OCTAVE SPECIALTY GROUP INC

Consolidated Results

A summary of our financial results is shown below:

Octave's results for the three months ended March 31, 2026 compared to the three months ended March 31, 2025, were impacted by the following:

•Acquisitions within the ID segment have had a significant impact on the comparability of results between 2026 and 2025.

•Effective October 31, 2025, Octave acquired 100% of ArmadaCare.

•Effective September 1, 2025, Octave exercised its option to convert its $3,500 convertible note investment in Pivix and now owns approximately 74%.

•On September 29, 2025, Octave completed the sale of AAC. AAC's results, including Octave's loss on the sale of AAC are reported within discontinued operations. Refer to Note 4.

Discontinued Operations of the Notes to Consolidated Financial Statements included in this Quarterly Report on Form 10-Q and Note 5. Discontinued Operations of the Notes to Consolidated Financial Statements in the Annual Report on Form 10-K for the year ended December 31, 2025, and for further details on the sale and results for the three months ended March 31, 2025. As a result of the sale, Octave repaid all of the outstanding debt used to acquire Octave Ventures, amounting to $150,000, and purchased AAC's co-investment in Octave Ventures of $62 million. Concurrent with the sale, OSG entered into a number of transactions as discussed in the Annual Report on Form 10-K for the year ended December 31, 2025, including transactions intended to lower the long term run-rate of corporate operating expenses.

The following describes the consolidated results of continuing operations of Octave and its subsidiaries for the three months ended March 31, 2026 and 2025.

Gross Premiums Written Gross premiums written increased $16,801 for the three months ended March 31, 2026 compared to the same period in the prior year.

The increase is primarily driven by growth in new and existing programs partially offset by the non-renewal of certain programs.

Net Premiums Written Net premiums written increased $14,445 for the three months ended March 31, 2026 compared to the same period in the prior year.

The increase is primarily driven by growth in new and existing programs, including certain programs with a high retention ratio partially offset by the non-renewal of certain programs.

Net Premiums Earned Net premiums earned increased $4,323 for the three months ended March 31, 2026 compared to the same period in the prior year.

The increase is primarily driven by growth in new and existing programs, including certain programs with a high retention ratio partially offset by the non-renewal of certain programs.

Commission Income and Commission Expense Commission increased $31,407 for the three months ended March 31, 2026 as compared to the same period in the prior year.

The increase was primarily due to organic growth in premiums placed as well as the acquisition of ArmadaCare in October of 2025. Commission income included profit commissions (based on underwriting performance) of $6,188 for the three months ended March 31, 2026, and $4,691 for the three months ended March 31, 2025. The increase for the three months ended March 31, 2026, was primarily driven by increase at Octave Ventures and Xchange Benefits.

Commission expense increased $3,640 for the three months ended March 31, 2026 as compared to the same period of the prior year. Commission expense represented approximately 22% and 32% of commission income for the three months ended March 31, 2026 and 2025, respectively. The decrease in commission expense relative to commission income in 2026

relative to 2025 is related to the Armada acquisition as majority of their business is produced internally and lower external broker commisison model as well as change in gross to net reporting at Octave Ventures. Because third parties are paid commissions to obtain business, the majority of Octave Ventures' commission income is reported net of any distribution and commission expenses, due to the nature of its program agreements. The majority of the ID segment's other MGA/Us report their commission income gross of distribution and commission expenses.

Program Fees Program fee revenues were $3,644 and $3,652 for the three months ended March 31, 2026 and 2025, respectively. Program fee revenues represent the recognition of ceding commissions in excess of direct acquisition costs received from reinsurers and minimum fees received from MGA/Us until related programs reach certain levels of premium ceded. Program fees are charged as a percentage of premiums ceded to reinsurers as a component of total ceding commissions. Program fees for three months ended March 31, 2026 are flat versus the three months ended March 31, 2025, due to growth in existing programs offset by impact of a shift to retained from fronted for certain programs.

Net Investment Income Net investment income consists of interest income, including the net effect of discount accretion and premium amortization, from fixed maturity securities classified as available for sale and net gains (losses) on pooled investment funds that are reported under the equity method. These funds and certain other investments are reported in Other investments on the Consolidated Balance Sheets. For further information about investment funds held, refer to Note 4. Investments of the Notes to Consolidated Financial Statements included this Quarterly Report on Form 10-Q.

Net investment income decreased $460 for the three months ended March 31, 2026 compared to the same period in the prior year due primarily to lower Corporate short-term investment yields and balances following the acquisition of ArmadaCare and lower average Everspan asset balances.

Servicing and Other Fees Servicing and other fees increased $4,398 for the three months ended March 31, 2026. Servicing and other fees include revenues earned for providing operational and administrative services to the Lloyd's syndicates managed by Octave Ventures as well as program administration, health connections, set-up and renewal fees related to ArmadaCare and Pivix.

