What changed in this filing

/stocks — the workspaceLOADING

Item 1A. Risk Factors

2026-03-09 compared with 2025-03-10 · 114 added, 105 removed, 585 unchanged (27% of the section changed)

9 unchanged sentences

Accordingly, our short-term results of operations may not be indicative of our long-term prospects.

A downgrade or withdrawal of our A.M.

Best ratings would materially and adversely affect our ability to implement our business strategy.

Best downgrades or withdraws either of our ratings, we could be severely limited or prevented from writing any new reinsurance contracts, which would materially and adversely affect our ability to implement our business strategy.

Additionally, if A.M.

Best downgrades or withdraws our ratings, we cannot provide assurance that our regulators, CIMA and the Central Bank of Ireland, would continue to authorize our current business strategy and investment strategy.

See “ — Risks Relating to Insurance and Other Regulations – Any suspension or revocation of our reinsurance licenses would materially and adversely impact our ability to do business and implement our business strategy .”

Greenlight Re’s A.M.

Best rating of “A- (Excellent)” is the fourth highest of 15 financial strength ratings that A.M.

In October 2024, A.M.

Best revised Greenlight Re’s outlooks to positive from stable.

Best periodically reviews our ratings and may revise one or more of our ratings downward or revoke them at its sole discretion based primarily on its analysis of our balance sheet strength, operating performance, and business profile.

Potential developments that may affect such an analysis include:

Best alters its capital adequacy assessment methodology in a manner that would adversely affect the rating of our reinsurance entities;

Best alters its approach regarding our Solasglas investment strategy or our Innovations investments;

● if our actual losses significantly exceed our loss reserves;

● if unfavorable financial or market trends impact us;

● if we change our business practices from our organizational business plan in a manner that no longer supports our A.M.

Best ratings;

● if we are unable to retain our senior management and other key personnel or implement succession plans;

● if our investments incur significant losses.

Substantially all of our assumed reinsurance contracts contain provisions that permit our clients to cancel the contract or require additional collateral in the event of a downgrade in our A.M.

Best ratings below specified levels or a reduction of our capital or surplus below specified levels over the course of the agreement.

Contracts containing such cancellation rights represented approximately 37% of gross premiums written during 2024.

Additional collateral in the event of a downgrade in our A.M.

Best ratings would be approximately $134.6 million at December 31, 2024.

We expect that similar provisions will also be included in future contracts.

Whether a client would exercise such cancellation rights would likely depend on, among other things, the prevailing market conditions, the degree of unexpired coverage, and the pricing and availability of replacement reinsurance coverage.

We cannot predict how many of our clients would ultimately exercise such rights.

The exercise of such rights in the aggregate could significantly affect our financial condition, results of operations, and our underwriting capacity.

Return to table of contents

If our losses and LAE greatly exceed our loss reserves, our financial condition may be materially and adversely affected.

14 unchanged sentences

Management’s Discussion and Analysis of Financial Condition and Results of Operations - Critical Accounting Estimates , Loss and Loss Adjustment Expense Reserves ”.

Our property and casualty reinsurance operations make us vulnerable to losses from catastrophes and may cause our results of operations to vary significantly from period to period.

Certain of our reinsurance operations expose us to claims arising out of unpredictable catastrophic events, including losses from severe weather and other natural catastrophes and man-made disasters such as acts of war or terrorism.

The incidence and severity of catastrophes are inherently unpredictable, with climate change continuing to add to such unpredictability as well as increasing the frequency and severity of events.

To the extent climate

Return to table of contents

change produces extreme changes in temperatures and weather patterns, it could impact the frequency or severity of weather including, but not limited to, hurricanes, tornadoes, freezes, droughts, other storms, and wildfires.

These changes in weather patterns could also affect the frequency and severity of other natural catastrophe events to which we may be exposed.

Further, such catastrophes could impact the affordability and availability of homeowners insurance, which could impact pricing.

Additionally, increases in the value and geographic concentration of insured property, particularly along coastal regions, could cause the cost of such losses to increase.

Catastrophic losses are a function of the insured exposure in the affected area and the event’s severity.

Claims from catastrophic events could cause substantial volatility in our financial results for any fiscal quarter or year and could materially and adversely affect our business, financial condition and results of operations.

Finally, given the scientific uncertainty of predicting the effect of climate cycles and global climate change on the frequency and severity of natural catastrophes and the lack of adequate predictive tools, we may not be able to adequately model the associated exposures and potential losses in connection with such catastrophes which could have a material adverse effect on our business, financial condition or operating results.

