AHL.PRE / Aspen Insurance Holdings Limited - Preferred Stock - Pengajuan SECLaporan Tahunan, Pernyataan Proksi

Aspen Insurance Holdings Limited - Preferred Stock
US ˙ NYSE ˙ BMG053842040

Mga Batayang Estadistika
LEI 549300YX6HECG9XQCQ75
CIK 1267395
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Aspen Insurance Holdings Limited - Preferred Stock
SEC Filings (Chronological Order)
Halaman ini menyediakan daftar lengkap dan kronologis dari Pengajuan SEC, tidak termasuk pengajuan kepemilikan yang kami sediakan di tempat lain.
September 2, 2025 EX-99.1

Aspen Declares Dividends on Preference Shares

Exhibit 99.1 PRESS RELEASE Aspen Declares Dividends on Preference Shares Hamilton, Bermuda, September 2, 2025 – Aspen Insurance Holdings Limited (“Aspen,” “our” or the “Company”) (NYSE: AHL) announced today that its Board of Directors has declared the following dividends on its Preference Shares: •Quarterly dividend of $0.3516 per share on its 5.625% Perpetual Non-Cumulative Preference Shares with

September 2, 2025 6-K

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 September 2025 Commission File Number: 001-

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 September 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 e

August 27, 2025 EX-99.1

AGREEMENT AND PLAN OF MERGER by and among ENDURANCE SPECIALTY INSURANCE LTD. AJAX LTD. ASPEN INSURANCE HOLDINGS LIMITED Dated as of August 27, 2025 TABLE OF CONTENTS

Exhibit 99.1 Execution Version AGREEMENT AND PLAN OF MERGER by and among ENDURANCE SPECIALTY INSURANCE LTD. AJAX LTD. and ASPEN INSURANCE HOLDINGS LIMITED Dated as of August 27, 2025 TABLE OF CONTENTS Page ARTICLE I DEFINITIONS AND TERMS Section 1.01 Definitions 2 Section 1.02 Interpretations 19 ARTICLE II THE MERGER Section 2.01 Merger 21 Section 2.02 Merger Effective Time 21 Section 2.03 Effects

August 27, 2025 6-K

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: 001-319

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 exec

August 27, 2025 EX-99.2

Sompo to Acquire Aspen for $3.5 Billion All outstanding Class A ordinary shares of Aspen to be redeemed for cash and delisted from NYSE; Aspen preference shares to remain outstanding Further diversifies Sompo’s portfolio geographically in high-growth

Exhibit 99.2 FOR IMMEDIATE RELEASE Sompo to Acquire Aspen for $3.5 Billion All outstanding Class A ordinary shares of Aspen to be redeemed for cash and delisted from NYSE; Aspen preference shares to remain outstanding Further diversifies Sompo’s portfolio geographically in high-growth international markets Strengthens underwriting expertise and presence in core specialty insurance and reinsurance

August 13, 2025 EX-99.1

FINANCIAL STATEMENTS TABLE OF CONTENTS

Note 7. Derivative Contracts FINANCIAL STATEMENTS TABLE OF CONTENTS Page Consolidated Balance Sheets 1 Consolidated Statements of Operations and Other Comprehensive Income (Loss) 2 Consolidated Statements of Changes in Shareholders’ Equity 3 Consolidated Statements of Cash Flows 4 Note 1. History and Organization 6 Note 2. Basis of Presentation and Significant Accounting Policies 6 Note 3. Segment

August 13, 2025 6-K

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: 001-319

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 exec

August 7, 2025 EX-99.2

ASPEN INSURANCE HOLDINGS LIMITED Table Of Contents Page Basis of Presentation 1 Cautionary Statement Regarding Forward-Looking Statements 2 Financial Highlights 3 Consolidated Statements of Operations - Quarterly Results 4 Consolidated Statements of

Exhibit 99.2 FINANCIAL SUPPLEMENT As of June 30, 2025 Aspen Insurance Holdings Limited 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

August 7, 2025 6-K

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: 001-319

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 exec

August 7, 2025 EX-99.1

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

Exhibit 99.1 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: •Improvement of 3.6 percentage points in the combined ratio of 85.1% compared to June 30, 2024, resulting in underw

July 17, 2025 EX-99.1

Aspen Appoints John Welch as Group Chief Underwriting Officer

Exhibit 99.1 PRESS RELEASE Aspen Appoints John Welch as Group Chief Underwriting Officer HAMILTON, Bermuda-(BUSINESS WIRE)-Aspen Insurance Holdings Limited (“Aspen”) (NYSE: AHL) has appointed John Welch as Group Chief Underwriting Officer. John brings over 30 years of experience in executive roles across global players including at AXA XL and XL Catlin Group, and originally joined Aspen as Chief U

July 17, 2025 6-K

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 July 2025 Commission File Number: 001-31909

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 July 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 execut

June 13, 2025 6-K

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 June 2025 Commission File Number: 001-31909

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 June 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 execut

June 13, 2025 EX-1.1

ASPEN INSURANCE HOLDINGS LIMITED 5.750% Senior Notes due 2030 UNDERWRITING AGREEMENT

Exhibit 1.1 Execution Version ASPEN INSURANCE HOLDINGS LIMITED $300,000,000 5.750% Senior Notes due 2030 UNDERWRITING AGREEMENT June 10, 2025 CITIGROUP GLOBAL MARKETS INC. LLOYDS SECURITIES INC. HSBC SECURITIES (USA) INC. As Representatives of the several Underwriters named in Schedule I c/o CITIGROUP GLOBAL MARKETS INC. 388 Greenwich Street New York, NY 10013 c/o LLOYDS SECURITIES INC. 1095 Avenu

June 13, 2025 EX-4.2

FIFTH SUPPLEMENTAL INDENTURE BY AND BETWEEN ASPEN INSURANCE HOLDINGS LIMITED, AS ISSUER DEUTSCHE BANK TRUST COMPANY AMERICAS, AS TRUSTEE

Exhibit 4.2 Execution Version FIFTH SUPPLEMENTAL INDENTURE BY AND BETWEEN ASPEN INSURANCE HOLDINGS LIMITED, AS ISSUER AND DEUTSCHE BANK TRUST COMPANY AMERICAS, AS TRUSTEE Dated as of June 13, 2025 $300,000,000 ASPEN INSURANCE HOLDINGS LIMITED 5.750% SENIOR NOTES DUE 2030 FIFTH SUPPLEMENTAL INDENTURE This Fifth Supplemental Indenture, dated as of June 13, 2025 (the “Fifth Supplemental Indenture”),

June 11, 2025 EX-99.1

Aspen Prices Public Offering of US$300,000,000 of Senior Notes

Exhibit 99.1 PRESS RELEASE Aspen Prices Public Offering of US$300,000,000 of Senior Notes Hamilton, Bermuda—June 10, 2025 – Aspen Insurance Holdings Limited (“Aspen” or the “Company”) (NYSE: AHL) has priced an underwritten public offering of US$300,000,000 aggregate principal amount of 5.750% senior notes due 2030 (the “Notes”). The Notes were priced at 99.870% of the principal amount and will mat

June 11, 2025 424B5

$300,000,000 Aspen Insurance Holdings Limited 5.750% Senior Notes due 2030

Filed Pursuant to Rule 424(b)(5) Registration No. 333-272650 Prospectus Supplement (To Prospectus dated June 26, 2023) $300,000,000 Aspen Insurance Holdings Limited 5.750% Senior Notes due 2030 This is an offering by Aspen Insurance Holdings Limited (“Aspen Holdings” or the “Issuer”) of $300,000,000 aggregate principal amount of 5.750% Senior Notes due 2030 (the “notes”). The notes will bear inter

June 11, 2025 6-K

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 June 2025 Commission File Number: 001-31909

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 June 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 execut

June 10, 2025 FWP

ASPEN INSURANCE HOLDINGS LIMITED $300,000,000 5.750% SENIOR NOTES DUE 2030 PRICING TERM SHEET June 10, 2025

Filed Pursuant to Rule 433 Dated June 10, 2025 Registration Statement on Form F-3 (No.

June 9, 2025 424B5

SUBJECT TO COMPLETION, DATED JUNE 9, 2025

Filed Pursuant to Rule 424(b)(5) Registration No. 333-272650 The information in this preliminary prospectus supplement is not complete and may be changed. This preliminary prospectus supplement and the accompanying prospectus are not an offer to sell these securities and we are not soliciting offers to buy these securities in any jurisdiction where the offer or sale is not permitted. SUBJECT TO CO

June 6, 2025 6-K

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 June 2025 Commission File Number: 001-31909

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 June 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 execut

June 3, 2025 EX-99.1

FINANCIAL STATEMENTS TABLE OF CONTENTS

Exhibit 99.1 FINANCIAL STATEMENTS TABLE OF CONTENTS Page Consolidated Balance Sheets 1 Consolidated Statements of Operations and Other Comprehensive Income (Loss) 2 Consolidated Statements of Changes in Shareholders’ Equity 3 Consolidated Statements of Cash Flows 4 Note 1. History and Organization 6 Note 2. Basis of Presentation and Significant Accounting Policies 6 Note 3. Segment Reporting 7 Not

June 3, 2025 EX-99.2

ASPEN INSURANCE HOLDINGS LIMITED Table Of Contents Page Basis of Presentation 1 Cautionary Statement Regarding Forward-Looking Statements 2 Financial Highlights 3 Consolidated Statements of Operations - Quarterly Results 4 Consolidated Statements of

Exhibit 99.2 FINANCIAL SUPPLEMENT As of March 31, 2025 Aspen Insurance Holdings Limited 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 wit

June 3, 2025 6-K

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 OF THE SECURITIES EXCHANGE ACT OF 1934 For the month of June 2025 Commission File Number: 001-31909 AS

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 OF THE SECURITIES EXCHANGE ACT OF 1934 For the month of June 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

June 2, 2025 6-K

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 June 2025 Commission File Number: 001-31909

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 June 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 execut

June 2, 2025 EX-99.1

Aspen Declares Dividends on Preference Shares

Exhibit 99.1 PRESS RELEASE Aspen Declares Dividends on Preference Shares Hamilton, Bermuda, June 2, 2025 – Aspen Insurance Holdings Limited (“Aspen,” “our” or the “Company”) (NYSE: AHL) announced today that its Board of Directors has declared the following dividends on its Preference Shares: •Quarterly dividend of $0.3516 per share on its 5.625% Perpetual Non-Cumulative Preference Shares with a $2

May 9, 2025 EX-99.1

Aspen Announces Closing of Upsized Initial Public Offering

EX-99.1 2 exhibit991-6xkclosing.htm EX-99.1 Exhibit 99.1 PRESS RELEASE Aspen Announces Closing of Upsized Initial Public Offering Hamilton, Bermuda, May 9, 2025 — Aspen Insurance Holdings Limited (“Aspen”) announced today the closing of its upsized initial public offering of 13,250,000 of its Class A ordinary shares, par value $0.001 per share (“ordinary shares”), at a price to the public of $30.0

May 9, 2025 6-K

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 May 2025 Commission File Number: 001-31909

6-K 1 aspen-6xkclosing.htm 6-K 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 May 2025 Commission File Number: 001-31909 ASPEN INSURANCE HOLDINGS LIMITED (Translation of registrant’s name into English) 141 Front Street Hamilton HM 19 Bermud

May 8, 2025 S-8

As filed with the Securities and Exchange Commission on May 8, 2025

As filed with the Securities and Exchange Commission on May 8, 2025 Registration No.

May 8, 2025 EX-99.1

Aspen Announces Pricing of Upsized Initial Public Offering

Exhibit 99.1 PRESS RELEASE Aspen Announces Pricing of Upsized Initial Public Offering Hamilton, Bermuda, May 7, 2025 — Aspen Insurance Holdings Limited (“Aspen”) announced today the pricing of its upsized initial public offering (“IPO”) of 13,250,000 of its Class A ordinary shares, par value $0.001 per share (“ordinary shares”), at a price to the public of $30.00 per ordinary share. The ordinary s

May 8, 2025 F-N

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM F-N APPOINTMENT OF AGENT FOR SERVICE OF PROCESS BY FOREIGN BANKS AND FOREIGN INSURANCE COMPANIES AND CERTAIN OF THEIR HOLDING COMPANIES AND FINANCE SUBSIDIARIES MAKING PUBLI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM F-N APPOINTMENT OF AGENT FOR SERVICE OF PROCESS BY FOREIGN BANKS AND FOREIGN INSURANCE COMPANIES AND CERTAIN OF THEIR HOLDING COMPANIES AND FINANCE SUBSIDIARIES MAKING PUBLIC OFFERINGS OF SECURITIES IN THE UNITED STATES A.Name of issuer or person filing (“Filer”): Aspen Insurance Holdings Limited B.This is (select one): ☒

May 8, 2025 EX-4.1

ASPEN INSURANCE HOLDINGS LIMITED 2025 EQUITY AND INCENTIVE PLAN I. INTRODUCTION

Exhibit 4.1 ASPEN INSURANCE HOLDINGS LIMITED 2025 EQUITY AND INCENTIVE PLAN I. INTRODUCTION 1.1 Purposes. The purposes of the 2025 Equity and Incentive Plan (this “Plan”) are to (i) align the interests of the Company’s shareholders and the recipients of awards under this Plan by increasing the proprietary interest of such recipients in the Company’s growth and success, (ii) advance the interests o

May 8, 2025 424B4

13,250,000 Class A Ordinary Shares Aspen Insurance Holdings Limited

Filed Pursuant to Rule 424(b)(4) Registration No. 333-276163 Prospectus 13,250,000 Class A Ordinary Shares Aspen Insurance Holdings Limited This is the initial public offering of the Class A ordinary shares, par value $0.001 per share, of Aspen Insurance Holdings Limited (the “ordinary shares”). The selling shareholders identified in this prospectus are offering 13,250,000 ordinary shares. We are

May 8, 2025 EX-FILING FEES

Calculation of Filing Fee Table FORM S-8 (Form Type) Aspen Insurance Holdings Limited (Exact Name of Registrant as Specified in its Charter) Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered Propose

Exhibit 107 Calculation of Filing Fee Table FORM S-8 (Form Type) Aspen Insurance Holdings Limited (Exact Name of Registrant as Specified in its Charter) Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee 1 Equity Class A Ordinary Shares, par value $0.

May 8, 2025 F-N

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM F-N APPOINTMENT OF AGENT FOR SERVICE OF PROCESS BY FOREIGN BANKS AND FOREIGN INSURANCE COMPANIES AND CERTAIN OF THEIR HOLDING COMPANIES AND FINANCE SUBSIDIARIES MAKING PUBLI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM F-N APPOINTMENT OF AGENT FOR SERVICE OF PROCESS BY FOREIGN BANKS AND FOREIGN INSURANCE COMPANIES AND CERTAIN OF THEIR HOLDING COMPANIES AND FINANCE SUBSIDIARIES MAKING PUBLIC OFFERINGS OF SECURITIES IN THE UNITED STATES A. Name of issuer or person filing (“Filer”): Aspen Insurance Holdings Limited B. This is (select one):

May 8, 2025 6-K

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 May 2025 Commission File Number: 001-31909

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 May 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 executi

May 7, 2025 F-1MEF

As filed with the Securities and Exchange Commission on May 7, 2025.

