ARGD / Argo Group U.S., Inc. - Preferred Security - Pengajuan SECLaporan Tahunan, Pernyataan Proksi

UNITED STATES

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 18, 2025 Argo Group International Holdings, Inc.

Argo Group International Holdings, Inc. Announces Full Redemption of Outstanding Depositary Shares Representing Interests in its 7.00% Resettable Fixed Rate Preferred Stock, Series A, and Full Redemption of Argo Group US, Inc.’s Outstanding 6.500% Se

Exhibit 99.1 Argo Group International Holdings, Inc. Announces Full Redemption of Outstanding Depositary Shares Representing Interests in its 7.00% Resettable Fixed Rate Preferred Stock, Series A, and Full Redemption of Argo Group US, Inc.’s Outstanding 6.500% Senior Notes Due September 15, 2042 and Intent to Voluntarily Delist and Deregister New York – August 15, 2025 – Argo Group International H

UNITED STATES SECURITIES AND EXCHANGE COMMISSION

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 15, 2025 Argo Group International Holdings, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended June 30, 2025 ☐ Transition report pu

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended June 30, 2025 or ☐ Transition report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 for the transition period from to Commission file number: 1-

Resignation Agreement, by and between Argo Group International Holdings, Inc. and Jessica Buss, dated April 2, 2025.

exhibit101 April 2, 2025 Jessica Buss Via Email Re: Resignation from the Argo Group Dear Jessica: Pursuant to our recent discussions, we acknowledge and accept your resignation from employment with the Argo Group (defined below), effective as of April 2, 2025 (the “Separation Date”).

Executive Long-Term Incentive Plan of Argo

1009497587v7 ARGO GROUP INTERNATIONAL HOLDINGS, INC. EXECUTIVE LONG-TERM INCENTIVE PLAN Introduction This Executive Long-Term Incentive Plan (the “Plan”) has been adopted by the Board of Directors (the “Board”) of Argo Group International Holdings, Inc. (the “Company”) effective as of October 16, 2024. The purpose of the Plan is to attract and retain senior management of the Company and its subsid

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended March 31, 2025 ☐ Transition report p

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended March 31, 2025 or ☐ Transition report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 for the transition period from to Commission file number: 1

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 8, 2025 (April 2, 2025) Argo Group International Holdings, Inc.

Argo Group Announces Leadership Changes

Exhibit 99.1 Argo Group Announces Leadership Changes New York – March 24, 2025 – Argo Group International Holdings, Inc. (“Argo” or “the company”), an underwriter of specialty insurance products, today announced the appointment of Chris Donahue as Chief Executive Officer. Mr. Donahue joined the company in November 2023 as Chief Financial Officer. “Chris has been integral to the transformation of A

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 27, 2025 (March 21, 2025) Argo Group International Holdings, Inc.

Offer Letter, by and between Argo Group International Holdings, Inc. and David Chan, dated March 24, 2025.

Exhibit 10.1 March 24, 2025 David Chan c/o [email protected] Dear David, Congratulations on your promotion to Chief Financial Officer of Argo Group International Holdings, Inc. (“Argo” or the “Company”). In your role, you will report to Christopher Donahue, Chief Executive Officer and will work out of the Company’s offices in New York, New York. Effective Date This offer and your role as

Insider Trading Policy

exhibit19 Exhibit 19 INSIDER TRADING POLICY Argo Group International Holdings, Inc.

Code of Business Conduct and Ethics.

Code of Business Conduct and Ethics Argo Group International Holdings, Inc. (the “Company”) As adopted by the Board of Directors, effective August 2, 2023 Introduction The Company is committed to conducting its business in accordance with all laws, rules and regulations that apply to the Company wherever it does business, as well as the highest standards of business ethics. Further, the Company is

Clawback Policy of Argo Group International Holdings, Inc. and Argo Group US, Inc.

Clawback Policy CLAWBACK POLICY September 6, 2024 Exhibit 97.1 Clawback Policy Scope This Clawback Policy (the “Policy”) applies to any individual who, at the relevant time, is or was an Executive Officer (as defined below) of Brookfield Wealth Solutions Ltd. (“Brookfield Wealth Solutions”) and/or any wholly-owned subsidiary of Brookfield Wealth Solutions, whose securities may be listed on a U.S.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ Annual report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2024 ☐ Transition report pursua

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ 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 Securities Exchange Act of 1934 for the transition period from to Commission file number: 1-1525

Amendment No. 1 to Deposit Agreement, dated as of April 19, 2024, by and between Argo Group International Holdings, Inc. and Equiniti Trust Company, LLC.

AMENDMENT NO. 1 TO DEPOSIT AGREEMENT This Amendment No. 1 to Deposit Agreement (this "Amendment"), effective as April 19, 2024, is entered into by and between Argo Group International Holdings, Inc., a Delaware corporation (formerly known as Argo Group International Holdings, Ltd., an exempted company organized under the laws of Bermuda) (the "Company"), and Equiniti Trust Company, LLC, a New York

Guaranteed Securities

Exhibit 22 Guarantor and Subsidiary Issuer of Registered Guaranteed Securities Securities Guarantor Argo Group US, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended September 30, 2024 ☐ Transition repo

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended September 30, 2024 or ☐ Transition report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 for the transition period from to Commission file numbe

Amended and Restated Bylaws of Argo Group International Holdings, Inc.

Exhibit 3.2 AMENDED AND RESTATED BYLAWS of ARGO GROUP INTERNATIONAL HOLDINGS, INC., a Delaware Corporation Effective November 30, 2023September 25, 2024 TABLE OF CONTENTS Page Article I - Stockholders 1   1.    Place of Meetings 1   2.    Annual Meeting 1   3.    Special Meetings 1   4.    Notice of Meetings 1   5.    Quorum 2   6.    Voting and Proxies 2   7.    Action at Meeting 2   8.    Presid

Amended and Restated Certificate of Incorporation of Argo Group International Holdings, Inc.

Exhibit 3.1 AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF ARGO GROUP INTERNATIONAL HOLDINGS, INC. FIRST: The name of this corporation shall be: Argo Group International Holdings, Inc. (the “Corporation”). SECOND: Its registered office in the State of Delaware is to be located at 251 Little Falls Drive, in the City of Wilmington, 19808, County of New Castle and its registered agent at such a

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): September 25, 2024 Argo Group International Holdings, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended June 30, 2024 ☐ Transition report pu

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended June 30, 2024 or ☐ Transition report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 for the transition period from to Commission file number: 1-

Letter of KPMG LLP, dated June 20, 2024.

Exhibit 16.1 KPMG LLP 345 Park Avenue New York, NY 10154-0102 June 20, 2024 Securities and Exchange Commission Washington, D.C. 20549 Ladies and Gentlemen: We were previously principal accountants for Argo Group International Holdings, Inc. and, under the date of March 18, 2024, we reported on the consolidated financial statements of Argo Group International Holdings, Inc. as of December 31, 2023

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 20, 2024 Argo Group Internatio

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 20, 2024 Argo Group International Holdings, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended March 31, 2024 ☐ Transition report p

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended March 31, 2024 or ☐ Transition report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 for the transition period from to Commission file number: 1

Form of Stock Certificate evidencing 7.00% Resettable Fixed Rate Preferred Stock, Series A, of Argo Group International Holdings, Inc.

Certificate Number: 01 Number of shares of Series A Preferred Stock: 6,000 CUSIP / ISIN NO.

Clawback Policy of Argo Group International Holdings, Inc.

1 ARGO GROUP INTERNATIONAL HOLDINGS, LTD. CLAWBACK POLICY The Board of Directors (the “Board”) of Argo Group International Holdings, Ltd. (the “Company”) believes that it is appropriate for the Company to adopt this Clawback Policy (the “Policy”) to be applied to the Covered Executives of the Company and adopts this Policy as of November 16, 2023, to be effective as of the Effective Date. 1. Defin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ Annual report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2023 ☐ Transition report pursua

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ 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 Securities Exchange Act of 1934 for the transition period from to Commission file number: 1-1525

Subsidiaries of Registrant

Exhibit 21 Subsidiaries of Argo Group International Holdings, Inc. Company Name Country/State of Incorporation PXRE Capital Statutory Trust II Connecticut PXRE Capital Statutory Trust VI Delaware Argo Re Ltd. Bermuda Argo Insurance Services Bermuda, Ltd. Bermuda Argo Irish Holdings I Ltd. Bermuda Argo Irish Holdings II Bermuda Argo Re Escritório de Representação no Brasil Ltda. Brazil PXRE Reinsur

Certificate of Designations of 7.00% Resettable Fixed Rate Prefer

TERMS, RIGHTS, RESTRICTIONS AND QUALIFICATIONS OF 7.00% RESETTABLE FIXED RATE PREFERRED STOCK, SERIES A OF ARGO GROUP INTERNATIONAL HOLDINGS, INC. Section 1.              Designation. The distinctive serial designation of the Series A Preferred Stock is “7.00% Resettable Fixed Rate Preferred Stock, Series A.” Each share of Series A Preferred Stock shall be identical in all respects to every other

Certificate of Designations of 7.00% Resettable Fixed Rate Preference Shares, Series A, of

Exhibit 4.5 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 Argo Group International Holdings, Inc. (“Argo Group,” “Company,” “we,” “us,” and “our”) has two classes of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”): (a) the 6.500% Senior Notes due 2042 (the “Notes”) i

Form of 6.500% Senior Notes due 2042, dated December 11, 2023.