We may need additional capital in the future in order to operate our business, and such capital may not be available to us or may not be available to us on favorable terms.

We may need to raise additional capital in the future through public or private equity or debt offerings or otherwise in order to:

● repay our debt;

● fund liquidity needs or replace lost capital resulting from underwriting or investment losses;

4 unchanged sentences

Additional capital may not be available on terms favorable to us, or at all.

Increases in interest rates could result in higher interest expense on our outstanding debt.

Increases in interest rates could result in higher interest expense on debt.

Further, any additional capital raised through the sale of equity could dilute existing ownership interest in our company and may cause the market price of our ordinary shares to decline.

Additional capital raised through the issuance of debt may result in creditors having rights, preferences, and privileges senior or otherwise superior to those of our ordinary shares.

Return to table of contents

Competitors with greater resources may make it difficult for us to effectively market our products or offer our products at a profit.

9 unchanged sentences

● the experience and reputation of the members of our underwriting team in the particular lines of reinsurance we seek to underwrite.

We cannot assure you that we will be able to compete successfully in the reinsurance market.

Our failure to compete effectively could materially and adversely affect our financial condition and results of operations, and may increase the likelihood that we will be deemed a passive foreign investment company or an investment company.

We cannot assure you that we will be able to continue to compete successfully in the reinsurance market.

Our failure to continue to compete effectively could materially and adversely affect our financial condition and results of

Return to table of contents

operations, and may increase the likelihood that we will be deemed a passive foreign investment company or an investment company.

See “— Risks Relating to Taxation — United States persons who own ordinary shares may be subject to United States federal income taxation on our undistributed earnings and may recognize ordinary income upon disposition of ordinary shares.

16 unchanged sentences

Recently, for instance, the U.S.

administration imposed and/or announced (and in some cases postponed) tariffs on imports from various countries and on certain products, which may lead to unpredictable economic consequences including inflation or trade wars.

administration imposed and/or announced (and in some cases postponed or changed) tariffs on imports from various countries and on certain products, which may lead to unpredictable economic consequences including inflation or trade wars.

Our operations are susceptible to inflation, and underestimating inflation levels could result in underpricing the risks we reinsure because premiums are established before the ultimate amounts of losses and LAE are known.

5 unchanged sentences

See “— Risks Related to Our Solasglas Investment Strategy ” and “— Risks Related to Our Innovations Strategy .”

Return to table of contents

Further, our results of operations and financial condition may also be materially adversely affected by a challenging political climate, including events such as military actions, invasions, wars, civil unrest and terrorist activities and the imposition of sanctions and importation limitations.

2 unchanged sentences

Due to the widespread impact of the ongoing conflict, it is likely to indirectly impact the markets in which we operate.

The effect of emerging claim and coverage issues on our business is uncertain.

Return to table of contents

Emerging claim and coverage issues have had and may continue to adversely impact our business and results.

As industry practices and social, political, legal, judicial, and regulatory conditions change, unexpected issues related to claims and coverage have emerged and adversely affected our results.

11 unchanged sentences

As a result, we may not be able to ascertain the full extent of our liabilities under our reinsurance contracts for many years following the issuance of our contracts.

The property and casualty reinsurance market may be affected by cyclical trends.

The property and casualty reinsurance market is affected by cyclical trends.

We write reinsurance in the property and casualty markets, which are subject to pricing cycles.

8 unchanged sentences

Return to table of contents

A downgrade or withdrawal of our A.M.

Best ratings would materially and adversely affect our ability to implement our business strategy.

Additionally, if A.M.

Best’s current rating for Greenlight Re is “A (Excellent”) and the outlook is stable.

Potential developments that may affect such an analysis include:

Best alters its capital adequacy assessment methodology in a manner that would adversely affect the rating of our reinsurance entities;

Best alters its approach regarding our Solasglas investment strategy or our Innovations investments;

● if our actual losses significantly exceed our loss reserves;

● if unfavorable financial or market trends impact us;

● if we change our business practices from our organizational business plan in a manner that no longer supports our A.M.

Best ratings;

● if we are unable to retain our senior management and other key personnel or implement succession plans;

● if our investments incur significant losses.

Substantially all of our assumed reinsurance contracts contain provisions that permit our clients to cancel the contract or require additional collateral in the event of a downgrade in our A.M.

Best ratings below specified levels (generally below “A-”) or a reduction of our capital or surplus below specified levels over the course of the agreement.

We expect that similar provisions will also be included in future contracts.

We cannot predict how many of our clients would ultimately exercise such rights.

