牛津桥控股有限公司美国存托凭证招股说明书（2026年6月22日版）

Oxbridge Re Holdings Limited Ordinary Shares We have entered into an At-the-Market Sales Agreement (the “Sales Agreement”) with Chardan Capital Markets LLC (“Chardan” or the “Sales Agent”), dated June 22,2026, relating to the sale of the ordinary shares offered by this prospectus supplement and the accompanying prospectus. In accordance with the terms of the SalesAgreement, under this prospectus supplement and the accompanying prospectus, we may offer and sell ordinary shares having an aggregate offering price of up to$1,678,301 from time to time through the Sales Agent, acting as our sales agent. Sales of our ordinary shares, if any, under this prospectus supplement and the accompanying prospectus may be made by any method permitted that is deemed an “atthe market offering” as defined in Rule 415 promulgated under the Securities Act of 1933, as amended (the “Securities Act”). If we and the Sales Agent agree on anymethod of distribution other than sales of our ordinary shares into The Nasdaq Capital Market or another existing trading market in the United States at market prices,we will file a further prospectus supplement providing all information about such offering as required by Rule 424(b) under the Securities Act. The Sales Agent is not The Sales Agent will be entitled to a commission equal to 3.0% of the gross sales price per share sold under the Sales Agreement. The amount of proceeds we willreceive from this offering, if any, will depend on the actual number of ordinary shares sold and the market price at which such ordinary shares are sold. Because there isno minimum offering amount required as a condition to close this offering, the actual total public offering amount, commissions and proceeds to us, if any, are not In connection with the sale of ordinary shares on our behalf, the Sales Agent will be deemed to be an “underwriter” within the meaning of the Securities Act and thecompensation of the Sales Agent will be deemed to be underwriting commissions or discounts. We have also agreed to provide indemnification and contribution to theSales Agent with respect to certain liabilities, including liabilities under the Securities Act. Our ordinary shares are listed on The Nasdaq Capital Market under the symbol “OXBR.” On June 17, 2026, the last reported sale price of our ordinary shares on TheNasdaq Capital Market was $1.03 per share. The aggregate market value of our outstanding ordinary shares held by non-affiliates pursuant to General Instruction I.B.6 of Form S-3 was approximately $7,446,329,which was calculated based on 8,101,374 ordinary shares outstanding as of June 19, 2026, of which 871,928 shares were held by affiliates, and a price of $1.03 pershare, which was the closing price of our ordinary shares on the Nasdaq Capital Market on June 17, 2026. Pursuant to General Instruction I.B.6 of Form S-3, in noevent will we sell securities in a public primary offering with a value exceeding more than one-third of our public float in any 12-month period so long as our public Investing in our ordinary shares involves a high degree of risk. You should read this prospectus supplement and the accompanying prospectus carefully beforeyou make your investment decision. See “Risk Factors” beginning on page S-4 of this prospectus supplement, as well as the documents we file with theSecurities and Exchange Commission that are incorporated by reference in this prospectus supplement and in the accompanying prospectus, including ourmost recent Annual Report on Form 10-K, our most recent Quarterly Report on Form 10-Q, and any subsequently filed Quarterly Reports on Form 10-Q and Neither the Securities and Exchange Commission nor any state securities commission has approved or disapproved of these securities or determined if thisprospectus supplement or the accompanying prospectus is truthful or complete. Any representation to the contrary is a criminal offense. Chardan Capital Markets LLC The date of this prospectus supplement is June 22, 2026. Prospectus Supplement We are offering to sell, and are seeking offers to buy, the securities only in jurisdictions where such offers and sales are permitted. The distribution of thisprospectus supplement and the accompanying prospectus and the offering of the securities in certain jurisdictions may be restricted by law. Persons outsidethe United States who come into possession of this prospectus supplement and the accompanying prospectus must inform themselves about and observe anyrestrictions relating to the offering of the securities and the distribution of this prospectus supplement and the accompanying prospectus outside the United About This Prospectus Supplement and Prospectus This prospectus supplement and the accompanying prospectus are part of a registration statement on Form S-3 (File No. 333-287186) that we filed with the Securitiesand Exchange Commission (“SEC”) and that was declared effective by the SEC on May 19, 2025. Under this shelf registrat