** | **Total fixed income securities - Available for sale** | **5146.3** | 5088.1 | 4692.2 | 4555.8 | 4384.1 | 4504.4 |
| **Short-term investments - Available for Sale** | **Short-term investments - Available for Sale** | **90.8** | 139.6 | 261.9 | 66.5 | 81.7 | 79.2 |
| **Privately-held investments - Available for sale** | **Privately-held investments - Available for sale** | **26.4** | 25.0 | 24.2 | 25.3 | 14.8 | 15.1 |
| **Total Investments - Available for sale** | **Total Investments - Available for sale** | $**5263.5** | $5252.7 | $4978.3 | $4647.6 | $4480.6 | $4598.7 |
| **Fixed Income Securities - Trading** | **Fixed Income Securities - Trading** |  |  |  |  |  |  |
| U.S. government securities | U.S. government securities | $**264.8** | $255.4 | $261.3 | $267.1 | $260.5 | $261.6 |
| Municipal securities | Municipal securities | **3.3** | 2.2 | 1.6 | 2.0 | 2.1 | 3.1 |
| Corporate securities | Corporate securities | **153.1** | 146.1 | 151.1 | 152.6 | 148.2 | 146.8 |
| Non-U.S. government securities | Non-U.S. government securities | **26.8** | 25.6 | 24.4 | 24.2 | 23.4 | 23.8 |
| Non-U.S. government-backed corporate securities | Non-U.S. government-backed corporate securities | **—** | 2.8 | 2.8 | 6.3 | 6.2 | 6.3 |
| Asset-backed securities | Asset-backed securities | **580.5** | 599.7 | 625.2 | 688.7 | 705.2 | 914.2 |
| Mortgage-backed securities | Mortgage-backed securities | **30.8** | 30.7 | 31.1 | 33.4 | 31.3 | 25.6 |
| High yield loans | High yield loans | **108.7** | 109.9 | 102.4 | 107.0 | 99.6 | 99.3 |
| **Total fixed income securities - Trading** | **Total fixed income securities - Trading** | **1168.0** | 1172.4 | 1199.9 | 1281.3 | 1276.5 | 1480.7 |
| **Short-term investments - Trading** | **Short-term investments - Trading** | **8.4** | 19.1 | 1.0 | 3.2 | 2.6 | 5.7 |
| **Catastrophe bonds - Trading** | **Catastrophe bonds - Trading** | **—** |  | 1.0 | 1.0 | 1.1 | 1.1 |
| **Privately-held investments - Trading** | **Privately-held investments - Trading** | **225.1** | 230.8 | 286.8 | 341.2 | 459.4 | 445.0 |
| **Total Investments - Trading** | **Total Investments - Trading** | $**1401.5** | $1422.3 | $1488.7 | $1626.7 | $1739.6 | $1932.5 |
| **Other Investments** | **Other Investments** | $**319.6** | $311.8 | $274.5 | $212.8 | $216.2 | $215.6 |
| **Total Investments** | **Total Investments** | $**6984.6** | $6986.8 | $6741.5 | $6487.1 | $6436.4 | $6746.8 |
| Cash and cash equivalents | Cash and cash equivalents | **939.0** | 845.2 | 914.2 | 1244.9 | 921.2 | 743.4 |
| Accrued interest | Accrued interest | **60.5** | 59.7 | 54.6 | 55.0 | 53.1 | 54.8 |
| **Total Cash and Accrued Interest** | **Total Cash and Accrued Interest** | $**999.5** | $904.9 | $968.8 | $1299.9 | $974.3 | $798.2 |
| **Total Cash, Accrued Interest and Investments** | **Total Cash, Accrued Interest and Investments** | $**7984.1** | $7891.7 | $7710.3 | $7787.0 | $7410.7 | $7545.0 |

