What changed in this filing

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Item 1. Financial Statements

2026-08-07 compared with 2026-05-11 · 272 added, 163 removed, 903 unchanged (33% of the section changed)

3 unchanged sentences

CONDENSED CONSOLIDATED BALANCE SHEETS (UNAUDITED)

March 31, 2026 December 31, 2025

June 30, 2026 December 31, 2025

($ in thousands, except share and per share amounts) (Unaudited)

33 unchanged sentences

Stockholders’ equity

Common stock, $ 0.01 par value, 500,000,000 shares authorized, 44,728,087 shares issued and 44,543,065 shares outstanding at March 31, 2026;

Common stock, $ 0.01 par value, 500,000,000 shares authorized, 44,827,499 shares issued and 44,396,493 shares outstanding at June 30, 2026;

40,511,222 shares issued and outstanding at December 31, 2025

8 unchanged sentences

AND SUBSIDIARIES

CONDENSED CONSOLIDATED STATEMENTS OF OPERATIONS

AND COMPREHENSIVE INCOME (UNAUDITED)

Three months ended March 31,

CONDENSED CONSOLIDATED STATEMENTS OF OPERATIONS AND COMPREHENSIVE INCOME (UNAUDITED)

Three months ended June 30, Six months ended June 30,

($ in thousands, except share and per share amounts) 2026 2025 2026 2025

3 unchanged sentences

Net investment income 30,727 18,704 57,782 38,126

Net investment gains 3,185 6,750

Net investment (losses) gains ( 601 ) 3,090 2,584 9,840

Other income 13 7 28 20

15 unchanged sentences

Net change in unrealized (losses) gains on investments, net of tax ( 625 ) 11,005 ( 17,842 ) 23,260

Reclassification adjustment for gains (losses) on securities no longer held, net of tax 502 ( 182 )

Reclassification adjustment for (losses) gains on securities no longer held, net of tax ( 490 ) ( 3,624 ) 12 ( 3,806 )

Foreign currency translation adjustment 150 — ( 718 ) —

11 unchanged sentences

CONDENSED CONSOLIDATED STATEMENTS OF STOCKHOLDERS’ EQUITY (UNAUDITED)

Three months ended March 31,

Three months ended June 30,

($ in thousands, except share amounts) 2026 2025

Common shares:

Balance at beginning of period 44,543,065 40,402,879

(Acquisition) issuance of common stock ( 146,572 ) 83,777

Balance at June 30, 44,396,493 40,486,656

Treasury shares:

Balance at beginning of period ( 185,022 ) —

Shares acquired ( 245,984 ) —

Balance at June 30, ( 431,006 ) —

Common stock:

Balance at beginning of period $ 484 $ 404

(Acquisition) issuance of common stock ( 36 ) 1

Balance at June 30, $ 448 $ 405

Treasury stock:

Balance at beginning of period $ ( 8,665 ) $ —

Issuance of treasury stock ( 10,762 ) —

Balance at June 30, $ ( 19,427 ) $ —

Additional paid-in capital:

Balance at beginning of period $ 922,311 $ 721,186

Issuance of common stock 5,379 2,973

Balance at June 30, $ 927,690 $ 724,159

Accumulated other comprehensive loss:

Balance at beginning of period $ ( 6,126 ) $ ( 10,047 )

Other comprehensive (loss) income, net of tax ( 965 ) 7,381

Balance at June 30, $ ( 7,091 ) $ ( 2,666 )

Retained earnings:

Balance at beginning of period $ 316,879 $ 139,178

Net income 49,038 38,839

Balance at June 30, $ 365,917 $ 178,017

Total stockholders’ equity $ 1,267,537 $ 899,915

The accompanying notes are an integral part of the consolidated financial statements.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

CONDENSED CONSOLIDATED STATEMENTS OF STOCKHOLDERS’ EQUITY (UNAUDITED)

Six months ended June 30,

($ in thousands, except share amounts) 2026 2025

Common shares:

Balance at beginning of year 40,511,222 40,127,908

Issuance of shares 3,885,271 358,748

Balance at March 31, 44,543,065 40,402,879

Balance at June 30, 44,396,493 40,486,656

Treasury shares:

1 unchanged sentence

Shares acquired ( 431,006 ) —

Balance at March 31, 185,022 —

Balance at June 30, ( 431,006 ) —

Common stock:

1 unchanged sentence

Issuance of common stock 43 4

Balance at March 31, $ 484 $ 404

Balance at June 30, $ 448 $ 405

Treasury stock:

1 unchanged sentence

Treasury stock acquired ( 19,427 ) —

Balance at March 31, $ ( 8,665 ) $ —

Balance at June 30, $ ( 19,427 ) $ —

Additional paid-in capital:

1 unchanged sentence

Issuance of common stock 197,135 5,561

Balance at March 31, $ 922,311 $ 721,186

Balance at June 30, $ 927,690 $ 724,159

Accumulated other comprehensive loss:

1 unchanged sentence

Other comprehensive (loss) income, net of tax ( 18,548 ) 19,454

Balance at March 31, $ ( 6,126 ) $ ( 10,047 )

Balance at June 30, $ ( 7,091 ) $ ( 2,666 )

Retained earnings:

1 unchanged sentence

Net income 98,769 80,897

Balance at March 31, $ 316,879 $ 139,178

Balance at June 30, $ 365,917 $ 178,017

Total stockholders’ equity $ 1,267,537 $ 899,915

3 unchanged sentences

CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS (UNAUDITED)

Three months ended March 31,

Six months ended June 30,

($ in thousands) 2026 2025

9 unchanged sentences

Investment in direct and indirect loans 3,164 13,435

Proceeds from the sales of (payments for the purchase of) property and equipment 1,654 ( 202 )

Purchase of property and equipment ( 965 ) ( 1,287 )

Proceeds from the sales of fixed maturity securities, available-for-sale 237,986 25,524

5 unchanged sentences

Change in receivable/payable for securities ( 15,762 ) —

Cash provided by deposit accounting 4,457 1,200

Net cash used in investment activities ( 361,844 ) ( 100,779 )

Cash (used in) provided by deposit accounting ( 8,026 ) 15,183

Net cash used in investing activities ( 382,620 ) ( 169,301 )

Cash flows from financing activities:

1 unchanged sentence

Proceeds from long term borrowings 371,089 —

Payments on long term borrowings ( 50,000 ) —

Treasury stock acquired ( 19,427 ) —

28 unchanged sentences

Description of Business

Skyward Specialty Insurance Group, Inc.

(the “Company”), an insurance holding company, is a Delaware corporation that was organized in 2006.

Skyward Specialty Insurance Group, Inc., an insurance holding company, is a Delaware corporation that was organized in 2006.

It is a specialty insurance company operating in two segments delivering commercial property and casualty products insurance coverages.

5 unchanged sentences

• Oklahoma Specialty Insurance Company (“OSIC”), a subsidiary of IIC, underwrites insurance on a non-admitted basis.

The Company has a wholly owned captive reinsurance company subsidiary, Skyward Re, that is domiciled in the Cayman Islands and assumed net reserves for certain divisions, related to a retroactive reinsurance contract, from the Company’s insurance companies and retroceded the net reserves to a third-party reinsurer.

The Company has a wholly owned captive reinsurance company subsidiary, Skyward Re, that is domiciled in the Cayman Islands.

The Company has three non-risk bearing wholly owned subsidiaries, (i) Skyward Underwriters Agency, Inc.

16 unchanged sentences

ASML may also earn profit commission under contractual arrangements with the capital providers to each syndicate.

Profit commission is contingent on syndicate profitability and is accrued in accordance with the contractual terms and the subsequent development of underwriting results at the balance sheet date.

Profit commissions are contingent on syndicate profitability and are accrued in accordance with the contractual terms and the subsequent development of underwriting results at the balance sheet date.

Amounts are generally not payable until the underlying underwriting results have substantially matured (typically around 36 months after inception), unless interim profit distributions permit earlier payments on account.

8 unchanged sentences

The functional currency for each business unit is determined by the local currency used for most economic activity in that area.

Movements in exchange rates related to transactions in currencies other than a business unit’s functional currency for monetary assets and liabilities are remeasured through the consolidated statements of operations and comprehensive income (loss) in other income (expense), except for currency movements related to available for sale fixed maturities securities, which are excluded from net income (loss) and accumulated in stockholder’s equity, net of deferred taxes.

