OCTAVE SPECIALTY GROUP INC

Consolidated Results

A summary of our financial results is shown below:

(1) Excludes $2,058 of commission income, $123 of policy acquisition costs and $1,622 of commission expense related to intersegment activities, which are eliminated for consolidation, for the three and six months ended June 30, 2026. Refer to Note 2. Segment Information for additional information.

Octave's results for the three and six months ended June 30, 2026, compared to the three and six months ended June 30, 2025, were materially impacted by the following:

•Transactions within the ID segment

◦Effective October 31, 2025, Octave acquired 100% of ArmadaCare. In connection with the acquisition, Octave borrowed $120,000 under a new bank funded credit facility. On April 1, 2026, Octave borrowed an additional $40,000 under the credit facility in connection with the acquisition of an additional 10% of Octave Ventures. Refer to Note 9. Debt of the Notes to Consolidated Financial Statements included in this Quarterly Report on Form 10-Q for further detail on these credit facility borrowings.

◦Effective September 1, 2025, Octave exercised its option to convert its $3,500 convertible note investment in a start-up MGA, resulting in an approximate 74% ownership interest and inclusion of the MGA in consolidated results.

◦Effective March 31, 2026, the minority owners of Octave Ventures exercised their option to put a portion of their remaining interest, representing 10% of Octave Ventures, to OSG.

•The sale of AAC

◦On September 29, 2025, Octave completed the sale of its legacy financial guarantee business. AAC's results, including Octave's loss on the sale of AAC are reported within discontinued operations. Refer to Note 3. 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 and six months ended June 30, 2025.

•Repayment of Debt

◦On September 29, 2025, Octave repaid all of the outstanding debt used to acquire its original 60% interest in Octave Ventures, amounting to $150,000, using the proceeds from the sale of AAC. 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 and six months ended June 30, 2026 and 2025.

Gross Premiums Written Gross premiums written decreased $1,545 and increased $15,256 for the three and six months ended June 30, 2026, respectively, compared to the same periods of the prior year.

The decrease for the three months ended June 30, 2026, related mostly to the shift in business mix and timing of premiums written compared to the three months ended June 30, 2025. The increase for the six months ended June 30, 2026, is primarily driven by growth in new and existing programs, partially offset by a reduction in participation of an assumed reinsurance transaction and the shift in the business mix.

Net Premiums Written Net premiums written increased $7,935 and $22,379 for the three and six months ended June 30, 2026, respectively, compared to the same periods of the prior year.

The increase is primarily driven by growth in new and existing programs, including certain programs with high retention ratios partially offset by a reduction in the participation rate on an assumed reinsurance program and the shift in the business mix.

Net Premiums Earned Net premiums earned increased $5,546 and $9,869 for the three and six months ended June 30, 2026, respectively, compared to the same periods of 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 shift in the business mix.

Commission Income and Commission Expense Commission income increased$19,406 and $50,813 for the three and six months ended June 30, 2026, respectively, as compared to the same period in the prior year.

The increase was primarily due to strong ID organic growth as well as the acquisition of ArmadaCare in October of 2025. Commission income included profit commissions (based on underwriting performance) of $5,620 and $2,266 for the three months ended June 30, 2026 and 2025, respectively, and $11,808 and $6,957 for the six months ended June 30, 2026 and 2025, respectively.

Commission expense increased $1,105 and $4,745 for the three and six months ended June 30, 2026, respectively, as compared to the same periods of the prior year. The lower commission expense relative to commission income in 2026 relative to 2025 is related primarily to the ArmadaCare acquisition partially offset by a change in gross-to-net reporting for one MGA. ArmadaCare produces a majority of their business internally and has a lower external broker commission model. 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 $3,293 and $3,497 for the three months ended June 30, 2026 and 2025, respectively, and $6,937 and $7,149 for the six months ended June 30, 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 and six months ended June 30, 2026 are slightly lower versus the three and six months ended June 30, 2025, due to the shift in net retention levels partially offset by growth in 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$732 and $1,192 for the three and six months ended June 30, 2026, respectively, compared to

the same periods of 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$1,441 and $5,839 for the three and six months ended June 30, 2026, respectively, compared to the same periods of the prior year. Servicing and other fees include revenues earned for providing operational and administrative services to our Lloyd's syndicates, managed by Statera, our Lloyd's Managing Agent; program administration; policy; and set-up and renewal fees.