As filed with the Securities and Exchange Commission on May 7, 2025. Registration No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form F-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 ASPEN INSURANCE HOLDINGS LIMITED (Exact Name of Registrant as Specified in its Charter) Bermuda 6331 98-0501000 (State or Other Jurisdiction of Incorporation or Organizatio

May 7, 2025 8-A12B

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(B) OR (G) OF THE SECURITIES EXCHANGE ACT OF 1934 ASPEN INSURANCE HOLDINGS LIMITED (Exact name of

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(B) OR (G) OF THE SECURITIES EXCHANGE ACT OF 1934 ASPEN INSURANCE HOLDINGS LIMITED (Exact name of registrant as specified in its charter) Bermuda 98-0501000 (State or other jurisdiction of (I.R.S. Employer Identification No.) incorporation or orga

May 7, 2025 EX-FILING FEES

Calculation of Filing Fee Tables Form F-1 (Form Type) Aspen Insurance Holdings Limited (Exact Name of Registrant as Specified in its Memorandum of Association) Table 1: Newly Registered and Carry Forward Securities

Exhibit 107 Calculation of Filing Fee Tables Form F-1 (Form Type) Aspen Insurance Holdings Limited (Exact Name of Registrant as Specified in its Memorandum of Association) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered(1) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee(3) Carry Forward Form Type Carry Forward File Number Carry Forward Initial Effective Date Filing Fee Previously Paid in Connection with Unsold Securities to be Carried Forward Newly Registered Securities Fees to be Paid Equity Class A Ordinary Shares, par value $0.

May 5, 2025 CORRESP

[Signature Page Follows]

May 5, 2025 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance Office of Finance 100 F.

May 5, 2025 CORRESP

Aspen Insurance Holdings Limited 141 Front Street Hamilton HM 19 May 5, 2025

Aspen Insurance Holdings Limited 141 Front Street Hamilton HM 19 Bermuda May 5, 2025 VIA EDGAR U.

April 29, 2025 EX-1.1

Aspen Insurance Holdings Limited Class A Ordinary Shares Underwriting Agreement

Exhibit 1.1 Aspen Insurance Holdings Limited Class A Ordinary Shares Underwriting Agreement [ ò ], 2025 Goldman Sachs & Co. LLC Citigroup Global Markets Inc. Jefferies LLC As representatives (the “Representatives”) of the several Underwriters named in Schedule I hereto c/o Goldman Sachs & Co. LLC 200 West Street New York, New York 10282 c/o Citigroup Global Markets Inc. 388 Greenwich Street New Yo

April 29, 2025 CORRESP

SIDLEY AUSTIN LLP

SIDLEY AUSTIN LLP 787 SEVENTH AVENUE NEW YORK, NY 10019 +1 212 839 5300 +1 212 839 5599 FAX AMERICA ASIA PACIFIC EUROPE April 29, 2025 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance Office of Finance 100 F Street, N.

April 29, 2025 EX-99.3

Consent of Independent Registered Public Accounting Firm

Exhibit 99.3 Consent of Independent Registered Public Accounting Firm We consent to the incorporation by reference in the Registration Statement (Form F-3 No. 333-272650) of Aspen Insurance Holdings Limited and in the related Prospectus of our report dated April 1, 2024, with respect to the consolidated financial statements of Aspen Insurance Holdings Limited for the year ended December 31, 2023,

April 29, 2025 EX-99.4

Aspen Announces Launch of Initial Public Offering

Exhibit 99.4 PRESS RELEASE Aspen Announces Launch of Initial Public Offering Hamilton, Bermuda, April 29, 2025 — Aspen Insurance Holdings Limited (“Aspen”) announced today the launch of its initial public offering (“IPO”) of 11,000,000 of its Class A ordinary shares, par value $0.001 per share (“ordinary shares”), all of which will be sold by certain entities managed by affiliates of Apollo Global

April 29, 2025 F-1/A

As filed with the Securities and Exchange Commission on April 29, 2025.

As filed with the Securities and Exchange Commission on April 29, 2025. Registration No. 333-276163 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 5 to Form F-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 ASPEN INSURANCE HOLDINGS LIMITED (Exact Name of Registrant as Specified in its Charter) Bermuda 6331 98-0501000 (State or Other Jurisdiction of

April 29, 2025 6-K

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 April 2025 Commission File Number: 001-3190

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 April 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 execu

April 29, 2025 EX-10.9

ASPEN INSURANCE HOLDINGS LIMITED 2025 EQUITY AND INCENTIVE PLAN I. INTRODUCTION

Exhibit 10.9 ASPEN INSURANCE HOLDINGS LIMITED 2025 EQUITY AND INCENTIVE PLAN I. INTRODUCTION 1.1 Purposes. The purposes of the 2025 Equity and Incentive Plan (this “Plan”) are to (i) align the interests of the Company’s shareholders and the recipients of awards under this Plan by increasing the proprietary interest of such recipients in the Company’s growth and success, (ii) advance the interests

April 29, 2025 6-K

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 April 2025 Commission File Number: 001-3190

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 April 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 execu

April 29, 2025 EX-99.1

INDEX TO THE CONSOLIDATED FINANCIAL STATEMENTS

Exhibit 99.1 INDEX TO THE CONSOLIDATED FINANCIAL STATEMENTS AUDITED ACCOUNTS Page REPORT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM (ERNST & YOUNG LTD.) F-2 REPORT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM (ERNST & YOUNG LLP) F-5 CONSOLIDATED BALANCE SHEETS F-6 CONSOLIDATED STATEMENTS OF OPERATIONS AND OTHER COMPREHENSIVE INCOME (LOSS) F-7 CONSOLIDATED STATEMENTS OF CHANGES IN SHAREHO

April 29, 2025 EX-99.2

Consent of Independent Registered Public Accounting Firm

Exhibit 99.2 Consent of Independent Registered Public Accounting Firm We consent to the incorporation by reference in the Registration Statement (Form F-3 No. 333-272650) of Aspen Insurance Holdings Limited and in the related Prospectus of our report dated March 19, 2025 (except for Note 26, as to which the date is April 29, 2025) with respect to the consolidated financial statements of Aspen Insu

April 29, 2025 EX-FILING FEES

Calculation of Filing Fee Tables Form F-1 (Form Type) Aspen Insurance Holdings Limited (Exact Name of Registrant as Specified in its Memorandum of Association) Table 1: Newly Registered and Carry Forward Securities

Exhibit 107 Calculation of Filing Fee Tables Form F-1 (Form Type) Aspen Insurance Holdings Limited (Exact Name of Registrant as Specified in its Memorandum of Association) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price(1) Fee Rate Amount of Registration Fee Carry Forward Form Type Carry Forward File Number Carry Forward Initial Effective Date Filing Fee Previously Paid in Connection with Unsold Securities to be Carried Forward Newly Registered Securities Fees to be Paid Equity Class A Ordinary Shares, par value $0.

March 20, 2025 EX-10.15

(1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.S. SERVICES INC. - and - (3) ASPEN BERMUDA LIMITED - and - (4) COGNIZANT WORLDWIDE LIMITED OUTSOURCING AGREEMENT

Exhibit 10.15 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.S. SERVICES INC. - and - (3) ASPEN BERMUDA LIMITED - and - (4) COGNIZANT WORLDWIDE LIMITED OUTSOURCING AGREEMENT CONTENTS PART A DEFINITIONS AND INTERPRETATION 6 1. DEFINITIONS 6 2. INTERPRETATION 6 PART B TERM AND SERVICE PROVISION 6 3. TERM 6 4. SERVICES 8 5. DELAY 10 6. ACCEPTANCE 11 7. TRANSITION 12 8. GOVERNAN

March 20, 2025 EX-24.2

POWER OF ATTORNEY

Exhibit 24.2 POWER OF ATTORNEY KNOW ALL PERSONS BY THESE PRESENTS, that each of the undersigned constitutes and appoints each of Mark Pickering and David Amaro, each acting alone, his true and lawful attorneys-in-fact and agents, with full power of substitution and resubstitution, for such person and in his name, place and stead, in any and all capacities, to sign the Registration Statement of Asp

March 20, 2025 EX-10.23

INVESTMENT MANAGEMENT AGREEMENT

Exhibit 10.23 INVESTMENT MANAGEMENT AGREEMENT This Investment Management Agreement (this “Agreement”) is entered into by and between Apollo Management International LLP, a limited liability partnership incorporated in England with registered number OC316197 (“AMI”), and [Aspen entity], a company domiciled in [ ] with registered number [ ] (“Client” and together with AMI, the “Parties” and each a “

March 20, 2025 EX-10.21

INVESTMENT MANAGEMENT AGREEMENT

Exhibit 10.21 Execution Version INVESTMENT MANAGEMENT AGREEMENT This Investment Management Agreement (this “Agreement”) is entered into by and between Apollo Asset Management Europe PC LLP, a limited liability partnership incorporated in England with registered number OC402344 (“AAME”), and Aspen American Insurance Company, a Texas corporation (“Client” and together with AAME, the “Parties”), on A

March 20, 2025 EX-3.4

THIRD AMENDED AND RESTATED BYE - LAWS ASPEN INSURANCE HOLDINGS LIMITED I N D E X

Exhibit 3.4 THIRD AMENDED AND RESTATED BYE - LAWS OF ASPEN INSURANCE HOLDINGS LIMITED I N D E X BYE-LAW SUBJECT PAGE 1 Interpretation 1 2 Registered Office 6 3 Share Capital 6 4-7 Alteration of Capital 9 8-12 Shares 10 13-14 Modification of Rights 11 15-18 Certificates 12 19-20 Register of Shareholders 13 21 Register of Directors and Officers 13 22-26 Transfer of Shares 13 27-30 Transmission of Sh

March 20, 2025 F-1/A

As filed with the Securities and Exchange Commission on March 20, 2025.

As filed with the Securities and Exchange Commission on March 20, 2025. Registration No. 333-276163 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 4 to Form F-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 ASPEN INSURANCE HOLDINGS LIMITED (Exact Name of Registrant as Specified in its Charter) Bermuda 6331 98-0501000 (State or Other Jurisdiction of

March 20, 2025 EX-10.22

Dated 24 January 2025 (1) APOLLO ASSET MANAGEMENT EUROPE PC LLP (2) APOLLO ASSET MANAGEMENT EUROPE LLP (3) ASPEN AMERICAN INSURANCE COMPANY DEED OF NOVATION

Exhibit 10.22 Execution Version EV Dated 24 January 2025 (1) APOLLO ASSET MANAGEMENT EUROPE PC LLP (2) APOLLO ASSET MANAGEMENT EUROPE LLP (3) ASPEN AMERICAN INSURANCE COMPANY DEED OF NOVATION 2 CONTENTS Clause Page 1. NOVATION 1 2. RELEASE AND DISCHARGE OF THE OUTGOING PARTY 2 3. COUNTERPARTS 2 4. GOVERNING LAW AND DISPUTES 2 ANNEX A 6 THIS DEED OF NOVATION is made on 24 January 2025 BETWEEN: (1)A

March 20, 2025 EX-21.1

SUBSIDIARIES OF THE COMPANY NAME OF SUBSIDIARY JURISDICTION OF INCORPORATION Acorn Limited Bermuda Aspen (UK) Holdings Limited United Kingdom Aspen American Insurance Company Texas Aspen Australia Service Company Pty Ltd. Australia Aspen Bermuda Limi

Exhibit 21.1 SUBSIDIARIES OF THE COMPANY NAME OF SUBSIDIARY JURISDICTION OF INCORPORATION Acorn Limited Bermuda Aspen (UK) Holdings Limited United Kingdom Aspen American Insurance Company Texas Aspen Australia Service Company Pty Ltd. Australia Aspen Bermuda Limited Bermuda Aspen Capital Management, Ltd Bermuda Aspen Cat Fund Limited Bermuda Aspen European Holdings Limited United Kingdom Aspen Ins

March 20, 2025 CORRESP

SIDLEY AUSTIN LLP 787 SEVENTH AVENUE NEW YORK, NY 10019 +1 212 839 5300 +1 212 839 5599 FAX AMERICA ASIA PACIFIC EUROPE

SIDLEY AUSTIN LLP 787 SEVENTH AVENUE NEW YORK, NY 10019 +1 212 839 5300 +1 212 839 5599 FAX AMERICA ASIA PACIFIC EUROPE March 20, 2025 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance Office of Finance 100 F Street, N.

March 19, 2025 EX-13.1

CERTIFICATION PURSUANT TO 18 U.S.C. SECTION 1350, AS ADOPTED PURSUANT TO SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002

Exhibit 13.1 CERTIFICATION PURSUANT TO 18 U.S.C. SECTION 1350, AS ADOPTED PURSUANT TO SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002 In connection with this Annual Report on Form 20-F of Aspen Insurance Holdings Limited (the “Company”) for the twelve months ended December 31, 2024 as filed with the Securities and Exchange Commission on the date hereof (the “Report”), Mark Cloutier as Chief Executiv

March 19, 2025 EX-15.1

Consent of Independent Registered Public Accounting Firm

Exhibit 15.1 Consent of Independent Registered Public Accounting Firm We consent to the incorporation by reference in the Registration Statement (Form F-3 No. 333-272650) of Aspen Insurance Holdings Limited and in the related Prospectus of our report dated March 19, 2025, with respect to the consolidated financial statements of Aspen Insurance Holdings Limited, included in this Annual Report (Form

March 19, 2025 EX-4.9

(1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.S. SERVICES INC. - and - (3) ASPEN BERMUDA LIMITED - and - (4) COGNIZANT WORLDWIDE LIMITED OUTSOURCING AGREEMENT

Exhibit 4.9 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.S. SERVICES INC. - and - (3) ASPEN BERMUDA LIMITED - and - (4) COGNIZANT WORLDWIDE LIMITED OUTSOURCING AGREEMENT CONTENTS PART A DEFINITIONS AND INTERPRETATION 6 1. DEFINITIONS 6 2. INTERPRETATION 6 PART B TERM AND SERVICE PROVISION 6 3. TERM 6 4. SERVICES 8 5. DELAY 10 6. ACCEPTANCE 11 7. TRANSITION 12 8. GOVERNANCE

March 19, 2025 EX-4.15

Dated 24 January 2025 (1)APOLLO ASSET MANAGEMENT EUROPE PC LLP (2)APOLLO ASSET MANAGEMENT EUROPE LLP (3)ASPEN AMERICAN INSURANCE COMPANY DEED OF NOVATION

EV Exhibit 14.17 Dated 24 January 2025 (1)APOLLO ASSET MANAGEMENT EUROPE PC LLP (2)APOLLO ASSET MANAGEMENT EUROPE LLP (3)ASPEN AMERICAN INSURANCE COMPANY DEED OF NOVATION CONTENTS Clause Page 2. RELEASE AND DISCHARGE OF THE OUTGOING PARTY 2 3. COUNTERPARTS 2 4. GOVERNING LAW AND DISPUTES 2 ANNEX A 5 UK-703494539.3 THIS DEED OF NOVATION is made on 24 January 2025 BETWEEN: (1)Apollo Asset Management

