CORRECTING and REPLACING Aspen and Ryan Specialty Announce Expanded Trading Relationship

Aspen materially expands participation in Ryan Specialty’s international MGU portfolio.

Second paragraph, third sentence of release should read: As part of this deal, Aspen will provide capacity across multiple platforms and geographies, with four programs in the U.S. and three programs in Europe (instead of ...with three programs in the U.S. and four programs in Europe.)

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The updated release reads:

ASPEN AND RYAN SPECIALTY ANNOUNCE EXPANDED TRADING RELATIONSHIP

Aspen materially expands participation in Ryan Specialty’s international MGU portfolio.

Aspen Insurance Holdings Limited (“Aspen”) is pleased to announce that it has entered into agreement with Ryan Specialty Group (“Ryan Specialty”) to support a diverse international portfolio of delegated underwriting authority business.

With effect from January 1, 2022, Aspen has joined an additional seven programs from Ryan Specialty Underwriting Managers’ MGU portfolio. This unique arrangement harnesses the full scope of Aspen’s capabilities, in Insurance, Reinsurance and Capital Markets. As part of this deal, Aspen will provide capacity across multiple platforms and geographies, with four programs in the U.S. and three programs in Europe.

Mark Cloutier, Executive Chairman and Group Chief Executive Officer, Aspen, said: “This expanded trading partnership showcases Aspen’s comprehensive capabilities, combining insurance, reinsurance and capital markets to deliver an innovative, risk transfer solution. We are grateful to the Ryan Specialty team for their trust and confidence and for the opportunity to bring this creative solution to bare, and in doing so further build on our strong trading relationship. We believe that this agreement is a blueprint for creative capital deployment, exemplifying our purpose to bring ‘clarity from complexity’”.

Pat Ryan, Founder, Chairman & CEO, Ryan Specialty, added: “We’re excited about our substantially broadened delegated authority relationship with Aspen. Moreover, we are appreciative of their confidence in our underwriting capabilities and of their commitment to progressive solutions.”

Bruce Eisler, CEO US, and Chief Underwriting Officer, Aspen Insurance, commented: “In conjunction with Ryan Specialty, we contemplated the existing structure of each binder and had to develop a creative solution relative to capital deployment through our U.S./U.K. companies and Lloyd’s Syndicate 4711 to bring this to fruition. The trading partnership is a great testament to our technical underwriting capabilities and strong collaboration across our global platforms and products.”

Miles Wuller, President and CEO of RSG Underwriting Managers, said: “We greatly appreciate Aspen’s innovation bringing coordinated insurance capital to support our $2.0bn¹ international Underwriting Managers business and its objectives. We now benefit from their syndicated support across nine of our MGUs. We thank the Aspen team for their trust of our delegated underwriting stewardship.”

About Aspen Insurance Holdings Limited

Aspen provides reinsurance and insurance coverage to clients in various domestic and global markets through wholly-owned subsidiaries and offices in Australia, Bermuda, Canada, Singapore, Switzerland, the United Kingdom and the United States. For the year ended December 31, 2020, Aspen reported $13.2 billion in total assets, $7.2 billion in gross reserves, $3.0 billion in total shareholders’ equity and $3.7 billion in gross written premiums. Aspen's operating subsidiaries have been assigned a rating of “A-” by Standard & Poor’s Financial Services LLC and an “A” (“Excellent”) by A.M. Best Company Inc. For more information about Aspen, please visit www.aspen.co.

About Ryan Specialty Group

Founded in 2010, Ryan Specialty is a rapidly growing service provider of specialty products and solutions for insurance brokers, agents and carriers. Ryan Specialty provides distribution, underwriting, product development, administration and risk management services by acting as a wholesale broker and a managing underwriter. Our mission is to provide industry-leading innovative specialty insurance solutions for insurance brokers, agents and carriers. ryansg.com (NYSE: RYAN) ©2021 Ryan Specialty Group, LLC www.ryansg.com

Cautionary Statement Regarding Forward-Looking Statements

This press release may contain written “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended, that are made pursuant to the “safe harbor” provisions of The Private Securities Litigation Reform Act of 1995. Forward-looking statements include all statements that do not relate solely to historical or current facts. In particular, statements using the words such as “expect,” “intend,” “plan,” “believe,” “aim,” “project,” “anticipate,” “seek,” “will,” “likely,” “assume,” “estimate,” “may,” “continue,” “guidance,” “objective,” “outlook,” “trends,” “future,” “could,” “would,” “should,” “target,” “predict,” “potential,” “on track” or their negatives or variations and similar terminology and words of similar import generally involve forward-looking statements.

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¹ Premium for RSG Underwriting Managers for the year ended 12/31/2020 (pro-forma for the All Risk transaction which closed 9/1/20).

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