$2,021,889 Oxbridge Re (NASDAQ: OXBR) ATM share program update

Rhea-AI Filing Summary

Oxbridge Re Holdings Limited is filing a prospectus supplement to register the offer and sale of up to $2,021,889 of its ordinary shares from time to time through Maxim Group LLC under an equity distribution (at-the-market) Sales Agreement. The company states that, under Form S-3 General Instruction I.B.6 limits and after selling approximately $4.58 million of securities in the prior 12 months, $1,672,714 of capacity remains available to be sold under this program. Its ordinary shares trade on the Nasdaq Capital Market under the symbol OXBR at a last reported price of $2.75 per share, with 7,635,922 ordinary shares outstanding as of September 15, 2025, of which 816,176 were held by affiliates.

Filed Pursuant to Rule 424(b)(5)

Registration No. 333-287186

PROSPECTUS SUPPLEMENT

(To Prospectus dated May 19, 2025 and

Prospectus Supplement dated July 9, 2025)

$2,021,889

Oxbridge Re Holdings Limited

Ordinary Shares

This prospectus supplement (“Prospectus Supplement No. 1”) amends and supplements the information in the prospectus supplement dated July 9, 2025 relating to the offer and sale of up to $2,021,889 of our ordinary shares, pursuant to the equity distribution agreement (the “Sales Agreement”) with Maxim Group LLC (the “Sales Agent”), dated July 9, 2025. This Prospectus Supplement No. 1 is registering the offer and sales of up to $2,021,889 of our ordinary shares from time to time through the Sales Agent, acting as agent. This Prospectus Supplement No. 1 is not complete without and may only be delivered or utilized in connection with the prospectus supplement dated July 9, 2025, the accompanying base prospectus, and any future amendments or supplements thereto.

Our ordinary shares are listed on The Nasdaq Capital Market under the symbol “OXBR.” On September 15, 2025, the last reported sale price of our ordinary shares on The Nasdaq Capital Market was $2.75 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 $18,754,301 which was calculated based on 7,635,922 ordinary shares outstanding as of September 15, 2025, of which 816,176 shares were held by affiliates, and a price of $2.75 per share, which was the closing price of our ordinary shares on the Nasdaq Capital Market on September 15, 2025. Pursuant to General Instruction I.B.6 of Form S-3, in no event 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 float remains below $75,000,000. We have sold approximately $4.58 million of securities pursuant to General Instruction I.B.6 of Form S-3 during the 12 calendar months prior to and including the date of this Prospectus Supplement No. 1, and therefore $1,672,714 remains available to be sold pursuant to this Prospectus Supplement No. 1 and the Sales Agreement.

Investing in our ordinary shares involves a high degree of risk. You should read this prospectus supplement dated July 9, 2025 and the accompanying prospectus carefully before you make your investment decision.

NEITHER THE SECURITIES AND EXCHANGE COMMISSION NOR ANY STATE SECURITIES COMMISSION HAS APPROVED OR DISAPPROVED OF THESE SECURITIES OR PASSED UPON THE ADEQUACY OR ACCURACY OF THIS PROSPECTUS SUPPLEMENT, THE PRIOR PROSPECTUS SUPPLEMENT OR THE ACCOMPANYING PROSPECTUS. ANY REPRESENTATION TO THE CONTRARY IS A CRIMINAL OFFENSE.

Maxim Group LLC

The date of this Prospectus Supplement No. 1 is September 16, 2025.

FAQ

What is Oxbridge Re (OXBR) registering in this 424B5 prospectus supplement?

Oxbridge Re is registering the offer and sale of up to $2,021,889 of its ordinary shares, to be sold from time to time through Maxim Group LLC under an equity distribution Sales Agreement.

Is the Oxbridge Re (OXBR) offering a primary at-the-market program?

Yes. The prospectus supplement covers a primary offering of ordinary shares by Oxbridge Re under an equity distribution (at-the-market) Sales Agreement with Maxim Group LLC acting as sales agent.

How much capacity remains under Oxbridge Res Form S-3 I.B.6 limit?

Oxbridge Re reports that it has sold approximately $4.58 million of securities under Form S-3 General Instruction I.B.6 in the prior 12 months, leaving $1,672,714 available to be sold under this prospectus supplement and the Sales Agreement.

What is Oxbridge Res public float and share count used in this filing?

The company states its public float is approximately $18,754,301, based on 7,635,922 ordinary shares outstanding as of September 15, 2025, of which 816,176 shares were held by affiliates at a price of $2.75 per share.

On which exchange are Oxbridge Re (OXBR) shares listed and what was the recent price?

Oxbridge Res ordinary shares are listed on the Nasdaq Capital Market under the symbol OXBR, and the last reported sale price on September 15, 2025 was $2.75 per share.

Does this Oxbridge Re prospectus supplement highlight any risks for investors?

Yes. The document states that investing in Oxbridge Res ordinary shares involves a high degree of risk and directs readers to carefully review the July 9, 2025 prospectus supplement and accompanying prospectus before making an investment decision.