March 19, 2025 20-F

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 20-F

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 20-F ☐ REGISTRATION STATEMENT PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECUR

March 19, 2025 EX-4.14

INVESTMENT MANAGEMENT AGREEMENT

EXECUTION VERSION Exhibit 4.16 INVESTMENT MANAGEMENT AGREEMENT This Investment Management Agreement (this “Agreement”) is entered into by and between Apollo Asset Management Europe PC LLP, a limited liability partnership incorporated in England with registered number OC402344 (“AAME”), and Aspen American Insurance Company, a Texas corporation (“Client” and together with AAME, the “Parties”), on Ap

March 19, 2025 EX-15.2

Consent of Independent Registered Public Accounting Firm

Exhibit 15.2 Consent of Independent Registered Public Accounting Firm We consent to the incorporation by reference in the Registration Statement (Form F-3 No. 333-272650) of Aspen Insurance Holdings Limited and in the related Prospectus of our report dated April 1, 2024, with respect to the consolidated financial statements of Aspen Insurance Holdings Limited for the year ended December 31, 2023,

March 19, 2025 EX-12.1

CERTIFICATION

Exhibit 12.1 CERTIFICATION I, Mark Cloutier, certify that: 1.I have reviewed this annual report on Form 20-F of Aspen Insurance Holdings Limited; 2.Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with

March 19, 2025 EX-11.1

Acknowledgment & Agreement

Exhibit 11.1 TABLE OF CONTENTS 1. INTRODUCTION 3 1.1. Ownership, Approval and Periodic Review 3 2. BACKGROUND AND SCOPE 3 2.1. Material Information 4 2.2. Non-Public Information 5 2.3. Hindsight 5 2.4. Transactions by Immediate Family Members 6 3. POLICY & PRINCIPLES 6 3.1. Prohibitions on Trading Securities 6 3.1.1. Prohibited Transactions in Aspen Securities 6 3.1.2. Close Periods 8 3.1.3. Hards

March 19, 2025 EX-12.2

CERTIFICATION

Exhibit 12.2 CERTIFICATION I, Mark Pickering, certify that: 1.I have reviewed this annual report on Form 20-F of Aspen Insurance Holdings Limited; 2.Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading wit

February 28, 2025 6-K

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 February 2025 Commission File Number: 001-3

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 February 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 ex

February 28, 2025 EX-99.1

Aspen Declares Dividends on Preference Shares

Exhibit 99.1 PRESS RELEASE Aspen Declares Dividends on Preference Shares Hamilton, Bermuda, February 28, 2025 – Aspen Insurance Holdings Limited (“Aspen,” “our” or the “Company”) announced today that its Board of Directors has declared the following dividends on its Preference Shares: •Quarterly dividend of $0.3516 per share on its 5.625% Perpetual Non-Cumulative Preference Shares with a $25 liqui

February 27, 2025 EX-99.1

Aspen Reports Results for the Three and Twelve Months Ended December 31, 2024 Net Income Available to Ordinary Shareholders of $235 million and Operating Income** of $145 million for the Three Months Ended December 31, 2024 Net Income Available to Or

Exhibit 99.1 PRESS RELEASE Aspen Reports Results for the Three and Twelve Months Ended December 31, 2024 Net Income Available to Ordinary Shareholders of $235 million and Operating Income** of $145 million for the Three Months Ended December 31, 2024 Net Income Available to Ordinary Shareholders of $431 million and Operating Income** of $433 million for the Twelve Months Ended December 31, 2024 An

February 27, 2025 6-K

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 February 2025 Commission File Number: 001-3

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 February 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 ex

January 2, 2025 EX-99.25

EX-99.25

NOTIFICATION OF THE REMOVAL FROM LISTING AND REGISTRATION OF THE STATED SECURITIES The New York Stock Exchange hereby notifies the SEC of its intention to remove the entire class of the stated securities from listing and registration on the Exchange at the opening of business on January 13, 2025, pursuant to the provisions of Rule 12d2-2 (a).

December 11, 2024 EX-3.7

CERTIFICATE OF DESIGNATION 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES ASPEN INSURANCE HOLDINGS LIMITED

Exhibit 3.7 CERTIFICATE OF DESIGNATION OF 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES OF ASPEN INSURANCE HOLDINGS LIMITED ASPEN INSURANCE HOLDINGS LIMITED, a Bermuda company (the “Company”), HEREBY CERTIFIES that pursuant to resolutions of duly authorized Directors adopted on September 12, 2016, the creation of the 5.625% Perpetual Non-Cumulative Preference Shares, with a liquidation prefere

December 11, 2024 EX-3.3

Registration No. 32164 The Companies Act 1981 CERTIFICATE OF DEPOSIT OF MEMORANDUM OF INCREASE OF SHARE CAPITAL that a Memorandum of Increase of Share Capital THIS IS TO CERTIFY of Aspen Insurance Holdings Limited was delivered to the Registrar of Co

Exhibit 3.3 Registration No. 32164 The Companies Act 1981 CERTIFICATE OF DEPOSIT OF MEMORANDUM OF INCREASE OF SHARE CAPITAL that a Memorandum of Increase of Share Capital THIS IS TO CERTIFY of Aspen Insurance Holdings Limited was delivered to the Registrar of Companies on the in accordance with8th day of April 2024 section 45(3) of (the "Act").the Companies Act 1981 Kenneth Joaquin Registrar of Co

December 11, 2024 EX-10.10

THIRD AMENDED AND RESTATED CREDIT AGREEMENT ASPEN INSURANCE HOLDINGS LIMITED, The Subsidiary Borrowers from Time to Time Parties Hereto, The Several Lenders from Time to Time Parties Hereto, THE BANK OF NEW YORK MELLON, as Collateral Agent, CITIBANK,

Exhibit 10.10 Execution Version THIRD AMENDED AND RESTATED CREDIT AGREEMENT among ASPEN INSURANCE HOLDINGS LIMITED, The Subsidiary Borrowers from Time to Time Parties Hereto, The Several Lenders from Time to Time Parties Hereto, THE BANK OF NEW YORK MELLON, as Collateral Agent, CITIBANK, N.A., as Syndication Agent, HSBC BANK USA, N.A., LLOYDS BANK CORPORATE MARKETS PLC AND WELLS FARGO BANK, NATION

December 11, 2024 EX-3.5

CERTIFICATE OF DESIGNATION 5.95% FIXED-TO-FLOATING RATE PERPETUAL NON-CUMULATIVE PREFERENCE SHARES ASPEN INSURANCE HOLDINGS LIMITED

Exhibit 3.5 CERTIFICATE OF DESIGNATION OF 5.95% FIXED-TO-FLOATING RATE PERPETUAL NON-CUMULATIVE PREFERENCE SHARES OF ASPEN INSURANCE HOLDINGS LIMITED ASPEN INSURANCE HOLDINGS LIMITED, a Bermuda company (the “Company”), HEREBY CERTIFIES that pursuant to resolutions of duly authorized Directors adopted on April 25, 2013, the creation of the 5.95% Fixed-to-Floating Rate Perpetual Non-Cumulative Prefe

December 11, 2024 EX-3.12

Form of Preference Shares Certificate 7.00% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY

Exhibit 3.12 Form of Preference Shares Certificate 7.00% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (“DTC”), NEW YORK, NEW YORK, TO THE COMPANY OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NA

December 11, 2024 EX-3.4

SECOND AMENDED AND RESTATED BYE - LAWS ASPEN INSURANCE HOLDINGS LIMITED I N D E X

Exhibit 3.4 SECOND AMENDED AND RESTATED BYE - LAWS OF ASPEN INSURANCE HOLDINGS LIMITED I N D E X BYE-LAW SUBJECT PAGE 1 Interpretation 1 2 Registered Office 5 3 Share Capital 5 4-7 Alteration of Capital 8 8-12 Shares 9 13-14 Modification of Rights 10 15-18 Certificates 11 19-20 Register of Shareholders 12 21 Register of Directors and Officers 12 22-26 Transfer of Shares 12 27-30 Transmission of Sh

December 11, 2024 EX-10.20

INDEMNIFICATION AGREEMENT

Exhibit 10.20 INDEMNIFICATION AGREEMENT THIS INDEMNIFICATION AGREEMENT (this “Agreement”) is made as of [insert month] [insert day], [insert year] (the “Effective Date”), by and between Aspen Insurance Holdings Limited, a Bermuda exempted company (the “Company”) and (the “Indemnitee”). WHEREAS, it is essential to the Company that it and its Subsidiaries (the “Aspen Group”) be able to retain and at

December 11, 2024 EX-10.16

BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL AMENDED AND RESTATED REINSURANCE AGREEMENT by and among ASPEN INSURANCE UK LIMITED, ASPEN MANAGING AGENCY LIMITED for and on behalf of the UNDERWRIT

Exhibit 10.16 CERTAIN IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THIS EXHIBIT BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL AMENDED AND RESTATED REINSURANCE AGREEMENT by and among ASPEN INSURANCE UK LIMITED, ASPEN MANAGING AGENCY LIMITED for and on behalf of the UNDERWRITING MEMBER(S) OF LLOYD’S SYNDICATE 4711, ASPEN BERMUDA LIMITED, ASPEN

December 11, 2024 CORRESP

* * * *

SIDLEY AUSTIN LLP 787 SEVENTH AVENUE NEW YORK, NY 10019 +1 212 839 5300 +1 212 839 5599 FAX AMERICA • ASIA PACIFIC • EUROPE December 11, 2024 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance Office of Finance 100 F Street, N.

December 11, 2024 EX-10.11

FIRST AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT

Exhibit 10.11 Execution Version FIRST AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT This FIRST AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT (this “Amendment”), dated as of January 6, 2023, is among Aspen Insurance Holdings Limited (“Aspen”), the undersigned Subsidiary Borrowers (together with Aspen, each a “Borrower” and collectively the “Borrowers”), the several banks that

December 11, 2024 EX-10.13

(1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.S. SERVICES, INC. - and - (3) ASPEN BERMUDA LIMITED - and - (4) GENPACT (UK) LIMITED

Exhibit 10.13 DATED MARCH 31, 2023 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.S. SERVICES, INC. - and - (3) ASPEN BERMUDA LIMITED - and - (4) GENPACT (UK) LIMITED AMENDED AND RESTATED OUTSOURCING AGREEMENT CONTENTS Part A DEFINITIONS AND INTERPRETATION 7 1. DEFINITIONS 7 2. INTERPRETATION 7 Part B TERM AND SERVICE PROVISION 8 3. TERM 8 4. SERVICES 8 5. DELAY 10 6. ACCEPT

December 11, 2024 EX-10.8

MANAGEMENT CONSULTING AGREEMENT

Exhibit 10.8 MANAGEMENT CONSULTING AGREEMENT MANAGEMENT CONSULTING AGREEMENT, dated March 28, 2019 (this “Agreement”), by and between ASPEN INSURANCE HOLDINGS LIMITED, a Bermuda exempted company (the “Company”), and APOLLO MANAGEMENT HOLDINGS, L.P., a Delaware limited partnership (the “Service Provider”). RECITALS WHEREAS, the Service Provider has expertise in the areas of finance, strategy, inves

December 11, 2024 EX-10.4

Form of Face of Receipt; Form of Reverse of Receipt

Exhibit 10.4 Form of Face of Receipt; Form of Reverse of Receipt UNLESS THIS RECEIPT IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (“DTC”), NEW YORK, NEW YORK, TO ASPEN INSURANCE HOLDINGS LIMITED OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY RECEIPT ISSUED IS REGISTERED IN THE NAME OF CEDE & CO. OR SUCH OTHER NAME AS

December 11, 2024 EX-10.7

DATED February 19, 2019 ASPEN INSURANCE HOLDINGS LIMITED MARK CLOUTIER SERVICE AGREEMENT

Exhibit 10.7 DATED February 19, 2019 ASPEN INSURANCE HOLDINGS LIMITED and MARK CLOUTIER SERVICE AGREEMENT CONTENTS Clause Page 1. DEFINITIONS AND INTERPRETATION 1 2. APPOINTMENT 3 3. TERM 3 4. DUTIES 4 5. INSIDE INFORMATION 5 6. REMUNERATION 6 7. TRAVEL AND EXPENSES 7 8. PENSION 7 9. BENEFITS 7 10. HOLIDAYS AND HOLIDAY PAY 7 11. SICKNESS, ABSENCE, DISABILITY OR DEATH 8 12. CONFIDENTIAL INFORMATION

December 11, 2024 EX-10.3

DEPOSIT AGREEMENT November 26, 2024 ASPEN INSURANCE HOLDINGS LIMITED, AS ISSUER, COMPUTERSHARE INC. AND COMPUTERSHARE TRUST COMPANY, N.A., AS DEPOSITARY, - and - The Holders from Time to Time of The Depositary Receipts Described Herein RELATING TO TH

Exhibit 10.3 DEPOSIT AGREEMENT Dated November 26, 2024 ASPEN INSURANCE HOLDINGS LIMITED, AS ISSUER, COMPUTERSHARE INC. AND COMPUTERSHARE TRUST COMPANY, N.A., AS DEPOSITARY, - and - The Holders from Time to Time of The Depositary Receipts Described Herein RELATING TO THE RECEIPTS, DEPOSITARY SHARES AND RELATED 7.00% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES OF THE ISSUER TABLE OF CONTENTS ARTICLE

December 11, 2024 EX-10.6

AGREEMENT AND PLAN OF MERGER by and among HIGHLANDS HOLDINGS, LTD. HIGHLANDS MERGER SUB, LTD. ASPEN INSURANCE HOLDINGS LIMITED Dated as of August 27, 2018 TABLE OF CONTENTS

Exhibit 10.6 EXECUTION VERSION AGREEMENT AND PLAN OF MERGER by and among HIGHLANDS HOLDINGS, LTD. HIGHLANDS MERGER SUB, LTD. and ASPEN INSURANCE HOLDINGS LIMITED Dated as of August 27, 2018 TABLE OF CONTENTS Page ARTICLE I. DEFINITIONS AND TERMS Section 1.01 Definitions 2 Section 1.02 Interpretations 19 ARTICLE II. THE MERGER Section 2.01 Merger 21 Section 2.02 Merger Effective Time 21 Section 2.0

December 11, 2024 EX-3.11

CERTIFICATE OF DESIGNATION 7.00% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES ASPEN INSURANCE HOLDINGS LIMITED

Exhibit 3.11 CERTIFICATE OF DESIGNATION OF 7.00% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES OF ASPEN INSURANCE HOLDINGS LIMITED ASPEN INSURANCE HOLDINGS LIMITED, a Bermuda company (the “Company”), HEREBY CERTIFIES that pursuant to resolutions of duly authorized Directors adopted on September 23, 2024, the creation of the 7.00% Perpetual Non-Cumulative Preference Shares, with a liquidation preferen

