This information shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that Section, or incorporated by reference into any filing under the Securities Act of 1933, as amended (the “Securities Act”), or the Exchange Act, except as shall be expressly set forth by specific reference in such filing.

This information shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that Section, or incorporated by reference into any filing under the Securities Act of 1933, as amended (the “Securities Act”), or the Exchange Act, except as shall be expressly set forth by specific reference in such filing.

Director — Franklin (Tad) Montross IV and Peter W. H. Tan: Two Class I directors decided not to stand for reelection at the annual general meeting.

President & Chief Executive Officer — Rob Gibbs: Mr. Rob Gibbs departed from his role as President & Chief Executive Officer with a severance agreement.

President & Chief Executive Officer of SiriusPoint International — Mr. Rob Gibbs: Mr. Rob Gibbs is leaving the Company as part of business structure changes.

This information shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that Section, or incorporated by reference into any filing under the Securities Act of 1933, as amended (the “Securities Act”), or the Exchange Act, except as shall be expressly set forth by specific reference in such filing.

Other Events. On October 31, 2025, a subsidiary of SiriusPoint Ltd. (the “Company”) completed the previously announced sale of all of the issued and outstanding limited liability company membership interests in ArmadaCorp Capital, LLC (“Armada”), the holding company of the Company’s wholly owned supplemental health insurance program manager, ArmadaCare, to a subsidiary of Ambac Financial Group Inc. (“Ambac”), pursuant to the Membership Interest Purchase Agreement (the “Purchase Agreement”), d…

This information shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that Section, or incorporated by reference into any filing under the Securities Act of 1933, as amended (the “Securities Act”), or the Exchange Act, except as shall be expressly set forth by specific reference in such filing.

Other Events. On October 28, 2025, the Audit Commitee of the Board of Directors of SiriusPoint Ltd. approved a quarterly cash dividend of $0.50 per share on its 8.00% Resettable Fixed Rate Preference Shares, Series B, $0.10 par value, $25.00 liquidation preference per share payable on November 28, 2025 to Series B shareholders of record as of November 13, 2025. A copy of the press release is attached hereto as Exhibit 99.4.

Chief Accounting Officer and principal accounting officer — Evan Cabat: Mr. Cabat resigned to pursue another opportunity.

Director — Martin Hudson: The filing discloses the appointment of a new independent director to the board, which is a routine governance event and not an executive departure.

The filing discloses the adoption of a new Executive Severance Plan, which is a compensatory arrangement rather than a specific management departure or appointment.

Other Events. On July 30, 2025, the Audit Commitee of the Board of Directors of SiriusPoint Ltd. approved a quarterly cash dividend of $0.50 per share on its 8.00% Resettable Fixed Rate Preference Shares, Series B, $0.10 par value, $25.00 liquidation preference per share payable on August 29, 2025 to Series B shareholders of record as of August 14, 2025. A copy of the press release is attached hereto as Exhibit 99.4.

This information shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that Section, or incorporated by reference into any filing under the Securities Act of 1933, as amended (the “Securities Act”), or the Exchange Act, except as shall be expressly set forth by specific reference in such filing.

Creation of a Direct Financial Obligation. On June 6, 2025 (the “ Closing Date ”), Sirius International Corporate Member Limited (the “ Borrower ”), a subsidiary of SiriusPoint Ltd. (the “ Company ”), entered into a $35,000,000 Tier 1 FAL Facility Agreement (the “ Facility ”) with Lloyds Bank PLC, as the administrative agent (“ Lloyds Bank ”), the lenders party thereto from time to time (the “ Lenders ”), and the Company. The Facility will mature on December 31, 2026, subject to an option, af…

Other Events. On May 1, 2025 , the Audit Commitee of the Board of Directors of SiriusPoint Ltd. approved a quarterly cash dividend of $0.50 per share on its 8.00% Resettable Fixed Rate Preference Shares, Series B, $0.10 par value, $25.00 liquidation preference per share payable on May 30, 2025 to Series B shareholders of record as of May 15, 2025. A copy of the press release is attached hereto as Exhibit 99.4.

This information shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that Section, or incorporated by reference into any filing under the Securities Act of 1933, as amended (the “Securities Act”), or the Exchange Act, except as shall be expressly set forth by specific reference in such filing.

Other Events. Closing of the CM Bermuda Securities Repurchase Immediately following the closing of the Secondary Offering (as defined below), on February 27, 2025, SiriusPoint Ltd. (the “Company”) (i) repurchased 45,720,732 common shares, par value $0.10 per share (the “Common Shares”), of the Company held by CM Bermuda Limited (“CM Bermuda” and, the shares repurchased, the “CM Bermuda Shares”) at a price of $14.25 per CM Bermuda Share into treasury and (ii) repurchased and cancelled 20,991,3…

This information shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that Section, or incorporated by reference into any filing under the Securities Act of 1933, as amended (the “Securities Act”), or the Exchange Act, except as shall be expressly set forth by specific reference in such filing.

Other Events. On January 25, 2025, the Audit Committee of the Board of Directors of SiriusPoint Ltd. approved a quarterly cash dividend of $0.50 per share on its 8.00% Resettable Fixed Rate Preference Shares, Series B, $0.10 par value, $25.00 liquidation preference per share payable on February 28, 2025 to Series B shareholders of record as of February 13, 2025. A copy of the press release is attached hereto as Exhibit 99.1.

Director — Meng Tee Saw: A director resigned contingent upon the closing of a securities purchase agreement, with no disagreement cited.

Entry Into a Material Definitive Agreement. On December 30, 2024, SiriusPoint Ltd. (“SiriusPoint”) entered into a Securities Purchase Agreement (the “Securities Purchase Agreement”) with CM Bermuda Limited (the “Seller”). The Securities Purchase Agreement provides that, subject to the satisfaction or waiver of certain customary conditions set forth therein, SiriusPoint will repurchase all common shares of SiriusPoint, par value $0.10 per share held by the Seller (the “Common Shares”), and all…

Creation of a Direct Financial Obligation. The information set forth in

Entry into a Material Definitive Agreement. On December 19, 2024, the Company entered into a $400.0 million senior unsecured revolving credit facility (the “Facility”) with JPMorgan Chase Bank, N.A. as administrative agent. The Facility will mature on December 29, 2028, subject to an option, after satisfaction of certain conditions including agreement of lenders representing greater than a majority of commitments, for the Company to request an extension by such lenders of the maturity date of…

Director — Meng Tee Saw: The filing discloses the appointment of a new director to fill a vacancy, which is a routine board composition change rather than the departure of a senior executive.