OCTAVE SPECIALTY GROUP INC

Consolidated Results

A summary of our financial results is shown below:

(1) Excludes $3,270 and $5,328 of commission income, $313 and$436 of policy acquisition costs and $2,722 and $4,344 of commission expense related to intersegment activities, which are eliminated for consolidation, for the three and nine months ended September 30, 2026, respectively. Refer to Note 2. Segment Information for additional information.

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

•Transactions within the ID segment

◦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.

◦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 start-up MGA Pivix Specialty Insurance Service, Inc. ("Pivix"), resulting in an approximate 74% ownership interest and inclusion of Pivix in our consolidated results.

•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 nine months ended September 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 nine months ended September 30, 2026 and 2025.

Gross Premiums Written Gross premiums written increased $1,657 and increased $16,913 for the three and nine months ended September 30, 2026, respectively, compared to the same periods of the prior year.

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

Net Premiums Written Net premiums written increased $7,856 and $30,236 for the three and nine months ended September 30, 2026, respectively, compared to the same periods of the prior year.

The increase is primarily driven by a shift in business mix including growth in new and existing programs, and higher retention levels in certain select programs, partially offset by a reduction in participation in an assumed reinsurance transaction. Programs with higher retention levels generally include slide commission structures to manage the impact of the programs loss performance.

Net Premiums Earned Net premiums earned increased $8,789 and $18,658 for the three and nine months ended September 30, 2026, respectively, compared to the same periods of the prior year.

The increase is primarily driven by a shift in business mix including growth in new and existing programs, and higher retention levels in certain programs, partially offset by a reduction in participation in an assumed reinsurance transaction. Programs with higher retention levels generally include slide commission structures to manage the impact of the programs loss performance.

Commission Income and Commission Expense Commission income increased $11,956 and $62,769 for the three and nine months ended September 30, 2026, respectively, as compared to the same period in the prior year.

The increase was primarily due to ID organic growth as well as the acquisition of ArmadaCare in October of 2025. Commission income included profit commissions (based on underwriting performance) of $4,816 and $1,940 for the three months ended September 30, 2026 and 2025, respectively, and $16,624 and $8,896 for the nine months ended September 30, 2026 and 2025, respectively.

Commission expense decreased $1,412 and increased $3,333 for the three and nine months ended September 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, and 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 $3,569 and $3,590 for the three months ended September 30, 2026 and 2025, respectively, and $10,506 and $10,739 for the nine months ended September 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 nine months ended September 30, 2026, were flat versus the three and nine months ended September 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 $632 and $1,824 for the three and nine months ended September 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 $2,125 and $7,964 for the three and nine months ended September 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 include (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 September 30, 2026 and 2025, of $(1,071) and $2,408, 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, the reversal of a CECL allowance in the third quarter of 2025, and a Corporate investment impairment charge in the third quarter of 2026. Other revenues for the nine months ended September 30, 2026 and 2025, of $(6) and $(862), 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, the reversal of a CECL allowance in the third quarter of 2025, and Corporate investment impairment charge in the third quarter of 2026.

Losses and Loss Adjustment Expenses (Benefit)

Loss and loss adjustment expenses incurred increased $345 and $11,896 for the three and nine months ended September 30, 2026, compared to the same periods of the prior year.

The higher loss and loss adjustment expenses for the three months ended September 30, 2026, is primarily due to the growth in our P&C program business and lower prior period development in the three months ended September 30, 2026 vs. the three months ended September 30, 2025. The higher loss and loss adjustment expenses for the nine months ended September 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, partially offset a business mix shift with a lower effective loss ratio.

General and Administrative Expenses (G&A) The following table provides a summary of G&A expenses:

The increase of $1,522 and $27,153 in compensation expenses during the three and nine months ended September 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, and (iii) the launch of our Lloyd's managing agency, increased employment costs, and incentive compensation at Octave Ventures.

The decrease in non-compensation G&A expenses of $3,235 for the three months ended September 30, 2026, was primarily due to cost reduction initiatives, including lower premise expenses and a legacy software write-off, partially offset by increased consulting and legal fees. The decrease in non-compensation G&A expenses of $3,367 for the nine months ended September 30, 2026, was primarily attributable to lower premises costs and reduced professional fees related to transaction and acquisition costs, partially offset by insurance costs recorded in Discontinued Operations in the prior-year period.

Intangible Amortization and Depreciation. The increase in intangible amortization and depreciation of $2,568 and $8,129 for the three and nine months ended September 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 $3,473 and $9,633 for the three and nine months ended September 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 $(521) for the three months ended September 30, 2026, compared to $(1,241) for the three months ended September 30, 2025. The provision (benefit) for income taxes was $(517) for the nine months ended September 30, 2026 compared to $(4,030) for the nine months ended September 30, 2025. The tax benefit recognized in the current year includes deferred tax benefits related to the recognition of deferred tax assets and amortization of finite-lived intangible assets, partially offset by current tax expense associated with our UK operations.