December 11, 2024 EX-10.14

AMENDMENT NUMBER 1 TO THE AMENDED AND RESTATED OUTSOURCING AGREEMENT DATED MARCH 31, 2023

Exhibit 10.14 AMENDMENT NUMBER 1 TO THE AMENDED AND RESTATED OUTSOURCING AGREEMENT DATED MARCH 31, 2023 This First Amendment to the Amended and Restated Outsourcing Agreement (“Amendment”) is entered into effective 01 January, 2024 (the “First Amendment Effective Date”) by and among Aspen Insurance UK Services Limited, Aspen Insurance U.S. Services, Inc., and Aspen Bermuda Limited (“Customer”), an

December 11, 2024 EX-3.10

Preference Shares Certificate 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY

Exhibit 3.10 Preference Shares Certificate 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (“DTC”), NEW YORK, NEW YORK, TO THE COMPANY OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NAME OF C

December 11, 2024 EX-10.17

BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL DATED May 27, 2022 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) MINDTREE LIMITED MASTER SERVICES AGREEMENT: ITO SERVICES TABLE OF CONTENTS

Exhibit 10.17 CERTAIN IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THIS EXHIBIT BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL DATED May 27, 2022 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) MINDTREE LIMITED MASTER SERVICES AGREEMENT: ITO SERVICES TABLE OF CONTENTS 1. INTERPRETATION 1 2. CALL OFF OF SERVICES 13 3. SERVICE PROVIDER'S RE

December 11, 2024 EX-10.18

TERM LOAN CREDIT AGREEMENT ASPEN INSURANCE HOLDINGS LIMITED, The Several Lenders from Time to Time Parties Hereto, HSBC BANK BERMUDA LIMITED, as Structuring Agent, LLOYDS BANK PLC, as Syndication Agent, and CITIBANK, N.A., as Administrative Agent Dat

Exhibit 10.18 Execution Version TERM LOAN CREDIT AGREEMENT among ASPEN INSURANCE HOLDINGS LIMITED, The Several Lenders from Time to Time Parties Hereto, HSBC BANK BERMUDA LIMITED, as Structuring Agent, LLOYDS BANK PLC, as Syndication Agent, and CITIBANK, N.A., as Administrative Agent Dated as of July 26, 2023 CITIBANK, N.A., HSBC BANK BERMUDA LIMITED AND LLOYDS BANK PLC, as Joint Lead Arrangers an

December 11, 2024 EX-10.5

ASPEN INSURANCE HOLDINGS LIMITED DEUTSCHE BANK TRUST COMPANY AMERICAS, Dated as of August 16, 2004 DEBT SECURITIES Table Of Contents

Exhibit 10.5 ASPEN INSURANCE HOLDINGS LIMITED TO DEUTSCHE BANK TRUST COMPANY AMERICAS, Trustee INDENTURE Dated as of August 16, 2004 DEBT SECURITIES Table Of Contents Page ARTICLE 1 DEFINITIONS 1 SECTION 1.1 CERTAIN TERMS DEFINED 1 ARTICLE 2 SECURITY FORMS 8 SECTION 2.1 FORMS GENERALLY 8 SECTION 2.2 FORM OF LEGEND FOR RESTRICTED SECURITIES 9 SECTION 2.3 FORM OF TRUSTEE'S CERTIFICATE OF AUTHENTICAT

December 11, 2024 EX-10.15

DATED 24 DECEMBER 2020 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.S. SERVICES INC. - and - (3) ASPEN BERMUDA LIMITED - and - (4) COGNIZANT WORLDWIDE LIMITED

Exhibit 10.15 Confidential DATED 24 DECEMBER 2020 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.S. SERVICES INC. - and - (3) ASPEN BERMUDA LIMITED - and - (4) COGNIZANT WORLDWIDE LIMITED OUTSOURCING AGREEMENT 1 Confidential CONTENTS PART A DEFINITIONS AND INTERPRETATION 6 1. DEFINITIONS 6 2. INTERPRETATION 7 PART B TERM AND SERVICE PROVISION 8 3. TERM 8 4. SERVICES 10 5. DE

December 11, 2024 EX-3.8

Form of Preference Shares Certificate 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY

Exhibit 3.8 Form of Preference Shares Certificate 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (“DTC”), NEW YORK, NEW YORK, TO THE COMPANY OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NA

December 11, 2024 EX-10.19

[Signature Page to First Amendment to Credit Agreement]

Exhibit 10.19 Execution Version FIRST AMENDMENT TO TERM LOAN CREDIT AGREEMENT This FIRST AMENDMENT TO TERM LOAN CREDIT AGREEMENT (this “Amendment”), dated as of December 18, 2023, is among Aspen Insurance Holdings Limited (the “Borrower”), the several banks that are parties hereto, and Citibank, N.A., as administrative agent (in such capacity, the “Administrative Agent”). Capitalized terms used bu

December 11, 2024 EX-3.9

CERTIFICATE OF DESIGNATION 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES ASPEN INSURANCE HOLDINGS LIMITED

Exhibit 3.9 CERTIFICATE OF DESIGNATION OF 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES OF ASPEN INSURANCE HOLDINGS LIMITED ASPEN INSURANCE HOLDINGS LIMITED, a Bermuda company (the “Company”), HEREBY CERTIFIES that pursuant to resolutions of duly authorized Directors adopted on May 29, 2019, the creation of the 5.625% Perpetual Non-Cumulative Preference Shares, with a liquidation preference of

December 11, 2024 EX-3.6

5.95% FIXED-TO-FLOATING RATE PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY

Exhibit 3.6 5.95% FIXED-TO-FLOATING RATE PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (“DTC”), NEW YORK, NEW YORK, TO THE COMPANY OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NAME OF CEDE & CO.

December 11, 2024 F-1/A

As filed with the Securities and Exchange Commission on December 11, 2024.

As filed with the Securities and Exchange Commission on December 11, 2024. Registration No. 333-276163 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 3 to Form F-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 ASPEN INSURANCE HOLDINGS LIMITED (Exact Name of Registrant as Specified in its Charter) Bermuda 6331 98-0501000 (State or Other Jurisdiction

December 11, 2024 EX-10.12

SECOND AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT

Exhibit 10.12 Execution Version SECOND AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT This SECOND AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT (this “Amendment”), dated as of June 29, 2023, is among Aspen Insurance Holdings Limited (“Aspen”), the undersigned Subsidiary Borrowers (together with Aspen, each a “Borrower” and collectively the “Borrowers”), the several banks that

November 29, 2024 6-K

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 November 2024 Commission File Number: 001-3

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 November 2024 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 ex

November 29, 2024 EX-99.2

Aspen Announces Redemption of 5.95% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares

Exhibit 99.2 PRESS RELEASE Aspen Announces Redemption of 5.95% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares Hamilton, Bermuda—November 29, 2024—Aspen Insurance Holdings Limited (“Aspen” or the “Company”) announced today that it has decided to call all 11,000,000 of its outstanding 5.95% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares (NYSE: AHLPRC; CUSIP: G05

November 29, 2024 EX-99.1

Aspen Declares Dividends on Preference Shares

Exhibit 99.1 PRESS RELEASE Aspen Declares Dividends on Preference Shares Hamilton, Bermuda, November 29, 2024 – Aspen Insurance Holdings Limited (“Aspen”) (NYSE:AHL) announced today that the Board of Directors has declared the following dividends on its Preference Shares: •Quarterly dividend of $0.6196 per share on its Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares with a $25 li

November 26, 2024 EX-4.2

Form of Preference Shares Certificate 7.00% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY

Exhibit 4.2 Form of Preference Shares Certificate 7.00% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (“DTC”), NEW YORK, NEW YORK, TO THE COMPANY OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NAM

November 26, 2024 6-K

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 November 2024 Commission File Number: 001-3

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 November 2024 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 ex

November 26, 2024 EX-4.1

CERTIFICATE OF DESIGNATION 7.00% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES ASPEN INSURANCE HOLDINGS LIMITED

Exhibit 4.1 CERTIFICATE OF DESIGNATION OF 7.00% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES OF ASPEN INSURANCE HOLDINGS LIMITED ASPEN INSURANCE HOLDINGS LIMITED, a Bermuda company (the “Company”), HEREBY CERTIFIES that pursuant to resolutions of duly authorized Directors adopted on September 23, 2024, the creation of the 7.00% Perpetual Non-Cumulative Preference Shares, with a liquidation preferenc

November 26, 2024 8-A12B

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) or (g) OF THE SECURITIES EXCHANGE ACT OF 1934 ASPEN INSURANCE HOLDINGS LIMITED (Exact Name of

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) or (g) OF THE SECURITIES EXCHANGE ACT OF 1934 ASPEN INSURANCE HOLDINGS LIMITED (Exact Name of Registrant as Specified in its Charter) Bermuda 98-0501000 (State or Other Jurisdiction of Incorporation or Organization) (I.R.S. Employer Identifica

November 26, 2024 EX-4.4

Form of Face of Receipt; Form of Reverse of Receipt

Exhibit 4.4 Form of Face of Receipt; Form of Reverse of Receipt UNLESS THIS RECEIPT IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (“DTC”), NEW YORK, NEW YORK, TO ASPEN INSURANCE HOLDINGS LIMITED OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY RECEIPT ISSUED IS REGISTERED IN THE NAME OF CEDE & CO. OR SUCH OTHER NAME AS I

November 26, 2024 EX-4.3

DEPOSIT AGREEMENT November 26, 2024 ASPEN INSURANCE HOLDINGS LIMITED, AS ISSUER, COMPUTERSHARE INC. AND COMPUTERSHARE TRUST COMPANY, N.A., AS DEPOSITARY, - and - The Holders from Time to Time of The Depositary Receipts Described Herein RELATING TO TH

Exhibit 4.3 DEPOSIT AGREEMENT Dated November 26, 2024 ASPEN INSURANCE HOLDINGS LIMITED, AS ISSUER, COMPUTERSHARE INC. AND COMPUTERSHARE TRUST COMPANY, N.A., AS DEPOSITARY, - and - The Holders from Time to Time of The Depositary Receipts Described Herein RELATING TO THE RECEIPTS, DEPOSITARY SHARES AND RELATED 7.00% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES OF THE ISSUER TABLE OF CONTENTS ARTICLE 1

November 26, 2024 EX-3.3

SECOND AMENDED AND RESTATED BYE - LAWS ASPEN INSURANCE HOLDINGS LIMITED I N D E X

Exhibit 3.3 SECOND AMENDED AND RESTATED BYE - LAWS OF ASPEN INSURANCE HOLDINGS LIMITED I N D E X BYE-LAW SUBJECT PAGE 1 Interpretation 1 2 Registered Office 5 3 Share Capital 5 4-7 Alteration of Capital 8 8-12 Shares 9 13-14 Modification of Rights 10 15-18 Certificates 11 19-20 Register of Shareholders 12 21 Register of Directors and Officers 12 22-26 Transfer of Shares 12 27-30 Transmission of Sh

November 25, 2024 424B5

8,000,000 Depositary Shares Aspen Insurance Holdings Limited Each Representing a 1/1,000th Interest in a Share of 7.00% Perpetual Non-Cumulative Preference Shares (Liquidation Preference $25,000 Per Preference Share)

Filed Pursuant to Rule 424(b)(5) Registration No. 333-272650 PROSPECTUS SUPPLEMENT (To Prospectus Dated June 26, 2023) 8,000,000 Depositary Shares Aspen Insurance Holdings Limited Each Representing a 1/1,000th Interest in a Share of 7.00% Perpetual Non-Cumulative Preference Shares (Liquidation Preference $25,000 Per Preference Share) We are selling 8,000,000 depositary shares (the “Depositary Shar

November 22, 2024 EX-99.1

Aspen Prices Public Offering of US$200 Million of Depositary Shares Representing Interests in Perpetual Non-Cumulative Preference Shares

Exhibit 99.1 PRESS RELEASE Aspen Prices Public Offering of US$200 Million of Depositary Shares Representing Interests in Perpetual Non-Cumulative Preference Shares Hamilton, Bermuda—November 21, 2024 – Aspen Insurance Holdings Limited (“Aspen” or the “Company”) has priced an underwritten public offering of 8,000,000 Depositary Shares (the “Depositary Shares”), each of which represents a 1/1,000th

November 22, 2024 EX-1.1

ASPEN INSURANCE HOLDINGS LIMITED 8,000,000 Depositary Shares, Each Representing a 1/1,000th Interest in a Share of 7.00% Perpetual Non-Cumulative Preference Shares (Liquidation Preference $25,000 Per Preference Share) UNDERWRITING AGREEMENT

Exhibit 1.1 ASPEN INSURANCE HOLDINGS LIMITED 8,000,000 Depositary Shares, Each Representing a 1/1,000th Interest in a Share of 7.00% Perpetual Non-Cumulative Preference Shares (Liquidation Preference $25,000 Per Preference Share) UNDERWRITING AGREEMENT November 21, 2024 WELLS FARGO SECURITIES, LLC 550 South Tryon Street Charlotte, North Carolina 28202 BOFA SECURITIES, INC. One Bryant Park New York

November 22, 2024 6-K

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 November 2024 Commission File Number: 001-3

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 November 2024 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 ex

November 21, 2024 FWP

Aspen Insurance Holdings Limited 8,000,000 Depositary Shares, Each Representing a 1/1,000th Interest in a Share of 7.00% Perpetual Non-Cumulative Preference Shares PRICING TERM SHEET

Filed Pursuant to Rule 433 Dated November 21, 2024 Registration Statement on Form F-3 (No.