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 June 30, 2026 and 2025, of $435 and $(2,146), respectively, were driven primarily by foreign exchange gains (losses) on non-functional currency operations of Octave Ventures, net of the offsetting effects of FX forward contracts. Other revenues for the six months ended June 30, 2026 and 2025, of $1,065 and $(3,270), respectively, were driven primarily 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 $2,368 and $11,551 for the three and six months ended June 30, 2026, compared to the same periods of the prior year.

The higher loss and loss adjustment expenses for the three months ended June 30, 2026, is primarily due to the growth in our P&C program business. The higher loss and loss adjustment expenses for the six months ended June 30, 2026, is due to the growth in our P&C program business and prior period development primarily related to (i) $2,125 of net losses and $5,787 of LAE (legal expenses) from the first quarter 2026 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 periods presented.

The increaseof $11,474 and 25,631 in compensation expenses during the three and six months ended June 30, 2026, respectively, was driven primarily by higher compensation costs due to (i) the acquisition of ArmadaCare and launch of new business, (ii) changes in performance factors and timing of long-

term incentive grants in 2025, (iii) the launch of our Lloyd's managing agency, and (iv) severance and related costs.

The decrease of $600 and $132 in non-compensation G&A expenses for the three and six months ended June 30, 2026, respectively, was driven primarily by lower premium related taxes and prior year costs associated with the sale of AAC, partially offset by the acquisition of ArmadaCare, launch of new business, and higher expenses related to data, AI and related systems.

Intangible Amortization and Depreciation. The increase in intangible amortization and depreciation of $2,523 and $5,561 for the three and six months ended June 30, 2026, respectively, as compared to the same periods of the prior year, was primarily due to the ArmadaCare acquisition.

Interest Expense The decrease in interest expense of $2,796 and $6,160 for the three and six months ended June 30, 2026, respectively, as compared to the same periods of the prior year, was due primarily to a lower loan balance and a reduced interest rate. Prior year interest expense also includes duration fees and extension fees.

Provision (Benefit) for Income Taxes The provision (benefit) for income taxes primarily relates to international operations and was $485 for the three months ended June 30, 2026, compared to $(2,172) for the three months ended June 30, 2025. The provision (benefit) for income taxes was $4 for the six months ended June 30, 2026 compared to $(2,789) for the six months ended June 30, 2025. The tax benefit recognized in the current year includes current tax expense associated with our UK operations, partially offset by the deferred tax benefits related to the recognition of UK deferred tax assets and amortization of finite-lived intangible assets.

Results of Operations by Segment

(1) Includes $7,700 premiums placed, as well as $2,058 of commission income and $1,622 of commission expense related to intersegment activities for the three and six months ended June 30, 2026. Refer to Note 2. Segment Information for additional information.

(2) 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 primarily 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.

For the three months ended June 30, 2026, the increase in premiums placed was driven by the acquisition of ArmadaCare and organic growth. The growth in premiums written, as well as the mix of business written, drove an increase in commission income and commission expense of 71% and 37%, respectively. For the six months ended June 30, 2026, commission income and commission expense increased 79% and 36%, respectively, driven by the same factors as those driving the increase for the three months ended June 30, 2026.

Commission income included profit commissions (based on underwriting performance) of $5,620 and $2,266 for the three months ended June 30, 2026 and 2025, respectively, and $11,808 and $6,957 for the six months ended June 30, 2026 and 2025, respectively. Excluding profit commissions, commission expense was approximately 21% and 26% of commission income for the three months ended June 30, 2026 and 2025, respectively, and

22% and 29% for the six months ended June 30, 2026 and 2025, respectively.

The increase in G&A expenses of $13,461 and $28,616 for the three and six months ended June 30, 2026, respectively, was primarily due to the acquisition of ArmadaCare, the launch of new MGAs and the Managing Agency business and organic staff increases.