Form of 6.500% Senior Note due 2042 THIS NOTE IS A GLOBAL SECURITY WITHIN THE MEANING OF THE INDENTURE HEREINAFTER REFERRED TO. UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY (“DTC”), A NEW YORK CORPORATION, TO ARGO GROUP US, INC. OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NAM

Clawback Policy of Argo Group US, Inc.

ARGO GROUP US, INC. CLAWBACK POLICY The Board of Directors (the “Board”) of Argo Group US, Inc. (the “Company”) believes that it is appropriate for the Company to adopt this Clawback Policy (the “Policy”) to be applied to the Covered Executives of the Company and adopts this Policy as of February 6, 2024, to be effective as of the Effective Date. 1. Definitions For purposes of this Policy, terms d

Guaranteed Securities

Exhibit 22 Guarantor and Subsidiary Issuer of Registered Guaranteed Securities Securities Guarantor Argo Group US, Inc.

Amendment No. 6 to the Credit Agreement, dated February 21, 2024, by and among Argo Group International Holdings, Inc. and Argo Group US, Inc., as Borrowers, JPMorgan Chase Bank, N.A., individually as a lender and as Administrative Agent, and the other financial institutions signatory thereto.

Exhibit 10.1 EXECUTION VERSION AMENDMENT NO. 6 TO CREDIT AGREEMENT This Amendment No. 6 to Credit Agreement (this “Amendment”) is dated as of February 21, 2024 by and among ARGO GROUP INTERNATIONAL HOLDINGS, INC., a Delaware corporation (f/k/a ARGO GROUP INTERNATIONAL HOLDINGS, LTD., a company organized under the laws of Bermuda) and ARGO GROUP US, INC., a Delaware corporation (each, a “Borrower”

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 21, 2024 Argo Group International Holdings, Inc.

ARGO / Argo Group International Holdings Ltd / DIMENSIONAL FUND ADVISORS LP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 13 )* Argo Group International Holdings Ltd (Name of Issuer) Common Stock (Title of Class of Securities) G0464B107 (CUSIP Number) December 29, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursua

Certificate of Incorporation of Argo Group International Holdings, Inc.

Exhibit 3.1 CERTIFICATE OF INCORPORATION OF ARGO GROUP INTERNATIONAL HOLDINGS, INC. FIRST: The name of this corporation shall be: Argo Group International Holdings, Inc. (the “Corporation”). SECOND: Its registered office in the State of Delaware is to be located at 251 Little Falls Drive, in the City of Wilmington, 19808, County of New Castle and its registered agent at such address is CORPORATION

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 30, 2023 ARGO GROUP INTE

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 30, 2023 ARGO GROUP INTERNATIONAL HOLDINGS, INC. (Exact Name of Registrant as Specified in its Charter) Delaware 001-15259 98-0214719 (State or Other Jurisdiction of Incorpor

Bylaws of Argo Group International Holdings, Inc.

  Exhibit 3.2   BYLAWS   of   ARGO GROUP INTERNATIONAL HOLDINGS, INC., a Delaware Corporation   Effective November 30, 2023         TABLE OF CONTENTS   Page Article I - Stockholders 1   1.    Place of Meetings 1   2.    Annual Meeting 1   3.    Special Meetings 1   4.    Notice of Meetings 1   5.    Quorum 2   6.    Voting and Proxies 2   7.    Action at Meeting 2   8.    Presiding Officer 2   9. 

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 15 CERTIFICATION AND NOTICE OF TERMINATION OF REGISTRATION UNDER SECTION 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR SUSPENSION OF DUTY TO FILE REPORTS UNDER SECTIONS 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 15 CERTIFICATION AND NOTICE OF TERMINATION OF REGISTRATION UNDER SECTION 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR SUSPENSION OF DUTY TO FILE REPORTS UNDER SECTIONS 13 AND 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. Commission File Number 001-15259 Argo Group International Holdings, Ltd. (Exact name of registrant

As filed with the Securities and Exchange Commission on November 16, 2023

As filed with the Securities and Exchange Commission on November 16, 2023 Registration No.

Retention Award Agreement, by and between Argo Group International Holdings, Ltd. and Jessica Snyder, dated November 16, 2023 (incorporated by reference to Exhibit 10.2 to the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on November 16, 2023).*

Exhibit 10.2 EXECUTION COPY RETENTION AWARD AGREEMENT This Retention Award Agreement (this “Agreement”) is made as of November 16, 2023 between ARGO GROUP INTERNATIONAL HOLDINGS, LTD. (the “Company”), and Jessica Snyder (“Executive”). A.            Cash Retention Award 1.            The Company hereby grants a cash award (the “Retention Award”) to Executive having a target value of $700,000 (the “

Brookfield Reinsurance Completes

Exhibit 99.1 Brookfield Reinsurance Completes $1.1 Billion Acquisition of Argo Group ● Jessica Snyder to serve as Argo Group CEO. Hamilton, Bermuda – NOVEMBER 16, 2023 – Argo Group international Holdings, Ltd. (“Argo”) today announced the completion of Brookfield Reinsurance’s acquisition of Argo in an all-cash transaction valued at approximately $1.1 billion. Under the terms of the transaction, B

As filed with the Securities and Exchange Commission on November 16, 2023

As filed with the Securities and Exchange Commission on November 16, 2023 Registration No.

Offer Letter, by and between Argo Group International Holdings, Ltd. and Christopher Donahue, dated November 16, 2023 (incorporated by reference to Exhibit 10.4 to the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on November 16, 2023).*

Exhibit 10.4 November 16, 2023 Christopher Donahue 42 Main St Apt 10F Brooklyn, NY 11201 Dear Chris, Congratulations, I am pleased to confirm our conditional offer of employment on behalf of Argonaut Management Services, Inc. (“AMSI”), as Chief Financial Officer (“CFO”). You will report to and work from Argo’s NYC office. Your start date will November 16, 2023. You will report to Jessica Snyder, C

Altered Memorandum of Association of Argo Group International Holdings, Ltd.

Exhibit 3.1 Amended November, 2023 Argo Group International Holdings, Ltd. Amended November, 2023 US$2,030,000,000 Amended November, 2023 A mended October, 2023

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 November 27, 2023, pursuant to the provisions of Rule 12d2-2 (a).

As filed with the Securities and Exchange Commission on November 16, 2023

As filed with the Securities and Exchange Commission on November 16, 2023 Registration No.

Offer Letter, by and between Argo Group International Holdings, Ltd. and Jessica Snyder, dated November 16, 2023 (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on November 16, 2023).*

Exhibit 10.1 EXECUTION VERSION CONFIDENTIAL November 16, 2023 Jessica Snyder Via Email Dear Jessica: We are very pleased to offer you the role of Chief Executive Officer of Argo Group International Holdings, Ltd. (the “Company”) on the terms and conditions outlined in this offer letter (“Letter”). 1.              Effective Date: This offer and your role as Chief Executive Officer of the Company wi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 16, 2023 ARGO GROUP INTE

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 16, 2023 ARGO GROUP INTERNATIONAL HOLDINGS, LTD. (Exact Name of Registrant as Specified in its Charter) Bermuda 001-15259 98-0214719 (State or Other Jurisdiction of Incorpora

As filed with the Securities and Exchange Commission on November 16, 2023

As filed with the Securities and Exchange Commission on November 16, 2023 Registration No.

Resignation Letter, by and between Argo Group International Holdings, Ltd. and Susan Comparato, dated November 16, 2023 (incorporated by reference to Exhibit 10.3 to the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on November 16, 2023).

Exhibit 10.3 Execution Copy Resignation Letter November 16, 2023 Argo Group International Holdings, Ltd. 90 Pitts Bay Road Pembroke, HM 08 Bermuda Ladies and Gentlemen: Reference is hereby made to that certain Agreement and Plan of Merger, by and among Argo Group International Holdings, Ltd., a Bermuda exempted company limited by shares (the “Company”), Brookfield Reinsurance Ltd., a Bermuda exemp

As filed with the Securities and Exchange Commission on November 16, 2023

As filed with the Securities and Exchange Commission on November 16, 2023 Registration No.

Letter Agreement, by and between Argo Group International Holdings, Ltd. and Scott Kirk, dated November 16, 2023 (incorporated by reference to Exhibit 10.5 to the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on November 16, 2023).

Exhibit 10.5 CONFIDENTIAL November 16, 2023 Scott Kirk Via Email Re: Resignation and Transition Dear Scott: Pursuant to our recent discussions, this letter (“Letter”) acknowledges your intent to resign from your employment with Argo International Holdings Ltd., successor in interests to Argo Management Services Limited, (“AIHL”) and to cease providing services to Argo Group International Holdings,

Amended and Restated Bye-laws of Argo Group International Holdings, Ltd.

Exhibit 3.2 BYE-LAWS of Argo Group International Holdings, Ltd. The undersigned HEREBY CERTIFIES that the attached Bye-Laws are a true copy of the Bye-Laws of Argo Group International Holdings, Ltd. (Company) adopted by the Shareholder of the Company on 16 November 2023. /s/ Allison Kiene Secretary BYE-LAWS Of Argo Group International Holdings, Ltd. Bye-Law Subject Page 1. Definitions and Interpre

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended September 30, 2023 ☐ Transition repo

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended September 30, 2023 or ☐ Transition report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 for the transition period from to Commission file numbe

Argo Group Reports Third Quarter 2023 Results Focused On Optimizing Business For Profitable Growth

Exhibit 99.1 Argo Group Reports Third Quarter 2023 Results Focused On Optimizing Business For Profitable Growth • Pending merger with Brookfield Reinsurance: The parties have received a majority of the required regulatory approvals. The merger agreement outside date for completing the transaction has been automatically extended from today to February 8, 2024, pursuant to the terms of the merger ag

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 8, 2023 Argo Group International Holdings, Ltd.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended June 30, 2023 ☐ Transition report pu

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended June 30, 2023 or ☐ Transition report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 for the transition period from to Commission file number: 1-

Argo Group Reports Second Quarter 2023 Results Focused On Optimizing Business For Profitable Growth

Exhibit 99.1 Argo Group Reports Second Quarter 2023 Results Focused On Optimizing Business For Profitable Growth • Pending merger with Brookfield Reinsurance: We continue to expect the merger to close the second half of 2023, subject to customary closing conditions, including receipt of required regulatory approvals • Low Catastrophe Losses: Total catastrophe losses were $3.1 million for second qu

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 7, 2023 Argo Group Internati

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 7, 2023 Argo Group International Holdings, Ltd.