The business units’ functional currency financial statements are translated to the Company’s reporting currency, U.S.

dollars, using the exchange rates at the end of period for the balance sheets and the average exchange rates in effect for the reporting period for the statements of operations and comprehensive income.

Gains and losses resulting from translating the foreign currency financial statements, net of deferred income taxes, are excluded from net income and accumulated as a separate component of accumulated other comprehensive income in stockholder’s equity.

Reclassifications

5 unchanged sentences

Goodwill and Intangible Assets

The following tables set forth the carrying amount and changes in the balance of goodwill by reporting unit at March 31, 2026 and 2025:

The following tables set forth the carrying amount and changes in the balance of goodwill by reporting unit at June 30, 2026 and 2025:

($ in thousands) Accident

3 unchanged sentences

Additions — — — 125,408 — 125,408

Net balance at March 31, 2026 $ 46,756 $ 6,781 $ 10,204 $ 125,408 $ 1,993 $ 191,142

Net balance at June 30, 2026 $ 46,756 $ 6,781 $ 10,204 $ 125,408 $ 1,993 $ 191,142

($ in thousands) Accident

2 unchanged sentences

Accumulated impairment at December 31, 2024 ( 44,821 ) — — ( 1,886 ) ( 46,707 )

Net balance at March 31, 2025 $ 46,756 $ 6,781 $ 10,204 $ 1,993 $ 65,734

The following tables set forth the carrying amount and changes in the balance of other intangible assets at March 31, 2026 and 2025:

Net balance at June 30, 2025 $ 46,756 $ 6,781 $ 10,204 $ 1,993 $ 65,734

The following tables set forth the carrying amount and changes in the balance of other intangible assets at June 30, 2026 and 2025:

($ in thousands) Agent

5 unchanged sentences

Amortization ( 2,513 ) — ( 1,750 ) — — ( 4,263 )

Net balance at March 31, 2026 $ 33,031 $ — $ 35,124 $ 200,000 $ 14,019 $ 282,174

Net balance at June 30, 2026 $ 31,775 $ — $ 34,249 $ 200,000 $ 14,019 $ 280,043

($ in thousands) Agent

3 unchanged sentences

Accumulated amortization at December 31, 2024 ( 17,895 ) ( 1,117 ) — — ( 19,012 )

Additions 2,000 — — — 2,000

Amortization ( 553 ) — — — ( 553 )

Net balance at March 31, 2025 $ 6,337 $ — $ 999 $ 14,019 $ 21,355

Net balance at June 30, 2025 $ 8,043 $ — $ 999 $ 14,019 $ 23,061

The Company’s indefinite lived intangible assets relate to insurance licenses, trademarks and Lloyd’s syndicates capacity.

Its finite lived intangible assets, which relate to policy renewals, agency relationships, within agent relationships, finite syndicates capacity relationships and non-compete/exclusivity agreements, within non-competes, have a weighted average useful life of approximately 9 years as of March 31, 2026.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

2 unchanged sentences

Goodwill and Intangible Assets (continued)

The Company recognized approximately $ 2.1 million and $ 0.3 million in amortization expense for the three months ended March 31, 2026 and 2025, respectively.

During the three and six months ended June 30, 2026, the Company recognized approximately $ 2.2 million and $ 4.3 million, respectively, of amortization expense, compared to $ 0.3 million and $ 0.6 million, respectively, for the same 2025 periods.

The following table sets forth the estimated future net amortization expense of intangible assets:

5 unchanged sentences

Year Ending December 31, 2030 8,025

The following tables set forth the amortized cost and the fair value by investment category at March 31, 2026 and December 31, 2025:

The following tables set forth the amortized cost and the fair value by investment category at June 30, 2026 and December 31, 2025:

($ in thousands) Amortized

Losses Allowance for Credit Losses Fair Value

March 31, 2026

June 30, 2026

Fixed maturity securities, available-for-sale:

28 unchanged sentences

Total fixed maturity securities, held-to-maturity $ 33,290 $ 829 $ ( 48 ) $ ( 468 ) $ 33,603

The following table sets forth the amortized cost and fair value of available-for-sale fixed maturity securities by contractual maturity at March 31, 2026:

The following table sets forth the amortized cost and fair value of available-for-sale fixed maturity securities by contractual maturity at June 30, 2026:

($ in thousands) Amortized

9 unchanged sentences

Also, changing interest rates, tax considerations or other factors may result in portfolio sales prior to maturity.

