American Overseas : Notice of 2024 Annual General Meeting

AMERICAN OVERSEAS GROUP LIMITED

(a Bermuda company)

Clarendon House

2 Church Street

Hamilton HM 11

Bermuda

NOTICE OF ANNUAL GENERAL MEETING

To Be Held Tuesday, June 18, 2024

Dear Members:

We are pleased to invite you to the 2024 Annual General Meeting of American Overseas Group Limited (the "Company"), which we refer to as the "Annual Meeting". We will hold the Annual Meeting at The Connaught Hotel, Carlos Place, Mayfair, London W1K 2AL, United Kingdom, on Tuesday, June 18, 2024, at 11:00 a.m. local time. The purpose of the Annual Meeting is:

1. To elect the directors of the Company to serve until the 2025 Annual General Meeting of the Company.
2. To ratify the appointment of Deloitte Ltd., Hamilton, Bermuda, as the Company's independent auditor for the financial year ending December 31, 2024, until the 2025 Annual General Meeting of the Company, and to authorize the directors of the Company to determine the independent auditor's fee.

Enclosed is our Proxy Statement, which explains the matters to be acted upon at the Annual Meeting, and our 2023 Annual Report, which includes our financial statements and schedules for the year ended December 31, 2023. The audited consolidated financial statements for the Company for the year ended December 31, 2023, and accompanying auditor's report will be presented at the Annual Meeting.

Members of record of common shares on the record date of April 22, 2024, (1) who are individuals, may attend and vote at the Annual Meeting in person or by proxy; or (2) that are corporations or other entities, may have their duly authorized representative attend and vote at the Annual Meeting in person or by proxy. A list of all members entitled to attend the Annual Meeting will be open for public examination during regular business hours beginning on or about May 6, 2024, at the registered office of the Company, located at Clarendon House, 2 Church Street, Hamilton HM 11, Bermuda.

By order of the board of directors,

Debra J. Roberts

President, Chief Executive Officer and Chair of the

Board

May 6, 2024

Hamilton, Bermuda

PROXY STATEMENT
TABLE OF CONTENTS
	Page
Information About Our Annual General Meeting	1
Information About Directors, Corporate Governance and Director Compensation	5
Information About Our Executive Officers and Executive Compensation	8
Information About the Owners of Our Common Shares	8
Proposals Recommended by the AOG Board	9
Additional Information	12

AMERICAN OVERSEAS GROUP LIMITED

(a Bermuda company)

Clarendon House

2 Church Street

Hamilton HM 11

Bermuda

PROXY STATEMENT

INFORMATION ABOUT OUR ANNUAL GENERAL MEETING

We are sending you this Proxy Statement because the board of directors of the Company (the "AOG Board") is soliciting your proxy to vote at the 2024 Annual General Meeting of American Overseas Group Limited ("the Company", "we", "us", or "our"), which we refer to as our "Annual Meeting".

Date, Time and Location of the Annual Meeting

We will hold the Annual Meeting at The Connaught Hotel, Carlos Place, Mayfair, London W1K 2AL, United Kingdom, on Tuesday, June 18, 2024, at 11:00 a.m. local time.

Proposals to be Voted on at the Annual Meeting

The proposals to be voted on at the Annual Meeting are:

1. To elect the directors of the Company to serve until the 2025 Annual General Meeting of the Company.
2. To (i) ratify the appointment of Deloitte Ltd., Hamilton, Bermuda, as the Company's independent auditor for the financial year ending December 31, 2024, until the 2025 Annual General Meeting of the Company; and (ii) to authorize the directors of the Company to determine the independent auditor's fee.

2023 Annual Report of the Company

We have enclosed our 2023 Annual Report with this Proxy Statement. The 2023 Annual Report is included for informational purposes and not as a means of soliciting your proxy. The 2023 Annual Report and financial statements for the year ended December 31, 2023 are available atwww.aoreltd.comby clicking on "Financial Information".

Mail Date

This Proxy Statement, and the accompanying Notice of Annual Meeting and Proxy, are first being mailed to members on or about May 6, 2024.