IGIC / International General Insurance Holdings Ltd / Argo Group International Holdings, Ltd. - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 4)* International General Insurance Holdings Ltd. (Name of Issuer) Common shares, par value $0.01 per share (Title of Class of Securities) G4809J106 (CUSIP Number) July 31, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 24, 2023 Argo Group Internatio

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 24, 2023 Argo Group International Holdings, Ltd.

Amendment No. 5 to the Credit Agreement, dated July 24, 2023, by and among Argo Group International Holdings, Ltd., Argo Group US, Inc., as Borrowers, and JPMorgan Chase Bank, N.A., individually and as Administrative Agent, and the other financial institutions signatory thereto.

  Exhibit 10.1   EXECUTION VERSION   AMENDMENT NO. 5 TO CREDIT AGREEMENT     This Amendment No. 5 to Credit Agreement (this “Amendment”) is dated as of July 24, 2023 by and among ARGO GROUP INTERNATIONAL HOLDINGS, LTD, a company organized under the laws of Bermuda and ARGO GROUP US, INC., a Delaware corporation (each, a “Borrower” and, collectively, the “Borrowers”), JPMORGAN CHASE BANK, N. A., in

Amendment No. 4 to the Credit Agreement, dated July 14, 2023, by and among Argo Group International Holdings, Ltd., Argo Group US, Inc., as Borrowers, and JPMorgan Chase Bank, N.A., individually and as Administrative Agent, and the other financial institutions signatory thereto (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on July 17, 2023).

Exhibit 10.1 Execution Version AMENDMENT NO. 4 TO CREDIT AGREEMENT This Amendment No. 4 to Credit Agreement (this “Amendment”) is dated as of July 14, 2023 by and among ARGO GROUP INTERNATIONAL HOLDINGS, LTD, a company organized under the laws of Bermuda (the “Parent”), and ARGO GROUP US, INC., a Delaware corporation (each, a “Borrower” and, collectively, the “Borrowers”), JPMORGAN CHASE BANK, N.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 14, 2023 Argo Group Internatio

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 14, 2023 Argo Group International Holdings, Ltd.

ARGO / Argo Group International Holdings Ltd / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SC 13G/A 1 tv0017-argogroupinternationa.htm SCHEDULE 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 11)* Name of issuer: Argo Group International Holdings Ltd. Title of Class of Securities: Common Stock CUSIP Number: G0464B107 Date of Event Which Requires Filing of this Statement: June 30, 2023 Check the approp

Form of Non-Employee Director Cash Award Agreement

Exhibit 10.2 Participant Name %%FIRSTNAMEMIDDLENAMELASTNAME%-% Grant Date %%OPTIONDATE,’Month DD, YYYY’%-% Total Cash Awarded CASH AWARD AGREEMENT This Cash Award Agreement (this “Agreement”) is made as of the date set forth above (“Grant Date”) between ARGO GROUP INTERNATIONAL HOLDINGS, LTD. (the “Company”), and the individual named above (“Participant”). RECITALS A.The Company’s 2019 Omnibus Inc

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended March 31, 2023 ☐ Transition report p

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended March 31, 2023 or ☐ Transition report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 for the transition period from to Commission file number: 1

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 8, 2023 Argo Group Internationa

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 8, 2023 Argo Group International Holdings, Ltd.

Argo Group Reports First Quarter 2023 Results Argo Shareholders Approve Proposed Merger with Brookfield Reinsurance

Exhibit 99.1 Argo Group Reports First Quarter 2023 Results Argo Shareholders Approve Proposed Merger with Brookfield Reinsurance • Reduced Catastrophe Losses: Total catastrophe losses of $3.6 million were 59% lower than the first quarter 2022; reflects volatility reduction efforts through exiting businesses with property catastrophe exposure. • Disciplined Expense Focus: Expense ratio of 35.1% imp

ARGO / Argo Group International Holdings Ltd / FourWorld Capital Management LLC Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Argo Group International Holdings, Ltd. (Name of Issuer) Common Stock (Title of Class of Securities) G0464B107 (CUSIP Number) April 6, 2023 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 ¨ TRAN

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) (Mark One) x 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 SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 1-15

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 19, 2023 ARGO GROUP INTERNA

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 19, 2023 ARGO GROUP INTERNATIONAL HOLDINGS, LTD. (Exact Name of Registrant as Specified in its Charter) Bermuda 001-15259 98-0214719 (State or Other Jurisdiction of Incorporatio

UNITED STATES SECURITIES AND EXCHANGE COMMISSION

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A INFORMATION (Rule 14a-101) Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1) Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted

ARGO / Argo Group International Holdings Ltd / PZENA INVESTMENT MANAGEMENT LLC - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G AMENDMENT NO 1 Under the Securities Exchange Act of 1934 ARGO GROUP INTERNATIONAL HOLDINGS Ltd (Name of Issuer) COMMON STOCK (Title of Class of Securities) G0464B107 (CUSIP Number) March 31, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to whi

ARGO / Argo Group International Holdings Ltd / Voce Capital Management LLC - ARGO GROUP INTERNATIONAL HOLDINGS, LTD. Activist Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 15)* Argo Group International Holdings, Ltd. (Name of Issuer) Common Shares, par value $1.00 per share (Title of Class of Securities) G0464B107 (CUSIP Number) J. Daniel Plants Voce Capital Management LLC One Embarcadero Center, Suite 1140 San Francisco, California 94111

ARGO / Argo Group International Holdings Ltd / Voce Capital Management LLC - ARGO GROUP INTERNATIONAL HOLDINGS, LTD. Activist Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 14)* Argo Group International Holdings, Ltd. (Name of Issuer) Common Shares, par value $1.00 per share (Title of Class of Securities) G0464B107 (CUSIP Number) J. Daniel Plants Voce Capital Management LLC One Embarcadero Center, Suite 1140 San Francisco, California 94111

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(A) OF THE SECURITIES EXCHANGE ACT OF 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(A) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defi

ARGO / Argo Group International Holdings Ltd / Voce Capital Management LLC Activist Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 13)* Argo Group International Holdings, Ltd. (Name of Issuer) Common Shares, par value $1.00 per share (Title of Class of Securities) G0464B107 (CUSIP Number) J. Daniel Plants Voce Capital Management LLC One Embarcadero Center, Suite 1140 San Francisco, California 94111

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨ Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨ Definitive Proxy State

Offer Letter, dated August 2, 2022,

ex103912312022 -""'ARGO GROUP PRIVILEGED AND CONFIDENTIAL August 2, 2022 Jessica Snyder Dear Jessica, Congratulations, I am pleased to confirm our conditional offer of employment on behalf of Argonaut Management Services, Inc.

Guaranteed Securities

Exhibit 22 Guarantor and Subsidiary Issuer of Registered Guaranteed Securities Securities Guarantor Argo Group U.

Subsidiaries of Registrant

Exhibit 21 Subsidiaries of Argo Group International Holdings, Ltd. Company Name Country/State of Incorporation The Argo Foundation Bermuda PXRE Capital Statutory Trust II Connecticut PXRE Capital Statutory Trust VI Delaware Argo Re Ltd. Bermuda Argo Insurance Services Bermuda, Ltd. Bermuda Argo Irish Holdings I Ltd. Bermuda Argo Irish Holdings II Bermuda Argo Re Escritório de Representação no Bras

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(A) OF THE SECURITIES EXCHANGE ACT OF 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(A) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defi

CALCULATION OF FILING FEE TABLES Schedule 14A (Form Type) Argo Group International Holdings, Ltd. (Exact Name of Registrant as Specified in its Charter) Table 1: Transaction Valuation

Exhibit 107 CALCULATION OF FILING FEE TABLES Schedule 14A (Form Type) Argo Group International Holdings, Ltd.

Offer Letter, dated August 22, 2018, between Argonaut Management Services, Inc. and Susan Comparato.

ex103812312022 �ARGO GROUP 22 August 2018 Susan Comparato Dear Susan, I am pleased to confirm our offer of employment on behalf of Argo Group, as an SVP, US General Counsel in our New York, NY office.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ Annual report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2022 ☐ Transition report pursua

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ 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 Securities Exchange Act of 1934 for the transition period from to Commission file number: 1-1525

Deed of Amendment, dated February 2, 2023, related to the Share Purchase Agreement for the sale and purchase of the entire issued share capital of Argo Underwriting Agency Limited dated September 8, 2022 by and between Argo International Holdings Limited as Seller and Ohio Farmers Insurance Company as Purchaser.

ex103412312022 1 From: Ohio Farmers Insurance Company 1 Park Circle, Westfield Center Ohio 44251 United States of America To: Argo International Holdings Limited 6 Devonshire Square London, EC2M 4YE United Kingdom 2 February 2023 Dear Sirs or Madams, Letter Deed of Amendment 1.

to the Company’s Annual Report on Form 10-K filed with the Securities and Exchange Commission on March 6, 2023).