Other Revenues Other revenues includes (i) net investment gains (losses) on securities sold or called, net of investment impairment charges; (ii) foreign exchange gains (losses) from the ID segment; and (iii) net gains (losses) on derivative contracts including FX forward contracts used to manage currency risk within the ID segment. Other revenues for the three months ended March 31, 2026, of $630 and for the three months ended March 31, 2025, of $(1,124) were driven primarily by by foreign exchange gains and (losses) on non-functional currency operations of Octave Ventures, net of the offsetting effects of FX forward contracts.

Losses and Loss Adjustment Expenses (Benefit)

Loss and loss adjustment expenses incurred increased $9,183 for the three months ended March 31, 2026 compared to the same period in the prior year.

The higher loss and loss adjustment expenses is due to the growth in existing and addition of new programs and prior period development primarily related to (i) $2,125 of net losses and $5,787 of LAE (legal expenses) from the settlement of a potential litigation matter related to an insurance claim, and (ii) slight reserve strengthening on an excess liability program and claim fees.

General and Administrative Expenses (G&A) The following table provides a summary of G&A expenses for the three months ended March 31, 2026 and 2025:

The increase of $14,157 in compensation expenses during the three months ended March 31, 2026, was driven primarily by higher compensation costs due to (i) the acquisitions of ArmadaCare and Pivix, (ii) changes in performance factors and timing of grants in 2025, (iii) expansion of Octave Venture's managing agency, and (iv) acceleration of RSUs & PSUs of terminated employees, and severance.

The increase of $467 in non-compensation G&A expenses for the three months ended March 31, 2026 as compared to the three months ended March 31, 2025, was driven primarily by integration expenses related to the ArmadaCare and Pivix acquisitions and costs associated with the build-out of the Octave Ventures managing agency, partially offset by a reduction in Corporate segment initiatives.

Intangible Amortization and Depreciation. The increase in intangible amortization and depreciation of $3,038 for the three months ended March 31, 2026 as compared to the three months ended March 31, 2025, was primarily due to the ArmadaCare acquisition.

Interest Expense The decrease in interest expense of $3,364 for the three months ended March 31, 2026 as compared to the three months ended March 31, 2025, was due to a lower loan balance, reduced interest rate, and prior year includes duration fees.

Provision for Income Taxes The provision (benefit) for income taxes primarily relates to international operations and was $(481) for the three months ended March 31, 2026 compared to $(617) for the three months ended March 31, 2025. The tax benefit recognized in the current year includes current tax expense associated with Octave Ventures UK operations, partially offset by deferred tax benefit related to the recognition of deferred tax assets generated by Octave Ventures US and amortization of finite-lived intangible assets associated with Octave Ventures UK and US operations.

Results of Operations by Segment

(1) Represents the share of Octave stockholders equity for each subsidiary within the ID segment, including intercompany eliminations.

Octave's ID companies are compensated for their services primarily by commissions paid by insurance carriers for underwriting, structuring and/or administering polices, and in some cases, the managing of claims under an agency agreement. Commission revenues are usually based on a percentage of the premiums placed. In addition, we are eligible to receive profit sharing contingent commissions based on the underwriting results of certain programs underwritten by our MGA/Us. These profit commissions may fluctuate from period to period resulting in some variability in revenue and earnings.

Higher premiums placed were driven by the acquisition of ArmadaCare and organic growth.

For the three months ended March 31, 2026, the increase in premiums placed and changes to the mix of business written led to the growth in commission income and commission expense of 85% and (35.1)%, respectively.

The increase in G&A expenses of $15,154 for the three months ended March 31, 2026 as compared to the three months ended March 31, 2025, was primarily due to the acquisition of ArmadaCare, launch of Pivix as well as increase in staffing for the build out of new businesses at Octave Ventures.

ID pretax income for the three months ended March 31, 2026, was $16,785 compared to a loss of $(2,243) for the three months ended March 31, 2025. The higher pretax income for the three months ended March 31, 2026, compared to the prior year period mostly related to higher Net Commissions and Fees related to the ArmadaCare acquisition and organic growth as well as lower interest expense, partially offset by higher intangible amortization.

The ID EBITDA for the three months ended March 31, 2026, was $30,817 compared to $12,083 for the three months ended March

31, 2025. The increase was primarily driven by an increase in commission income due to acquisitions and organic growth.

ID businesses may experience seasonal impacts on their revenues and net results. For example, our A&H businesses collectively produce the majority of their business in the first quarter of each year resulting in revenue and earnings concentrations in the first quarter. Similar concentrations of production, revenue and earnings also occurs in the fourth quarter, driven by our non-A&H businesses, but generally to a lesser degree. Seasonal impacts on the ID segment, and therefore Octave's results, may increase or decrease and shift over time depending on the relative growth of certain classes of business, impact of acquisitions, impact of de-novo MGAs and market conditions.

(1)Retention ratio is defined as net premiums written divided by gross premiums written.