November 21, 2024 424B2

Subject to Completion, dated November 21, 2024

Filed Pursuant to Rule 424(b)(2) Registration No. 333-272650 The information in this preliminary prospectus supplement is not complete and may be changed. This preliminary prospectus supplement and the accompanying prospectus are not an offer to sell these securities and we are not soliciting offers to buy these securities in any jurisdiction where the offer or sale is not permitted. Subject to Co

November 14, 2024 EX-99.1

Aspen Reports Results Three and Nine Months Ended September 30, 2024 Net Income Available to Ordinary Shareholders of $43 million and Operating Income of $87 million for the Three Months Ended September 30, 2024 Net Income Available to Ordinary Share

Exhibit 99.1 PRESS RELEASE Aspen Reports Results Three and Nine Months Ended September 30, 2024 Net Income Available to Ordinary Shareholders of $43 million and Operating Income of $87 million for the Three Months Ended September 30, 2024 Net Income Available to Ordinary Shareholders of $196 million and Operating Income of $288 million for the Nine Months Ended September 30, 2024 Operating Return

November 14, 2024 6-K

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 November 2024 Commission File Number: 001-3

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 November 2024 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 ex

November 14, 2024 6-K

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 November 2024 Commission File Number: 001-3

Table of Contents 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 November 2024 Commission File Number: 001-31909 ASPEN INSURANCE HOLDINGS LIMITED (Translation of registrant’s name into English) 141 Front Street Hamilton HM 19 Bermuda (Addre

August 30, 2024 6-K

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 2024 Commission File Number: 001-319

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 2024 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 exec

August 30, 2024 EX-99.1

Aspen Declares Dividends on Preference Shares

Exhibit 99.1 PRESS RELEASE Aspen Declares Dividends on Preference Shares Hamilton, Bermuda, August 30, 2024 – Aspen Insurance Holdings Limited (“Aspen”) (NYSE:AHL) announced today that the Board of Directors has declared the following dividends on its Preference Shares: •Quarterly dividend of $0.6129 per share on its Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares with a $25 liqu

August 14, 2024 EX-99.1

Aspen Reports Results For the Three and Six Months Ended June 30, 2024 Net Income Available to Ordinary Shareholders of $55 million and Operating Income of $98 million for the Three Months Ended June 30, 2024 Net Income Available to Ordinary Sharehol

Exhibit 99.1 PRESS RELEASE Aspen Reports Results For the Three and Six Months Ended June 30, 2024 Net Income Available to Ordinary Shareholders of $55 million and Operating Income of $98 million for the Three Months Ended June 30, 2024 Net Income Available to Ordinary Shareholders of $154 million and Operating Income of $201 million for the Six Months Ended June 30, 2024 Operating Return on Averag

August 14, 2024 6-K

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 2024 Commission File Number: 001-319

Table of Contents 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 2024 Commission File Number: 001-31909 ASPEN INSURANCE HOLDINGS LIMITED (Translation of registrant’s name into English) 141 Front Street Hamilton HM 19 Bermuda (Address

August 14, 2024 6-K

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 2024 Commission File Number: 001-319

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 2024 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 exec

July 29, 2024 EX-99.1

Aspen appoints Christian Dunleavy as Group President and Mark Pickering as Group Chief Financial Officer & Treasurer

Exhibit 99.1 PRESS RELEASE Aspen appoints Christian Dunleavy as Group President and Mark Pickering as Group Chief Financial Officer & Treasurer Hamilton, Bermuda, 29 July, 2024 – Aspen (NYSE: AHL) today announces changes to its leadership, effective August 1, 2024, to create stronger, more accountable executive roles that are more responsive to the current priorities of Aspen. Under the new struct

July 29, 2024 6-K

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 July 2024 Commission File Number: 001-31909

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 July 2024 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 execut

July 12, 2024 EX-99.1

Securities and Exchange Commission 12 July 2024

Securities and Exchange Commission 12 July 2024 100 F Street, N.E. Washington, DC 20549 Ladies and Gentlemen: We have read the Form 6-K dated 12 July 2024 for Aspen Insurance Holdings Limited and are in agreement with the statements contained therein in relation to the resignation of the independent registered public accounting firm. We have no basis to agree or disagree with other statements of t

July 12, 2024 6-K

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 July 2024 Commission File Number: 001-31909

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 July 2024 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 execut

June 13, 2024 6-K

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 June 2024 Commission File Number: 001-31909

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 June 2024 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 execut

May 30, 2024 6-K

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 May 2024 Commission File Number: 001-31909

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 May 2024 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 executi

May 30, 2024 EX-99.1

Aspen Declares Dividends on Preference Shares

Exhibit 99.1 PRESS RELEASE Aspen Declares Dividends on Preference Shares Hamilton, Bermuda, May 30, 2024 – Aspen Insurance Holdings Limited (“Aspen”) (NYSE:AHL) announced today that the Board of Directors has declared the following dividends on its Preference Shares: •Quarterly dividend of $0.6063 per share on its 5.95% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares with a $25 l

April 29, 2024 6-K

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 April 2024 Commission File Number: 001-3190

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 April 2024 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 execu

April 5, 2024 CORRESP

* * * *

SIDLEY AUSTIN LLP 787 SEVENTH AVENUE NEW YORK, NY 10019 +1 212 839 5300 +1 212 839 5599 FAX AMERICA • ASIA PACIFIC • EUROPE April 5, 2024 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance Office of Finance 100 F Street, N.

April 5, 2024 EX-10.4

AGREEMENT AND PLAN OF MERGER by and among HIGHLANDS HOLDINGS, LTD. HIGHLANDS MERGER SUB, LTD. ASPEN INSURANCE HOLDINGS LIMITED Dated as of August 27, 2018 TABLE OF CONTENTS

Exhibit 10.4 EXECUTION VERSION AGREEMENT AND PLAN OF MERGER by and among HIGHLANDS HOLDINGS, LTD. HIGHLANDS MERGER SUB, LTD. and ASPEN INSURANCE HOLDINGS LIMITED Dated as of August 27, 2018 TABLE OF CONTENTS Page ARTICLE I. DEFINITIONS AND TERMS Section 1.01 Definitions 2 Section 1.02 Interpretations 19 ARTICLE II. THE MERGER Section 2.01 Merger 21 Section 2.02 Merger Effective Time 21 Section 2.0

April 5, 2024 EX-10.16

BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL DATED May 27, 2022 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) MINDTREE LIMITED MASTER SERVICES AGREEMENT: ITO SERVICES TABLE OF CONTENTS

Exhibit 10.16 CERTAIN IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THIS EXHIBIT BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL DATED May 27, 2022 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) MINDTREE LIMITED MASTER SERVICES AGREEMENT: ITO SERVICES TABLE OF CONTENTS 1. INTERPRETATION 1 2. CALL OFF OF SERVICES 13 3. SERVICE PROVIDER'S RE

April 5, 2024 F-1/A

As filed with the Securities and Exchange Commission on April 5, 2024.

As filed with the Securities and Exchange Commission on April 5, 2024. Registration No. 333-276163 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 2 to Form F-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 ASPEN INSURANCE HOLDINGS LIMITED (Exact Name of Registrant as Specified in its Charter) Bermuda 6331 98-0501000 (State or Other Jurisdiction of I

April 5, 2024 EX-10.5

DATED February 19, 2019 ASPEN INSURANCE HOLDINGS LIMITED MARK CLOUTIER SERVICE AGREEMENT

Exhibit 10.5 DATED February 19, 2019 ASPEN INSURANCE HOLDINGS LIMITED and MARK CLOUTIER SERVICE AGREEMENT CONTENTS Clause Page 1. DEFINITIONS AND INTERPRETATION 1 2. APPOINTMENT 3 3. TERM 3 4. DUTIES 4 5. INSIDE INFORMATION 5 6. REMUNERATION 6 7. TRAVEL AND EXPENSES 7 8. PENSION 7 9. BENEFITS 7 10. HOLIDAYS AND HOLIDAY PAY 7 11. SICKNESS, ABSENCE, DISABILITY OR DEATH 8 12. CONFIDENTIAL INFORMATION

April 5, 2024 EX-10.19

INDEMNIFICATION AGREEMENT

Exhibit 10.19 INDEMNIFICATION AGREEMENT THIS INDEMNIFICATION AGREEMENT (this “Agreement”) is made as of [insert month] [insert day], [insert year] (the “Effective Date”), by and between Aspen Insurance Holdings Limited, a Bermuda exempted company (the “Company”) and (the “Indemnitee”). WHEREAS, it is essential to the Company that it and its Subsidiaries (the “Aspen Group”) be able to retain and at

April 5, 2024 EX-10.13

AMENDMENT NUMBER 1 TO THE AMENDED AND RESTATED OUTSOURCING AGREEMENT DATED MARCH 31, 2023

Exhibit 10.13 AMENDMENT NUMBER 1 TO THE AMENDED AND RESTATED OUTSOURCING AGREEMENT DATED MARCH 31, 2023 This First Amendment to the Amended and Restated Outsourcing Agreement (“Amendment”) is entered into effective 01 January, 2024 (the “First Amendment Effective Date”) by and among Aspen Insurance UK Services Limited, Aspen Insurance U.S. Services, Inc., and Aspen Bermuda Limited (“Customer”), an

April 5, 2024 EX-10.10

FIRST AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT

Exhibit 10.10 Execution Version FIRST AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT This FIRST AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT (this “Amendment”), dated as of January 6, 2023, is among Aspen Insurance Holdings Limited (“Aspen”), the undersigned Subsidiary Borrowers (together with Aspen, each a “Borrower” and collectively the “Borrowers”), the several banks that

April 5, 2024 EX-10.15

BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL AMENDED AND RESTATED REINSURANCE AGREEMENT by and among ASPEN INSURANCE UK LIMITED, ASPEN MANAGING AGENCY LIMITED for and on behalf of the UNDERWRIT

Exhibit 10.15 CERTAIN IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THIS EXHIBIT BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL AMENDED AND RESTATED REINSURANCE AGREEMENT by and among ASPEN INSURANCE UK LIMITED, ASPEN MANAGING AGENCY LIMITED for and on behalf of the UNDERWRITING MEMBER(S) OF LLOYD’S SYNDICATE 4711, ASPEN BERMUDA LIMITED, ASPEN

April 5, 2024 EX-10.17

TERM LOAN CREDIT AGREEMENT ASPEN INSURANCE HOLDINGS LIMITED, The Several Lenders from Time to Time Parties Hereto, HSBC BANK BERMUDA LIMITED, as Structuring Agent, LLOYDS BANK PLC, as Syndication Agent, and CITIBANK, N.A., as Administrative Agent Dat

Exhibit 10.17 \Execution Version TERM LOAN CREDIT AGREEMENT among ASPEN INSURANCE HOLDINGS LIMITED, The Several Lenders from Time to Time Parties Hereto, HSBC BANK BERMUDA LIMITED, as Structuring Agent, LLOYDS BANK PLC, as Syndication Agent, and CITIBANK, N.A., as Administrative Agent Dated as of July 26, 2023 CITIBANK, N.A., HSBC BANK BERMUDA LIMITED AND LLOYDS BANK PLC, as Joint Lead Arrangers a

April 5, 2024 EX-21.1

SUBSIDIARIES OF THE COMPANY

Exhibit 21.1 SUBSIDIARIES OF THE COMPANY NAME OF SUBSIDIARY JURISDICTION OF INCORPORATION Acorn Limited Bermuda APJ Asset Protection Jersey Limited Jersey Aspen (UK) Holdings Limited United Kingdom Aspen American Insurance Company Texas Aspen Australia Service Company Pty Ltd Australia Aspen Bermuda Limited Bermuda Aspen Capital Management, Ltd Bermuda Aspen Cat Fund Limited Bermuda Aspen European

April 5, 2024 EX-10.11

SECOND AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT

Exhibit 10.11 Execution Version SECOND AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT This SECOND AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT (this “Amendment”), dated as of June 29, 2023, is among Aspen Insurance Holdings Limited (“Aspen”), the undersigned Subsidiary Borrowers (together with Aspen, each a “Borrower” and collectively the “Borrowers”), the several banks that

April 5, 2024 EX-10.14

DATED 24 DECEMBER 2020 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.S. SERVICES INC. - and - (3) ASPEN BERMUDA LIMITED - and - (4) COGNIZANT WORLDWIDE LIMITED

Exhibit 10.14 Confidential DATED 24 DECEMBER 2020 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.S. SERVICES INC. - and - (3) ASPEN BERMUDA LIMITED - and - (4) COGNIZANT WORLDWIDE LIMITED OUTSOURCING AGREEMENT 1 Confidential CONTENTS PART A DEFINITIONS AND INTERPRETATION 6 1. DEFINITIONS 6 2. INTERPRETATION 7 PART B TERM AND SERVICE PROVISION 8 3. TERM 8 4. SERVICES 10 5. DE

April 5, 2024 EX-10.9

THIRD AMENDED AND RESTATED CREDIT AGREEMENT ASPEN INSURANCE HOLDINGS LIMITED, The Subsidiary Borrowers from Time to Time Parties Hereto, The Several Lenders from Time to Time Parties Hereto, THE BANK OF NEW YORK MELLON, as Collateral Agent, CITIBANK,

Exhibit 10.9 Execution Version THIRD AMENDED AND RESTATED CREDIT AGREEMENT among ASPEN INSURANCE HOLDINGS LIMITED, The Subsidiary Borrowers from Time to Time Parties Hereto, The Several Lenders from Time to Time Parties Hereto, THE BANK OF NEW YORK MELLON, as Collateral Agent, CITIBANK, N.A., as Syndication Agent, HSBC BANK USA, N.A., LLOYDS BANK CORPORATE MARKETS PLC AND WELLS FARGO BANK, NATIONA

April 5, 2024 EX-10.6

MANAGEMENT CONSULTING AGREEMENT

Exhibit 10.6 MANAGEMENT CONSULTING AGREEMENT MANAGEMENT CONSULTING AGREEMENT, dated March 28, 2019 (this “Agreement”), by and between ASPEN INSURANCE HOLDINGS LIMITED, a Bermuda exempted company (the “Company”), and APOLLO MANAGEMENT HOLDINGS, L.P., a Delaware limited partnership (the “Service Provider”). RECITALS WHEREAS, the Service Provider has expertise in the areas of finance, strategy, inves

April 5, 2024 EX-10.18

[Signature Page to First Amendment to Credit Agreement]

Exhibit 10.18 Execution Version FIRST AMENDMENT TO TERM LOAN CREDIT AGREEMENT This FIRST AMENDMENT TO TERM LOAN CREDIT AGREEMENT (this “Amendment”), dated as of December 18, 2023, is among Aspen Insurance Holdings Limited (the “Borrower”), the several banks that are parties hereto, and Citibank, N.A., as administrative agent (in such capacity, the “Administrative Agent”). Capitalized terms used bu

April 5, 2024 EX-10.12

(1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.S. SERVICES, INC. - and - (3) ASPEN BERMUDA LIMITED - and - (4) GENPACT (UK) LIMITED

Exhibit 10.12 DATED MARCH 31, 2023 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.S. SERVICES, INC. - and - (3) ASPEN BERMUDA LIMITED - and - (4) GENPACT (UK) LIMITED AMENDED AND RESTATED OUTSOURCING AGREEMENT CONTENTS Part A DEFINITIONS AND INTERPRETATION 7 1. DEFINITIONS 7 2. INTERPRETATION 7 Part B TERM AND SERVICE PROVISION 8 3. TERM 8 4. SERVICES 8 5. DELAY 10 6. ACCEPT

April 1, 2024 EX-15.2

Consent of Independent Registered Public Accounting Firm

Consent of Independent Registered Public Accounting Firm We consent to the incorporation by reference in the Registration Statement (Form F-3 No.

April 1, 2024 EX-4.7

FIRST AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT

Execution Version FIRST AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT This FIRST AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT (this “Amendment”), dated as of January 6, 2023, is among Aspen Insurance Holdings Limited (“Aspen”), the undersigned Subsidiary Borrowers (together with Aspen, each a “Borrower” and collectively the “Borrowers”), the several banks that are parties hereto, and Barclays Bank PLC, as administrative agent (in such capacity, the “Administrative Agent”).