TRANSACTION BONUS Exhibit 10.40 March 3, 2023 Thomas A. Bradley Dear Tom: As you know, Argo Group International Holdings, Ltd. (together with its successors, the “Company”) has entered into an Agreement and Plan of Merger with Brookfield Reinsurance Ltd., and BNRE Bermuda Merger Sub Ltd. (“Merger Sub”), dated as of February 8, 2023, pursuant to which the Company will merge with Merger Sub and be t

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING (Check One): x Form 10-K ¨ Form 20-F ¨ Form 11-K ¨ Form 10-Q ¨ Form 10-D ¨ Form N-CEN ¨ Form N-CSR For Period Ended: December 31, 2022 ¨ Transition Report on Form 10-K ¨ Transition Report on Form 20-F ¨ Transition Report on Form 11-K ¨ Transition Report on Form 10-Q For the Transition Pe

Argo Group Reports Fourth Quarter and Full Year 2022 Results Completed Strategic Alternatives Review; Entered into a Definitive Merger Agreement to be Acquired by Brookfield Reinsurance for Approximately $1.1 Billion

Exhibit 99.1 Argo Group Reports Fourth Quarter and Full Year 2022 Results Completed Strategic Alternatives Review; Entered into a Definitive Merger Agreement to be Acquired by Brookfield Reinsurance for Approximately $1.1 Billion • Simplified Business Model: Completed sale of Argo Underwriting Agency Limited and its Lloyd's Syndicate 1200 on February 2, 2023, transforming Argo into a focused, pure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 27, 2023 Argo Group Intern

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 27, 2023 Argo Group International Holdings, Ltd.

ARGO / Argo Group International Holdings, Ltd. / Voce Capital Management LLC - ARGO GROUP INTERNATIONAL HOLDINGS, LTD. Activist Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 12)* Argo Group International Holdings, Ltd. (Name of Issuer) Common Shares, par value $1.00 per share (Title of Class of Securities) G0464B107 (CUSIP Number) J. Daniel Plants Voce Capital Management LLC One Embarcadero Center, Suite 1140 San Francisco, California 94111

Argo Group Announces J. Daniel Plants to Step Down from Board of Directors

Exhibit 99.1 Argo Group Announces J. Daniel Plants to Step Down from Board of Directors HAMILTON, Bermuda – February 13, 2023 – Argo Group International Holdings, Ltd. (NYSE: ARGO) (“Argo”) today announced that J. Daniel Plants, a member of the Argo Board of Directors (the “Board”) and Chairman of its Strategic Review Committee, has notified the company of his intention to step down from the Board

IGIC / International General Insurance Holdings Ltd. Ordinary Share / Argo Group International Holdings, Ltd. - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 3)* International General Insurance Holdings Ltd. (Name of Issuer) Common shares, par value $0.01 per share (Title of Class of Securities) G4809J106 (CUSIP Number) December 31, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropri

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 13, 2023 ARGO GROUP INTE

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 13, 2023 ARGO GROUP INTERNATIONAL HOLDINGS, LTD. (Exact Name of Registrant as Specified in its Charter) Bermuda 001-15259 98-0214719 (State or Other Jurisdiction of Incorpora

ARGO / Argo Group International Holdings, Ltd. / DIMENSIONAL FUND ADVISORS LP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 12 )* Argo Group International Holdings Ltd (Name of Issuer) Common Stock (Title of Class of Securities) G0464B107 (CUSIP Number) December 30, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursua

ARGO / Argo Group International Holdings, Ltd. / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 10)* Name of issuer: Argo Group International Holdings Ltd. Title of Class of Securities: Common Stock CUSIP Number: G0464B107 Date of Event Which Requires Filing of this Statement: December 30, 2022 Check the appropriate box to designate the rule pursuant to which this

ARGO / Argo Group International Holdings, Ltd. / Voce Capital Management LLC - ARGO GROUP INTERNATIONAL HOLDINGS, LTD. Activist Investment

SC 13D/A 1 p23-0570sc13da.htm ARGO GROUP INTERNATIONAL HOLDINGS, LTD. SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 11)* Argo Group International Holdings, Ltd. (Name of Issuer) Common Shares, par value $1.00 per share (Title of Class of Securities) G0464B107 (CUSIP Number) J. Daniel Plants Voce Capital Management

Brookfield Reinsurance to Acquire Argo in $1.1 Billion Transaction

Exhibit 99.1 Brookfield Reinsurance to Acquire Argo in $1.1 Billion Transaction Argo Shareholders to Receive $30.00 per Share in Cash BROOKFIELD, NEWS, FEBRUARY 8, 2023 – Brookfield Reinsurance (NYSE, TSX:BNRE) and Argo Group International Holdings, Ltd. (“Argo”) (NYSE: ARGO) today announced they have entered into a definitive merger agreement whereby Brookfield Reinsurance will acquire Argo in an

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Information Required in Proxy Statement Schedule 14A Information Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Information Required in Proxy Statement Schedule 14A Information Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Information Required in Proxy Statement Schedule 14A Information Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Information Required in Proxy Statement Schedule 14A Information Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 8, 2023 ARGO GROUP INTERNATIONAL HOLDINGS, LTD. (Exact Name of Registrant as Specified in its Charter) Bermuda 001-15259 98-0214719 (State or Other Jurisdiction of Incorporat

. and Voce Capital Management LLC (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on February 8, 2023).

Exhibit 10.1 EXECUTION VERSION VOTING AND SUPPORT AGREEMENT This Voting and Support Agreement (this “Agreement”) is made and entered into as of February 8, 2023 (the “Agreement Date”), by and among Brookfield Reinsurance Ltd., a Bermuda exempted company limited by shares (“Parent”), Argo Group International Holdings, Ltd., a Bermuda exempted company limited by shares (the “Company”), and Voce Capi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 8, 2023 ARGO GROUP INTER

DEFA14A 1 tm235943d2defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 8, 2023 ARGO GROUP INTERNATIONAL HOLDINGS, LTD. (Exact Name of Registrant as Specified in its Charter) Bermuda 001-15259 98-0214719 (S

Agreement and Plan of Merger, dated as of February 8, 2023, by and among Argo Group International Holdings, Ltd.,

Exhibit 2.1 EXECUTION VERSION AGREEMENT AND PLAN OF MERGER by and among ARGO GROUP INTERNATIONAL HOLDINGS, LTD. BROOKFIELD REINSURANCE LTD. and BNRE Bermuda Merger Sub Ltd. Dated as of February 8, 2023 TABLE OF CONTENTS Page ARTICLE I DEFINITIONS AND TERMS Section 1.01 Definitions 5 Section 1.02 Interpretation 18 ARTICLE II The Merger Section 2.01 Merger 19 Section 2.02 Merger Effective Time 19 Se

Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 2, 2023 ARGO GROUP INTERNATIONAL HOLDINGS, LTD. (Exact Name of Registrant as Specified in its Charter) Bermuda 001-15259 98-0214719 (State or Other Jurisdiction of Incorporat

Argo Group Announces Closing of Lloyd’s Syndicate 1200 Transaction

Exhibit 99.1 Argo Group Announces Closing of Lloyd’s Syndicate 1200 Transaction HAMILTON, Bermuda-( BUSINESS WIRE)- Argo Group International Holdings, Ltd. (NYSE: ARGO) (“Argo”) today announced the completion of its previously announced sale of Argo Underwriting Agency Limited and its Lloyd’s Syndicate 1200 to Westfield. “We are pleased to complete this transaction,” said Thomas A. Bradley, Argo’s

ARGO / Argo Group International Holdings, Ltd. / PZENA INVESTMENT MANAGEMENT LLC - SC 13G Passive Investment

SC 13G 1 pzn-sc13g.htm SC 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 ARGO GROUP INTERNATIONAL HOLDINGS Ltd (Name of Issuer) COMMON STOCK (Title of Class of Securities) G0464B107 (CUSIP Number) December 31, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the ru

Amendment No. 3 to the Credit Agreement, dated December 20, 2022, by and among Argo Group International Holdings, Ltd., Argo Group U.S., Inc., Argo International Holdings Limited and Argo Underwriting Agency Limited, as Borrowers, and JPMorgan Chase Bank, N.A., individually and as Administrative Agent, and the other financial institutions signatory thereto.

Exhibit 10.1 EXECUTION VERSION AMENDMENT NO. 3 TO CREDIT AGREEMENT This Amendment No. 3 to Credit Agreement (this ?Amendment?) is dated as of December 20, 2022 by and among ARGO GROUP INTERNATIONAL HOLDINGS, LTD, a company organized under the laws of Bermuda, ARGO GROUP US, INC., a Delaware corporation, ARGO INTERNATIONAL HOLDINGS LIMITED, a corporation organized under the laws of the United Kingd

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 20, 2022 Argo Group International Holdings, Ltd.

