OXBRIDGE RE HOLDINGS Ltd

Previous wording

The following is a discussion and analysis of our results of operations for the three-and six-month periods ended June 30, 2025 and 2024 and our financial condition as of June 30, 2025 and December 31, 2024. The following discussion should be read in conjunction with our consolidated financial statements and related notes included elsewhere in this Quarterly Report on Form 10-Q and in our Form 10-K filed with the Securities and Exchange Commission (“SEC”) on March 26, 2025. References to “we,” “us,” “our,” “our company,” or “the Company” refer to Oxbridge Re Holdings Limited and its subsidiaries, Oxbridge Reinsurance Limited, Oxbridge Re NS, SurancePlus Holdings Ltd., SurancePlus, Inc. and DSN Blockchain Technologies Ltd., unless the context dictates otherwise.

Current wording

The following is a discussion and analysis of our results of operations for the three-and nine-month periods ended September 30, 2025 and 2024 and our financial condition as of September 30, 2025 and December 31, 2024. The following discussion should be read in conjunction with our consolidated financial statements and related notes included elsewhere in this Quarterly Report on Form 10-Q and in our Form 10-K filed with the Securities and Exchange Commission (“SEC”) on March 26, 2025. References to “we,” “us,” “our,” “our company,” or “the Company” refer to Oxbridge Re Holdings Limited and its subsidiaries, Oxbridge Reinsurance Limited, Oxbridge Re NS, SurancePlus Holdings Ltd., SurancePlus, Inc. and DSN Blockchain Technologies Ltd., unless the context dictates otherwise.

Previous wording

During the period ended June 30, 2025, we have sold 97,715 ordinary shares under the ATM program for gross proceeds of $448,858 at an average price of $4.59 per share. After deducting commissions related to the ATM offering of $13,465, the net proceeds we received from the transactions were $435,393. The proceeds from the ATM sales are being used for general corporate purposes.

Current wording

During the period ended September 30, 2025, we have sold 287,915 ordinary shares under the ATM program for gross proceeds of $900,531 at an average price of $3.13 per share. After deducting commissions related to the ATM offering of $27,016, the net proceeds we received from the transactions were $873,515. The proceeds from the ATM sales are being used for general corporate purposes.

Previous wording

Income from our investments is primarily comprised of net realized and unrealized (losses) gains interest income and dividends on investment securities. Such income is primarily from the Company’s investments, which includes other investments in Jet.AI and investments held in trust accounts that collateralize the reinsurance policies that we write. The investment parameters for trust accounts are generally be established by the cedant for the relevant policy.

Current wording

Income from our investments is primarily comprised of net realized and unrealized (losses) gains interest income and dividends on investment securities. Such income is primarily from the Company’s investments, which includes investments held in trust accounts that collateralize the reinsurance policies that we write. The investment parameters for trust accounts are generally be established by the cedant for the relevant policy.

Previous wording

During the six-month period June 30, 2025, the Company’s subsidiary, SurancePlus, effectively entered into subscription agreements for the sale of ZetaCat Re and EtaCat Re Participation Shares representing fractionalized interest in reinsurance contracts underwritten by Oxbridge Re NS. The ZetaCat Re and EtaCat Re Tokens were issued on the Avalanche blockchain.

Current wording

During the nine-month period September 30, 2025, the Company’s subsidiary, SurancePlus, effectively entered into subscription agreements for the sale of ZetaCat Re and EtaCat Re Participation Shares representing fractionalized interest in reinsurance contracts underwritten by Oxbridge Re NS. The ZetaCat Re and EtaCat Re Tokens were issued on the Avalanche blockchain.

Previous wording

The following is our consolidated statement of operations and performance ratios for the three- and six-month periods ended June 30, 2025 and 2024 (dollars in thousands, except per share amounts):

Current wording

The following is our consolidated statement of operations and performance ratios for the three- and nine-month periods ended September 30, 2025 and 2024 (dollars in thousands, except per share amounts):

Previous wording

General. Net loss for the quarter ended June 30, 2025 was $1.87 million, or ($0.25) basic and diluted loss per share compared to a net loss of $821,000, or ($0.14) basic and diluted loss per share, for the quarter ended June 30, 2024. The increase in net loss is primarily due to the recording of full limit loss on one of the reinsurance contracts during the quarter ended June 30, 2025 when compared with the prior period.