Results of Operations by Segment

(1) Includes $11,957 and $19,657 premiums placed, as well as $3,270 and $5,328 of commission income and $2,722 and $4,344 of commission expense related to intersegment activities for the three and nine months ended September 30, 2026, respectively. 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 September 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 42% and 12%, respectively. For the nine months ended September 30, 2026, commission income and commission expense increased 66% and 27%, respectively, driven by the same factors as those driving the increase for the three months ended September 30, 2026.

Commission income included profit commissions (based on underwriting performance) of $4,816 and $1,940 for the three months ended September 30, 2026 and 2025, respectively, and $16,624 and $8,896 for the nine months ended September 30, 2026 and 2025, respectively. Excluding profit commissions, commission expense was approximately 26% and 31% of commission income for the three months ended September 30,

2026 and 2025, respectively, and 23% and 30% for the nine months ended September 30, 2026 and 2025, respectively. The decrease is related primarily to the inclusion of ArmadaCare in 2026, as the majority of their business is produced internally and their external brokers have a low commission model. Additionally, changes in certain capacity provider agreements resulted in associated program revenue being reported on a net basis in 2026.

The increase in G&A expenses of $12,645 and $41,264 for the three and nine months ended September 30, 2026, respectively, was primarily due to the acquisition of ArmadaCare, the launch of new MGAs, consulting and start-up costs, build out of the Managing Agency business and organic staff increases.

ID pretax income (loss) for the three months ended September 30, 2026, was $(3,640) compared to a loss of $(5,747) for the three months ended September 30, 2025. ID pretax income for the nine months ended September 30, 2026, was $12,299 compared to a loss of $(18,159) for the nine months ended September 30, 2025. The higher pretax income for the three and nine months ended September 30, 2026, mostly related to higher net commissions and fees related to the ArmadaCare acquisition, organic growth, higher profit commissions, as well as lower interest expense, offset partially by higher G&A expenses and intangible amortization.

The ID EBITDA increase of $1,187 and $29,106 during the three and nine months ended September 30, 2026, respectively, was primarily driven by an increase in commission income due to the ArmadaCare 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 typically 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 grown 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 third quarter of 2026 while many of our underlying ID MGAs grew, certain other of our MGAs, such as our niche specialty and auto specialty focused MGAs, reduced their underwriting activity resulting in lower commission revenues period over period.

(1)Includes $313 and $436 of policy acquisition costs related to intersegment activity for the three and nine months ended September 30, 2026, respectively. 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. Thirty programs were authorized to issue policies as of September 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 gross and net premiums written, net premiums earned, losses and loss expenses incurred and policy acquisition costs in the three and nine months ended September 30, 2026, compared to the same periods of the prior year. Partially offsetting this increase was a reduction in participation percentage of an assumed reinsurance program. Additionally, although losses and loss expenses have increased,

the shift in Everspan's net business mix and retention changes have led to an improved loss ratio.

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 generally 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 September 30, 2026, was driven by a shift in business mix and retention changes in addition to lower prior year reserve strengthening. The change in the Loss and LAE ratio during the nine months ended September 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 and retention changes. The nine months ended September 30, 2026, contained prior years loss strengthening equating to 14.4% of which 11.7% relates to this settlement. The three and nine months ended September 30, 2025, contained prior years loss strengthening equating to 23.2% and 8.8%, respectively, driven primarily by commercial auto liability loss experience on programs that are in runoff, and 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.

Policy acquisition costs increased for the three and nine months ended September 30, 2026 as compared to the three and nine months ended September 30, 2025, due to a shift in business mix, including an increase in retention of certain programs. Programs with higher retention levels include slide commission structures to manage the impact of the programs loss performance. For the three and nine months ended September 30, 2026, compared to the same prior year periods, acquisition costs were affected by sliding scale commission arrangements with program partners.

Sliding scale commissions decreased the Specialty Property and Casualty Insurance segment's expense ratio by 0.3% and increased the expense ratio by 0.6% during the three and nine months ended September 30, 2026, respectively. During the three and nine months ended September 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 6.9% and 3.3%, 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 increase in G&A expenses of $2,330 for the three months ended September 30, 2026, was primarily due to increase in compensation related to new hires and the impact of changes in performance factors on incentive compensation. Additionally increases in non-compensation were driven by higher legal fees associated with the pending sale of PWIC, recruiting fees related to staffing hires, timing difference of costs associated with subscriptions and dues and higher software costs. The increase of $3,767 for the nine months ended September 30, 2026, was primarily driven by severance, impact of performance factors on incentive compensation, increased recruiting fees and higher software costs, partially offset by lower professional fees.

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 $(652) and $610 for the three months ended September 30, 2026 and 2025, respectively, and $(75) and $1,723 for the nine months ended September 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, and a Corporate investment impairment in the third quarter of 2026. The investment impairment resulted from OSG's agreement in principle to sell one of its minority MGA

investments. The sale is subject to final documentation and other closing conditions.

The decrease in G&A expenses of $16,688 for the three months ended September 30, 2026, and $21,245 for the nine months ended September 30, 2026, were mainly due to cost reduction initiatives, including lower premise expenses following our NY corporate office re-location and reduced acquisition and restructuring related costs.