The exercise of such rights in the aggregate could significantly affect our financial condition, results of operations, and our underwriting capacity.

Modeling risks are inherent in our business.

6 unchanged sentences

Furthermore, these models typically rely on either cedent or industry data, which may be incomplete or may be subject to errors.

Accordingly, these models, and the assumptions and judgements made in connection therewith, may understate the exposures we are assuming, and our financial results may be materially and adversely impacted.

Accordingly, these models, and the assumptions and judgments made in connection therewith, may understate the exposures we are assuming, and our financial results may be materially and adversely impacted.

Technology breaches or failures, including those resulting from a malicious ransomware or cyber-attack on us or our business partners and service providers, could disrupt or otherwise negatively impact our business.

1 unchanged sentence

We have also licensed certain systems and data from third parties.

We cannot be certain that we will have access to these service providers or that our information technology or application systems will continue to operate as intended.

Return to table of contents

be certain that we will have access to these service providers or that our information technology or application systems will continue to operate as intended.

In addition, we cannot be certain that we would be able to replace these systems without slowing our underwriting response time.

12 unchanged sentences

Cybersecurity .”

Our property and casualty reinsurance operations make us vulnerable to losses from catastrophes and may cause our results of operations to vary significantly from period to period.

The incidence and severity of catastrophes are inherently unpredictable, with climate change continuing to add to that inherent unpredictability as well as increasing the frequency and severity of events.

To the extent climate change produces extreme changes in temperatures and weather patterns, it could impact the frequency or severity of weather including, but not limited to, hurricanes, tornadoes, freezes, droughts, other storms, and wildfires.

These changes in weather patterns could also affect the frequency and severity of other natural catastrophe events to which we may be exposed.

Further, such catastrophes could impact the affordability and availability of homeowners insurance, which could impact pricing.

Additionally, increases in the value and geographic concentration of insured property, particularly along coastal regions, could cause the cost of such losses to increase.

Catastrophic losses are a function of the insured exposure in the affected area and the event’s severity.

Return to table of contents

The loss of significant brokers or customers, could materially and adversely affect our business, financial condition and results of operations.

1 unchanged sentence

For the Open Market segment, our four largest brokers each accounted for more than 10% of our gross written premiums, and in the aggregate, they accounted for approximately 70.5% of the segment’s gross premiums written in 2025.

For the Innovations segment, we had two customer that accounted for 37.8% of the segment’s gross premiums written in 2024.

For the Innovations segment, we had six customers that accounted for 53.6% of the segment’s gross premiums written in 2025.

Accordingly, we are exposed to concentration risk for both Open Market and Innovations segments.

10 unchanged sentences

Consequently, we assume a degree of credit risk associated with brokers.

We are also exposed to the credit risk of our cedents and agents, who, pursuant to their contracts with us, may be required to pay us profit commission, additional premiums, reinstatement premiums, and adjustments to ceding commissions over a period of time, which in some cases may extend beyond the initial period of risk coverage.

Return to table of contents

commissions over a period of time, which in some cases may extend beyond the initial period of risk coverage.

Insolvency, liquidity problems, distressed financial condition, or the general effects of an economic recession may increase the risk that our cedents or agents may not pay some or all of their obligations to us.

1 unchanged sentence

While we generally seek to mitigate this risk through, among other things, collateral agreements, funds withheld, corporate guarantees, and the right to offset receivables against any losses payable, an increased inability of customers to fulfill their obligations to us could have an adverse effect on our financial condition and results of operations.

Our reinsurance balances receivable from brokers and cedents at December 31, 2024 totaled $704.5 million, which included premiums, ceding commissions receivable, and funds at Lloyd’s, a majority of which are not collateralized (see Part II, Item 8.

Our reinsurance balances receivable from brokers and cedents at December 31, 2025 totaled $664.4 million, which included premiums, funds withheld balances (including FAL), and profit commission receivable, a majority of which are not collateralized (see Part II, Item 8.

“ Commitments and Contingencies ” to the consolidated financial statements).

3 unchanged sentences

As part of our risk management, from time to time, we seek to purchase reinsurance for certain liabilities we reinsure to mitigate the effect of a potential concentration of losses upon our financial condition.

At December 31, 2024, total loss recoverables were $85.8 million, a majority of which are not collateralized (see Part II, Item 8.

Note 8 “ Retrocession ” to the

Return to table of contents

consolidated financial statements).

At December 31, 2025, total loss recoverables were $81.4 million, a majority of which were from highly-rated reinsurers and not collateralized (see Part II, Item 8.

