ARGO Argo Group International Holdings Ltd

21 September 8, 2022 Relaunch of buyer outreach OVERVIEW OF SIGNIFICANT TRANSACTIONS RESULTING FROM ONGOING STRATEGIC REVIEW PROCESS 1 Purchase price will vary up / down based on tangible book value at closing relative to the $107mm level. Excludes transaction r elated costs. Summary of Transactions Resulting from Strategic Review Process ◼ U.S. LPT: Enstar to reinsure a number of Argo’s direct U.S. casualty insurance portfolios, including construction, relating to the accident years 2011 to 2019 — Enstar’s subsidiary providing ground up cover of $746 million of U.S. Casualty reserves at inception ◼ Pending sale of Syndicate 1200 business: Argo entered into a definitive agreement for the sale of Argo Underwriting Agency Limited (including each of its subsidiaries), which incorporates Argo’s Lloyd’s Syndicate 1200 business to Westfield — Total purchase price of $125mm 1 — Westfield to replace Funds at Lloyd’s, including the FAL supported by Argo Re Ltd. of $136.9mm ◼ Other selected divestitures in 2022: Completed sale of Brazilian operations, agreement on LPT transaction for Syndicate 1200’s reserves for 2018 and 2019 years of account, and the sale of Malta business Summary of Current Strategic Review Process Board continues to actively consider a range of options for Argo, including a potential sale of the whole Company April 28, 2022 Announcement of strategic review April 28, 2022 Initial buyer outreach August 8, 2022 Announcement of U.S. LPT transaction September 8, 2022 Announcement of Syndicate 1200 sale Post - October 2022 ◼ Completion of U.S. LPT transaction on November 9, 2022 ◼ Plan to close Syndicate 1200 sale ◼ Continued effort on strategic alternatives process Argo management and Board focused on Syndicate 1200 and U.S. LPT transactions

22 LOSS PORTFOLIO TRANSFER OF PORTION OF U.S. CASUALTY RESERVES TRANSACTION OVERVIEW Key Points Accelerates Argo’s Derisking Plans ◼ Enstar will reinsure a number of Argo’s direct U.S. casualty insurance portfolios, including construction, relating to the accident years 2011 to 2019 ◼ Provides protection against reserve volatility and provides Argo with additional regulatory capital flexibility ◼ Allows Argo to remain focused on pursuing profitable growth as a U.S. specialty insurer with leading positions in specialty markets Transaction Structure ◼ Enstar’s subsidiary will provide ground up cover of $746 million of U.S. Casualty reserves at inception — Additional $275 million of cover in excess of $821 million — Policy limit of $1.1 billion — Argo retains a loss corridor of $75 million above the $746 million of reserves ◼ Argo anticipates recognizing an after - tax charge for approximately $100 million in connection with this transaction Timing ◼ Enstar announced the completion of the LPT transaction on November 9, 2022

24 BOARD IS UNDERTAKING A COMPREHENSIVE STRATEGIC REVIEW PROCESS Outreach Summary Overview ◼ Since the exploration of strategic alternatives was announced on April 28, 2022, Argo has progressed significantly under the Board’s Strategic Review Committee — Executed on strategic transactions with Westfield and Enstar — Transactions have simplified corporate structure, enhanced fundamentals of Argo’s core U.S. specialty businesses, strengthened capital and reduced reserve volatility ◼ J. Daniel Plants, Chief Investment Officer of Voce Capital Management LLC, Argo’s largest shareholder at approximately 9.5%, appointed as independent member of the Company’s board of directors and Chairperson of the Strategic Review Committee ◼ The Board has reached out to a broad range of parties regarding a potential transaction, which may include a whole Company sale — Through these discussions, it is evident that the parties have found the latest developments and progress of transformation initiatives impressive, acknowledging that Argo is a healthier, streamlined business — Select bidders who have put forward preliminary, non - binding proposals have been given access to a data room containing over 60,000 pages of documents, and are conducting due diligence meetings with management Outreach to 80+ Parties Balanced Mix of Financial Sponsors and Strategic Buyers Select International Players with Interest in U.S. Platforms

ARGO HAS THE RIGHT GOVERNANCE PROFILE AND BOARD IN PLACE 4

26 ARGO’S BOARD IS NOT ONE THAT NEEDS ADDITIONAL CHANGE AT THIS TIME Best - in - Class Governance Profile 1 Highly Skilled and Independent Directors 2 Significant Recent Refreshment of the Board 3 Highly Engaged and Responsive Board and Management Team 4 Capital Returns’ Nominees Do Not Offer Skills and Experiences the Board Needs at This Time 5

