Hires industry veteran as strategic advisor

Argo Group International Holdings, Ltd. (NYSE: ARGO) ("Argo" or the "company") today announced an agreement, effective immediately, with North American insurer, Trisura Group, Ltd. to support its surety underwriting operations as it works to revamp and grow its surety business. Trisura will provide surety underwriting services and other services to support Argo’s surety operations. Argo will retain surety claims management responsibilities. The two companies intend to partner on and are actively negotiating appropriate terms related to shared surety and co-surety arrangements as well as fronting arrangements.

"This partnership is an important step as we work to evolve Argo Surety,” said Argo Executive Chairman and Chief Executive Officer, Thomas A. Bradley. “Trisura’s underwriting philosophy aligns with Argo Surety’s history of close partnerships, in-depth industry knowledge and commitment to creating specialty solutions for hard-to-place business. Through this partnership, we will build on our commitment to the surety business for our valuable broker partners while expanding our capacity for new business.”

As one of the largest surety writers in Canada, Trisura is an experienced surety underwriter with more than 16 years in the business and deep expertise in underwriting commercial, contract and international surety.

“Trisura is excited to partner with Argo to provide underwriting support and the same high level of service to Argo’s brokers and agents as they have come to expect from Argo,” said President and CEO Trisura Canada, Chris Sekine. “We are pleased to partner with Argo and believe the collaboration will expand support for both Argo and Trisura stakeholders. For Trisura’s North American surety platform, we are excited to continue negotiations to finalize terms to access Argo’s licensed and Treasury Listed paper in all U.S. jurisdictions and assess co-surety and shared surety opportunities together. The strategic partnership will advance both of our businesses across North America.”

The terms of the agreement were not disclosed.

Argo brings on accomplished leader to advise on its surety business

Effective immediately, former RLI Surety leader Greg Chilson will join Argo in an advisory role. Chilson will work directly with Argo Surety Interim Head, Steve Boughal in developing and executing the company’s surety business strategy, including evaluation of its in-force portfolio, reviewing underwriting guidelines, providing guidance on organizational design, and mentoring junior staff.

“We are thrilled to have Greg on the team as we look to build upon the great success of Argo’s surety business,” said Boughal. “Greg’s deep industry knowledge and experience will provide tremendous value to the organization.”

Chilson retired as vice president overseeing RLI's Surety Division at the end of 2021. RLI Corp. is a specialty insurer serving diverse, niche property, casualty and surety markets.

The company has also contracted with MacColl Strategic Advisors to provide strategic advice and counsel in regard to its surety operations.

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.

ABOUT TRISURA GROUP, LTD.

Trisura Group Ltd. is a specialty insurance provider operating in the surety, risk solutions, corporate insurance, fronting and reinsurance segments of the market. Trisura has investments in wholly owned subsidiaries through which it conducts insurance and reinsurance operations. Those operations are primarily in Canada (“Trisura Canada”) and the United States (“Trisura US”). Trisura Group Ltd. is listed on the Toronto Stock Exchange under the symbol “TSU”.

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

Trisura Group Contacts: Tania Washchuk Director, Marketing and Communications 416.607.0145 tania.washchuk@trisura.com

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