Note 9 “ Retrocession ” to the consolidated financial statements).

The insolvency or inability or refusal of a retrocessionaire to make payments under the terms of its agreement with us could have an adverse effect on us because our obligations to our clients would remain.

11 unchanged sentences

Business - Regulations ”, we are required to provide letters of credit or collateral to jurisdictions in which we are not licensed or admitted as a reinsurer.

In addition to the CIBC LOC facility entered in late 2023, we expanded the available letters of credit facilities by adding the Uncommitted HSBC LC Facility and the Uncommitted Citibank LC Facility in late 2024.

(see Note 16 “ Commitments and Contingencies - Letters of Credit and Trusts ” of the consolidated financial statements).

Neither the Uncommitted Citibank LC Facility nor the Uncommitted HSBC LC Facility are a committed facility, which means Citibank and HSBC can decide not to issue the LC under the respective facility when we attempt to draw upon it.

In addition, we cannot assure you that we will be able to obtain additional credit facilities in the future on favorable terms or at all.

In addition to the CIBC LC facility entered in late 2023, we expanded the available letters of credit facilities by adding the Uncommitted HSBC LC Facility and the Uncommitted Citibank LC Facility in late 2024 and the Citibank FAL Facility in 2025 (see Note 10 “ Debt and Credit Facilities ” of the consolidated financial statements).

The Uncommitted Citibank LC Facility, Uncommitted HSBC LC Facility and Citibank FAL Facility are not committed facilities, which means Citibank and HSBC can decide not to issue the LC under the respective facility when we attempt to draw upon it.

In addition, we cannot assure you that we will be able to increase existing credit facilities or add additional credit facilities in the future on favorable terms or at all.

Return to table of contents

If we lose or are unable to retain or implement succession plans for our senior management and other key personnel, our ability to implement our business strategy could be delayed or hindered, which, in turn, could materially and adversely affect our business, financial condition and results of operations.

4 unchanged sentences

Our ability to implement our business strategy could be adversely affected by Cayman Islands employment restrictions.

Under Cayman Islands law, persons who are not Caymanian, do not possess Caymanian status, or are not otherwise entitled to reside and work in the Cayman Islands pursuant to provisions of the Immigration Act (as amended) of the Cayman Islands, which we refer to as the Immigration Act, may not engage in any gainful occupation in the Cayman Islands without an appropriate governmental work permit.

Such a work permit may be granted or extended on a continuous basis for a maximum period of nine years (after having been legally and ordinarily resident in the Cayman Islands for a period of eight years a person may apply for permanent residence in accordance with the provisions of the Immigration Act) upon showing that, after proper public advertisement, no Caymanian or person of Caymanian status, or other person legally and ordinarily resident in the Cayman Islands who meets the minimum standards for the advertised position is available.

The failure of these work permits to be granted or extended could prevent us from continuing to implement our business strategy.

Return to table of contents

Compliance with Cayman Islands’ immigration requirements may adversely impact a company’s ability to meet its business goals.

Under Cayman Islands law, specifically the Immigration (Transition) Act (as amended), no person may work in the Islands unless they are Caymanian, a permanent resident with the right to work (including a person married to, or in a civil partnership with, a Caymanian), the holder of a 25-year Residency Certificate that affords the right to work, or a work permit.

It is a criminal offence to work or to employ someone without such authorisation.

Work permits are the most common form of employment authorisation for non-Caymanian workers.

They are generally granted for periods of one to three years at a time, though the maximum length of time a worker may be granted work permits is nine years, after which they must leave the Islands for at least one year.

All work permit holders who have resided legally in Cayman Islands for a continuous period of eight years have however the right to apply for permanent residence with the right to work, though if unsuccessful, must leave the Islands for at least one year.

Approval of work permits cannot be guaranteed:

the employing company must first demonstrate before applying for a work permit, and before each subsequent renewal application, by way of advertising the position on a government jobs portal for fourteen days, that there is no qualified Caymanian or permanent resident available to fill the position.

If it is considered that there is such a person available, the application will be refused.

Further uncertainty is created by processing times for full work permit applications.

Reforms to immigration policy approved by Parliament in December 2025, and which are expected to come into effect later in 2026, aim to prioritize Caymanian employment, tighten employment mobility for foreign workers, and restructure aspects of the work permit system to enhance oversight and accountability.

For businesses, this could mean higher compliance obligations, increased work permit-related costs, reduced flexibility in hiring and transferring employees from other jurisdictions, and longer processing times, all of which impacts strategic planning and business certainty.