Current wording

General. Net loss for the quarter ended September 30, 2025 was $187,000, or ($0.02) basic and diluted loss per share compared to a net loss of $540,000, or ($0.09) basic and diluted loss per share, for the quarter ended September 30, 2024. The decrease in net loss is primarily due to the decrease in unrealized loss on other investments during the quarter ended September 30, 2025 when compared with the prior period.

Previous wording

Net loss for the six-months ended June 30, 2025 was $2.01 million, or ($0.28) basic and diluted loss per share compared to a net loss of $1.73 million, or ($0.29) basic and diluted loss per share, for the six months ended June 30, 2024. The increase in net loss is primarily due to the recording of full limit loss on one of the reinsurance contracts during the quarter ended June 30, 2025 when compared with the prior period.

Current wording

Net loss for the nine-months ended September 30, 2025 was $2.19 million, or ($0.30) basic and diluted loss per share compared to a net loss of $2.27 million, or ($0.37) basic and diluted loss per share, for the nine-months ended September 30, 2024. The decrease in net loss is primarily due to the decrease in unrealized loss on other investments during the nine-month period ended September 30, 2025 when compared with the prior period.

Previous wording

Net premiums earned for the quarter ended June 30, 2025 increased to $582,000 from $564,000 for the quarter ended June 30, 2024. The increase is due to the rates on contracts that were in force in the quarter ended June 30, 2025 when compared to the contracts in force in the prior-year period.

Current wording

Net premiums earned for the quarter ended September 30, 2025 decreased to $555,000 from $595,000 for the quarter ended September 30, 2024. The decrease is due to lower weighted average rate on reinsurance contracts in force during the quarter ended September 30, 2025, when compared to the prior period.

Previous wording

Net premiums earned for the six-months ended June 30, 2025 increased to $1.18 million from $1.11 million for the quarter ended June 30, 2024. The increase is due to the rates on contracts that were in force in the quarter ended June 30, 2025 when compared to the contracts in force in the prior-year period.

Current wording

Net premiums earned for the nine-months ended September 30, 2025 increased to $1.73 million from $1.71 million for the nine-month period ended September 30, 2024. The increase is due to higher weighted average rate on reinsurance contracts in force during the nine-month period ending September 30, 2025, when compared to the prior period.

Previous wording

Losses Incurred. During the three-month period ending June 30, 2025, one of our reinsurance contracts experienced adverse loss development stemming from Hurricane Milton, and we recognized a full limit loss of $2.3 million. There were no losses incurred during the three month period ending June 30, 2024.

Current wording

Losses Incurred. There were no losses incurred during the three-month period ending September 30, 2025 and September 30, 2024, respectively.

Previous wording

During the six-month period ending June 30, 2025, one of our reinsurance contracts experienced adverse loss development stemming from Hurricane Milton, and we recognized a full limit loss of $2.3 million. There were no losses incurred during the six-month period ending June 30, 2024. The net impact of the Hurricane Milton’s loss on the Company’s equity, after accounting for the portion of losses borne by external tokenholders’, is $1.18 million.

Current wording

During the nine-month period ending September 30, 2025, one of our reinsurance contracts experienced adverse loss development stemming from Hurricane Milton, and we recognized a full limit loss of $2.3 million. There were no losses incurred during the nine-month period ending September 30, 2024. The net impact of the Hurricane Milton’s loss on the Company’s equity, after accounting for the portion of losses borne by external tokenholders’, is $1.18 million.

Previous wording

Policy Acquisition Costs. Acquisition costs represent the amortization of the brokerage fees and federal excise taxes incurred on reinsurance contracts placed. Policy acquisition costs for the quarter ended June 30, 2025 increased to $64,000 from $62,000 for the quarter ended June 30, 2024. The increase is due to the rates on contracts in force in the quarter ended June 30, 2025, and the resulting acquisition costs, when compared to the rates on contracts in the prior-year period.

Current wording

Policy Acquisition Costs. Acquisition costs represent the amortization of the brokerage fees and federal excise taxes incurred on reinsurance contracts placed. Policy acquisition costs for the quarter ending September 30, 2025 decreased to $61,000 from $66,000 for the quarter ending September 30, 2024. The decrease is due to the rates on contracts in force in the quarter ended September 30, 2025, and the resulting acquisition costs, when compared to the rates on contracts in the prior-year period.