27 Independent Leadership and Oversight Shareholder - Friendly Bye - Laws and Charter Management Compensation Aligned with Shareholder Interest Embedded Sustainability Focus into Our Board Decision Making ARGO POSSESSES A BEST - IN - CLASS GOVERNANCE PROFILE ✓ Fully independent Board (except CEO) ✓ Lead Independent Director ✓ Annual review of director independence ✓ No classified board ✓ Shareholders holding 10% of shares have right to call a special meeting ✓ Shareholder right to remove any director without cause ✓ Majority vote standard for director elections ✓ No poison pill ✓ Annual “say - on - pay” vote ✓ Compensation Clawback policy ✓ Prohibition on pledging and hedging of shares ✓ Equity ownership guidelines and share retention requirements ✓ Sustainability Working Group oversees sustainability and ESG policies ✓ Dedicated Board oversight on ESG efforts by the Nominating and Governance Committee

28 ARGO’S NOMINEES BRING DEEP EXPERIENCE AND THE RIGHT SKILLS TO DRIVE VALUE CREATION UNDER THE NEW ARGO Bernard C. Bailey President, Paraquis Solutions Jodie McLean CEO & Director, EDENS Thomas O’Toole Clinical Professor of Marketing, Kellogg School of Management Independent Director since 2020 Lead Independent Director since 2022 Thomas A. Bradley CEO, Argo Dymphna A. Lehane Former Global Managing Partner (Insurance), Accenture Carol A. McFate Former Chief Investment Officer, Xerox Corporation Independent Director since 2017 Chair of Human Resources Comm. since 2020 Independent Director since 2020 Chair of Investment Comm. since 2021 Samuel G. Liss Managing Partner, Whitegate Partners Independent Director since 2019 Chair of Nom & Gov Comm. since 2020 J. Daniel Plants Chief Investment Officer, Voce Capital Management Independent Director since 2022 Chair of Strategic Review Comm. since 2022 Al - Noor Ramji Former Group Chief Digital Officer, Prudential PLC Independent Director since 2017 Chair of Risk Comm. since 2020 Director since 2018 Chief Executive Officer since 2022 ✓ 6 of 7 Are Independent (86%) ✓ 5 of 7 Appointed since 2018 (71%) Other Public Company Board Experience Insurance Industry Expertise Received > 95% support at the 2021 AGM Source: Company filings. 1 Includes gender, ethnic, and disabled military diversity. ✓ 4 of 7 Offer Diversity 1 (57%) ✓ 60+ Board Meetings in 2022

29 BOARD HAS UNDERGONE SIGNIFICANT DIRECTOR REFRESHMENT TO ASSEMBLE ITS CURRENT MIX OF SKILLS AND EXPERIENCES ~43% of the Directors Joined over the Past 3 Years Source: Company filings Current Board Is Led by Highly - Qualified Directors with the Relevant Skills and Experience to Provide Robust Oversight Knowledge, Skills & Experience # of Existing Directors Executive Leadership Business Strategy / Operations Risk Management Industry Knowledge International Operations / Global Markets Accounting and Finance Corporate Governance Technology / Cybersecurity Investment Management Legal / Regulatory Directors by Year Joined 2 1 1 2 1 2017 2018 2019 2020 2021 2022

30 ARGO MANAGEMENT AND BOARD HAVE BEEN HIGHLY ENGAGED AND RESPONSIVE TO CAPITAL RETURNS Engagement with Capital Returns ◼ Capital Returns first reached out to management in the fall of 2021 ◼ Over the past year of interactions between Argo and Capital Returns, Capital Returns has repeatedly requested that Argo take the following two actions 1. Commence a strategic review process 2. Put Capital Returns’ two director nominees on the Board (first introduced in February 2022) ◼ The Board, after receiving input from other shareholders and outside advisors, determined to announce the strategic review, as requested by Capital Returns ◼ With respect to their second request, given the total level of rotation on the Board and the Board’s belief after having interviewed both of Capital Returns nominees that they would not be additive to the Board’s current mix of skills and experiences, the Board determined that adding Capital Returns’ nominees would diminish the level of expertise and diversity on the Board and would potentially disrupt or hinder the ongoing strategic review process just as it enters its most critical phase ◼ The Argo Board and management team have engaged extensively with Capital Returns for more than a year in an attempt to foster a constructive dialogue ◼ Most recently, Mr. Bradley and Mr. Kirk met with Mr. Bobman in late September 2022 to provide an update on the ongoing strategic review process and discuss a potential resolution to the proxy contest initiated by Capital Returns ◼ During this meeting, Mr. Bradley and Mr. Kirk reinforced that Argo was actively exploring strategic alternatives, as previously requested by Capital Returns, including executing on transactions specifically suggested by Capital Returns such as the sale of the Syndicate 1200 business ◼ Despite Argo already executing upon the suggestions Capital Returns has previously raised, Capital Returns has insisted on proceeding with a costly proxy contest and all the while Capital Returns has been selling blocks of Argo stock since April 2022 Broader Shareholder Engagement Efforts ◼ Regularly meets with investors throughout the year at major financial services industry conferences and events sponsored by the Company ◼ Board receives regular briefings on shareholder meetings ◼ Provides shareholders with means to communicate with the Board