We may face risks arising from future strategic transactions such as acquisitions, dispositions, mergers, or joint ventures.

12 unchanged sentences

or assume businesses with internal control deficiencies.

Risk-mitigating provisions that we put in place in the course of negotiating and executing these transactions, such as due diligence efforts and indemnification provisions, may not be sufficient to fully address these risks and contingencies.

Risk-mitigating provisions that we put in place in the course of

Return to table of contents

negotiating and executing these transactions, such as due diligence efforts and indemnification provisions, may not be sufficient to fully address these risks and contingencies.

Non-compliance with laws, regulations, and taxation regarding transactions with international counterparties may adversely affect our business.

24 unchanged sentences

Any such suspension or revocation of our license would negatively impact our reputation in the (re)insurance marketplace, could have a material adverse effect on any potential license application and would materially and adversely affect our business, financial condition and results of operations.

Return to table of contents

CIMA and the CBI may take a number of actions, including suspending or revoking a reinsurance license whenever the regulatory body believes that a licensee is or may become unable to meet its financial obligations, is carrying on business in a manner likely to be detrimental to the public interest or the interest of its creditors or policyholders, has contravened the terms of the Act, or has otherwise behaved in such a manner so as to cause such regulatory body to call into question the licensee’s fitness to conduct regulated activity.

Further, based on statutes, regulations, and policies in their respective jurisdictions, CIMA and CBI may suspend or revoke our licenses if certain events occur, including without limitation:

Return to table of contents

● we cease to carry on reinsurance business;

21 unchanged sentences

These restrictions could adversely impact the Company.

Return to table of contents

We are subject to the risk of possibly becoming an investment company under U.S.

3 unchanged sentences

As we hold ourselves out as a global specialty property and casualty reinsurer and we do not propose to engage primarily in the business of investing or trading in securities, we believe the exemption applies.

Return to table of contents

Accordingly, we do not believe that we are, or are likely to become in the future, an investment company under the Investment Company Act.

26 unchanged sentences

Failure to comply with, or to obtain desired authorizations and/or exemptions under, any applicable laws could result in restrictions on our ability to do business or undertake activities that are regulated in one or more of the jurisdictions in which we operate and could subject us to fines and other sanctions.

The MAA includes amendments that provide for a specific administrative fines framework whereby CIMA has been granted the power to issue monetary penalties of up to 1 million Cayman Islands Dollars for a very serious breach.

Return to table of contents

MAA includes amendments that provide for a specific administrative fines framework whereby CIMA has been granted the power to issue monetary penalties of up to 1 million Cayman Islands Dollars for a very serious breach.

In addition, governmental authorities worldwide have become increasingly interested in potential risks posed by the insurance industry as a whole, and to the commercial and financial systems in general.

2 unchanged sentences

There are differences between Cayman Islands corporate law and Delaware corporate law with respect to interested party transactions, which may benefit certain of our shareholders at the expense of other shareholders.

As a matter of Cayman Islands law, a director of a Cayman Islands company is in the position of a fiduciary with respect to the company and therefore it is considered that they owe certain duties to the company, including the following:

As a matter of Cayman Islands law, a director of a Cayman Islands company is in the position of a fiduciary with respect to the company and therefore they owe certain duties to the company, including the following:

a duty to act in good faith and in what they consider to be in the best interests of the company;

48 unchanged sentences

Results for the Solasglas investment portfolio could differ from those of other funds managed by DME Advisors and its affiliates due to restrictions imposed by our investment guidelines and other factors.

Return to table of contents

Potential conflicts of interest with DME Advisors and its affiliates may exist that could adversely affect us.

4 unchanged sentences

Accordingly, his involvement as a member of the Boards of Directors of Greenlight Capital Re and Greenlight Re may lead to a conflict of interest.

Return to table of contents

DME Advisors and its affiliates may also manage accounts whose advisory fee schedules, investment objectives, and policies differ from those of Solasglas, which may cause DME Advisors and its affiliates to effect trading in one account that may have an adverse effect on another account, including Solasglas.

14 unchanged sentences

These performance compensation arrangements may incentivize DME Advisors to engage in transactions that focus on the potential for short-term gains rather than long-term growth or that are particularly risky or speculative.

Return to table of contents

DME Advisors’ representatives’ service on boards and committees may place trading restrictions on our investments and may subject us to indemnification liability.