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 15, 2022 ARGO GROUP INTERNATIONAL HOLDINGS, LTD. (Exact Name of Registrant as Specified in its Charter) Bermuda 001-15259 98-0214719 (State or Other Jurisdiction of Incorpora

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

DEFA14A 1 tm2229047d23defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ¨ Check the appropriate box: ¨ Preliminary proxy statement ¨ Confidential, for use of the Commission only (as permitted by

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ? Check the appropriate box: ? Preliminary proxy statement ? Confidential, for use of the Commission only (as permitted by Rule 14a-6(e)(2)) ? Definitive proxy state

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Ame

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confide

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

DEFA14A 1 tm2229047d21defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ¨ Check the appropriate box: ¨ Preliminary proxy statement ¨ Confidential, for use of the Commission only (as permitted by

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ? Check the appropriate box: ? Preliminary proxy statement ? Confidential, for use of the Commission only (as permitted by Rule 14a-6(e)(2)) ? Definitive proxy state

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

DEFA14A 1 tm2229047d18defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ¨ Check the appropriate box: ¨ Preliminary proxy statement ¨ Confidential, for use of the Commission only (as permitted by

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

DEFA14A 1 tm2229047d19defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ¨ Check the appropriate box: ¨ Preliminary proxy statement ¨ Confidential, for use of the Commission only (as permitted by

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ? Check the appropriate box: ? Preliminary proxy statement ? Confidential, for use of the Commission only (as permitted by Rule 14a-6(e)(2)) ? Definitive proxy state

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Ame

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confide

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ? Check the appropriate box: ? Preliminary proxy statement ? Confidential, for use of the Commission only (as permitted by Rule 14a-6(e)(2)) ? Definitive proxy state

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ? Check the appropriate box: ? Preliminary proxy statement ? Confidential, for use of the Commission only (as permitted by Rule 14a-6(e)(2)) ? Definitive proxy state

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Ame

DFAN14A 1 dfan14a1273000411172022.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☐ Filed by a Party other than the Registrant ☒ Check the appropriate box: ☐

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

DEFA14A 1 tm2229047d12defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ¨ Check the appropriate box: ¨ Preliminary proxy statement ¨ Confidential, for use of the Commission only (as permitted by

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

DEFA14A 1 tm2229047d13defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ¨ Check the appropriate box: ¨ Preliminary proxy statement ¨ Confidential, for use of the Commission only (as permitted by

Enhancing Shareholder Value with New Board Members PRESENTATION TO ARGO GROUP SHAREHOLDERS NOVEMBER 2022

Exhibit 1 Enhancing Shareholder Value with New Board Members PRESENTATION TO ARGO GROUP SHAREHOLDERS NOVEMBER 2022 CAPITAL RETURNS 2 INVESTOR PRESENTATION 2 Important Information The materials contained herein (the ?Materials?) represent the opinions of Capital Returns Master Ltd.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Ame

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confide

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Ame

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☐ Filed by a Party other than the Registrant ☒ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confide

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ? Check the appropriate box: ? Preliminary proxy statement ? Confidential, for use of the Commission only (as permitted by Rule 14a-6(e)(2)) ? Definitive proxy state

Amended and Restated Loss Portfolio Transfer Reinsurance Agreement by and between Argonaut Insurance Company and Cavello Bay Reinsurance Limited dated November 9, 2022 with an effective date of January 1, 2022 (incorporated by reference to Exhibit 10.1 to the Company’s Quarterly Report on Form 10-Q filed with the Securities and Exchange Commission on November 9, 2022).**

Exhibit 10.1 Execution Version Certain identified information marked with ?[***]? has been omitted from this document because it is both (i) not material and (ii) the type that the registrant treats as private or confidential. AMENDED AND RESTATED LOSS PORTFOLIO TRANSFER REINSURANCE AGREEMENT by and between ARGONAUT INSURANCE COMPANY of Illinois and CAVELLO BAY REINSURANCE LIMITED Hamilton, Bermud

Share Purchase Agreement for the sale and purchase of the entire issued share capital of Argo Underwriting Agency Limited dated September 8, 2022 by and between Argo International Holdings Limited as Seller and Ohio Farmers Insurance Company as Purchaser (incorporated by reference to Exhibit 10.2 to the Company’s Quarterly Report on Form 10-Q filed with the Securities and Exchange Commission on November 9, 2022).**

EXECUTION VERSION Exhibit10.2 Certain identified information marked with ?[***]? has been omitted from this document because it is both (i) not material and (ii) the type that the registrant treats as private or confidential. DATED 8 SEPTEMBER 2022 ARGO INTERNATIONAL HOLDINGS LIMITED and OHIO FARMERS INSURANCE COMPANY SHARE PURCHASE AGREEMENT FOR THE SALE AND PURCHASE OF THE ENTIRE ISSUED SHARE CA

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

DEFA14A 1 tm2229047d10defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ¨ Check the appropriate box: ¨ Preliminary proxy statement ¨ Confidential, for use of the Commission only (as permitted by

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended September 30, 2022 ☐ Transition repo

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended September 30, 2022 or ? Transition report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 for the transition period from to Commission file numbe

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Ame

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confide

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

DEFA14A 1 tm2229047d7defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ¨ Check the appropriate box: ¨ Preliminary proxy statement ¨ Confidential, for use of the Commission only (as permitted by R

Argo Group Reports Third Quarter 2022 Results Execution on Strategic Priorities Continues to Benefit Results

Exhibit 99.1 Argo Group Reports Third Quarter 2022 Results Execution on Strategic Priorities Continues to Benefit Results ? Simplified Business Model: As announced in September the company entered into a definitive agreement for the sale of Argo Underwriting Agency Limited and its Lloyd's Syndicate 1200. ? Continued Growth in Ongoing Business: U.S. Operations earned premiums increased approximatel

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 7, 2022 Argo Group International Holdings, Ltd.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Ame

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confide

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Ame

DEFC14A 1 defc14a1273000410312022.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☐ Filed by a Party other than the Registrant ☒ Check the appropriate box: ☐

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

DEFA14A 1 tm2229047d5defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x                 Filed by a party other than the registrant ¨ Check the appropriate box: ¨ Preliminary proxy statement ¨ Confidential, for use of the Commission only (a

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant ☒                 Filed by a party other than the registrant ☐ Check the appropriate box: ☐ Preliminary proxy statement ☐ Confidential, for use of the Commission only (as permitted by Rule 14a

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

DEFA14A 1 tm2229047d6defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ¨ Check the appropriate box: ¨ Preliminary proxy statement ¨ Confidential, for use of the Commission only (as permitted by R

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant ☒                 Filed by a party other than the registrant ☐ Check the appropriate box: ☐ Preliminary proxy statement ☐ Confidential, for use of the Commission only (as permitted by Rule 14a-6(e)(2)) ☐ Defini

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Ame

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Amendment No. 2) Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confid

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

DEFA14A 1 tm2229047-4defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant ☒                 Filed by a party other than the registrant ☐ Check the appropriate box: ☐ Preliminary proxy statement ☐ Confidential, for use of the Commission only (a

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 24, 2022 ARGO GROUP INTERNATIONAL HOLDINGS, LTD. (Exact Name of Registrant as Specified in its Charter) Bermuda 001-15259 98-0214719 (State or Other Jurisdiction of Incorporat

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ? Check the appropriate box: x Preliminary proxy statement ? Confidential, for use of the Commission only (as permitted by Rule 14a-6(e)(2)) ? Definitive proxy state

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 24, 2022 ARGO GROUP INTER

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 24, 2022 ARGO GROUP INTERNATIONAL HOLDINGS, LTD. (Exact Name of Registrant as Specified in its Charter) Bermuda 001-15259 98-0214719 (State or Other Jurisdiction of Incorporat

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Ame

PRRN14A 1 prrn14a1273000410172022.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Amendment No. 1) Filed by the Registrant ☐ Filed by a Party other than the Registrant ☒ Check the appropriate box:

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant x Filed by a party other than the registrant ? Check the appropriate box: x Preliminary proxy statement ? Confidential, for use of the Commission only (as permitted by Rule 14a-6(e)(2)) ? Definitive proxy state

$ Impact (in millions)

CORRESP 1 filename1.htm October 5, 2022 VIA EDGAR Division of Corporation Finance Office of Finance U.S. Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Re: Argo Group International Holdings, Ltd. Form 10-K for Fiscal Year Ended December 31, 2020 Filed March 15, 2021 File No. 001-15259 Dear Division of Corporation Finance: Please find below the responses of Argo Group

Argo Group Executes on Strategic Review Opportunities

Exhibit 99.1 Argo Group Executes on Strategic Review Opportunities ? The board of directors continues to actively explore strategic alternatives to maximize shareholder value. ? Sale of Lloyd?s Syndicate will position Argo as U.S.-focused specialty insurer: The transaction will result in a simplified corporate structure, drive greater efficiencies with increased focus on core U.S. businesses, and

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): September 8, 2022 Argo Group International Holdings, Ltd.

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): September 8, 2022 Argo Group International Holdings, Ltd.