ELECTION OF CAPITAL RETURNS’ NOMINEES WOULD REMOVE SUPERIOR TALENT AND CRITICAL SKILLS FROM THE BOARD 5

32 Ronald D. Bobman David W. Michelson Public Board Experience O Superior Specialty Insurance Experience 1 O ~ Sufficient Time for Commitment ~ O Claimed Skills & Experience “Investment and leadership experience in the insurance industry” “Leadership and board experience in the insurance industry” BOARD DETERMINED THAT CAPITAL RETURNS’ CANDIDATES DO NOT OFFER SKILLS AND EXPERIENCES THE BOARD NEEDS AT THIS TIME Capital Returns’ Nominees Offer No Incremental Value to Argo’s Board • Executive Leadership (7 / 7 existing directors) • Insurance industry knowledge (6 / 7 existing directors) • Investment Management (3 / 7 existing directors) • Mr. J. Daniel Plants, the CIO of Voce Capital Management (the Company's largest shareholder ), currently serves as a director and Chair of the Strategic Review Committee Source: Public filings, Capital IQ. Market data as of 31 - Oct - 2022. 1 As compared to Argo’s nominees. (Currently serves as director at FedNat , which has suffered a ~98% stock price decline , been delisted from Nasdaq, triggered a default on over $120 million of senior notes and had one of its insurance subsidiaries placed into receivership by the Florida Department of Financial Services during Mr. Michelson’s tenure ) (Director and advisor to at least six other companies) Skills and perspectives of Capital Returns’ candidates are already well represented on the Board and at a higher caliber ~

33 ELECTION OF CAPITAL RETURNS’ NOMINEES WOULD REMOVE SUPERIOR TALENT AND CRITICAL SKILLS FROM THE BOARD An exchange of Mr. Bailey and / or Mr. Ramji for Capital Returns’ nominees would result in a loss of superior talent and experience and a degradation in the quality of Board dialogue just as it enters its most critical phase Source: Public filings. 1 Point Blank Solutions 8 - K/A filing on 15 - Jun - 2009. Bernard C. Bailey Al - Noor Ramji Public Board Experience Select Professional Experience ◼ Former CEO, Authentix , a PE - backed enterprise later sold to Blue Water Energy ◼ Former CEO, Viisage Technology (during his tenure the Company executed 9 acquisitions) ◼ Has served as director of nine publicly - traded companies ◼ Former Group Chief Digital Officer, Prudential ◼ Former Managing Director, Northgate Capital ◼ Former Chief Strategy Officer, Calypso Technology Capital Returns’ Criticisms ? Questions qualifications to serve on the Board ? Has not invested beyond the minimum requirement ? Director at Point Blank Solutions at time of bankruptcy ? Unique responsibility for Company performance ? Suitability of insurance experience to serve as Chair of Risk and Capital Committee ◼ Brings absolutely critical M&A experience to the Board in the Company's ongoing strategic review process; has been pivotal in the Company's recent transition to a U.S. specialty insurer ◼ As Chairman of the Board, has led the successful sale of two publicly - traded companies - Analogic Corporation and Lasercard Corporation ◼ Invested almost $100K of own capital; never sold Argo shares; ownership in line with other independent directors ◼ Resigned from the Board of Point Blank Solutions due to concerns over the governance of the company a year prior to the bankruptcy filing 1 ◼ During Mr. Ramji’s tenure, Argo has substantially de - risked its portfolio, including the sale of its international operations and the recently closed LPT transaction ◼ Brings 6 years of experience as an executive team member at Prudential plc, applying technology to solve risk and manage challenges across the portfolio, to his Risk & Capital Committee chair role at Argo Rebuttals to Capital Returns