---

22&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

---

| | | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Investment Analysis | Investment Analysis | Investment Analysis | Investment Analysis | Investment Analysis | Investment Analysis |  |
| **(in US$ millions except for percentages)** | **(in US$ millions except for percentages)** | **Q2 2025** | **Q1 2025** | **Q4 2024** | **Q3 2024** | **Q2 2024** | **Q1 2024** |
| Fixed income securities - Available for sale | Fixed income securities - Available for sale | $**53.5** | $50.5 | $44.5 | $40.7 | $40.8 | $35.5 |
| Fixed income securities - Trading | Fixed income securities - Trading | **16.6** | 17.9 | 18.9 | 21.5 | 23.2 | 24.6 |
| Short term investments - Available for sale | Short term investments - Available for sale | **0.8** | 1.8 | 2.0 | 0.7 | 0.9 | 0.9 |
| Short term investments - Trading | Short term investments - Trading | **0.1** | 0.1 |  |  |  | 0.1 |
| Fixed term deposits (included in cash and cash equivalents) | Fixed term deposits (included in cash and cash equivalents) | **8.7** | 8.5 | 12.1 | 12.1 | 9.6 | 11.5 |
| Privately-held investments - Available for sale | Privately-held investments - Available for sale | **0.4** | 0.3 | 0.5 | 0.3 | 0.2 | 0.2 |
| Privately-held investments - Trading | Privately-held investments - Trading | **4.1** | 5.3 | 5.2 | 8.7 | 9.7 | 11.3 |
| Other investments, at fair value | Other investments, at fair value | **(0.1)** | (5.1) | (1.8) | (2.3) | 1.6 | (3.7) |
| **Total investment income** | **Total investment income** | $**84.1** | $79.3 | $81.4 | $81.7 | $86.0 | $80.4 |
| Investment expenses | Investment expenses | **(3.6)** | (3.4) | (2.3) | (2.1) | (3.5) | (3.6) |
| **Net investment income** | **Net investment income** | $**80.5** | $75.9 | $79.1 | $79.6 | $82.5 | $76.8 |
| Net realized and unrealized investment (losses)/gains | Net realized and unrealized investment (losses)/gains | **(9.3)** | (0.3) | (28.5) | 6.1 | (26.1) | (1.0) |
| Change in unrealized gains/(losses) on available for sale investments (before tax)  | Change in unrealized gains/(losses) on available for sale investments (before tax)  | **61.8** | 69.8 | (69.4) | 120.6 | 9.6 | (26.7) |
| Total return on investments | Total return on investments | $**133.0** | $145.4 | $(18.8) | $206.3 | $66.0 | $49.1 |
| **Portfolio Characteristics** | **Portfolio Characteristics** |  |  |  |  |  |  |
| Fixed income portfolio book yield | Fixed income portfolio book yield | **4.4%** | 4.3% | 4.2% | 4.0% | 4.0% | 4.0% |
| Fixed income portfolio duration | Fixed income portfolio duration | **3.2 years** | 3.3 years | 2.9 years | 2.5 years | 2.5 years | 2.4 years |

---

23&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

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| | | | | | |
|:---|:---|:---|:---|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED | ASPEN INSURANCE HOLDINGS LIMITED |  |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Operating Income Reconciliation | Operating Income Reconciliation | Operating Income Reconciliation | Operating Income Reconciliation |  |
| Net income is adjusted to exclude after-tax change in net foreign exchange gains and losses, realized gains and losses in investments and non-operating items. | Net income is adjusted to exclude after-tax change in net foreign exchange gains and losses, realized gains and losses in investments and non-operating items. | Net income is adjusted to exclude after-tax change in net foreign exchange gains and losses, realized gains and losses in investments and non-operating items. | Net income is adjusted to exclude after-tax change in net foreign exchange gains and losses, realized gains and losses in investments and non-operating items. |  |  |
|  |  | **Three Months Ended** | **Three Months Ended** | **Six Months Ended** | **Six Months Ended** |
| **(in US$ millions except where stated)** | **(in US$ millions except where stated)** | **June 30, 2025** | **June 30, 2024** | **June 30, 2025** | **June 30, 2024** |
| Net income | Net income | $**46.5** | $69.0 | $**83.3** | $180.8 |
| Preference share dividends | Preference share dividends | **(11.0)** | (13.7) | **(23.5)** | (27.3) |
| Preference share redemption | Preference share redemption | **—** |  | **(4.4)** |  |
| Net income available to Aspen Insurance Holdings Limited's ordinary shareholders | Net income available to Aspen Insurance Holdings Limited's ordinary shareholders | **35.5** | 55.3 | **55.4** | 153.5 |
| Add/(deduct) items before tax: | Add/(deduct) items before tax: |  |  |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;Net foreign exchange losses/(gains) | &nbsp;&nbsp;&nbsp;&nbsp;Net foreign exchange losses/(gains) | **31.9** | (1.9) | **44.8** | (11.0) |
| &nbsp;&nbsp;&nbsp;&nbsp;Net realized and unrealized investment losses | &nbsp;&nbsp;&nbsp;&nbsp;Net realized and unrealized investment losses | **9.3** | 26.1 | **9.6** | 27.1 |
| &nbsp;&nbsp;&nbsp;&nbsp;Non-operating expenses | &nbsp;&nbsp;&nbsp;&nbsp;Non-operating expenses | **47.3** | 5.5 | **55.6** | 11.7 |
| &nbsp;&nbsp;&nbsp;&nbsp;Impact of the LPT | &nbsp;&nbsp;&nbsp;&nbsp;Impact of the LPT | **5.6** | 13.5 | **14.6** | 15.0 |
| &nbsp;&nbsp;&nbsp;&nbsp;Variable interest on the LPT funds withheld | &nbsp;&nbsp;&nbsp;&nbsp;Variable interest on the LPT funds withheld | **2.5** | 5.2 | **5.4** | 11.5 |
| &nbsp;&nbsp;&nbsp;&nbsp;Non-operating income tax (benefit) | &nbsp;&nbsp;&nbsp;&nbsp;Non-operating income tax (benefit) | **(21.2)** | (6.1) | **(28.5)** | (6.8) |
| &nbsp;&nbsp;&nbsp;&nbsp;Preference share redemption costs | &nbsp;&nbsp;&nbsp;&nbsp;Preference share redemption costs | **—** |  | **4.4** |  |
| Operating income | Operating income | $**110.9** | $97.6 | $**161.3** | $201.0 |