1 September 8, 2022 ARGO GROUP Strategic Update 2 Forward-Looking Statements This presentation and any related oral statements may include forward-looking statements, both with respect to Argo Group International Holdings, Ltd. (“Argo Group”, “we”, o

Exhibit 99.2 1 September 8, 2022 ARGO GROUP Strategic Update 2 Forward-Looking Statements This presentation and any related oral statements may include forward-looking statements, both with respect to Argo Group International Holdings, Ltd. (?Argo Group?, ?we?, or ?our?) and its industry, that reflect our current views with respect to future events and financial performance. Forward-looking statem

Argo Group Announces Sale of Lloyd’s Syndicate 1200 to Westfield

Exhibit 99.1 FOR IMMEDIATE RELEASE Argo Group Announces Sale of Lloyd?s Syndicate 1200 to Westfield ? Argo to receive total cash proceeds of approximately $125 million. ? Transaction will simplify corporate structure and drive greater efficiencies with increased focus on core U.S. businesses. ? Transaction expected to close in first half of 2023. HAMILTON, Bermuda ? September 8, 2022 ? Argo Group

Argo Group appoints Jessica Snyder as President, U.S. Insurance

Exhibit 99.1 Argo Group appoints Jessica Snyder as President, U.S. Insurance Hamilton, Bermuda ? August 15, 2022 ? Argo Group International Holdings, Ltd. (NYSE: ARGO), an underwriter of specialty insurance, today announced Jessica Snyder has been appointed to serve as president, U.S. insurance, effective immediately. Snyder will report to Tom Bradley, Argo?s executive chairman and chief executive

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 15, 2022 Argo Group International Holdings, Ltd.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended June 30, 2022 ☐ Transition report pu

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended June 30, 2022 or ? Transition report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 for the transition period from to Commission file number: 1-

Argo Group Announces Appointment of J. Daniel Plants to Board of Directors Mr. Plants will join Strategic Review and Human Resources Committees

Exhibit 99.1 Argo Group Announces Appointment of J. Daniel Plants to Board of Directors Mr. Plants will join Strategic Review and Human Resources Committees HAMILTON, Bermuda ? August 8, 2022 ? Argo Group International Holdings, Ltd. (NYSE: ARGO) (?Argo? or ?the Company?) today announced the August 4, 2022 appointment of J. Daniel Plants as an independent member of the Company?s board of directors

ARGO / Argo Group International Holdings, Ltd. / Voce Capital Management LLC - ARGO GROUP INTERNATIONAL HOLDINGS, LTD. Activist Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 10)* Argo Group International Holdings, Ltd. (Name of Issuer) Common Shares, par value $1.00 per share (Title of Class of Securities) G0464B107 (CUSIP Number) J. Daniel Plants Voce Capital Management LLC One Embarcadero Center, Suite 1140 San Francisco, California 94111

Argo Group Reports Second Quarter 2022 Results Well-Positioned for Continued Profitable Growth

Exhibit 99.1 Argo Group Reports Second Quarter 2022 Results Well-Positioned for Continued Profitable Growth ? Reduced Volatility: Total catastrophe losses were $2.5 million in the second quarter 2022; reflecting our strategy to reduce catastrophe exposure despite continued industry catastrophe losses this quarter. ? Achieved Further Strategic Growth: While net earned premiums decreased 3.4% from t

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 8, 2022 Argo Group International Holdings, Ltd.

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 4, 2022 Argo Group International Holdings, Ltd.

Amendment No. 2 to the Credit Agreement, dated July 15, 2022, by and among Argo Group International Holdings, Ltd., Argo Group U.S., Inc., Argo International Holdings Limited and Argo Underwriting Agency Limited, as Borrowers, and JPMorgan Chase Bank, N.A., individually and as Administrative Agent, and the other financial institutions signatory thereto.

Exhibit 10.1 AMENDMENT NO. 2 TO CREDIT AGREEMENT This Amendment No. 2 to Credit Agreement (this ?Amendment?) is dated as of July 15, 2022 and effective as of April 1, 2022 (such effective date, the ?Amendment No. 2 Effective Date?) by and among ARGO GROUP INTERNATIONAL HOLDINGS, LTD, a company organized under the laws of Bermuda, ARGO GROUP US, INC., a Delaware corporation, ARGO INTERNATIONAL HOLD

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 15, 2022 Argo Group International Holdings, Ltd.

. dated June 23, 2022 (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on June 23, 2022).*

Exhibit 10.1 SEPARATION AND RELEASE AGREEMENT This SEPARATION AND RELEASE AGREEMENT (this ?Separation Agreement?) is executed and entered into by and between, Argo Group International Holdings, Ltd., together with its subsidiaries and affiliates (the ?Company?) and Kevin J. Rehnberg, an individual resident of the state of Minnesota (the ?Executive?). The Company and the Executive shall be collecti

. and Thomas A. Bradley (incorporated by reference to Exhibit 10.2 to the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on June 23, 2022).*

Exhibit 10.2 Participant Name Thomas A. Bradley Grant Date June 23, 2022 Total Number of Restricted Shares Awarded 78,760 RESTRICTED STOCK AWARD AGREEMENT This Restricted Stock Award Agreement (this ?Agreement?) is made as of the date set forth above between ARGO GROUP INTERNATIONAL HOLDINGS, LTD. (the ?Company?), and the individual named above (the ?Participant?). RECITALS A. The Company?s 2019 O

. and Thomas A. Bradley (incorporated by reference to Exhibit 10.3 to the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on June 23, 2022).*

Exhibit 10.3 STOCK APPRECIATION RIGHT AGREEMENT This Stock Appreciation Right Agreement (?Agreement?) is made as of June 23, 2022 (the ?Grant Date?) between ARGO GROUP INTERNATIONAL HOLDINGS, LTD. (the ?Company?), and Thomas A. Bradley (the ?Participant?). R E C I T A L S A. The Company?s 2019 Omnibus Incentive Plan (as amended from time to time, the ?Plan?) provides for the granting of equity awa

Argo Group appoints Thomas A. Bradley as CEO Former CEO Kevin J. Rehnberg Departs

Exhibit 99.1 Argo Group appoints Thomas A. Bradley as CEO Former CEO Kevin J. Rehnberg Departs HAMILTON, Bermuda ? June 23, 2022 ? Argo Group International Holdings, Ltd. (NYSE: ARGO) (?Argo? or ?the company?), an underwriter of specialty insurance products, today announced the appointment of Thomas A. Bradley, who has served as Argo?s chairman since 2020, and who has been serving as interim chief

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 23, 2022 Argo Group International Holdings, Ltd.

Financial Statements and Exhibits, Changes in Registrant's Certifying Accountant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 1, 2022 ARGO GROUP INTERNATIONAL HOLDINGS, LTD.

Letter of Ernst & Young LLP, dated June 6, 2022

Exhibit 16.1 June 6, 2022 Securities and Exchange Commission 100 F Street, N.E. Washington, DC 20549 Ladies and Gentlemen: We have read Item 4.01 of Form 8-K dated June 6, 2022, of Argo Group International Holdings, Ltd. and are in agreement with the statements contained in the last sentence of the first paragraph, the third and fourth paragraphs and the first sentence of the fifth paragraph there

Retention Letter and Extension of Service Agreement, dated May 5, 2022, by and between Scott Kirk and Argo Management Services Limited (incorporated by reference to the Exhibit 10.2 to the Company’s Quarterly Report on Form 10-Q filed with the Securities and Exchange Commission on May 6, 2022).*

Exhibit 10.2 May 5, 2022 Scott Kirk By e-mail: Dear Scott, It is important to Argo Group International Holdings, Ltd. (together with its subsidiaries, "Argo Group") that key, high-performing employees are incentivised and encouraged to progress their careers with us. To that end, it is my pleasure to inform you that our Board of Directors has decided to: 1.offer you a cash retention award in the a

Argo Group International Holdings, Ltd. Executive Service Plan, effective January 1, 2021, amended and restated April 26, 2022†

Exhibit 10.1 ARGO GROUP INTERNATIONAL HOLDINGS, LTD. EXECUTIVE SEVERANCE PLAN Plan Document and Summary Plan Description Effective January 1, 2021 Amended and Restated April 26, 2022 TABLE OF CONTENTS Page ARTICLE One FOREWORD 1 Section 1.01 Purpose of the Plan 1 ARTICLE Two DEFINITIONS 1 Section 2.01 ?Accounting Firm? 1 Section 2.02 ?Affiliate? 1 Section 2.03 ?Amendment Date? 1 Section 2.04 ?Argo

Argonaut Supplemental Executive Retirement Plan and subsequent amendments thereto dated each of September 2009, April 2010, and September 2010 (incorporated by reference to the Exhibit 10.4 to the Company’s Quarterly Report on Form 10-Q filed with the Securities and Exchange Commission on May 6, 2022).*

ARGONAUT SUPPLEMENTAL EXECUTIVE RETIREMENT PLAN WHEREAS, Argonaut Group, Inc. (the "Company") heretofore adopted the "Argonaut Supplemental Executive Retirement Plan" (the "Plan"), an unfunded plan maintained for the purpose of providing deferred compensation for a select group of management or ,highly compensared employees within the meaning of the United Scares Code of Federal Regular ions Secri

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended March 31, 2022 ☐ Transition report p

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended March 31, 2022 or ? Transition report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 for the transition period from to Commission file number: 1

Form of U.S. Named Executive Officer Retention Award Agreement (incorporated by reference to the Exhibit 10.3 to the Company’s Quarterly Report on Form 10-Q filed with the Securities and Exchange Commission on May 6, 2022).*

Exhibit 10.3 RETENTION AWARD1 [Date] [NAME] By e-mail: [EMAIL ADDRESS] Dear [FIRST NAME], It is important to Argo Group International Holdings, Ltd. (together with its subsidiaries, ?Argo Group?) that key, high-performing employees are incentivised and encouraged to progress their careers with us. To that end, it is my pleasure to inform you that our Board of Directors has decided to offer you a c

Argo Group Reports First Quarter 2022 Results Further Progression of Strategic Plan Driving Improvement in Results

Exhibit 99.1 Argo Group Reports First Quarter 2022 Results Further Progression of Strategic Plan Driving Improvement in Results ? Continued Strategic Growth: Net earned premium increased 3.1% in the first quarter 2022; strong net earned premium growth in our ongoing business1 of approximately 20.8% ? Disciplined Expense Focus: Expense ratio of 36.0% for the first quarter 2022 improved 1.8 percenta

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 2, 2022 Argo Group International Holdings, Ltd.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 ☐ TRANSITION REPORT PURS

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Mark One) ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 1-15259 ARGO GROUP INT

Regulation FD Disclosure, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 28, 2022 ARGO GROUP INTERNATIONAL HOLDINGS, LTD. (Exact Name of Registrant as Specified in its Charter) Bermuda 001-15259 98-0214719 (State or Other Jurisdiction of Incorporatio

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Exhibit 99.1 Argo Group Board of Directors Announces Exploration of Strategic Alternatives to Maximize Shareholder Value HAMILTON, Bermuda ? April 28, 2022 ? Argo Group International Holdings, Ltd. (NYSE: ARGO) (?Argo? or the ?Company?) today announced that its board of directors has initiated an exploration of strategic alternatives. As part of this process, the board will consider a wide range o

UNITED STATES SECURITIES AND EXCHANGE COMMISSION

DEFA14A 1 tm2213795-1defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A INFORMATION (Rule 14a-101) Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for U

Offer Letter, dated May 15, 2020, between Argonaut Management Services, Inc. and Allison D. Kiene (incorporated by reference to the Exhibit 10.23 to the Company’s Annual Report on Form 10-K filed with the Securities and Exchange Commission on March 16, 2022).*

,,, ARGO GROUP -JS 2020 Cnar AlliSon, I am pleased to oonfinn our concfitional offer of employment on behalf of Argonaut Managet"Mf1t Services.