34 ELECTION OF CAPITAL RETURNS’ NOMINEES WOULD BRING NO ADDITIVE SKILLS & WOULD REDUCE THE BOARD’S DIVERSITY Source: Public filings Bernard C. Bailey Al - Noor Ramji ◼ Mr. Bailey’s career spans over three decades of business and management experience, including his role as a public company CEO, along with his extensive board experience ◼ Mr. Ramji’s extensive information technology background and digital strategy knowledge serve as unique skills on your Board ◼ Mr. Ramji also has significant business and management experience, including extensive experience serving on public company boards ◼ Former President and CEO of Viisage Technology, Inc.; during his four years of leadership, Viisage’s market capitalization grew from $60 million to $1 billion ◼ As Group Chief Digital Officer at Prudential plc, Mr. Ramji led the company’s transformation into the leading digital ecosystem platform across its US, European, Asian and African markets; his risk management expertise is a critical oversight component of Argo’s operations ◼ He has led numerous transactions in his previous roles, including leading Viisage through nine acquisitions, bringing significant operational and M&A experience to the Board ◼ His track record of successfully leveraging IT to achieve business objectives has won him numerous industry awards, including the CIO 100 Award, CIO Insight IT Leader of the Year 2009 and the British Computer Society CIO of the Year ◼ Mr. Bailey has served on the boards of nine publicly - traded companies, including as Chairman of both Analogic and Lasercard , where he led the successful sale of both companies to a private equity and strategic buyer, respectively. Of the nine public companies, four of them were ultimately acquired while Mr. Bailey was a serving director ◼ Earlier in his career, he served as CEO and Group CIO for BT Group for over six years and in technology leadership roles at Qwest Communications (CTO), Dresdner Kleinwort Benson (Global CIO) and Swiss Bank Corporation (COO) ◼ Mr. Bailey has also served on the management teams and boards of private equity - backed investments ◼ He has also served on the management teams and boards of both public companies and private equity - backed investments where he oversaw multiple sale processes, including Prudential plc, Northgate Capital, Calypso Technology, Tata Motors, Nation Media Group, Virtusa, EVRY ASA, MISYS plc and iSoftStone Information Service Corporation ◼ From 2012 to 2018, Mr. Bailey served as CEO of Authentix . Under his leadership, Authentix was acquired in 2017 by Blue Water Energy ◼ More specifically, as CEO of the Design and Innovate Division at BT Group, he delivered major multi - billion - dollar programs such as the fiber and software driven network for Britain as well as savings of 240 million British pounds annually; as General Manager and EVP of Banking at MISYS, he led all P&L and a global sales force of over 700 people and renewed all banking and capital markets and risk management software products for major financial institutions around the world ◼ Mr. Bailey’s vast leadership and corporate governance experience allows him to be an active member of the Board, as a member of the Audit, Human Resources, Nominating and Corporate Governance and Strategic Review committees. These qualifications led the Board to appoint him Lead Independent Director upon Mr. Bradley’s permanent appointment as CEO ◼ Mr. Ramji’s background in applying technology to solve risk and management challenges is critical to the Board’s Risk & Capital Committee, where he serves as Chair

36 Claim REALITY “Piecemeal asset sales” ➔ What Capital Returns would attempt to portray as “piecemeal” asset sales is actually a direct result of a thorough and probing review process where Argo listened carefully to bidders and its advisors; the result of those transactions allowed Argo to restart a more robust strategic review process in September, which is ongoing ➔ After our initial outreach to bidders in April and May, we received feedback that we would need to further advance the simplification of Argo’s portfolio and exit international business lines for suitors to seriously consider a potential acquisition or strategic transaction of the Company ➔ Argo took action to respond to this feedback throughout the ongoing strategic review process, entering into the LPT with Enstar and entering into a definitive agreement for the sale of Argo Underwriting Agency Limited and its Lloyd’s Syndicate 1200 to Westfield ➔ Now, Argo is finally in the position to entertain bids for the remaining U.S specialty insurance business ➔ We also find it characteristically inconsistent of Mr. Bobman to claim credit for the idea of asset divestitures, including pending sale of Syndicate 1200, and then to criticize the Board for executing the same “piecemeal” sales he advocated “Delayed the annual meeting” ➔ Argo’s Board has met over 60 times YTD ➔ Argo’s management team has devoted a very significant portion of their time to the strategic review process ➔ We delayed our annual meeting in order to focus on the very issue which Mr. Bobman wanted the Board and management team to address – a strategic review ➔ Mr. Bobman’s problem is not with the delay. His problem is with the Board’s assessment that he and Mr. Michelson are unfit to be on the Board – in relative experience and temperament to existing directors MR. BOBMAN’S NAÏVE CLAIMS VS. REALITY (CONT).

38 SUMMARY OF KEY MESSAGES Through the actions of this Board and the dedicated management team, Argo has successfully transformed into a U.S. specialty insurer Board has taken decisive actions to strengthen the U.S. specialty insurance business and those actions are demonstrating positive results Board has been proactive and transparent with shareholders in its announcements and execution of the ongoing strategic review and is open to considering any and all credible proposals to maximize shareholder value Argo interviewed both of Capital Returns’ nominees and found their skills and experiences to be inferior to Argo’s existing directors An exchange of either Capital Returns’ nominees for one of Mr. Bailey or Mr. Ramji would result in a degradation of board capabilities, dialogue, diversity, and could disrupt or hinder the ongoing strategic review

VOTE “FOR” ALL OF ARGO’S EXTREMELY QUALIFIED DIRECTOR NOMINEES ON THE BLUE PROXY CARD TODAY