Our Voting Securities

The record date for our Annual Meeting is April 22, 2022 (hereinafter the "Record Date"). Pursuant to the Company's Bye-laws, only registered holders of common shares of the Company at the close of business on the Record Date are entitled to attend and vote at the Annual Meeting. On the Record Date, 46,979 of our common shares (net of treasury shares held by the Company) were issued. The common shares are our only class of equity securities in issue and entitled to vote at the Annual Meeting.

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Number of Votes for each Common Share

In general, you have one vote for each common share owned at the Record Date. The following exceptions may apply:

Reduction or Increase of Voting Power Under our Bye-laws

Under our Bye-laws, if you are a U.S. member who controls, directly, indirectly or constructively, as described in our Bye-laws, more than 9.9% of our common shares, your total voting power will be reduced to 9.9% of the total voting power of our common shares. The determination of control is made under the relevant provisions of the Internal Revenue Code of 1986, as amended (the "Code"). These provisions include certain attribution or "constructive ownership" rules under which you may be treated as owning shares that are owned by other persons or entities. In addition, the AOG Board may otherwise limit your voting rights if the AOG Board believes it is necessary to do so to avoid adverse tax, legal or regulatory consequences.

If the voting power of any of our members is reduced under our Bye-laws, this reduction may increase another member's voting power to more than 9.9%. In this case, our Bye-laws would repeatedly reduce the voting power of all affected members until no U.S. member, has voting power of more than 9.9%. If we believe you are a U.S. member who may control more than 9.9% of our common shares, we may ask you to provide us with additional information so that we can verify your ownership and determine if your voting power needs to be reduced. We may disregard the votes of any member who fails to respond to a request for further information or who, in our judgment, submits incomplete or inaccurate information. In addition, because we may not know about your ownership, we request that you contact us promptly if you believe you may control more than 9.9% of the common shares. When you submit your proxy, we will consider the submission confirmation that, to your knowledge, you do not control, and you are not acting on behalf of a member who controls, more than 9.9% of our common shares.

Quorum Requirement

The presence of two (2) or more persons, representing in person or by proxy shares carrying more than 50% of the voting power of our issued common shares as of the Record Date, is necessary to constitute a quorum at the Annual Meeting. Assuming that a quorum is present, the affirmative vote of the holders of a simple majority of the common shares voted at the Annual Meeting in person or by proxy will be required to approve each of the matters to be voted upon at the Annual Meeting.

Attendance at the Annual Meeting

Pursuant to our Bye-laws, only members that are registered in our register of members as of the Record Date ("Registered Members") are entitled to attend this meeting. If you are a Registered Member and intend to attend and exercise your right to vote in person at the Annual Meeting, you must request an admission ticket in advance. Your request must be received no later than May 31, 2024. You can request an admission ticket by sending a request to the Company addressed to Assistant Secretary, American Overseas Group Limited, Clarendon House, 2 Church Street, Hamilton, HM 11 Bermuda. Upon confirmation that you are a Registered Member as of the Record Date, an admission ticket will be sent to you for your use at the meeting. All attendees will be required to present the admission ticket and a valid, government-issued photo identification (e.g. driver's license or passport) to enter the meeting.

Seating at the Annual Meeting will begin at 10:45 a.m. local time. Prior to entering the meeting, all bags will be subject to search and all persons may be subject to a metal detector and/or hand wand search. Cameras, recording devices and other electronic devices will not be permitted at the meeting. The security procedures may require additional time, so please plan accordingly. We suggest arriving at least 45 minutes early. Registration will close ten minutes before the meeting begins. If you do not provide an admission ticket and valid, government-issuedphoto identification or do not comply with the other registration and security procedures described above, you will not be admitted to the Annual Meeting. The Company reserves the right to remove persons from the Annual Meeting who disrupt the meeting or who do not comply with the rules and procedures for the conduct of the Annual Meeting.

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Possible travel restrictions may apply for travelers arriving in the UK from other countries. Members are encouraged to confirm round trip requirements or restrictions prior to their departure.