The Company’s fixed maturity securities, held-to-maturity, at March 31, 2026 consisted entirely of asset backed securities that were not due at a single maturity date.

At March 31, 2026, the Company had U.S.

The Company’s fixed maturity securities, held-to-maturity, at June 30, 2026 consisted entirely of asset-backed securities that were not due at a single maturity date.

At June 30, 2026, the Company had U.S.

government agencies mortgage-backed fixed maturity securities, with a carrying value of approximately $ 65.8 million pledged as collateral for a loan (the “FHLB Loan”) from the Federal Home Loan Bank of Dallas (“FHLB”) pursuant to an Advances and Security Agreement between the Company and FHLB (the “Advances and Security Agreement”).

In accordance with the terms of the FHLB Loan, the Company retains all rights regarding these pledged securities.

At March 31, 2026, the Company had assets with fair values of approximately $ 77.5 million pledged as collateral for performance obligations under reinsurance agreements.

At June 30, 2026, the Company had assets with fair values of approximately $ 88.5 million pledged as collateral for performance obligations under reinsurance agreements.

In accordance with the terms of the trust agreements, the Company retains all rights regarding these securities, of which $ 71.3 million are residential mortgage-backed securities, $ 15.0 million of cash and cash equivalents and other assets and $ 2.2 million of short-term investments.

3 unchanged sentences

Investments (continued)

The following tables set forth the gross unrealized losses and the corresponding fair values of investments, aggregated by length of time that individual securities had been in a continuous unrealized loss position as of March 31, 2026 and 2025:

Less than 12 Months 12 Months or More Total

($ in thousands) Fair Value Gross Unrealized Losses Fair Value Gross Unrealized Losses Fair Value Gross Unrealized Losses

March 31, 2026

June 30, 2026

Fixed maturity securities, available-for-sale:

23 unchanged sentences

Total $ 234,953 $ ( 1,484 ) $ 185,663 $ ( 15,394 ) $ 420,616 $ ( 16,878 )

The Company regularly monitors its available-for-sale fixed maturity securities that have fair values less than cost or amortized cost for signs of impairment, an assessment that requires significant management judgment regarding the evidence known.

Such judgments could change in the future as more information becomes known, which could negatively impact the amounts reported.

Among the factors that management considers for fixed maturity securities are the financial condition of the issuer including receipt of scheduled principal and interest cash flows, and intent to sell, including if it is more likely than not that the Company will be required to sell the investments before recovery.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

2 unchanged sentences

Investments (continued)

Such judgments could change in the future as more information becomes known, which could negatively impact the amounts reported.

As of March 31, 2026, the Company had 1,057 lots of fixed maturity securities in an unrealized loss position.

As of June 30, 2026, the Company had 987 lots of fixed maturity securities in an unrealized loss position.

The Company does not have an intent to sell these securities and it is not more likely than not that the Company will be required to sell these securities before maturity or recovery of its cost basis.

The Company reviewed its investments at March 31, 2026 and determined that for two available-for-sale securities in the “corporate securities and miscellaneous” category, credit impairments existed, based on new recovery analysis that showed deteriorating conditions raising credit concerns.

The Company reviewed its investments at June 30, 2026 and determined that for two available-for-sale securities in the “corporate securities and miscellaneous” category, credit impairments existed, based on new recovery analysis that showed deteriorating conditions raising credit concerns.

Other than the securities discussed previously, the Company determined that no other credit impairment existed in the gross unrealized holding losses, due to the reasons discussed below:

16 unchanged sentences

Therefore, the Company does not consider these impaired securities.