Previous wording

Policy acquisition costs for the six months ended June 30, 2025 increased from $122,000 to $129,000 for the six-moths ended June 30, 2025. The increase is due to the rates on contracts in force in the quarter ended June 30, 2025, and the resulting acquisition costs, when compared to the rates on contracts in the prior-year period.

Current wording

Policy acquisition costs for the nine-months ended September 30, 2025 increased from $188,000 to $191,000 for the nine-months ended September 30, 2025. The increase is due to the rates on contracts in force in the quarter ended September 30, 2025, and the resulting acquisition costs, when compared to the rates on contracts in the prior-year period.

Previous wording

General and Administrative Expenses. General and administrative expenses for the quarter ended June 30, 2025 increased to $1.3 million from $566,000 for the quarter ended June 30, 2024. The increase is primarily due to increased professional costs relating to investor relations, our web3 subsidiary tokenization costs, renewed S-3 related costs, increased human resources and personnel costs and legal expenditures.

Current wording

General and Administrative Expenses. General and administrative expenses for the quarter ended September 30, 2025 increased to $754,000 from $432,000 for the quarter ended September 30, 2024. The increase is primarily due to increased professional costs relating to investor relations, our web3 subsidiary tokenization costs, S-3 related costs, increased human resources and personnel costs and legal expenditures.

Previous wording

General and administrative expenses for the six months ended June 30, 2025 increased to $1.8 million , from $1.1 million for the six months ended June 30, 2024. The increase is primarily due to increased professional costs relating to investor relations, our web3 subsidiary tokenization costs, renewed S-3 related costs, increased human resources and personnel costs and legal expenditures.

Current wording

General and administrative expenses for the nine-months ended September 30, 2025 increased to $2.52 million, from $1.49 million for the nine-months ended September 30, 2024. The increase is primarily due to increased professional costs relating to investor relations, our web3 subsidiary tokenization costs, S-3 related costs, increased human resources and personnel costs and legal expenditures.

Previous wording

***Loss Ratio.***The loss ratio is the ratio of losses and loss adjustment expenses incurred to premiums earned and measures the underwriting profitability of our reinsurance business. The loss ratio increased to 394% and 194.8% for the quarter and six-month periods ended June 30, 2025, when compared with the prior comparative periods. This was due to the full limit loss on one of our reinsurance contracts affected by Hurricane Milton.

Current wording

***Loss Ratio.***The loss ratio is the ratio of losses and loss adjustment expenses incurred to premiums earned and measures the underwriting profitability of our reinsurance business. The loss ratio remained consistent at 0% for the three-month period ended September 2025 when compared with prior comparative period. The loss ratio increased to 132.4% for the nine-month period ended September 30, 2025, when compared with the prior comparative period. This was due to the full limit loss on one of our reinsurance contracts affected by Hurricane Milton.

Previous wording

The acquisition cost ratio remained consistent at 11.0% for the quarter end and six-month periods ended June 30, 2025 compared with the quarter and six-month periods ended June 30, 2024.

Current wording

The acquisition cost ratio remained consistent at 11.0% for the quarter end and nine-month periods ended September 30, 2025 compared with the quarter and nine-month periods ended September 30, 2024.

Previous wording

***Expense Ratio.***The expense ratio is the ratio of policy acquisition costs and general and administrative expenses to net premiums earned. We use the expense ratio to measure our operating performance. For the three-month period ended June 30, 2025, the expense ratio increased to 227%, from 111.3% for the three-month period ended June 30, 2024. For the six-month period ended June 30, 2025, the expense ratio increased to 160.7%, from 105.7% for the six-month period ended June 30, 2024. The increases are primarily due to increased professional costs relating to investor relations and our web3 subsidiary marketing and operations, renewed S-3 related costs, increased human resources and personnel costs and legal expenditures during the quarter ended June 30, 2025, when compared with the prior comparable periods.

Current wording

***Expense Ratio.***The expense ratio is the ratio of policy acquisition costs and general and administrative expenses to net premiums earned. We use the expense ratio to measure our operating performance. For the three-month period ended September 30, 2025, the expense ratio increased to 146.8%, from 83.7% for the three-month period ended September 30, 2024. For the nine-month period ended September 30, 2025, the expense ratio increased to 156.2%, from 98% for the nine-month period ended September 30, 2024. The increases are primarily due to increased professional costs relating to investor relations and our web3 subsidiary marketing and operations, renewed S-3 related costs, increased human resources and personnel costs and legal expenditures during the quarter ended September 30, 2025, when compared with the prior comparable periods.