April 1, 2024 EX-4.10

AMENDMENT NUMBER 1 TO THE AMENDED AND RESTATED OUTSOURCING AGREEMENT DATED MARCH 31, 2023

AMENDMENT NUMBER 1 TO THE AMENDED AND RESTATED OUTSOURCING AGREEMENT DATED MARCH 31, 2023 This First Amendment to the Amended and Restated Outsourcing Agreement (“Amendment”) is entered into effective 01 January, 2024 (the “First Amendment Effective Date”) by and among Aspen Insurance UK Services Limited, Aspen Insurance U.

April 1, 2024 EX-13.1

CERTIFICATION PURSUANT TO 18 U.S.C. SECTION 1350, AS ADOPTED PURSUANT TO SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002

Exhibit 13.1 CERTIFICATION PURSUANT TO 18 U.S.C. SECTION 1350, AS ADOPTED PURSUANT TO SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002 In connection with this Annual Report on Form 20-F of Aspen Insurance Holdings Limited (the “Company”) for the twelve months ended December 31, 2022 as filed with the Securities and Exchange Commission on the date hereof (the “Report”), Mark Cloutier as Chief Executiv

April 1, 2024 EX-4.9

(1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.S. SERVICES, INC. - and - (3) ASPEN BERMUDA LIMITED - and - (4) GENPACT (UK) LIMITED

DATED 2023 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.S. SERVICES, INC. - and - (3) ASPEN BERMUDA LIMITED - and - (4) GENPACT (UK) LIMITED AMENDED AND RESTATED OUTSOURCING AGREEMENT CONTENTS The table of contents is empty. Heading styles must be applied in the document and be selected in the table of contents properties panel. 2 SCHEDULES Schedule 1 Definitions Schedule

April 1, 2024 EX-97.1

ASPEN INSURANCE HOLDINGS LIMITED POLICY ON RECOUPMENT OF INCENTIVE COMPENSATION

Exhibit 97.1 ASPEN INSURANCE HOLDINGS LIMITED POLICY ON RECOUPMENT OF INCENTIVE COMPENSATION Introduction The Board of Directors (the “Board”) of Aspen Insurance Holdings Limited (the “Company”) has adopted this Policy on Recoupment of Incentive Compensation (this “Policy”), which provides for the recoupment of compensation in certain circumstances in the event of a restatement of financial result

April 1, 2024 EX-4.8

SECOND AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT

Execution Version SECOND AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT This SECOND AMENDMENT TO THIRD AMENDED AND RESTATED CREDIT AGREEMENT (this “Amendment”), dated as of June 29, 2023, is among Aspen Insurance Holdings Limited (“Aspen”), the undersigned Subsidiary Borrowers (together with Aspen, each a “Borrower” and collectively the “Borrowers”), the several banks that are parties hereto, and Barclays Bank PLC, as administrative agent (in such capacity, the “Administrative Agent”).

April 1, 2024 6-K

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 April 2024 Commission File Number: 001-3190

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 April 2024 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 execu

April 1, 2024 20-F

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 20-F ☐ REGISTRATION STATEMENT PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 20-F ☐ REGISTRATION STATEMENT PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECUR

April 1, 2024 EX-4.11

DATED 24 DECEMBER 2020 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.S. SERVICES INC. - and - (3) ASPEN BERMUDA LIMITED - and - (4) COGNIZANT WORLDWIDE LIMITED

Confidential DATED 24 DECEMBER 2020 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) ASPEN INSURANCE U.

April 1, 2024 EX-15.1

Consent of Independent Registered Public Accounting Firm

Consent of Independent Registered Public Accounting Firm We consent to the incorporation by reference in the registration statement (No. 333-272650) on Form F-3 of our report dated May 16, 2022, with respect to the consolidated financial statements of Aspen Insurance Holdings Limited. /s/ KPMG LLP London, United Kingdom April 1, 2024

April 1, 2024 EX-4.14

among ASPEN INSURANCE HOLDINGS LIMITED, The Several Lenders from Time to Time Parties Hereto, HSBC BANK BERMUDA LIMITED, as Structuring Agent, LLOYDS BANK PLC, as Syndication Agent, and CITIBANK, N.A., as Administrative Agent Dated as of July 26, 202

Execution Version TERM LOAN CREDIT AGREEMENT among ASPEN INSURANCE HOLDINGS LIMITED, The Several Lenders from Time to Time Parties Hereto, HSBC BANK BERMUDA LIMITED, as Structuring Agent, LLOYDS BANK PLC, as Syndication Agent, and CITIBANK, N.

April 1, 2024 EX-12.2

CERTIFICATION

Exhibit 12.2 CERTIFICATION I, Christopher Coleman, certify that: 1.I have reviewed this annual report on Form 20-F of Aspen Insurance Holdings Limited; 2.Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleadin

April 1, 2024 EX-12.1

CERTIFICATION

Exhibit 12.1 CERTIFICATION I, Mark Cloutier, certify that: 1.I have reviewed this annual report on Form 20-F of Aspen Insurance Holdings Limited; 2.Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with

April 1, 2024 EX-4.15

FIRST AMENDMENT TO TERM LOAN CREDIT AGREEMENT

Execution Version FIRST AMENDMENT TO TERM LOAN CREDIT AGREEMENT This FIRST AMENDMENT TO TERM LOAN CREDIT AGREEMENT (this “Amendment”), dated as of December 18, 2023, is among Aspen Insurance Holdings Limited (the “Borrower”), the several banks that are parties hereto, and Citibank, N.

April 1, 2024 EX-99.1

Aspen Reports Results for the Three and Twelve Months Ended December 31, 2023 Net Income Available to Ordinary Shareholders of $216 million and Operating Income of $98 million for the Three Months Ended Net Income Available to Ordinary Shareholders o

Exhibit 99.1 PRESS RELEASE Aspen Reports Results for the Three and Twelve Months Ended December 31, 2023 Net Income Available to Ordinary Shareholders of $216 million and Operating Income of $98 million for the Three Months Ended Net Income Available to Ordinary Shareholders of $485 million and Operating Income of $368 million for the Twelve Months Ended Operating Return on Average Equity of 20.2%

March 1, 2024 EX-99.1

Aspen Declares Dividends on Preference Shares

Exhibit 99.1 PRESS RELEASE Aspen Declares Dividends on Preference Shares Hamilton, Bermuda, March 1, 2024 – Aspen Insurance Holdings Limited (“Aspen”) (NYSE:AHL) announced today that the Board of Directors has declared the following dividends on its Preference Shares: •Quarterly dividend of $0.5996 per share on its 5.95% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares with a $25

March 1, 2024 6-K

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 March 2024 Commission File Number: 001-3190

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 March 2024 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 execu

February 1, 2024 CORRESP

* * * *

SIDLEY AUSTIN LLP 787 SEVENTH AVENUE NEW YORK, NY 10019 +1 212 839 5300 +1 212 839 5599 FAX AMERICA • ASIA PACIFIC • EUROPE February 1, 2024 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance Office of Finance 100 F Street, N.

February 1, 2024 F-1/A

As filed with the Securities and Exchange Commission on February 1, 2024.

As filed with the Securities and Exchange Commission on February 1, 2024. Registration No. 333-276163 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 1 to Form F-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 ASPEN INSURANCE HOLDINGS LIMITED (Exact Name of Registrant as Specified in its Charter) Bermuda 6331 98-0501000 (State or Other Jurisdiction o

January 17, 2024 6-K

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 January 2024 Commission File Number: 001-31

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 January 2024 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 exe

January 17, 2024 EX-99.1

ASPEN APPOINTS SARAH STANFORD AS INTERIM CEO, ASPEN UK

Exhibit 99.1 PRESS RELEASE ASPEN APPOINTS SARAH STANFORD AS INTERIM CEO, ASPEN UK Hamilton, Bermuda, 17 January 2024 - Aspen Insurance Holdings Limited (“Aspen”) today announces the appointment of Sarah Stanford as interim CEO, Aspen UK, effective immediately. Sarah is currently Active Underwriter, Lloyd’s Syndicate 4711, which represents approximately 75% of Aspen’s UK business. Under her leaders

December 20, 2023 EX-10.17

ANNEX ONE REINSURANCE DEPOSIT AGREEMENT (CHARGE FORM – CITIBANK, N.A. AS CUSTODIAN) (FORM 12) SCHEDULE TWO

Exhibit 10.17 11 October, 2006 Aspen Insurance Limited Attn Bryan Astwood Maxwell Roberts Building 1 Church Street Hamilton HM 11 Bermuda Dear Sirs (1) Reinsurance Deposit Agreement (Charge Form – Citibank, N.A. as Custodian) (Form 12) registered against Aspen Insurance Limited by and in favour of Citibank Ireland Financial Services plc (whose name has since been changed to Citibank Europe plc) da

December 20, 2023 EX-10.9

ASPEN INSURANCE U.S. SERVICES INC. NONQUALIFIED DEFERRED COMPENSATION PLAN

Exhibit 10.9 ASPEN INSURANCE U.S. SERVICES INC. NONQUALIFIED DEFERRED COMPENSATION PLAN This document is drafted with the intent that it comply with Internal Revenue Code Section 409A and regulations promulgated thereunder. NFP Executive Benefits has provided you this specimen document strictly in its capacity as an employee benefits consulting firm and plan record keeper. NFP Executive Benefits d

December 20, 2023 EX-10.24

[signature page follows]

Exhibit 10.24 AMENDED AND RESTATED PLEDGE AGREEMENT AMENDED AND RESTATED PLEDGE AGREEMENT, dated as of December 18, 2014 (as may be amended, restated or otherwise modified from time to time, this “Agreement”), made among ASPEN BERMUDA LIMITED, a company organized and existing under the laws of Bermuda whose address of its registered or principal office is at 141 Front Street, Hamilton, HM19 Bermud

December 20, 2023 EX-10.27

BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL AMENDED AND RESTATED REINSURANCE AGREEMENT by and among ASPEN INSURANCE UK LIMITED, ASPEN MANAGING AGENCY LIMITED for and on behalf of the UNDERWRIT

Exhibit 10.27 CERTAIN IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THIS EXHIBIT BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL AMENDED AND RESTATED REINSURANCE AGREEMENT by and among ASPEN INSURANCE UK LIMITED, ASPEN MANAGING AGENCY LIMITED for and on behalf of the UNDERWRITING MEMBER(S) OF LLOYD’S SYNDICATE 4711, ASPEN BERMUDA LIMITED, ASPEN

December 20, 2023 EX-10.8

MANAGEMENT CONSULTING AGREEMENT

Exhibit 10.8 MANAGEMENT CONSULTING AGREEMENT MANAGEMENT CONSULTING AGREEMENT, dated March 28, 2019 (this “Agreement”), by and between ASPEN INSURANCE HOLDINGS LIMITED, a Bermuda exempted company (the “Company”), and APOLLO MANAGEMENT HOLDINGS, L.P., a Delaware limited partnership (the “Service Provider”). RECITALS WHEREAS, the Service Provider has expertise in the areas of finance, strategy, inves

December 20, 2023 EX-10.6

AGREEMENT AND PLAN OF MERGER by and among HIGHLANDS HOLDINGS, LTD. HIGHLANDS MERGER SUB, LTD. ASPEN INSURANCE HOLDINGS LIMITED Dated as of August 27, 2018 TABLE OF CONTENTS

Exhibit 10.6 EXECUTION VERSION AGREEMENT AND PLAN OF MERGER by and among HIGHLANDS HOLDINGS, LTD. HIGHLANDS MERGER SUB, LTD. and ASPEN INSURANCE HOLDINGS LIMITED Dated as of August 27, 2018 TABLE OF CONTENTS Page ARTICLE I. DEFINITIONS AND TERMS Section 1.01 Definitions 2 Section 1.02 Interpretations 19 ARTICLE II. THE MERGER Section 2.01 Merger 21 Section 2.02 Merger Effective Time 21 Section 2.0

December 20, 2023 EX-10.5

Article 1 DEFINITIONS AND OTHER PROVISIONS OF GENERAL APPLICATION

Exhibit 10.5 FOURTH SUPPLEMENTAL INDENTURE, dated June 27, 2019 (this “Fourth Supplemental Indenture”), between Aspen Insurance Holdings Limited, an exempted company formed under the laws of Bermuda, having its principal executive office located at 141 Front Street, Hamilton HM 19, Bermuda (the “Company”), and Deutsche Bank Trust Company Americas, a New York banking corporation duly organized and

December 20, 2023 EX-3.4

CERTIFICATE OF DESIGNATION 5.95% FIXED-TO-FLOATING RATE PERPETUAL NON-CUMULATIVE PREFERENCE SHARES ASPEN INSURANCE HOLDINGS LIMITED

Exhibit 3.4 CERTIFICATE OF DESIGNATION OF 5.95% FIXED-TO-FLOATING RATE PERPETUAL NON-CUMULATIVE PREFERENCE SHARES OF ASPEN INSURANCE HOLDINGS LIMITED ASPEN INSURANCE HOLDINGS LIMITED, a Bermuda company (the “Company”), HEREBY CERTIFIES that pursuant to resolutions of duly authorized Directors adopted on April 25, 2013, the creation of the 5.95% Fixed-to-Floating Rate Perpetual Non-Cumulative Prefe

December 20, 2023 EX-10.7

DATED February 19, 2019 ASPEN INSURANCE HOLDINGS LIMITED MARK CLOUTIER SERVICE AGREEMENT

Exhibit 10.7 DATED February 19, 2019 ASPEN INSURANCE HOLDINGS LIMITED and MARK CLOUTIER SERVICE AGREEMENT CONTENTS Clause Page 1. DEFINITIONS AND INTERPRETATION 1 2. APPOINTMENT 3 3. TERM 3 4. DUTIES 4 5. INSIDE INFORMATION 5 6. REMUNERATION 6 7. TRAVEL AND EXPENSES 7 8. PENSION 7 9. BENEFITS 7 10. HOLIDAYS AND HOLIDAY PAY 7 11. SICKNESS, ABSENCE, DISABILITY OR DEATH 8 12. CONFIDENTIAL INFORMATION

December 20, 2023 EX-10.22

DEED OF AMENDMENT

Exhibit 10.22 DEED OF AMENDMENT Date: 20 September 2019 Between: (1) Citibank Europe plc (“Citibank”); and (2) Aspen Bermuda Limited (the “Company”). 1. Background 1.1 On 30 July 2012 a Committed Facility Letter for Issuance of Payment Instruments was signed between Citibank and the Company, as amended by a Letter of Amendment dated 30 June 2014 and a Letter of Amendment dated 30 June 2016 and a D

December 20, 2023 EX-10.21

DEED OF AMENDMENT

Exhibit 10.21 DEED OF AMENDMENT Date: 29 June 2018 Between: (1) Citibank Europe plc (“Citibank”); and (2) Aspen Bermuda Limited (the “Company”). 1. Background 1.1 On 30 July 2012 a Committed Facility Letter for Issuance of Payment Instruments was signed between Citibank and the Company, as amended by a Letter of Amendment dated 30 June 2014 and a Letter of Amendment dated 30 June 2016 (the “Commit

