Cuprina Holdings (Cayman) LTD

PROXY SOLICITATION

This Proxy Statement is furnished in connection with the solicitation of proxies by the Board of Directors (the “Board” or the “Board of Directors”) of Cuprina Holdings (Cayman) Limited (the “Company,” “we,” “us,” or “our”) for the Annual General Meeting of Shareholders on May 14, 2026, at 9:00 p.m., local time (i.e., 9 a.m. May 14, 2026 E.T.) and for any adjournment or postponement thereof, for the purposes set forth in the accompanying Notice of Annual General Meeting (the “Meeting” or “AGM”) of Shareholders. Eligible shareholders, directors, as well as duly appointed proxyholders will be able to attend, participate and vote at the Meeting. Any shareholder giving such a proxy has the power to revoke it at any time before it is voted. Written notice of such revocation should be forwarded directly to the Chairman of the Board of Directors of the Company, at the above stated address. Proxies may be solicited through the mails or direct communication with certain shareholders or their representatives by Company officers, directors, or employees, who will receive no additional compensation therefor.

If the enclosed proxy is properly executed and returned, the shares represented thereby will be voted in accordance with the directions thereon and otherwise in accordance with the judgment of the persons designated as proxies. Any proxy on which no direction is specified will be voted in favor of the actions described in this Proxy Statement.

The Company will bear the entire cost of preparing, assembling, printing and mailing this Proxy Statement, the accompanying proxy form, and any additional material that may be furnished to shareholders. The date on which this Proxy Statement and the accompanying Proxy Form will first be mailed or given to the Company’s shareholders is on or about May 1, 2026.

We have elected to provide access to our proxy materials both by sending you this full set of proxy materials, including the notice of our Meeting, this Proxy Statement and a proxy card to Shareholders.

Your vote is important. Whether or not you expect to attend the Meeting in person, you are urged to complete, sign, date and return the accompanying proxy form as promptly as possible to ensure your representation at such meeting. Shareholders who execute proxies retain the right to revoke them at any time prior to the voting thereof, and may nevertheless vote online at the Meeting. If you hold your shares in street name and wish to vote your shares at the Meeting, you should contact your broker, bank, custodian or other nominee holder about getting a legal proxy appointing you to vote your shares.