---

24&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

------

---

| | |
|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Non-GAAP Financial Measures |

---

---

| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
| | **Three Months Ended June 30, 2025** | **Three Months Ended June 30, 2025** | **Three Months Ended June 30, 2025** | **Three Months Ended June 30, 2024** | **Three Months Ended June 30, 2024** | **Three Months Ended June 30, 2024** |
| | **Insurance** | **Reinsurance** | **Total** | **Insurance** | **Reinsurance** | **Total** |
| | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** |
| **Underwriting Revenues** | | | | | | |
| Gross written premiums | $**693.5** | $**545.4** | $**1238.9** | $684.2 | $566.2 | $1250.4 |
| Net written premiums | $**390.4** | $**325.1** | $**715.5** | $425.3 | $385.8 | $811.1 |
| Net earned premiums | $**395.8** | $**279.1** | $**674.9** | $378.3 | $327.1 | $705.4 |
| **Underwriting Expenses** |  |  |  |  |  |  |
| Current accident year net losses and loss expenses | $**(224.8)** | $**(135.4)** | $**(360.2)** | $(229.6) | $(136.0) | $(365.6) |
| Catastrophe losses | **(11.3)** | **(12.3)** | **(23.6)** | (5.0) | (43.2) | (48.2) |
| Prior year reserve development, post LPT years | **0.5** | **9.7** | **10.2** | 3.5 | 3.7 | 7.2 |
| Adjusted losses and loss adjustment expenses <sup>(1)</sup> | **(235.6)** | **(138.0)** | **(373.6)** | (231.1) | (175.5) | (406.6) |
| Impact of the LPT <sup>(2)</sup> | **(3.7)** | **(1.8)** | **(5.5)** | (0.1) | (13.5) | (13.6) |
| **Losses and loss adjustment expenses** | **(239.3)** | **(139.8)** | **(379.1)** | (231.2) | (189.0) | (420.2) |
| Acquisition costs | **(45.2)** | **(44.8)** | **(90.0)** | (48.2) | (57.4) | (105.6) |
| General and administrative expenses | **(67.1)** | **(38.3)** | **(105.4)** | (63.4) | (35.9) | (99.3) |
| **Underwriting income** <sup>(1)</sup> | $**44.2** | $**56.2** | $**100.4** | $35.5 | $44.8 | $80.3 |
| Adjusted underwriting income <sup>(1)</sup> | $**47.9** | $**58.0** | $**105.9** | $35.6 | $58.3 | $93.9 |
| **Ratios** |  |  |  |  |  |  |
| Current accident year loss ratio, excluding catastrophe losses | **56.8%** | **48.5%** | **53.4%** | 60.7% | 41.6% | 51.9% |
| Current accident year catastrophe loss ratio | **2.9** | **4.4** | **3.5** | 1.3 | 13.2 | 6.8 |
| Current accident year loss ratio | **59.7** | **52.9** | **56.9** | 62.0 | 54.8 | 58.7 |
| Prior year reserve development ratio, post LPT years | **(0.2)** | **(3.5)** | **(1.5)** | (0.9) | (1.1) | (1.1) |
| Adjusted loss ratio <sup>(1)</sup> | **59.5** | **49.4** | **55.4** | 61.1 | 53.7 | 57.6 |
| Impact of the LPT <sup>(2)</sup> | **1.0** | **0.7** | **0.8** |  | 4.1 | 2.0 |
| **Loss ratio** | **60.5** | **50.1** | **56.2** | 61.1 | 57.8 | 59.6 |
| Acquisition cost ratio | **11.4** | **16.1** | **13.3** | 12.7 | 17.5 | 15.0 |
| General and administrative expense ratio | **17.0** | **13.7** | **15.6** | 16.8 | 11.0 | 14.1 |
| **Combined ratio** | **88.9%** | **79.9%** | **85.1%** | 90.6% | 86.3% | 88.7% |
| Adjusted combined ratio <sup>(1)</sup> | **87.9%** | **79.2%** | **84.3%** | 90.6% | 82.2% | 86.7% |

---

(1) Adjusted losses and loss adjustment expenses, underwriting income, adjusted underwriting income, 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.