December 20, 2023 EX-10.14

THIRD AMENDED AND RESTATED CREDIT AGREEMENT ASPEN INSURANCE HOLDINGS LIMITED, The Subsidiary Borrowers from Time to Time Parties Hereto, The Several Lenders from Time to Time Parties Hereto, THE BANK OF NEW YORK MELLON, as Collateral Agent, CITIBANK,

Exhibit 10.14 Execution Version THIRD AMENDED AND RESTATED CREDIT AGREEMENT among ASPEN INSURANCE HOLDINGS LIMITED, The Subsidiary Borrowers from Time to Time Parties Hereto, The Several Lenders from Time to Time Parties Hereto, THE BANK OF NEW YORK MELLON, as Collateral Agent, CITIBANK, N.A., as Syndication Agent, HSBC BANK USA, N.A., LLOYDS BANK CORPORATE MARKETS PLC AND WELLS FARGO BANK, NATION

December 20, 2023 EX-10.23

DEED OF AMENDMENT

Exhibit 10.23 DEED OF AMENDMENT Date: June 26, 2020 Between: (1) Citibank Europe plc (“Citibank”); and (2) Aspen Bermuda Limited (the “Company”). 1. Background 1.1 On 30 July 2012 a Committed Facility Letter for Issuance of Payment Instruments was signed between Citibank and the Company, as amended by Letters of Amendment dated 30 June 2014 and 30 June 2016, and Deeds of Amendment dated 21 June 20

December 20, 2023 EX-10.2

CUSIP NO.: G05384204 ASPEN INSURANCE HOLDINGS LIMITED RECEIPT FOR DEPOSITARY SHARES Each Representing a 1/1,000th Interest in a Share of 5.625% Perpetual Non-Cumulative Preference Shares (par value $0.0015144558 per share) (liquidation preference $25

Exhibit 10.2 UNLESS THIS RECEIPT IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (“DTC”), NEW YORK, NEW YORK, TO ASPEN INSURANCE HOLDINGS LIMITED OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY RECEIPT ISSUED IS REGISTERED IN THE NAME OF CEDE & CO. OR SUCH OTHER NAME AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF DTC

December 20, 2023 EX-10.20

1 North Wall Quay

Exhibit 10.20 1 North Wall Quay Dublin 1 Ireland T +353 1 622 2000 F +353 1 622 2222 Niall Tuckey Citibank Europe plc Director 1 North Wall Quay ILOC Product Dublin 1, Ireland Tel+353 (1) 622 7430 Fax+353 (1) 622 2741 [email protected] FROM: Citibank Europe plc (the “Bank”) TO: Aspen Bermuda Limited (the “Company”) 141 Front Street Hamilton HM19 Bermuda Attention: Mark Pickering DATE: 30 June

December 20, 2023 EX-3.6

CERTIFICATE OF DESIGNATION 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES ASPEN INSURANCE HOLDINGS LIMITED

Exhibit 3.6 CERTIFICATE OF DESIGNATION OF 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES OF ASPEN INSURANCE HOLDINGS LIMITED ASPEN INSURANCE HOLDINGS LIMITED, a Bermuda company (the “Company”), HEREBY CERTIFIES that pursuant to resolutions of duly authorized Directors adopted on September 12, 2016, the creation of the 5.625% Perpetual Non-Cumulative Preference Shares, with a liquidation prefere

December 20, 2023 EX-10.3

ASPEN INSURANCE HOLDINGS LIMITED DEUTSCHE BANK TRUST COMPANY AMERICAS, Dated as of August 16, 2004 DEBT SECURITIES Table Of Contents

Exhibit 10.3 ASPEN INSURANCE HOLDINGS LIMITED TO DEUTSCHE BANK TRUST COMPANY AMERICAS, Trustee INDENTURE Dated as of August 16, 2004 DEBT SECURITIES Table Of Contents Page ARTICLE 1 DEFINITIONS 1 SECTION 1.1 CERTAIN TERMS DEFINED 1 ARTICLE 2 SECURITY FORMS 8 SECTION 2.1 FORMS GENERALLY 8 SECTION 2.2 FORM OF LEGEND FOR RESTRICTED SECURITIES 9 SECTION 2.3 FORM OF TRUSTEE'S CERTIFICATE OF AUTHENTICAT

December 20, 2023 EX-10.18

1 North Wall Quay

Exhibit 10.18 1 North Wall Quay Dublin 1 Ireland Niall Tuckey Vice President ILOC Product Citibank Europe plc 1 North Wall Quay Dublin 1, Ireland Date 30 July 2012 Aspen Bermuda Limited 141 Front Street Hamilton HM19 Bermuda Attention: Bryan Astwood Dear Bryan 1.Committed letter of credit facility Further to recent discussions, Citibank Europe plc (the “Bank”) is pleased to confirm its committed l

December 20, 2023 EX-10.12

FIRST AMENDMENT TO SECOND AMENDED AND RESTATED CREDIT AGREEMENT

Exhibit 10.12 FIRST AMENDMENT TO SECOND AMENDED AND RESTATED CREDIT AGREEMENT This FIRST AMENDMENT TO SECOND AMENDED AND RESTATED CREDIT AGREEMENT (this “Amendment”), dated as of March 11, 2020, is among Aspen Insurance Holdings Limited (“Aspen”), the undersigned Subsidiary Borrowers (together with Aspen, each a “Borrower” and collectively the “Borrowers”), the several banks that are parties heret

December 20, 2023 EX-10.16

ASSIGNMENT AGREEMENT (THIS “AGREEMENT”) October 11, 2006

Exhibit 10.16 ASSIGNMENT AGREEMENT (THIS “AGREEMENT”) October 11, 2006 Reference is made to the following documents (collectively referred to as the “Original Agreements”): (1)INSURANCE LETTERS OF CREDIT MASTER AGREEMENT, dated December 15, 2003 and attached hereto as Exhibit I (the “Master Agreement”) among Citibank Ireland Financial Services plc (whose name has since been changed to Citibank Eur

December 20, 2023 EX-3.8

CERTIFICATE OF DESIGNATION 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES ASPEN INSURANCE HOLDINGS LIMITED

Exhibit 3.8 CERTIFICATE OF DESIGNATION OF 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES OF ASPEN INSURANCE HOLDINGS LIMITED ASPEN INSURANCE HOLDINGS LIMITED, a Bermuda company (the “Company”), HEREBY CERTIFIES that pursuant to resolutions of duly authorized Directors adopted on May 29, 2019, the creation of the 5.625% Perpetual Non-Cumulative Preference Shares, with a liquidation preference of

December 20, 2023 EX-3.1

[LOGO OMITTED] CERTIFICATE OF INCORPORATION

Exhibit 3.1 REGISTRATION NO. 32164 [LOGO OMITTED] BERMUDA CERTIFICATE OF INCORPORATION I hereby in accordance with section 14 of the Companies Act 1981 issue this Certificate of Incorporation and do certify that on the 23rd day of May, 2002 EXALI REINSURANCE HOLDINGS LIMITED was registered by me in the Register maintained by me under the provisions of the said section and that the status of the sa

December 20, 2023 EX-10.19

1 North Wall Quay

Exhibit 10.19 1 North Wall Quay T +353 1 622 2000 Dublin 1 F +353 1 622 2222 Ireland Niall Tuckey Director ILOC Product Citibank Europe plc 1 North Wall Quay Dublin 1, Ireland Tel+353 (1) 622 7430 Fax+353 (1) 622 2741 [email protected] FROM: Citibank Europe plc (the “Bank”) TO: Aspen Bermuda Limited (the “Company”) 141 Front Street Hamilton HM19 Bermuda Attention: Jazmin Da Ponte DATE: 30th Ju

December 20, 2023 EX-3.3

A M E N D E D A N D R E S T A T E D B Y E — L A W S ASPEN INSURANCE HOLDINGS LIMITED

Exhibit 3.3 A M E N D E D A N D R E S T A T E D B Y E — L A W S OF ASPEN INSURANCE HOLDINGS LIMITED INTERPRETATION 1.1 In these Bye-Laws, unless the context otherwise requires: 1.1.1 “Affiliate” means, in relation to any undertaking, any other undertaking that controls, is controlled by or is under common control with such first undertaking. For the purpose of this definition, the term “control” m

December 20, 2023 EX-FILING FEES

Calculation of Filing Fee Tables Form F-1 (Form Type) Aspen Insurance Holdings Limited (Exact Name of Registrant as Specified in its Memorandum of Association) Table 1: Newly Registered and Carry Forward Securities

Exhibit 107 Calculation of Filing Fee Tables Form F-1 (Form Type) Aspen Insurance Holdings Limited (Exact Name of Registrant as Specified in its Memorandum of Association) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price(1)(2) Fee Rate Amount of Registration Fee Carry Forward Form Type Carry Forward File Number Carry Forward Initial Effective Date Filing Fee Previously Paid in Connection with Unsold Securities to be Carried Forward Newly Registered Securities Fees to be Paid Equity Ordinary Shares, par value $0.

December 20, 2023 EX-10.1

DEPOSIT AGREEMENT August 13, 2019 ASPEN INSURANCE HOLDINGS LIMITED, AS ISSUER, COMPUTERSHARE INC. AND COMPUTERSHARE TRUST COMPANY, N.A., AS DEPOSITARY, - and - The Holders from Time to Time of The Depositary Receipts Described Herein RELATING TO THE

Exhibit 10.1 DEPOSIT AGREEMENT Dated August 13, 2019 ASPEN INSURANCE HOLDINGS LIMITED, AS ISSUER, COMPUTERSHARE INC. AND COMPUTERSHARE TRUST COMPANY, N.A., AS DEPOSITARY, - and - The Holders from Time to Time of The Depositary Receipts Described Herein RELATING TO THE RECEIPTS, DEPOSITARY SHARES AND RELATED 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES OF THE ISSUER TABLE OF CONTENTS ARTICLE 1

December 20, 2023 F-1

As filed with the Securities and Exchange Commission on December 20, 2023.

As filed with the Securities and Exchange Commission on December 20, 2023. Registration No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form F-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 ASPEN INSURANCE HOLDINGS LIMITED (Exact Name of Registrant as Specified in its Charter) Bermuda 6331 98-0501000 (State or Other Jurisdiction of Incorporation or Organ

December 20, 2023 EX-3.2

THE COMPANIES ACT 1981 MEMORANDUM OF ASSOCIATION OF COMPANY LIMITED BY SHARES Section 7(1) and (2) MEMORANDUM OF ASSOCIATION ASPEN INSURANCE HOLDINGS LIMITED (hereinafter referred to as the "Company")

Exhibit 3.2 FORM No. 2 BERMUDA THE COMPANIES ACT 1981 MEMORANDUM OF ASSOCIATION OF COMPANY LIMITED BY SHARES Section 7(1) and (2) MEMORANDUM OF ASSOCIATION OF ASPEN INSURANCE HOLDINGS LIMITED (hereinafter referred to as the "Company") 1.The liability of the members of the Company is limited to the amount (if any) for the time being unpaid on the shares respectively held by them. 2.We, the undersig

December 20, 2023 EX-10.11

SECOND AMENDED AND RESTATED CREDIT AGREEMENT ASPEN INSURANCE HOLDINGS LIMITED, The Subsidiary Borrowers from Time to Time Parties Hereto, The Several Lenders from Time to Time Parties Hereto, THE BANK OF NEW YORK MELLON, as Collateral Agent, CITIBANK

Exhibit 10.11 SECOND AMENDED AND RESTATED CREDIT AGREEMENT among ASPEN INSURANCE HOLDINGS LIMITED, The Subsidiary Borrowers from Time to Time Parties Hereto, The Several Lenders from Time to Time Parties Hereto, THE BANK OF NEW YORK MELLON, as Collateral Agent, CITIBANK, N.A., as Syndication Agent, DEUTSCHE BANK SECURITIES INC., THE BANK OF NEW YORK MELLON and LLOYDS SECURITIES INC., As Co-Documen

December 20, 2023 EX-10.10

ASPEN INSURANCE U.S. SERVICES INC. NONQUALIFIED DEFERRED COMPENSATION PLAN AMENDED AND RESTATED EFFECTIVE AUGUST 1, 2014

Exhibit 10.10 ASPEN INSURANCE U.S. SERVICES INC. NONQUALIFIED DEFERRED COMPENSATION PLAN AMENDED AND RESTATED EFFECTIVE AUGUST 1, 2014 This document is drafted with the intent that it comply with Internal Revenue Code Section 409A and regulations promulgated thereunder. NFP Executive Benefits has provided you this specimen document strictly in its capacity as an employee benefits consulting firm a

December 20, 2023 EX-10.28

BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL DATED May 27, 2022 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) MINDTREE LIMITED MASTER SERVICES AGREEMENT: ITO SERVICES TABLE OF CONTENTS

Exhibit 10.28 CERTAIN IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THIS EXHIBIT BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL DATED May 27, 2022 (1) ASPEN INSURANCE UK SERVICES LIMITED - and - (2) MINDTREE LIMITED MASTER SERVICES AGREEMENT: ITO SERVICES TABLE OF CONTENTS 1. INTERPRETATION 1 2. CALL OFF OF SERVICES 13 3. SERVICE PROVIDER'S RE

December 20, 2023 EX-3.7

Form of Preference Shares Certificate 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY

Exhibit 3.7 Form of Preference Shares Certificate 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (“DTC”), NEW YORK, NEW YORK, TO THE COMPANY OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NA

December 20, 2023 F-N

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM F-N APPOINTMENT OF AGENT FOR SERVICE OF PROCESS BY FOREIGN BANKS AND FOREIGN INSURANCE COMPANIES AND CERTAIN OF THEIR HOLDING COMPANIES AND FINANCE SUBSIDIARIES MAKING PUBLI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM F-N APPOINTMENT OF AGENT FOR SERVICE OF PROCESS BY FOREIGN BANKS AND FOREIGN INSURANCE COMPANIES AND CERTAIN OF THEIR HOLDING COMPANIES AND FINANCE SUBSIDIARIES MAKING PUBLIC OFFERINGS OF SECURITIES IN THE UNITED STATES A.Name of issuer or person filing (“Filer”): Aspen Insurance Holdings Limited B.This is (select one): ☒

December 20, 2023 EX-3.5

5.95% FIXED-TO-FLOATING RATE PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY

Exhibit 3.5 5.95% FIXED-TO-FLOATING RATE PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (“DTC”), NEW YORK, NEW YORK, TO THE COMPANY OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NAME OF CEDE & CO.