Voting Methods

If you are a Registered Member, you may exercise your vote by completing, signing and returning by mail the enclosed form of proxy so that it is received at least 24 hours before the Annual Meeting, or in person at the Annual Meeting. When you exercise your vote by using the form of proxy, you are instructing another person to vote your shares for you at the Annual Meeting in the manner that you indicate. These persons, called proxies, are named on your proxy card. If you have signed but have not provided instructions in the proxy, your shares will be voted FOR each of the proposals described in this Proxy Statement and set forth on the form of proxy, and in accordance with the proxy holder's discretion as to any other business as may properly come before the Annual Meeting.

If, like many members, you are a beneficial owner and hold your shares in "street name," meaning that you hold your shares through a bank, broker, nominee or other institution, you must instruct that institution how to vote your shares. Such an institution will usually provide you with an appropriate voting instruction form when it sends you this Proxy Statement.

Revocation of Proxy

If you are a Registered Member and you use the enclosed form of proxy, you can revoke your proxy or change your voting instructions in one of these ways:

1. By delivering another proxy dated after your prior proxy no less than 24 hours before the Annual Meeting to the Assistant Secretary of the Company at the address above;
2. By attending the Annual Meeting and voting in person; or
3. By delivering a written notice of revocation of your proxy no less than 24 hours before the Annual Meeting to the Assistant Secretary of the Company at the address above.

If you are a beneficial owner, you should contact the institution that holds your shares directly to change your voting instructions.

Voting in Person

If you are a Registered Member, you may vote your shares in person even if you have returned a proxy. If you choose to vote your shares in person at the Annual Meeting, please bring your admission ticket, the enclosed proxy card and proof of identification. Even if you plan to attend the Annual Meeting, we recommend that you submit your vote in advance, as described above, so that your vote will be counted if you are unable to attend the Annual Meeting.

Abstentions

If you are a Registered Member and abstain from voting on a proposal, your vote will not count as a vote cast, but the abstention will be represented at the Annual Meeting and will count toward establishing a quorum.

If you are a Registered Member and you do not vote, your shares will not be represented at the Annual Meeting and will not affect the outcome of our proposals. If you are a Registered Member and return a blank but signed proxy card, your shares will be voted in the manner recommended by the AOG Board, which is FOR Proposals 1 and 2. This will generally also be the case for beneficial owners, as explained in more detail below.

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Broker non-votes

If you are a beneficial owner and you do not give voting instructions to your broker, your broker may have discretionary authority to vote your shares for you on certain proposals that are considered routine matters. Brokers who have discretionary authority generally vote in the manner recommended by the AOG Board. When a client does not provide voting instructions for non-routine matters that may not be voted by the broker, the missing votes are called broker non-votes. If broker non-votes occur at the Annual Meeting, the shares in this category will count toward the establishment of a quorum, but the broker non-votes will have no effect on the outcome of those proposals on which the broker does not or cannot vote.

Availability of the Proxy Statement and Annual Report online

This Proxy Statement and our 2023 Annual Report are available at www.aoreltd.comby clicking on "Financial Information".

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INFORMATION ABOUT DIRECTORS, CORPORATE GOVERNANCE

AND DIRECTOR COMPENSATION

Composition of the AOG and AORE Boards

There are currently three (3) directors on the AOG Board. The total number of directors who may serve on the AOG Board at any given time is currently set by the AOG Board at three (3), but this number may increase up to a maximum of eleven (11) members. The AOG Board will continue to consist of three (3) directors following the Annual Meeting.

It is proposed that the following three (3) nominees be elected by the members to the AOG Board, as contemplated by Proposal 1.1:

1. Ronald J. Ballard
2. Andrew J. Kirkpatrick
3. Debra J. Roberts

Director Biographies

Set forth below is biographical information concerning each current director and director nominee of the Company and AORE including each such individual's principal occupation and the period during which such person has served as a director of the Company or AORE, if applicable. Information about share ownership of certain directors and executive officers as of December 31, 2023, can be found under "Directors and Executive Officers-Security Ownership of Executive Officers and Directors" in our 2023 Annual Report delivered herewith.