ID pretax income (loss) for the three months ended June 30, 2026, was $(846) compared to a loss of $(10,173) for the three months ended June 30, 2025. ID pretax income for the six months ended June 30, 2026, was $15,939 compared to a loss of $(12,416) for the six months ended June 30, 2025. The higher pretax income for the three and six months ended June 30, 2026, mostly related to higher net commissions and fees related to the ArmadaCare acquisition and organic growth as well as lower interest expense, offset partially by higher G&A expenses and intangible amortization.

The ID EBITDA increase of $9,189 and $27,923 during the three and six months ended June 30, 2026, respectively, was primarily driven by an increase in commission income due to the Armada acquisition and organic growth.

Our 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. In addition, while our ID business has experienced strong organic growth in 2026, it is important to note that nominal and organic growth rates will fluctuate from period to period due to a number of factors related to our specific businesses as well as macro and industry conditions, including but not limited to the timing and size of new program launches, renewals, market pricing cycles, shifts in capacity availability and risk appetite, and changes in insured exposures.. Furthermore, not all of our ID businesses may grow simultaneously. For example, during the second quarter of 2026 while our ID business produced strong nominal and organic growth rates, certain of our MGAs, such as our property focused MGAs, reduced their underwriting activity resulting in lower commission revenues period over period.

(1)Includes $123 of policy acquisition costs related to intersegment activity for the three and six months ended June 30, 2026. Refer to Note 2. Segment Information for additional information.

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

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

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

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

(6)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-seven programs were authorized to issue policies as of June 30, 2026, including Everspan participating in certain programs as a reinsurer. Everspan continued to build its production levels in 2026 with growth in new and existing programs. Additionally, Everspan's business mix shifted resulting lower loss ratios and a higher net retention ratio. This growth and business mix shift has resulted in an increase in net premiums written, net premiums earned, losses and loss expenses incurred, policy acquisition costs in the three and six months ended June 30, 2026, compared to the same periods of the prior year. Gross premiums decreased in the three months ended June 30, 2026 and increased in the six months ended June 30, 2026. The decrease in the three months ended June 30, 2026, is primarily due to the timing differences related to premium production for one

significant program and a reduction in participation percentage of an assumed reinsurance program whereas the increase in the six months ended June 30, 2026 is due to growth in new and existing programs. Although losses and loss expenses have increased, the shift in Everspan's net business 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 June 30, 2026, was driven by a shift in business mix. The change in the Loss and LAE ratio during the six months ended June 30, 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 shift in business mix. The six months ended June 30, 2026, contained prior years loss strengthening equating to 21.7% of which 19.0% relates this settlement. The remaining amount primarily relates to an excess liability claim and ULAE. The three and six months ended June 30, 2025, contained minimal prior years loss strengthening equating to 1.0% and 1.0%, respectively, driven primarily by excess liability loss experience.

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.

For the three and six months ended June 30, 2026, compared to the same prior year periods, acquisition costs were affected by sliding scale commission arrangements with program partners. Sliding scale commissions increased the Specialty Property and Casualty Insurance segment's expense ratio by 1.0% and 1.2% during the three and six months ended June 30, 2026, respectively. During the three and six months ended June 30, 2025, there was a benefit from sliding scale commission

arrangements with program partners resulting in a decrease to acquisition costs that reduced the expense ratio by 2.6% and 1.3%, 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 decrease in G&A expenses of $763 for the three months ended June 30, 2026 was primarily due to a decrease in premium taxes. The increase of $1,437 for the six months ended June 30, 2026 was primarily due to severance and related costs; partially offset by a premium tax true-up in the prior year.

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 $232 and $526 for the three months ended June 30, 2026 and 2025, respectively, and $577 and $1,113 for the six months ended June 30, 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. The decline in revenue for both periods is primarily due to lower average invested assets as a result of 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.

The decrease in G&A expenses of $1,825 for the three months ended June 30, 2026, and $4,554 for the six months ended June 30, 2026, were mainly due to cost reduction initiatives, including lower premise expenses following our NY corporate office re-location and reduced acquisition-related costs.