7 unchanged sentences

Issuers or borrowers whose securities or debt Solasglas holds, customers, reinsurers, clearing agents, exchanges, clearing houses, and other financial intermediaries and guarantors may default on their obligations to us and/or Solasglas due to bankruptcy, insolvency, lack of liquidity, adverse economic conditions, operational failure, fraud or other reasons.

Return to table of contents

defaults could have a significant and negative effect on us and/or Solasglas and, correspondingly, our investment portfolio and our results of operations, financial condition, and cash flows.

Such defaults could have a significant and negative effect on us and/or Solasglas and, correspondingly, our investment portfolio and our results of operations, financial condition, and cash flows.

Solasglas effectuates short sales that subject our capital accounts to material and adverse loss potential.

16 unchanged sentences

In the event of the counterparty’s default, Solasglas will generally only rank as an unsecured creditor and risk the loss of all or a portion of the amounts Solasglas is contractually entitled to receive.

Return to table of contents

Risks Relating to Our Innovations Strategy

1 unchanged sentence

Additionally, we have a material concentration in our top five holdings at December 31, 2025.

Our Innovations investments include private investments and unlisted equities in early-stage or start-up entities for which no active market may exist.

Our Innovations investments include investments in private equities for which no active market may exist.

We carry these investments on our consolidated balance sheets at cost, less impairment, plus or minus observable price changes (see “ Critical Accounting Estimates - “Investments” under “Part II, Item 8.

6 unchanged sentences

Any of the foregoing could result in a decline in our investment performance and capital resources and, accordingly, could materially and adversely affect our financial results and results of operations.

Refer to “Part II, Item 7.

Management’s Discussion and Analysis of Financial Condition and Results of Operations - Innovations Segment ” for total impairment charge in 2025.

Our Innovations investments carry higher risks due to illiquidity.

2 unchanged sentences

As such, there is a high liquidity risk due to the lack of active markets.

Return to table of contents

not be able to sell timely, or at all, illiquid holdings of early-stage companies facing significant challenges operationally and financially subsequent to our initial investment (see below “ Investments in privately held early-stage companies involve significant risks ”).

We may not be able to sell timely, or at all, illiquid holdings of early-stage companies facing significant challenges operationally and financially subsequent to our initial investment (see below “Investments in privately held early-stage companies involve significant risks” ).

Accordingly, this could materially and adversely affect our business, financial condition and results of operations.

6 unchanged sentences

Investments in privately held early-stage companies involve a number of significant risks, including the following:

Return to table of contents

● these companies may have limited financial resources and may be unable to meet their operating obligations;

21 unchanged sentences

After repaying such holders, the entity may not have any remaining assets for repaying its obligation to us.

In the case of securities

Return to table of contents

ranking equally with our investments, we would have to share on an equal basis any distributions with other security holders in the event of an insolvency, liquidation, dissolution, reorganization or bankruptcy of the relevant entity.

In the case of securities ranking equally with our investments, we would have to share on an equal basis any distributions with other security holders in the event of an insolvency, liquidation, dissolution, reorganization or bankruptcy of the relevant entity.

As a minority equity investor, we are often not in a position to influence the entity, and other equity holders and management of such entity may make decisions that could decrease the value of our investment in such entity.

2 unchanged sentences

As a result, an entity may make decisions that could decrease the value of our investment.

Return to table of contents

Our Innovations investments are in entities that may be highly leveraged.

5 unchanged sentences

(1) increase or maintain in whole or in part our equity ownership percentage;

(2) exercise warrants, options or convertible securities that we acquired in the original or subsequent financing or (3) attempt to preserve or enhance the value of our investment.

(2) exercise warrants, options or convertible securities that we acquired in the original or subsequent financing;

(3) protect our liquidation preference rights or (4) attempt to preserve or enhance the value of our investment.

We may elect not to make follow-on investments, be constrained in our ability to employ available funds, or otherwise lack sufficient funds to make those investments.

9 unchanged sentences

Our level of debt may have an adverse impact on our liquidity, restrict our current and future operations, particularly our ability to respond to business opportunities, and increase our vulnerability to adverse economic and industry conditions.

At December 31, 2024, we had $60.7 million of debt outstanding that matures on August 1, 2026.

Our level of debt and the provisions of such debt could have significant consequences, which include, but are not limited to, the following:

While we had $4.7 million of debt outstanding at December 31, 2025, we have the ability to borrow up to $50 million under the Revolving Credit Facility (see Note 10 “ Debt and Credit Facilities ” of our consolidated financial statements).