Debra J. Roberts	Ms. Roberts is the President and Chief Executive Officer of the Company, and also
Age 70	serves as Chair of the AOG Board. She also serves as Chairperson and/or Chief
Director since 2011	Executive Officer of all of the Company's subsidiaries in Barbados and the United
	States. Since 1993, Ms. Roberts has served as the Chief Executive Officer of Debra
	Roberts & Associates, Inc. which provides risk transfer consulting and arbitration-
	related services to the domestic and international reinsurance industries. From 1981
	through 1993, Ms. Roberts held various senior positions at three companies within
	the Swiss Reinsurance Group. She holds an MBA from Fordham University
	Graduate School of Business and is a Chartered Financial Analyst.
Andrew J. Kirkpatrick	Mr. Kirkpatrick is a director of the Company. Mr. Kirkpatrick is President and
Age 50	director of two of the Company's U.S. subsidiaries: Old American County Mutual
Director since 2018	Fire Insurance Company and Old American Indemnity Company. Mr. Kirkpatrick
	received a BBA in Finance and a BA in Psychology from Southern Methodist
	University. Mr. Kirkpatrick also holds an Associate in Reinsurance and an Associate
	in Risk Management designation.
Ronald J. Ballard	Mr. Ballard is Chief Financial Officer of the Company, and also an officer of various
Age 56	direct and indirect subsidiaries of the Company in Barbados and the United
Director since 2020	States. Mr. Ballard has over 30 years of experience in the property and casualty
	insurance industry. Mr. Ballard was most recently CFO of the non-standard
	automobile and commercial vehicle business for Kemper Corp, and has held a variety
	of financial and business leadership roles across the property and casualty spectrum
	at Kemper Corp, f/k/a Unitrin, Inc. Mr. Ballard has a BA in Economics from The
	University of Texas and a BBA in Accounting from Texas A&M University.

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As a Bermuda company, we hold our AOG Board meetings outside of the United States. As of September of 2014, the Company re-domesticated to the United Kingdom for tax purposes. The AOG Board held three general meetings during the financial year ended December 31, 2023: April 18, 2023, June 20, 2023, and September 20, 2023. The AOG Board generally meets in executive session for part of each regularly scheduled meeting.

All directors nominated for re-election to the AOG Board pursuant to this Proxy Statement, attended all of the general meetings of the AOG Board held during the term of their directorship in person in 2023.

Director Attendance at Annual Meetings

Each director of the Company is expected to be present at Annual General Meetings of the Company, absent exigent circumstances that prevent attendance. All of our directors nominated for re-election to the AOG Board pursuant to this Proxy Statement were present in person at the 2023 Annual General Meeting of the Company.

Committees

The Company does not have a separate Audit Committee, Governance Committee, and Risk Management Committee. Instead, the functions of these committees are the responsibility of and are carried on by the AOG Board.

Director Compensation

For information regarding equity compensation of our directors, please refer to "Directors and Executive Officers-Equity Compensation of Directors" and "Directors and Executive Officers - Equity Compensation of Executive Officers" in our 2023 Annual Report delivered herewith.

Member Nomination of Directors

It is the policy of our AOG Board that members may suggest director candidates for consideration by the AOG Board by writing to the AOG Board, care of the Assistant Secretary, American Overseas Group Limited, Clarendon House, 2 Church Street, Hamilton HM 11 Bermuda. The AOG Board evaluates all director candidates in the same manner and in accordance with the same criteria, regardless of whether they are nominated by members or identified by the AOG Board.

If a member wishes to propose a director candidate for nomination at the Annual Meeting, then the member must comply with the procedures set forth in the Company's Bye-laws and Bermuda law, as summarized below under "Additional Information - Member Proposals".

Member and Other Communications to the Directors

The AOG Board has instructed the Assistant Secretary to perform an initial review of all communications directed to them. Communications that are not relevant to the duties and responsibilities of the AOG Board, such as spam, junk mail and advertisements, are not reported to the AOG Board.

Any communications related to the Company's accounting, internal accounting controls or auditing matters will be referred promptly to the Chairman of the AOG Board. Any allegations pertaining to a serious accounting infraction involving senior managers of the Company or any other potentially material complaint would then be investigated as directed by the AOG Board and the results of such investigation would be reported to the AOG Board.

All other communications received by the Assistant Secretary will be forwarded promptly to the specific director(s) to whom they are addressed or otherwise to the non-management directors as a group.

