Industry veterans Rod Williams and Paul Drakontaidis also join the company

Argo Group International Holdings, Ltd. (NYSE: ARGO) ("Argo" or the "company") today announced Greg Chilson as president of Argo Surety, effective September 1. Chilson has served as a strategic advisor to the business since May.

“Greg joins the company with a tremendous amount of industry experience as we look to build on Argo Surety’s track record as a very profitable, growth-oriented business,” said Argo’s President of U.S. Insurance, Jessica Snyder. “Over the past few months, Greg has assisted us as we worked to implement our strategy to evolve the business, including the evaluation of Argo’s in-force portfolio, reviewing underwriting guidelines and providing guidance on organizational design.

“He was very much involved in building this leadership team. The quality of the team and the positive momentum we are seeing in this business is a testament to Greg’s leadership and promising future potential for Argo Surety.”

Chilson will report to Snyder with Williams and Drakontaidis reporting to him.

Chilson joins Argo from RLI Insurance Company where he led the surety business and held various roles during his 27-year tenure. He also served as controller at Underwriters Indemnity and in financial reporting at American General. Chilson attended the United States Military Academy West Point and earned a bachelor’s degree from the University of Texas.

This announcement follows the appointment of Rod Williams as head of contract surety and Paul Drakontaidis as the head of commercial surety announced earlier this month.

Williams has extensive experience in underwriting, financial analysis, management, strategic planning, training and development. Most recently, he served as vice president and director, Enterprise Risk Management at Markel Surety. Prior to that, he held similar roles at Liberty Mutual Surety, Safeco and Aetna. He earned his bachelor’s degree from the University of Tennessee, Knoxville and his master’s in business administration from Middle Tennessee State University.

Drakontaidis has more than 17 years of experience in surety underwriting. Most recently, serving as senior regional vice president-commercial surety bonds at Zurich Surety. Prior to that, he held similar roles at Liberty Mutual Surety and Safeco. He earned his bachelor’s degree from Loyola University of Chicago.

ABOUT ARGO GROUP INTERNATIONAL HOLDINGS, LTD.

Argo Group International Holdings, Ltd. (NYSE: ARGO) is an underwriter of specialty insurance products in the property and casualty market. Argo offers a full line of products and services designed to meet the unique coverage and claims-handling needs of businesses in two primary segments. Argo and its insurance subsidiaries are rated ‛A-’ by Standard and Poor’s. Argo’s insurance subsidiaries are rated ‛A-’ by A.M. Best. More information on Argo and its subsidiaries is available at www.argogroup.com.

FORWARD-LOOKING STATEMENTS

This press release and related oral statements may include forward-looking statements that reflect our current views with respect to future events and financial performance. Forward-looking statements include all statements that do not relate solely to historical or current facts, and can be identified by the use of words such as "expect," "intend," "plan," "believe," “do not believe,” “aim,” "project," "anticipate," “seek,” "will," “likely,” “assume,” “estimate,” "may," “continue,” “guidance,” “growth,” “objective,” “remain optimistic,” “improve,” “progress,” "path toward," "looking forward," “outlook,” “trends,” “future,” “could,” “would,” “should,” “target,” “on track” and other expressions of a future or forward-looking nature.

Such statements are subject to certain risks and uncertainties that could cause actual events or results to not occur or differ materially, including, but not limited to, recent changes in interest rates and inflation, the outcome of the partnership with Trisura on the surety business, the adequacy of our projected loss reserves, employee retention and changes in key personnel, the ability of our insurance subsidiaries to meet risk-based capital and solvency requirements, the outcome of legal and regulatory proceedings, investigations, inquiries, claims and litigation, and other risks and uncertainties discussed in our filings with the Securities and Exchange Commission (the "SEC"). For a more detailed discussion of such risks and uncertainties, see Item 1A, “Risk Factors” in Argo’s Annual Report on Form 10-K for the fiscal year ended December 31, 2022 and in other filings with the SEC. The inclusion of a forward-looking statement herein should not be regarded as a representation by Argo that its objectives will be achieved. Any forward-looking statements speak only as of the date of this press release. Argo undertakes no obligation to publicly update forward-looking statements, whether as a result of new information, future events or otherwise. You should not place undue reliance on any such statements.

Argo Group Contacts: Andrew Hersom Head of Investor Relations 860.970.5845 andrew.hersom@argogroupus.com

David Snowden Senior Vice President, Communications 210.321.2104 david.snowden@argogroupus.com

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