Previous wording

***Combined Ratio.***We use the combined ratio to measure our underwriting performance. The combined ratio is the sum of the loss ratio and the expense ratio. For the three-month period ended June 30, 2025, the combined ratio increased to 621%, from 111.3% for the three-month period ended June 30, 2024. For the six-month period ended June 30, 2025, the combined ratio increased to 355.5%, from 105.7% for the six-month period ended June 30, 2024.. The increase is due to higher general and administrative expenses and the losses incurred during the three-month and six-month periods ended June 30, 2025, when compared with the prior comparable periods.

Current wording

***Combined Ratio.***We use the combined ratio to measure our underwriting performance. The combined ratio is the sum of the loss ratio and the expense ratio. For the three-month period ended September 30, 2025, the combined ratio increased to 146.8%, from 83.7% for the three-month period ended September 30, 2024. For the nine-month period ended September 30, 2025, the combined ratio increased to 288.6%, from 98% for the nine-month period ended September 30, 2024. The increase is due to higher general and administrative expenses and the losses incurred during the three-month and nine-month periods ended September 30, 2025, when compared with the prior comparable periods.

Previous wording

**Restricted Cash and Cash Equivalents.**As of June 30, 2025, our restricted cash and cash equivalents increased by $760,000 or 12.90%, to $6.7 million, from $5.9 million as of December 31, 2024. The increase is the net result of premium deposits made during the six-months ending June 30, 2025, the registered direct offering that generated $2.7 million net of expenses, and payment of Hurricane Milton losses and general administrative expenses.

Current wording

**Restricted Cash and Cash Equivalents.**As of September 30, 2025, our restricted cash and cash equivalents increased by $1.28 million or 21.7%, to $7.18 million, from $5.9 million as of December 31, 2024. The increase is the net result of premium deposits made during the nine-months ending September 30, 2025, the registered direct offering and ATM program that generated $3.5 million net of expenses, and payment of Hurricane Milton losses and general administrative expenses.

Previous wording

**Investments.**As of June 30, 2025, our total investments decreased by $9,000 or 7.96% to $104,000, from $113,000 as of December 31, 2024. The decrease is primarily a result of the decrease in value of the equity securities during the six-month period ended June 30, 2025.

Current wording

**Investments.**As of September 30, 2025, our total investments increased by $2,000 or 1.77% to $115,000, from $113,000 as of December 31, 2024. The increase is primarily a result of the increase in value of the equity securities during the nine-month period ended September 30, 2025.

Previous wording

***Unearned Premiums Reserve.***As of June 30, 2025, our unearned premiums reserve increased by $1.04 million, to $2.03 million from $991,000 at December 31, 2024. The increase is due to the new reinsurance contracts placed for the 2025 2026 treaty year.

Current wording

***Unearned Premiums Reserve.***As of September 30, 2025, our unearned premiums reserve increased by $490,000, to $1.48 million from $991,000 at December 31, 2024. The increase is due to the new reinsurance contracts placed for the 2025 2026 treaty year.

Previous wording

Our sources of funds primarily consist of premium receipts (net of brokerage fees and federal excise taxes, where applicable) and investment income, including interest, dividends and realized gains. We use cash to pay losses and loss adjustment expenses, other underwriting expenses, dividends, and general and administrative expenses. Substantially all our surplus funds, net of funds required for cash liquidity purposes, are invested in accordance with our business plan and investment guidelines. Our investment portfolio, except for our investment in Jet.AI, is primarily comprised of cash and highly liquid securities, which can be liquidated, if necessary, to meet current liabilities. We believe that we have sufficient flexibility to liquidate any securities that we own to generate liquidity.

Current wording

Our sources of funds primarily consist of premium receipts (net of brokerage fees and federal excise taxes, where applicable) and investment income, including interest, dividends and realized gains. We use cash to pay losses and loss adjustment expenses, other underwriting expenses, dividends, and general and administrative expenses. Substantially all our surplus funds, net of funds required for cash liquidity purposes, are invested in accordance with our business plan and investment guidelines. Our investment portfolio is primarily comprised of cash and highly liquid securities, which can be liquidated, if necessary, to meet current liabilities. We believe that we have sufficient flexibility to liquidate any securities that we own to generate liquidity.