Members and other interested parties who wish to communicate with the Company's directors should direct correspondence to a particular director or to the directors as a group, by e-mail at [e-mail] or by regular mail to the Assistant Secretary, American Overseas Group Limited, Clarendon House, 2 Church Street, Hamilton HM 11, Bermuda.

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Transactions with Related Persons, Promoters and Certain Control Persons

In October of 2014, the Company entered into an Amalgamation Agreement whereby Orpheus Group Limited ("OGL") became a wholly-owned subsidiary of the Company. In connection with the amalgamation, the former members of OGL received shares of the Company and promissory notes in the aggregate principal amount of $43.9 million. Former directors Clement S. Dwyer, Jr., Shelley P. Fyfe, Steven J. Tynan and James L. Zech, and current directors Debra J. Roberts and Andrew J. Kirkpatrick, and/or their respective family members, owned approximately 75% of OGL in the aggregate at the time of the amalgamation. They or their family members received shares and/or notes or a combination of both in connection with the amalgamation. The notes issued by the Company mature on October 28, 2039. Interest on the notes is payable in quarterly installments at a fixed rate of 9.0% per annum. As of December 31, 2023, the aggregate principal amount of the Notes was $6.0 million and directors of certain AOG subsidiaries and/or their respective family members held notes payable in the aggregate principal amount of approximately $2.6 million. In connection with a series of restructuring actions undertaken by the Company in April 2021, the Company transferred and conveyed all of its rights, title, interest, duties and obligations under these notes to its subsidiary, Old American Capital Corporation, a Delaware corporation. Also as part of the restructuring, OGL was liquidated and dissolved on July 9, 2021.

Prior to the amalgamation, Old American Capital Corporation ("OACC"), issued a note in the principal amount of $20 million to Gabriele's Pence LLC, with a maturity date of October 28, 2039, with interest on the note being payable in quarterly installments at a fixed rate of 12.0% per annum. On January 1, 2015, OACC issued a series of Secured Senior Notes to the members of Gabriele's Pence, LLC which replaced and superseded the note issued to Gabriele's Pence, LLC. These notes will mature on January 1, 2040 and interest is payable in quarterly installments at a fixed rate of 12.0% per annum. As of December 31, 2023, the aggregate principal amount of the Senior Secured Notes was $14.8 million and directors of OACC and/or their respective family members held notes payable in the aggregate principal amount of approximately $10.4 million.

Effective April 1, 2016, OACC entered into individual Consultancy Agreements with Clement S. Dwyer, Jr. and James L. Zech (the "Consultants") for the Consultants to assist with general corporate issues, as well as loss mitigation strategies for the Company. As of July 1, 2022, under the amended terms of the Consultancy Agreements, the Consultants each receive a fee of $164,004 per contract year, as well as a car allowance of $3,000 per month for the lease of a vehicle.

Code of Conduct

Our Code of Conduct, which is our code of ethics applicable to all directors, employees and consultants, embodies our principles and practices relating to the ethical conduct of our business and our commitment to honesty, fair dealing and full compliance with all laws affecting our business. A member or any other party may follow the procedures set forth above under "Member and Other Communications to Directors" to anonymously and confidentially report a suspected or actual violation of the Code of Conduct.

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INFORMATION ABOUT OUR EXECUTIVE OFFICERS AND EXECUTIVE COMPENSATION

Executive Biographies

For biographical information regarding our executive officers, Debra J. Roberts, the President and Chief Executive Officer of the Company, and Ronald J. Ballard the Chief Financial Officer of the Company, please refer to the "Director Biographies" section of this Proxy Statement.

Executive Compensation

For information regarding equity compensation of our executive officers, please refer to "Directors and Executive Officers-Equity Compensation of Executive Officers" in our 2023 Annual Report delivered herewith.

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INFORMATION ABOUT THE OWNERS OF OUR COMMON SHARES

Security Ownership of Certain Executive Officers and Directors

For information regarding the beneficial ownership of our common shares by our executive officers and directors as of December 31, 2023, please refer to "Directors and Executive Officers - Security Ownership of Executive Officers and Directors" in our 2023 Annual Report delivered herewith.

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