Guaranteed Securities

Exhibit 22 Guarantor and Subsidiary Issuer of Registered Guaranteed Securities Securities Guarantor Argo Group U.

End of International Assignment, dated June 24, 2020, between Argo

Andrew Borst By email 24 June 2020 Dear Andy, End of International Assignment ? US to UK I am writing to confirm the below details following the end of your international assignment to the UK as discussed and agreed.

International Assignment, dated March 14, 2019, between Argonaut Management Services, Inc. and Andrew Borst.*

ARGOGLOBAL Member Argo Group Andrew Borst 26 Ellridge Place Ellington CT 06029 United States of America 14 March 2019 Dear Andy, International Assignment - US to UK - 2 years I would like to confirm our offer to you regarding your temporary international assignment to the UK.

Subsidiaries of Registrant

Exhibit 21 Subsidiaries of Argo Group International Holdings, Ltd. Company Name Country/State of Incorporation The Argo Foundation Bermuda PXRE Capital Statutory Trust II Connecticut PXRE Capital Statutory Trust VI Delaware Argo Re Ltd. Bermuda Argo Insurance Services Bermuda, Ltd. Bermuda Argo Irish Holdings I Ltd. Bermuda Argo Irish Holdings II Bermuda Argo Re Escrit?rio de Representa??o no Bras

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 1-15259 ARGO GROUP INTER

Form of Employee Restricted Stock Award Agreement (incorporated by reference to the Exhibit 10.11 to the Company’s Annual Report on Form 10-K filed with the Securities and Exchange Commission on March 16, 2022).*

Exhibit 10.11 Participant Name Grant Date Total Restricted Shares Awarded RESTRICTED STOCK AWARD AGREEMENT This Restricted Stock Award Agreement (this ?Agreement?) is made as of the date set forth above between ARGO GROUP INTERNATIONAL HOLDINGS, LTD. (the ?Company?), and the individual named above (the ?Participant?). R E C I T A L S A. The Company's 2019 Omnibus Incentive Plan (as amended from ti

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Ame

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confide

From: Tom Bradley

Exhibit 99.2 From: Tom Bradley To: Employees Subject Line: Recent Engagement with Argo Shareholder As you may have read, one of our shareholders, Capital Returns Management, made a filing with the SEC, expressing its views regarding our company and announcing the nomination of two candidates to the Argo Board of Directors. You can read our response here: https://www.argolimited.com/news-release/ar

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 14, 2022 Argo Group International Holdings, Ltd.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A INFORMATION (Rule 14a-101) Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A INFORMATION (Rule 14a-101) Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted b

Argo Group Comments on Director Nominations from Capital Returns Management No Shareholder Action Required at This Time

Exhibit 99.1 FOR IMMEDIATE RELEASE Argo Group Comments on Director Nominations from Capital Returns Management No Shareholder Action Required at This Time HAMILTON, Bermuda ? March 14, 2022 ? Argo Group International Holdings, Ltd. (NYSE: ARGO) (?Argo? or the ?Company?) today issued the following statement regarding the nomination by Capital Returns Management, LLC (together with its affiliates, ?

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Ame

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confide

Chairman email to employees

Exhibit 99.1 Chairman email to employees From: Thomas A. Bradley To: Employees [Subject Line] Kevin Rehnberg ? Temporary Medical Leave of Absence ? Board Chairman to serve as acting CEO ? No change in daily operations Dear Colleagues, Earlier today, we announced Argo Group Chief Executive Officer Kevin Rehnberg is taking a temporary medical leave of absence. During this time, the board of director

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 2, 2022 Argo Group International Holdings, Ltd.

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 2, 2022 Argo Group International Holdings, Ltd.

Amendment No. 1 to the Credit Agreement, dated March 2, 2022, by and among Argo Group International Holdings, Ltd., Argo Group US, Inc., Argo International Holdings Limited and Argo Underwriting Agency Limited, as Borrowers, and JPMorgan Chase Bank, N.A., individually and as Administrative Agent, and the other financial institutions signatory thereto (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on March 4, 2022).

Exhibit 10.1 AMENDMENT NO. 1 TO CREDIT AGREEMENT This Amendment No. 1 to Credit Agreement (this ?Amendment?) is entered into as of March 2, 2022 by and among ARGO GROUP INTERNATIONAL HOLDINGS, LTD, a company organized under the laws of Bermuda, ARGO GROUP US, INC., a Delaware corporation, ARGO INTERNATIONAL HOLDINGS LIMITED, a corporation organized under the laws of the United Kingdom, and ARGO UN

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING (Check One): ☒ Form 10-K ☐ Form 20-F ☐ Form 11-K ☐ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended: December 31, 2021 ☐ T

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING (Check One): ? Form 10-K ? Form 20-F ? Form 11-K ? Form 10-Q ? Form 10-D ? Form N-CEN ? Form N-CSR For Period Ended: December 31, 2021 ? Transition Report on Form 10-K ? Transition Report on Form 20-F ? Transition Report on Form 11-K ? Transition Report on Form 10-Q For the Transition Pe

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 23, 2022 Argo Group International Holdings, Ltd.

A U.S.-Focused Specialty Insurer A distinctive U.S.-focused specialty insurer with well-established businesses operating in key specialty markets ARGO GROUP ~90% of Companywide Premium from U.S. Domiciled Risks U.S. Operations Differentiated Excess &

February 2022 ARGO GROUP Investor Presentation Exhibit 99.1 Forward-Looking Statements This presentation includes forward-looking statements, both with respect to Argo Group International Holdings, Ltd. (?Argo Group?, ?we?, or ?our?) and its industry, that reflect our current views with respect to future events and financial performance. Forward-looking statements include all statements that do no

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 18, 2022 Argo Group International Holdings, Ltd.

Argo Group Reports 2021 Fourth Quarter and Full Year Results Results Reflect Continued Progression of Strategic Plan

Exhibit 99.1 Argo Group Reports 2021 Fourth Quarter and Full Year Results Results Reflect Continued Progression of Strategic Plan ? Continued Strategic Growth: Net earned premium increased 4.2% in the fourth quarter of 2021; Strong net earned premium growth in our ongoing business1 of approximately 19.8%, supported by favorable market conditions ? Expense Ratio Improvement: Expense ratio of 35.3%

ARGO / Argo Group International Holdings, Ltd. / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 9)* Name of issuer: Argo Group International Holdings Ltd. Title of Class of Securities: Common Stock CUSIP Number: G0464B107 Date of Event Which Requires Filing of this Statement: December 31, 2021 Check the appropriate box to designate the rule pursuant to which this S

Argo Group Comments on Preliminary Fourth Quarter 2021 Financial Results

Exhibit 99.1 Argo Group Comments on Preliminary Fourth Quarter 2021 Financial Results (HAMILTON, Bermuda) February 8, 2022 ? Argo Group International Holdings, Ltd. (?Argo?) (NYSE: ARGO), announced today that its results for the fourth quarter of 2021, which ended December 31, 2021, will be negatively affected by adverse prior year reserve development and non-operating charges, summarized in more

ARGO / Argo Group International Holdings, Ltd. / DIMENSIONAL FUND ADVISORS LP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 11 )* Argo Group International Holdings Ltd (Name of Issuer) Common Stock (Title of Class of Securities) G0464B107 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursua

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 8, 2022 Argo Group International Holdings, Ltd.

* * * * *

CORRESP 1 filename1.htm January 24, 2022 VIA EDGAR Division of Corporation Finance Office of Finance U.S. Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Re: Argo Group International Holdings, Ltd. Form 10-K for Fiscal Year Ended December 31, 2020 Filed March 15, 2021 File No. 001-15259 Dear Division of Corporation Finance: Please find below the responses of Argo Group

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 20, 2021 Argo Group International Holdings, Ltd.

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Exhibit 99.1 Argo Group Announces Sale of ArgoGlobal SE HAMILTON, BERMUDA ? Dec. 20, 2021 ? Argo Group International Holdings Ltd. (NYSE: ARGO), an underwriter of specialty insurance, today announced an agreement to sell its Malta business operations, ArgoGlobal Holdings (Malta) Ltd. and its subsidiaries, to Riverstone Holdings Limited (part of the RiverStone International group), an industry-lead

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended September 30, 2021 or ? Transition report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 for the transition period from to Commission file numbe

Separation Agreement and General Release between Argo Management Services, Inc. and Timothy Carter, dated August 27, 2021

1 SEPARATION AGREEMENT AND GENERAL RELEASE This SEPARATION AGREEMENT AND RELEASE (this ?Agreement?) is entered into by and between Argonaut Management Services, Inc.