The level of debt and the provisions of such debt could have significant consequences, which include, but are not limited to, the following:

● limit our ability to obtain additional financing in the future for working capital, capital expenditures, acquisitions, or other general corporate purposes;

• require a substantial portion of our cash flows to be dedicated to debt service payments instead of other purposes, thereby reducing the amount of cash flows available for working capital, capital expenditures,

Return to table of contents

acquisitions, and other general corporate purposes;

● require a substantial portion of our cash flows to be dedicated to debt service payments instead of other purposes, thereby reducing the amount of cash flows available for working capital, capital expenditures, acquisitions, and other general corporate purposes;

● discourage an acquisition of us by a third party;

2 unchanged sentences

We cannot assure you that we will be able to refinance our indebtedness debt upon maturity on acceptable terms or at all.

Return to table of contents

A shareholder may be required to sell its ordinary shares.

43 unchanged sentences

A shareholder may have a direct right of action against us where the individual rights of that shareholder have been infringed or are about to be infringed, and may have a direct right of action against us in circumstances where our Board of Directors exercise their powers for an improper purpose (or are about to exercise their powers for an improper purpose).

Subject to limited exceptions, under Cayman Islands law, a minority shareholder may not bring a derivative action against our Board of Directors.

Return to table of contents

Subject to limited exceptions, under Cayman Islands law, a minority shareholder may not bring a derivative action against our Board of Directors.

We do not intend to pay dividends on our ordinary shares and, consequently, your ability to achieve a return on your investment will depend on appreciation in the price of our common shares.

6 unchanged sentences

Risks Relating to Taxation

We may become subject to taxation in the Cayman Islands, which would negatively affect our results.

The Government of the Cayman Islands, does not, under existing legislation, impose any income, corporate or capital gains tax, estate duty, inheritance tax, gift tax or withholding tax upon Greenlight Re, GLRE or Viridis Re.

Each of Greenlight Re, GLRE and Viridis Re have applied for and received an undertaking from the Governor-in-Cabinet of the Cayman Islands that, in accordance with Section 6 of the Tax Concessions Act (as revised) of the Cayman Islands, for a period of 20 years from the date of the undertaking (until December 2043 in the case of Viridis Re and until January 2045 in the case of Greenlight Re and GLRE), each company will be exempt from any law which is enacted in the Cayman Islands imposing any tax on profits, income, gains or appreciations of Greenlight Re, GLRE or Viridis Re or their operations.

We cannot be assured that after the expiration of the respective certificates that we would not be subject to any such tax.

As the law currently stands, upon the expiration of the current exemption, it will be possible for us to apply for another 20 year exemption for each of Greenlight Re, GLRE and Viridis Re, which we plan to do.

If we were to become subject to taxation in the Cayman Islands, our financial condition and results of operations could be materially and adversely affected.

We may be subject to United States federal income taxation.

14 unchanged sentences

A qualifying insurance corporation is an insurance company which has applicable insurance liabilities, as reported on its annual financial statement, exceeding 25% of its total assets.

Return to table of contents

insurance liabilities means, with respect to our property and casualty reinsurance business, reserves for loss and loss adjustment expenses, and excluding unearned premium reserves.

Applicable insurance liabilities means, with respect to our property and casualty reinsurance business, reserves for loss and loss adjustment expenses, and excluding unearned premium reserves.

The exception for insurance companies is intended to ensure that a qualifying insurance entity’s income is not treated as passive income, except to the extent such income is attributable to financial reserves in excess of the reasonable needs of the insurance business.

We intend to operate our business with financial reserves and applicable insurance liabilities at levels that should not cause us to be deemed PFICs, although we cannot provide definitive assurance that we will be successful in structuring our operations to meet such levels nor can we ensure that the IRS will not successfully challenge our status.

We intend to operate our business with financial reserves and

Return to table of contents

applicable insurance liabilities at levels that should not cause us to be deemed PFICs, although we cannot provide definitive assurance that we will be successful in structuring our operations to meet such levels nor can we ensure that the IRS will not successfully challenge our status.

If we are unable to underwrite sufficient amount of risks and maintain a sufficient amount of applicable insurance liabilities, any of Greenlight Capital Re, Greenlight Re, Viridis Re or GRIL may become a PFIC.

24 unchanged sentences

In addition, the shareholder will be required to comply with certain reporting requirements, regardless of the amount of shares owned by the direct or indirect United States shareholder.

Although not free from doubt, we believe these rules should not apply to dispositions of ordinary shares because Greenlight Capital Re is not directly engaged in the insurance business and because proposed United States Treasury regulations applicable to this situation appear to apply only in the case of

Return to table of contents

shares of corporations that are directly engaged in the insurance business.

of corporations that are directly engaged in the insurance business.