Previous wording

Our cash flows from operating, investing, and financing activities for the six-month periods ended June 30, 2025 and 2024 are summarized below.

Current wording

Our cash flows from operating, investing, and financing activities for the nine-month periods ended September 30, 2025 and 2024 are summarized below.

Previous wording

Cash Flows for the Six months ended June 30, 2025 (in thousands)

Current wording

Cash Flows for the Nine months ended September 30, 2025 (in thousands)

Previous wording

Net cash used in operating activities for the six months ended June 30, 2025 totaled$1,899, which consisted primarily of cash received net written premiums less cash disbursed for operating expenses. Net provided by investing activities was $63, which consisted of consideration received on sale of investment in Jet.AI. Net cash provided by financing activities was $2,596 which consisted of net proceeds from issuance of ordinary shares through the Company’s ATM facility and the registered direct offering completed during the period.

Current wording

Net cash used in operating activities for the nine-months ended September 30, 2025 totaled $1,781, which consisted primarily of cash received net written premiums less cash disbursed for operating expenses. Net provided by investing activities was $63, which consisted of consideration received on sale of investment in Jet.AI. Net cash provided by financing activities was $3,001 which consisted of net proceeds from issuance of ordinary shares through the Company’s ATM facility and the registered direct offering completed during the period.

Previous wording

Cash Flows for the Six months ended June 30, 2024 (in thousands)

Current wording

Cash Flows for the Nine months ended September 30, 2024 (in thousands)

Previous wording

Net cash used in operating activities for the six months ended June 30, 2024 totaled $311, which consisted primarily of cash received net written premiums less cash disbursed for operating expenses. Net provided by investing activities of $448 which was due to the repayment of the note receivable by Jet.AI and the proceeds from the sale of two of our equity securities. Net cash provided by financing activities was $103 which consisted primarily of net proceeds from Epsilon Cat Re participation shares represented by digital tokens offset by the payments made to DeltaCat Re tokenholders.

Current wording

Net cash used in operating activities for the nine-months ended September 30, 2024 totaled $53 which consisted primarily of cash received net written premiums less cash disbursed for operating expenses. Net cash provided by investing activities of $448 which was due to the repayment of the note receivable by Jet.AI and the proceeds from the sale of two of our equity securities. Net cash provided by financing activities was $681 which consisted primarily of net proceeds from Epsilon Cat Re participation shares represented by digital tokens offset by the payments made to DeltaCat Re tokenholders.

Previous wording

We are required to make estimates and assumptions in certain circumstances that affect amounts reported in our consolidated financial statements and related footnotes. We evaluate these estimates and assumptions on an on-going basis based on historical developments, market conditions, industry trends and other information that we believe to be reasonable under the circumstances. These accounting policies pertain to fair value measurements, particular with respect to our beneficial interest in Jet.AI., premium revenues and risk transfer, reserve for loss and loss adjustment expenses, and deferred acquisition costs.

Current wording

We are required to make estimates and assumptions in certain circumstances that affect amounts reported in our consolidated financial statements and related footnotes. We evaluate these estimates and assumptions on an on-going basis based on historical developments, market conditions, industry trends and other information that we believe to be reasonable under the circumstances. These accounting policies pertain to fair value measurements, premium revenues and risk transfer, reserve for loss and loss adjustment expenses, and deferred acquisition costs.

Previous wording

During the quarter and six months ended June 30, 2025, the attachment layer reinsured by the Company under one of its contract was penetrated as a result of adverse loss development from Hurricane Milton. As a result, at June 30, 2025, the Company has recorded a reserve for losses and LAE of $175,000 based on the contractual maximum loss ($2,293) the Company can suffer under of the contracts, less advanced payments made during the quarter and six months ended June 30, 2025 relating to loss suffered by Hurricane Milton. The net impact of the Hurricane Milton’s loss on the Company’s equity, after accounting for the portion of losses borne by external tokenholders’, is $1.18 million.

Current wording

During the quarter and nine-months ended September 30, 2025, the attachment layer reinsured by the Company under one of its contract was penetrated as a result of adverse loss development from Hurricane Milton. The net impact of the Hurricane Milton’s loss on the Company’s equity, after accounting for the portion of losses borne by external tokenholders’, is $1.18 million.