Forward-Looking Statements This presentation may include forward-looking statements, both with respect to Argo Group International Holdings, Ltd. (“Argo Group”, “we”, or “our”) and its industry, that reflect our current views with respect to future e

November 2021 ARGO GROUP Earnings Supplement Exhibit 99.1 Forward-Looking Statements This presentation may include forward-looking statements, both with respect to Argo Group International Holdings, Ltd. (?Argo Group?, ?we?, or ?our?) and its industry, that reflect our current views with respect to future events and financial performance. Forward-looking statements include all statements that do n

Argo Group Reports 2021 Third Quarter Results Net Income EPS of $0.56 per diluted common share and Operating Income EPS of $0.91 per diluted common share driven by continued strong growth in the ongoing business, reduced catastrophe exposure and incr

Exhibit 99.1 Argo Group Reports 2021 Third Quarter Results Net Income EPS of $0.56 per diluted common share and Operating Income EPS of $0.91 per diluted common share driven by continued strong growth in the ongoing business, reduced catastrophe exposure and increased investment income ? Continued Growth: Strong growth from the ongoing business in both the U.S. and International segments reflectin

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 3, 2021 Argo Group International Holdings, Ltd.

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 2, 2021 Argo Group International Holdings, Ltd.

IGIC / International General Insurance Holdings Ltd. Ordinary Share / Argo Group International Holdings, Ltd. - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 2)* International General Insurance Holdings Ltd. (Name of Issuer) Common shares, par value $0.01 per share (Title of Class of Securities) G4809J106 (CUSIP Number) September 30, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropr

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 4, 2021 Argo Group International Holdings, Ltd.

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Exhibit 99.1 Argo Group Announces Sale of Brazilian Business HAMILTON, BERMUDA ? Oct. 4, 2021 ? Argo Group International Holdings, Ltd. (NYSE: ARGO), an underwriter of specialty insurance, today announced an agreement to sell its Brazilian operations, Argo Seguros Brasil S.A. (?Argo Brazil?), to Spice Private Equity Ltd. (?Spice PE?), an investment company focused on global private equity investme

Separation Agreement by and between Matthew Harris and Argo Management Services Limited dated August 9, 2021*

Exhibit 10.1 WITHOUT PREJUDICE AND SUBJECT TO CONTRACT DATED AUGUST 9, 2021 MATT HARRIS (1) - and - ARGO MANAGEMENT SERVICES LIMITED (2) SEPARATION AGREEMENT Ref:cm2ecb Hogan Lovells International LLP Atlantic House, Holborn Viaduct, London EC1A 2FG Hogan Lovells CONTENTS CLAUSE PAGE 1. TERMINATION 1 2. PERIOD UP TO THE TERMINATION DATE 1 3. TERMINATION PAYMENT 2 4. TAX 2 5. EXPENSES 2 6. REFERENC

Argo Group announces Susan Comparato as chief administrative officer and other key leadership roles •  Appointments support strategic goals outlined for investors •  Streamlines management structure and reduces expense

EX-99 3 d340796dex991.htm EX-99.1 Exhibit 99.1 Argo Group announces Susan Comparato as chief administrative officer and other key leadership roles •  Appointments support strategic goals outlined for investors •  Streamlines management structure and reduces expense HAMILTON, BERMUDA – August 12, 2021 – Argo Group International Holdings, Ltd. (NYSE: ARGO), an underwriter of specialty insurance, tod

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 6, 2021 Argo Group International Holdings, Ltd.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended June 30, 2021 or ? Transition report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 for the transition period from to Commission file number: 1-

Service Agreement between Argo Management Services Limited and Matt Harris, dated August 1, 2017

Argo Management Services Limited Exchequer Court, 33 St Mary Axe London, EC3A 8AA, UK T +44 (0)20 7712 7600 F +44 (0)20 7712 7601 W www.

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 2, 2021 Argo Group International Holdings, Ltd.

Argo Group Reports 2021 Second Quarter Results Net Income EPS of $1.92 per diluted common share and Operating EPS of $1.60 per diluted common share driven by strong underwriting results and investment income

Exhibit 99.1 Argo Group Reports 2021 Second Quarter Results Net Income EPS of $1.92 per diluted common share and Operating EPS of $1.60 per diluted common share driven by strong underwriting results and investment income ? Underwriting Results: Improved underwriting margins and reduced catastrophe losses resulted in a combined ratio of 95.4%, Argo's best quarterly combined ratio in more than two y

Quarterly Report - ARGO GROUP INTERNATIONAL HOLDINGS, LTD. FORM 10-Q - MARCH 31, 2021

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? Quarterly report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the quarterly period ended March 31, 2021 or ? Transition report pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 for the transition period from to Commission file number: 1

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 6, 2021 Argo Group International Holdings, Ltd.

Argo Group Reports 2021 First Quarter Results Results Reflect Continued Underlying Margin Improvement and Strong Investment Income

Exhibit 99.1 Argo Group Reports 2021 First Quarter Results Results Reflect Continued Underlying Margin Improvement and Strong Investment Income ? Underlying Margin Expansion: Strategic actions and favorable market conditions driving continued progress in current accident year, ex-catastrophe margins, including better loss and expense ratios. ? Strategic Growth: Underlying growth in targeted areas

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 3, 2021 Argo Group International Holdings, Ltd.

Argo Group Comments on Results for First Quarter 2021

Exhibit 99.1 Argo Group Comments on Results for First Quarter 2021 HAMILTON, Bermuda ? April 21, 2021 ? Argo Group International Holdings, Ltd. (?Argo? or the ?company?) (NYSE: ARGO), announced today that its results for the first quarter of 2021 will be adversely affected by estimated catastrophes losses of approximately $47 million. Argo expects to report natural catastrophe losses of approximat

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 21, 2021 Argo Group International Holdings, Ltd.

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DEFA14A 1 d165675ddefa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant ☒ Filed by a party other than the registrant ☐ Check the appropriate box: ☐ Preliminary proxy statement ☐ Confidential, for use of the Commission only (as permitted by Rule

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Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant ? Filed by a party other than the registrant ? Check the appropriate box: ? Preliminary proxy statement ? Confidential, for use of the Commission only (as permitted by Rule 14a-6(e)(2)) ? Defi

. and Jay S. Bullock (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K filed with the Securities and Exchange Commission on March 25, 2021).*

Exhibit 10.1 SEPARATION AND TRANSITION AGREEMENT AND GENERAL RELEASE This SEPARATION AND TRANSITION AGREEMENT AND RELEASE (this ?Agreement?), dated as of March 23, 2021, is entered into by and between Argo Group International Holdings, Ltd. (the ?Company,? and together with its parents, subsidiaries and affiliates, the ?Argo Group?) and Jay S. Bullock (?I? or ?my? or ?me?) (collectively, the ?Part

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DEFA14A 1 d130980ddefa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the registrant ☒ Filed by a party other than the registrant ☐ Check the appropriate box: ☐ Preliminary proxy statement ☐ Confidential, for use of the Commission only (as permitted by Rule

Argo Group announces board retirements

EX-99.1 Exhibit 99.1 Argo Group announces board retirements HAMILTON, Bermuda – March 25, 2021 – Argo Group International Holdings, Ltd. (NYSE: ARGO) (“Argo” or “the company”), an underwriter of specialty insurance, today announced the retirements of Kathleen Nealon and John Tonelli from the board of directors effective immediately following the company’s Annual General Meeting scheduled for May 6

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 23, 2021 Argo Group International Holdings, Ltd.

Form of Incentive Award Agreement (Restricted Stock Awards and Cash Awards) - 2019 Omnibus Incentive Plan.*

-1- INCENTIVE AWARD AGREEMENT This Incentive Award Agreement (this ?Agreement?) is made as of %%OPTIONDATE,?MONTH DD, YYYY?%-%, between ARGO GROUP INTERNATIONAL HOLDINGS, LTD.

Argo Group International Holdings, Ltd. Executive Severance Plan*

\\NY - 040113/000001 - 10232859 v4 ARGO GROUP INTERNATIONAL HOLDINGS, LTD. EXECUTIVE SEVERANCE PLAN Effective January 1, 2021 Exhibit 10.6 i TABLE OF CONTENTS Page ARTICLE ONE FOREWORD ....................................................................................................... 1 Section 1.01 Purpose of the Plan ............................................................................

Annual Report - ARGO GROUP INTERNATIONAL HOLDINGS, LTD. FORM 10-K - DECEMBER 31, 2020

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 1-15259 ARGO GROUP INTER

Description of Securities Registered Pursuant to Section 12 of the Securities Exchange Act of 1934 (each representing a 1/1,000th interest in a 7.00% Resettable Fixed Rate Preference Share, Series A, par value $1.00 per share).

DESCRIPTION OF THE REGISTRANT?S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 Argo Group International Holdings, Ltd.

Subsidiaries of Registrant

Exhibit 21 Subsidiaries of Argo Group International Holdings, Ltd. Company Name Country/State of Incorporation The Argo Foundation Bermuda PXRE Capital Statutory Trust II Connecticut PXRE Captial Statutory Trust VI Delaware Argo International Holdings AG Switzerland Argonaut Services GmbH Switzerland Argo Re Ltd. Bermuda Argo Insurance Services Bermuda, Ltd. Bermuda Argo Irish Holdings I Ltd. Berm