December 20, 2023 EX-10.15

Insurance Letters of Credit − Master Agreement Insurance/Reinsurance Companies or Brokers

Exhibit 10.15 Execution Version Insurance Letters of Credit − Master Agreement Form 3/CIFS To: Citibank Ireland Financial Services plc Insurance Letter of Credit Department 2nd Floor 1 North Wall Quay Dublin 1 Republic of Ireland Dear Sirs, Insurance Letters of Credit − Master Agreement Insurance/Reinsurance Companies or Brokers The purpose of this letter is to record our agreement (the ‘‘Agreemen

December 20, 2023 EX-10.13

SECOND AMENDMENT TO SECOND AMENDED AND RESTATED CREDIT AGREEMENT

Exhibit 10.13 Execution Version SECOND AMENDMENT TO SECOND AMENDED AND RESTATED CREDIT AGREEMENT 1.This SECOND AMENDMENT TO SECOND AMENDED AND RESTATED CREDIT AGREEMENT (this “Amendment”), dated as of April 28, 2020, is among Aspen Insurance Holdings Limited (“Aspen”), the undersigned Subsidiary Borrowers (together with Aspen, each a “Borrower” and collectively the “Borrowers”), the several banks

December 20, 2023 EX-10.4

THIRD SUPPLEMENTAL INDENTURE BY AND BETWEEN ASPEN INSURANCE HOLDINGS LIMITED, AS ISSUER DEUTSCHE BANK TRUST COMPANY AMERICAS, AS TRUSTEE Dated as of November 13, 2013 ASPEN INSURANCE HOLDINGS LIMITED 4.650% SENIOR NOTES DUE 2023 THIRD SUPPLEMENTAL IN

Exhibit 10.4 THIRD SUPPLEMENTAL INDENTURE BY AND BETWEEN ASPEN INSURANCE HOLDINGS LIMITED, AS ISSUER AND DEUTSCHE BANK TRUST COMPANY AMERICAS, AS TRUSTEE Dated as of November 13, 2013 $300,000,000 ASPEN INSURANCE HOLDINGS LIMITED 4.650% SENIOR NOTES DUE 2023 THIRD SUPPLEMENTAL INDENTURE This Third Supplemental Indenture, dated as of November 13, 2013 (the “Third Supplemental Indenture”), to the In

December 20, 2023 EX-21.1

SUBSIDIARIES OF THE COMPANY

Exhibit 21.1 SUBSIDIARIES OF THE COMPANY NAME OF SUBSIDIARY JURISDICTION OF INCORPORATION Acorn Limited Bermuda APJ Asset Protection Jersey Limited Jersey Aspen (UK) Holdings Limited United Kingdom Aspen (US) Holdings Limited United Kingdom Aspen American Insurance Company Texas Aspen Australia Service Company Pty Ltd Australia Aspen Bermuda Limited Bermuda Aspen Capital Management, Ltd Bermuda As

December 20, 2023 EX-3.9

Preference Shares Certificate 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY

Exhibit 3.9 Preference Shares Certificate 5.625% PERPETUAL NON-CUMULATIVE PREFERENCE SHARES FACE OF SECURITY UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION (“DTC”), NEW YORK, NEW YORK, TO THE COMPANY OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NAME OF CE

November 30, 2023 6-K

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 November 2023 Commission File Number: 001-3

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 November 2023 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 ex

November 30, 2023 EX-99.1

Aspen Declares Dividends on Preference Shares

Exhibit 99.1 PRESS RELEASE Aspen Declares Dividends on Preference Shares Hamilton, Bermuda, November 30, 2023 – Aspen Insurance Holdings Limited (“Aspen”) (NYSE:AHL) announced today that the Board of Directors has declared the following dividends on its Preference Shares: •Quarterly dividend of $0.6129 per share on its 5.95% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares with a

November 22, 2023 EX-99.1

Aspen Reports Results for the Three and Nine Months Ended September 30, 2023 Net Income Available to Common Shareholders of $86 million and Operating Income of $79 million for the Three Months Ended Net Income Available to Common Shareholders of $305

Exhibit 99.1 PRESS RELEASE Aspen Reports Results for the Three and Nine Months Ended September 30, 2023 Net Income Available to Common Shareholders of $86 million and Operating Income of $79 million for the Three Months Ended Net Income Available to Common Shareholders of $305 million and Operating Income of $270 million for the Nine Months Ended Hamilton, Bermuda, November 22, 2023 - Aspen Insura

November 22, 2023 6-K

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 November 2023 Commission File Number: 001-3

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 November 2023 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 ex

September 1, 2023 6-K

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 September 2023 Commission File Number: 001-

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 September 2023 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 e

September 1, 2023 EX-99

Aspen Declares Dividends on Preference Shares

Exhibit 99.1 PRESS RELEASE Aspen Declares Dividends on Preference Shares Hamilton, Bermuda, September 1, 2023 – Aspen Insurance Holdings Limited (“Aspen”) (NYSE:AHL) announced today that the Board of Directors has declared the following dividends on its Preference Shares: •Quarterly dividend of $0.5996 per share on its 5.95% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares with a

August 22, 2023 6-K

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 August 22, 2023 Commission File Number: 001-31909 ASPEN INSU

Table of Contents 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 August 22, 2023 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

August 22, 2023 EX-99.1

Six Months Ended June 30, 2023 Reinsurance Insurance Total Gross written premiums $ 875.7 $ 1,249.5 $ 2,125.2 Net written premiums 605.0 745.5 1,350.5 Gross earned premiums 755.7 1,203.6 1,959.3 Net earned premiums 572.0 715.4 1,287.4 Losses and loss

Exhibit 99.1 PRESS RELEASE Aspen Reports Strong Financial Results for the First Six Months of 2023 •Net income increased by 352% to $219 million (June 30, 2022: $48 million) •Operating income* increased by 47% to $191 million (June 30, 2022: $130 million) •Annualized operating return on average equity* of 22% (June 30, 2022: 14%) •Underwriting income increased by 33% to $208 million (June 30, 2022

August 22, 2023 6-K

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 2023 Commission File Number: 001-319

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 2023 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 exec

June 22, 2023 6-K

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 June 2023 Commission File Number: 001-31909

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 June 2023 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 execut

June 22, 2023 CORRESP

Aspen Insurance Holdings Limited 141 Front Street Hamilton, HM 19

Aspen Insurance Holdings Limited 141 Front Street Hamilton, HM 19 Bermuda June 22, 2023 VIA EDGAR Division of Corporation Finance Securities and Exchange Commission 100 F Street, N.

June 15, 2023 F-N

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM F-N APPOINTMENT OF AGENT FOR SERVICE OF PROCESS BY FOREIGN BANKS AND FOREIGN INSURANCE COMPANIES AND CERTAIN OF THEIR HOLDING COMPANIES AND FINANCE SUBSIDIARIES MAKING PUBLI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM F-N APPOINTMENT OF AGENT FOR SERVICE OF PROCESS BY FOREIGN BANKS AND FOREIGN INSURANCE COMPANIES AND CERTAIN OF THEIR HOLDING COMPANIES AND FINANCE SUBSIDIARIES MAKING PUBLIC OFFERINGS OF SECURITIES IN THE UNITED STATES A. Name of issuer or person filing (“Filer”): Aspen Insurance Holdings Limited B. This is (select one):

June 14, 2023 F-3

As filed with the Securities and Exchange Commission on June 14, 2023 Registration No. 333- SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form F-3 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 ASPEN INSURANCE HOLDINGS LIMITED (E

As filed with the Securities and Exchange Commission on June 14, 2023 Registration No.

June 14, 2023 EX-FILING FEES

Calculation of Filing Fee Tables Form F-3 (Form Type) Aspen Insurance Holdings Limited (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities and Carry Forward Securities

Exhibit 107 Calculation of Filing Fee Tables Form F-3 (Form Type) Aspen Insurance Holdings Limited (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities and Carry Forward Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount

June 14, 2023 EX-25.1

_____________________________________________________________________________ UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 ____________________ FORM T-1 STATEMENT OF ELIGIBILITY UNDER THE TRUST INDENTURE ACT OF 1939 OF A CO

exh251 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM T-1 STATEMENT OF ELIGIBILITY UNDER THE TRUST INDENTURE ACT OF 1939 OF A CORPORATION DESIGNATED TO ACT AS TRUSTEE CHECK IF AN APPLICATION TO DETERMINE ELIGIBILITY OF A TRUSTEE PURSUANT TO SECTION 305(b)(2) DEUTSCHE BANK TRUST COMPANY AMERICAS (formerly BANKERS TRUST COMPANY) (Exact name of trustee as specified in it

June 14, 2023 EX-25.2

_____________________________________________________________________________ UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 ____________________ FORM T-1 STATEMENT OF ELIGIBILITY UNDER THE TRUST INDENTURE ACT OF 1939 OF A CO

exh252 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM T-1 STATEMENT OF ELIGIBILITY UNDER THE TRUST INDENTURE ACT OF 1939 OF A CORPORATION DESIGNATED TO ACT AS TRUSTEE CHECK IF AN APPLICATION TO DETERMINE ELIGIBILITY OF A TRUSTEE PURSUANT TO SECTION 305(b)(2) DEUTSCHE BANK TRUST COMPANY AMERICAS (formerly BANKERS TRUST COMPANY) (Exact name of trustee as specified in it

June 13, 2023 6-K

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 June 2023 Commission File Number: 001-31909

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 June 2023 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 execut

June 13, 2023 EX-99

ASPEN APPOINTS JOHN WELCH AS CHIEF UNDERWRITING OFFICER, REINSURANCE

Exhibit 99.1 PRESS RELEASE ASPEN APPOINTS JOHN WELCH AS CHIEF UNDERWRITING OFFICER, REINSURANCE Hamilton, Bermuda, June 13, 2023 – Aspen Insurance Holdings Limited (“Aspen”) has appointed John Welch as Chief Underwriting Officer, Reinsurance, starting on June 26. John brings over 30 years of global experience in reinsurance, including executive roles across global players. He was most recently Chi

June 7, 2023 6-K

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 June 2023 Commission File Number: 001-31909

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 June 2023 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 execut

June 1, 2023 6-K

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 June 2023 Commission File Number: 001-31909

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 June 2023 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 execut

June 1, 2023 EX-99

Aspen Declares Dividends on Preference Shares

Exhibit 99.1 PRESS RELEASE Aspen Declares Dividends on Preference Shares Hamilton, Bermuda, June 1, 2023 – Aspen Insurance Holdings Limited (“Aspen”) (NYSE:AHL) announced today that the Board of Directors has declared the following dividends on its Preference Shares: •Quarterly dividend of $0.3719 per share on its 5.95% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares with a $25 l

May 18, 2023 6-K

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 May 2023 Commission File Number: 001-31909

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 May 2023 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 executi

April 20, 2023 EX-4.24

BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL DATED May 27, 2022 2022

CONFIDENTIAL CERTAIN IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THIS EXHIBIT BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL DATED May 27, 2022 2022 (1)ASPEN INSURANCE UK SERVICES LIMITED - and - (2)MINDTREE LIMITED MASTER SERVICES AGREEMENT: ITO SERVICES 34744018 CONFIDENTIAL TABLE OF CONTENTS INTERPRETATION 1 CALL OF OF SERVICES 13 SERVICE

April 20, 2023 20-F

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 20-F ☐ REGISTRATION STATEMENT PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 20-F ☐ REGISTRATION STATEMENT PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECUR

April 20, 2023 EX-12.1

CERTIFICATION

Exhibit 12.1 CERTIFICATION I, Mark Cloutier, certify that: 1.I have reviewed this annual report on Form 20-F of Aspen Insurance Holdings Limited; 2.Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with

April 20, 2023 EX-2.1

DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934

Exhibit 2.1 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 As of the date of the Annual Report on Form 20-F of which this exhibit is a part, Aspen Insurance Holdings Limited (“Aspen”, “AHL,” “Aspen Holdings,” “we,” “us,” “our,” and the “Company”) has three classes of securities registered under Section 12 of the Securities Exchan

April 20, 2023 EX-4.23

BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL AMENDED AND RESTATED REINSURANCE AGREEMENT by and among ASPEN INSURANCE UK LIMITED, ASPEN MANAGING AGENCY LIMITED for and on behalf of the UNDERWRIT

EXECUTION COPY CERTAIN IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THIS EXHIBIT BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL AMENDED AND RESTATED REINSURANCE AGREEMENT by and among ASPEN INSURANCE UK LIMITED, ASPEN MANAGING AGENCY LIMITED for and on behalf of the UNDERWRITING MEMBER(S) OF LLOYD’S SYNDICATE 4711, ASPEN BERMUDA LIMITED, ASPEN AMERICAN INSURANCE COMPANY, ASPEN SPECIALTY INSURANCE COMPANY, ASPEN INSURANCE HOLDINGS LIMITED (solely for the purposes of Sections 11.

April 20, 2023 EX-12.2

CERTIFICATION

Exhibit 12.2 CERTIFICATION I, Christopher Coleman, certify that: 1.I have reviewed this annual report on Form 20-F of Aspen Insurance Holdings Limited; 2.Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleadin

April 20, 2023 EX-13.1

CERTIFICATION PURSUANT TO 18 U.S.C. SECTION 1350, AS ADOPTED PURSUANT TO SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002

Exhibit 13.1 CERTIFICATION PURSUANT TO 18 U.S.C. SECTION 1350, AS ADOPTED PURSUANT TO SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002 In connection with this Annual Report on Form 20-F of Aspen Insurance Holdings Limited (the “Company”) for the twelve months ended December 31, 2022 as filed with the Securities and Exchange Commission on the date hereof (the “Report”), Mark Cloutier as Chief Executiv

April 19, 2023 6-K

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 April 2023 Commission File Number: 001-3190

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 April 2023 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 execu

April 19, 2023 EX-99.1

Twelve Months Ended December 31, 2022 Reinsurance Insurance Total Gross written premiums $ 1,807.0 $ 2,531.7 $ 4,338.7 Net written premiums 1,426.4 1,469.6 2,896.0 Gross earned premiums 1,617.2 2,370.8 3,988.0 Net earned premiums 1,251.8 1,436.9 2,68

Exhibit 99.1 PRESS RELEASE Aspen Reports Net Income of $51 million, Operating Income of $202 million and a Combined Ratio of 93.0% for the Twelve Months Ended December 31, 2022 •Gross written premiums increased by 10% to $4,339 million (2021: $3,938 million) •Underwriting income* of $190 million (2021: $(30) million) •Total fee income generated by Aspen Capital Markets of $104 million (2021: $61 m

March 8, 2023 EX-99

ASPEN APPOINTS NEW DIRECTOR

Exhibit 99.1 PRESS RELEASE ASPEN APPOINTS NEW DIRECTOR 8 March 2023 Hamilton, Bermuda – Aspen Insurance Holdings Limited (“Aspen”) is pleased to announce the appointment of David Altmaier to its Board as a Non-Executive Director, subject to receipt of any required regulatory approvals. David was previously the Commissioner of Insurance for the State of Florida, leading the Office of Insurance Regu

March 8, 2023 6-K

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 March 2023 Commission File Number: 001-3190

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 March 2023 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 execu

March 1, 2023 EX-99

Aspen Declares Dividends on Preference Shares

Exhibit 99.1 PRESS RELEASE Aspen Declares Dividends on Preference Shares Hamilton, Bermuda, March 1, 2023 – Aspen Insurance Holdings Limited (“Aspen”) (NYSE:AHL) announced today that the Board of Directors has declared the following dividends on its Preference Shares: •Quarterly dividend of $0.3719 per share on its 5.95% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares with a $25

March 1, 2023 6-K

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 March 2023 Commission File Number: 001-3190

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 March 2023 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 execu

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