(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.

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| | |
|:---|:---|
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED |
| ![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Non-GAAP Financial Measures |

---

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| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
| | **Six Months Ended June 30, 2025** | **Six Months Ended June 30, 2025** | **Six Months Ended June 30, 2025** | **Six Months Ended June 30, 2024** | **Six Months Ended June 30, 2024** | **Six Months Ended June 30, 2024** |
| | **Insurance** | **Reinsurance** | **Total** | **Insurance** | **Reinsurance** | **Total** |
| | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** | **($ in millions, except for percentages)** |
| **Underwriting Revenues** | | | | | | |
| Gross written premiums | $**1380.0** | $**1146.1** | $**2526.1** | $1301.2 | $1180.6 | $2481.8 |
| Net written premiums | $**768.3** | $**698.9** | $**1467.2** | $763.7 | $788.3 | $1552.0 |
| Net earned premiums | $**799.5** | $**578.1** | $**1377.6** | $739.3 | $631.8 | $1371.1 |
| **Underwriting Expenses** |  |  |  |  |  |  |
| Current accident year net losses and loss expenses | $**(453.5)** | $**(270.6)** | $**(724.1)** | $(451.7) | $(264.6) | $(716.3) |
| Catastrophe losses | **(28.3)** | **(86.7)** | **(115.0)** | (16.6) | (64.0) | (80.6) |
| Prior year reserve development, post LPT years | **2.4** | **16.8** | **19.2** | 3.5 | 3.7 | 7.2 |
| Adjusted losses and loss adjustment expenses <sup>(1)</sup> | **(479.4)** | **(340.5)** | **(819.9)** | (464.8) | (324.9) | (789.7) |
| Impact of the LPT <sup>(2)</sup> | **(7.8)** | **(6.7)** | **(14.5)** | 4.5 | (19.5) | (15.0) |
| **Losses and loss adjustment expenses** | **(487.2)** | **(347.2)** | **(834.4)** | (460.3) | (344.4) | (804.7) |
| Acquisition costs | **(95.3)** | **(90.4)** | **(185.7)** | (83.9) | (114.6) | (198.5) |
| General and administrative expenses | **(141.6)** | **(88.3)** | **(229.9)** | (125.6) | (72.5) | (198.1) |
| **Underwriting income** <sup>(1)</sup> | $**75.4** | $**52.2** | $**127.6** | $69.5 | $100.3 | $169.8 |
| Adjusted underwriting income <sup>(1)</sup> | $**83.2** | $**58.9** | $**142.1** | $65.0 | $119.8 | $184.8 |
| **Ratios** |  |  |  |  |  |  |
| Current accident year loss ratio, excluding catastrophe losses | **56.7%** | **46.8%** | **52.6%** | 61.2% | 41.9% | 52.2% |
| Current accident year catastrophe loss ratio | **3.5** | **15.0** | **8.3** | 2.2 | 10.1 | 5.9 |
| Current accident year loss ratio | **60.2** | **61.8** | **60.9** | 63.4 | 52.0 | 58.1 |
| Prior year reserve development ratio, post LPT years | **(0.3)** | **(2.9)** | **(1.4)** | (0.5) | (0.6) | (0.5) |
| Adjusted loss ratio <sup>(1)</sup> | **59.9** | **58.9** | **59.5** | 62.9 | 51.4 | 57.6 |
| Impact of the LPT <sup>(2)</sup> | **1.0** | **1.2** | **1.1** | (0.6) | 3.1 | 1.1 |
| **Loss ratio** | **60.9** | **60.1** | **60.6** | 62.3 | 54.5 | 58.7 |
| Acquisition cost ratio | **11.9** | **15.6** | **13.5** | 11.3 | 18.1 | 14.5 |
| General and administrative expense ratio | **17.7** | **15.3** | **16.7** | 17.0 | 11.5 | 14.4 |
| **Combined ratio** | **90.5%** | **91.0%** | **90.8%** | 90.6% | 84.1% | 87.6% |
| Adjusted combined ratio <sup>(1)</sup> | **89.5%** | **89.8%** | **89.7%** | 91.2% | 81.0% | 86.5% |

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(1) Adjusted losses and loss adjustment expenses, underwriting income, adjusted underwriting income, 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.