(2)Loss and LAE ratio is defined as losses and loss expenses incurred divided by net premiums earned.

(3)Expense Ratio is defined as acquisition costs and general and administrative expenses, reduced by program fees divided by net premiums earned.

(4)Combined ratio is defined as Loss and LAE ratio plus Expense Ratio.

(5)Represents Octave stockholders equity in the Specialty Property and Casualty Insurance segment, including intercompany eliminations.

The Specialty Property and Casualty Insurance segment has grown significantly since underwriting its first program in May 2021. Twenty-four programs were authorized to issue policies as of March 31, 2026, including Everspan participating in certain programs as a reinsurer. In 2026, Everspan's continues to see its production levels build with growth in new and existing programs. This growth has resulted in an increase in gross and net premiums written, net premiums earned, losses and loss

expenses incurred, policy acquisition costs and a shift in Everspan's retention ratio in the three months ended March 31, 2026 compared to the three months ended March 31, 2025. Although losses and loss expenses have increased, the shift in Everspan's net portfolio mix has led to an improved loss ratio on active programs.

Consistent with its strategy to generate sustainable and profitable, long-term specialty property and casualty program insurance business with a focus on diverse classes of risks, Everspan may source select programs as a reinsurer. Accessing programs as a reinsurer provides Everspan the ability to diversify its risk profile (temporarily or long-term), efficiently manage its exposure limits and underwrite programs in a cost efficient manner, amongst other benefits. Everspan may participate as a reinsurer on up to 30% of a program, which is in line with its strategy to retain up to 30% per program. Participation as a reinsurer will affect the retention ratio as Everspan's portion of assumed premiums is reflected fully in both Gross and Net premiums written.

The change in the Loss and LAE ratio during the three months ended March 31, 2026, was driven by $2,125 of net losses and $5,787 of LAE (legal expenses) from the settlement of a potential litigation matter related to an insurance claim, partially offset by a shirt in business mix. The three months ended March 31, 2026, contained prior years loss strengthening equating to 44.5% of which 39.6% relates this settlement. The remaining amount primarily relates to an excess liability claim and ULAE. The three months ended March 31, 2025, contained minimal prior years loss strengthening equating to 1.1%.

Loss and loss adjustment expenses incurred, and Everspan's associated Loss and LAE ratio, may be adversely impacted by economic and social inflation. The impact of inflation on ultimate loss reserves is difficult to estimate, particularly in light of recent disruptions to the judicial system, supply chains and labor markets. Going forward, we may not be able to offset the impact of inflation on our loss costs with sufficient price increases. The estimation of loss reserves may also be more difficult during extreme events, such as a pandemic, or during the persistence of volatile or uncertain economic conditions, due to, amongst other reasons, unexpected changes in behavior of judiciaries, claimants and policyholders, including fraudulent reporting of exposures and/or losses. Due to the inherent uncertainty underlying loss reserve estimates, the final resolution of the estimated liability for loss and loss adjustment expenses will likely be higher or lower than the related loss reserves at the reporting date. In addition, our estimate of losses and loss expenses may change. These additional liabilities or increases in estimates, or a range of either, could vary significantly from period to period.

In addition to the increase in the Loss and LAE ratio for the three months ended March 31, 2026, compared to the three months ended March 31, 2025, there was a charge to acquisition costs resulting from sliding scale commission arrangements with program partners. Such charge increased the Specialty Property and Casualty Insurance segment's expense ratio by 1.4% and —% for the three months ended March 31, 2026 and 2025, respectively. Certain Everspan programs were structured to include sliding scale commission arrangements within a loss ratio range. These sliding scale arrangements help mitigate losses, protect underwriting results and limit earnings volatility.

The increase in G&A expenses of $2,201 for the three months ended March 31, 2026 as compared to the three months ended March 31, 2025, was primarily due to severance and accelerated incentive compensation in addition to higher premium taxes driven by increased premiums written.

Corporate

Corporate consists of our holding company and shared services operations ("Corporate"). Corporate provides financial, legal, technological and human resources to Octave's two segments and is responsible for the function of OSG as a publicly-traded company.

Corporate revenues totaled $345 and $587 for the three months ended March 31, 2026 and 2025, respectively. Corporate revenue is mostly generated from investment of OSG's liquid resources and investment results from its previously made strategic investments, including certain minority investments in MGA/Us and an insurtech fund. Investment revenues comprised of net investment income and net investment gains (losses), including impairments, were $398 and $597 for the three months ended March 31, 2026 and 2025, respectively. The decline is primarily due to lower average invested assets due to the use of funds for the acquisition of ArmadaCare and share repurchases in the fourth quarter of 2025, as well as lower yields on short-term invested assets in 2026.

Corporate expenses were $11,919 and $14,650 for the three months ended March 31, 2026 and 2025 respectively. The decrease is mainly due to cost reduction initiatives, including lower premise expenses following the corporate office re-location, and reduced acquisition-related costs.