We cannot provide assurance, however, that the IRS will interpret the proposed regulations in this manner or that the proposed regulations will not be promulgated in final form in a manner that would cause these rules to apply to dispositions of ordinary shares.

25 unchanged sentences

The tax laws and interpretations regarding whether an entity is engaged in a United States trade or business, is a CFC, has related party insurance income or is a PFIC are subject to change, possibly on a retroactive basis.

New regulations or pronouncements interpreting or clarifying such rules may be forthcoming from the IRS.

We are not able to predict if, when or in what form such guidance will be provided and whether such guidance will have a retroactive effect.

Return to table of contents

regulations or pronouncements interpreting or clarifying such rules may be forthcoming from the IRS.

We are not able to predict if, when or in what form such guidance will be provided and whether such guidance will have a retroactive effect.

The TCJA may have a detrimental effect on the Company and its assets.

14 unchanged sentences

There are no immediate regulatory, tax, trade or other legal impacts to the Company, but we are not able to predict any future EU actions.

On October 8, 2021, the OECD announced an accord endorsing and providing an implementation plan for a global minimum tax rate of at least 15% for large multinational corporations on a jurisdiction-by-jurisdiction basis, known as “Pillar Two.” While the Company is not currently aware of any definitive actions being taken in the Cayman Islands to implement a minimum tax, in Ireland, a bill implementing Pillar Two was signed into law on December 18, 2023, including an “undertaxed profit rule” that will come into effect in 2025.

In the United Kingdom, legislation implementing an “undertaxed profit rule” under Pillar Two with effect as of 2025 was included in the Finance Bill 2024-2025.

On October 8, 2021, the OECD announced an accord endorsing and providing an implementation plan for a global minimum tax rate of at least 15% for large multinational corporations on a jurisdiction-by-jurisdiction basis, known as “Pillar Two.” While the Company is not currently aware of any definitive actions being taken in the Cayman Islands to implement a minimum tax, Ireland and the United Kingdom have enacted legislation implementing Pillar Two, including an “undertaxed profit rule” that came into effect in both countries in 2025.

If the Cayman Islands does not adopt a minimum tax, the undertaxed profits rule may allow Irish or United Kingdom tax authorities to collect more tax from our Irish or United Kingdom companies.

The global minimum tax rules implemented in different jurisdictions (including the undertaxed profit rule) would apply to overseas profits of multinational firms with annual revenue of more than €750 million.

While these global minimum tax rules are not expected to apply to the Company as currently proposed and being implemented in jurisdictions applicable to the Company’s operations, due to the Company’s revenues currently falling below the proposed annual revenue threshold, adjustments to the threshold or continued growth of the Company’s revenues could impact the Company in future periods.

Further, even if the Company did eventually meet the applicable threshold due to continued revenue growth or otherwise, then given the size and structure of the Company, the Company may be eligible to meet an initial phase transitional safe harbor provided for in the model rules of the accord (and incorporated into the Irish and UK legislation), which provides relief from taxation under the accord for a period of up to five additional years after the Company comes within the scope of the rules.

While these global minimum tax rules are not expected to apply to the Company in 2026 as currently proposed and being implemented in jurisdictions applicable to the Company’s operations, due to the Company’s revenues currently falling below the applicable revenue threshold test (that tests meeting the annual €750 million revenue threshold for at least two of the four fiscal years immediately preceding the tested fiscal year), adjustments to the threshold or continued growth of the Company’s revenues could impact the Company’s Pillar Two position in future periods beyond 2026.

Further, even if the Company did eventually meet the applicable

Return to table of contents

threshold due to meeting the revenue test in at least two fiscal years within a four-year period, then given the size and structure of the Company, the Company may be eligible to meet an initial phase transitional safe harbor provided for in the model rules of the accord (and incorporated into the Irish and UK legislation), which provides relief from taxation under the undertaxed profit rule for a period of up to five additional years after the Company comes within the scope of the rules.

We may become subject to taxation in the Cayman Islands, which would negatively affect our results.

We cannot be assured that after the expiration of the respective certificates that we would not be subject to any such tax.

If we were to become subject to taxation in the Cayman Islands, our financial condition and results of operations could be materially and adversely affected.

Compared sentence by sentence after normalising whitespace, quotation marks, case and digits, so re-formatting and restated figures do not read as changed language. Wording changes appear as one removal and one addition. The current filing and the prior one are authoritative.

What changed 10-K

Item 1A. Risk Factors