(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.

26&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;

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| | |
|:---|:---|
| <br>![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | ASPEN INSURANCE HOLDINGS LIMITED |
| <br>![aspen_leafxiconxblackxrgbxa.jpg](aspen_leafxiconxblackxrgbxa.jpg) | Derivatives |

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The following tables summarize information on the location and amounts of derivative fair values on the consolidated balance sheet as at June 30, 2025 and December 31, 2024:

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| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
| | | **As at June 30, 2025** | **As at June 30, 2025** | | **As at December 31, 2024** | **As at December 31, 2024** |
|<br>**Derivatives Not Designated as Hedging Instruments Under ASC 815** |<br>**Balance Sheet Location** | **Notional<br>Amount** | **Fair<br>Value** | | **Notional<br>Amount** | **Fair<br>Value** |
| | | **($ in millions)** | **($ in millions)** | | **($ in millions)** | **($ in millions)** |
| Foreign Exchange Contracts | Derivative assets | $740.6 | $23.8 |  | $550.0 | $17.0 |
| Foreign Exchange Contracts | Derivative liabilities | $981.1 | $(21.7) | <sup>(1)</sup>  | $1036.9 | $(41.7) |
| Loss Portfolio Transfer Liability - Embedded Derivative | Derivative liabilities | $— | $(0.7) | <sup>(2)</sup> | $— | $(3.6) |

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<sup>(1)&nbsp;&nbsp;&nbsp;&nbsp;</sup>Net of $1.0 million cash collateral (December 31, 2024 — $0.8 million)

<sup>(2)&nbsp;&nbsp;&nbsp;&nbsp;</sup>The LPT contains an embedded derivative within the contract in relation to the variable interest crediting rate.

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| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
| | | **As at June 30, 2025** | **As at June 30, 2025** | | **As at December 31, 2024** | **As at December 31, 2024** |
|<br>**Derivatives Designated as Hedging Instruments Under ASC 815** |<br>**Balance Sheet Location** | **Notional<br>Amount** | **Fair<br>Value** | | **Notional<br>Amount** | **Fair<br>Value** |
| | | **($ in millions)** | **($ in millions)** | | **($ in millions)** | **($ in millions)** |
| Foreign Exchange Contracts | Derivative assets | $79.1 | $4.3 |  | $— | $— |
| Foreign Exchange Contracts | Derivative liabilities | $— | $— | <sup>(1)</sup> | $158.0 | $(4.2) |

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<sup>(1)&nbsp;&nbsp;&nbsp;&nbsp;</sup>Net of $Nil cash collateral (December 31, 2024 — $2.0 million)

The following table provides the unrealized and realized gains/(losses) recorded in the statements of operations and other comprehensive income for derivatives that are not designated or designated as hedging instruments under ASC 815 - "Derivatives and Hedging" for the three and six months ended June 30, 2025 and 2024.

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| | | | | | |
|:---|:---|:---|:---|:---|:---|
| | | **Amount of Gain/(Loss) Recognized on Derivatives** | **Amount of Gain/(Loss) Recognized on Derivatives** | **Amount of Gain/(Loss) Recognized on Derivatives** | **Amount of Gain/(Loss) Recognized on Derivatives** |
| | | **Three Months Ended** | **Three Months Ended** | **Six Months Ended** | **Six Months Ended** |
| |<br>**Location of Gain/(Loss) Recognized on Derivatives** | **June 30, 2025** | **June 30, 2024** | **June 30, 2025** | **June 30, 2024** |
|<br><br>**Derivatives not designated as hedges** | | **($ in millions)** | **($ in millions)** | **($ in millions)** | **($ in millions)** |
| Foreign Exchange Contracts | Change in Fair Value of Derivatives | 19.5 | (4.9) | 43.0 | (22.4) |
| Loss Portfolio Transfer Liability - Embedded Derivative | Change in Fair Value of Derivatives | 0.5 | 2.9 | 2.9 | 6.8 |
| **Derivatives designated as hedges** |  |  |  |  |  |
| Foreign Exchange Contracts | General, administrative and corporate expenses | 0.4 |  | (0.4) |  |
| Foreign Exchange Contracts | Net change gross of tax from current period hedged transactions | 5.3 | 0.3 | 10.5 | (0.2) |

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