The following table sets forth the changes in the allowance for credit losses on available-for-sale securities and held-to-maturity securities during the three months ended March 31, 2026 and 2025:

The following table sets forth the changes in the allowance for credit losses on available-for-sale securities and held-to-maturity securities during the six months ended June 30, 2026 and 2025:

($ in thousands) Fixed Maturity Securities, Available-For-Sale Fixed Maturity Securities, Held-to-Maturity

2 unchanged sentences

Balance at March 31, 2026 $ 6,500 $ 301

Fixed Maturity Securities, Held-to-Maturity

Write-offs — 1,955

Recoveries of amounts previously written off ( 272 ) —

Balance at June 30, 2026 $ 6,228 $ 2,256

Fixed Maturity Securities, Available-For-Sale Fixed Maturity Securities, Held-to-Maturity

Balance at December 31, 2024 $ — $ 243

1 unchanged sentence

Balance at March 31, 2025 $ — $ 250

Current period provision for credit losses 6,150 18

Balance at June 30, 2025 $ 6,150 $ 268

SKYWARD SPECIALTY INSURANCE GROUP, INC.

2 unchanged sentences

Investments (continued)

The following table sets forth the components of net investment gains for the three months ended March 31, 2026 and 2025:

The following table sets forth the components of net investment (losses) gains for the three and six months ended June 30, 2026 and 2025:

Three months ended June 30, Six months ended June 30,

($ in thousands) 2026 2025 2026 2025

2 unchanged sentences

Equity securities — 15,441 — 17,186

Other ( 1,964 ) 596 ( 1,789 ) 626

Total ( 625 ) 16,489 1,182 18,717

8 unchanged sentences

Other 1,927 5,918 3,636 10,395

Net investment gains

Net investment (losses) gains

$ ( 601 ) $ 3,090 $ 2,584 $ 9,840

The following table sets forth the proceeds from sales of available-for-sale fixed maturity securities and equity securities for the three months ended March 31, 2026 and 2025:

The following table sets forth the proceeds from sales of available-for-sale fixed maturity securities and equity securities for the six months ended June 30, 2026 and 2025:

Six months ended June 30,

($ in thousands) 2026 2025

1 unchanged sentence

Equity securities — 67,495

The following table sets forth the components of net investment income for the three months ended March 31, 2026 and 2025:

The following table sets forth the components of net investment income for the three and six months ended June 30, 2026 and 2025:

Three months ended June 30, Six months ended June 30,

($ in thousands) 2026 2025 2026 2025

15 unchanged sentences

Investments (continued)

The following table sets forth the change in net unrealized gains (losses) on the Company’s investment portfolio, net of deferred income taxes, included in other comprehensive loss for the three months ended March 31, 2026 and 2025:

Three months ended June 30, Six months ended June 30,

($ in thousands) 2026 2025 2026 2025

9 unchanged sentences

The Company classifies its financial instruments into the following three-level hierarchy:

Level 1 - Inputs are unadjusted, quoted prices for identical assets or liabilities in active markets at the measurement

Level 2 - Inputs are other than quoted prices included in Level 1 that are observable for the asset or liability through

corroboration with market data at the measurement date.

Level 3 - Unobservable inputs that reflect management’s best estimate of what market participants would use in

pricing the asset or liability at the measurement date.

Level 1 - Inputs are unadjusted, quoted prices for identical assets or liabilities in active markets at the measurement date.

Level 2 - Inputs are other than quoted prices included in Level 1 that are observable for the asset or liability through corroboration with market data at the measurement date.

Level 3 - Unobservable inputs that reflect management’s best estimate of what market participants would use in pricing the asset or liability at the measurement date.

The following methods and assumptions were used in estimating the fair value disclosures for financial instruments in the accompanying consolidated financial statements and in these notes:

18 unchanged sentences

Fair Value Measurements (continued)

The following table sets forth the range of the discount rate as of March 31, 2026 and December 31, 2025:

March 31, 2026 December 31, 2025

The following table sets forth the range of the discount rate as of June 30, 2026 and December 31, 2025:

June 30, 2026 December 31, 2025

High 12.78 % 11.10 %

6 unchanged sentences

The spread represents the incremental cost of capital based on the borrower’s ability to make future payments and the value of the collateral relative to the loan balance and is subject to judgment and uncertainty.

The following table sets forth the range and weighted average, weighted by relative fair value, of the spread as of March 31, 2026 and December 31, 2025:

March 31, 2026 December 31, 2025

The following table sets forth the range and weighted average, weighted by relative fair value, of the spread as of June 30, 2026 and December 31, 2025:

June 30, 2026 December 31, 2025

High 8.09 % 8.34 %

8 unchanged sentences

Fair Value Measurements (continued)

The following tables set forth the Company’s investments and derivatives within the fair value hierarchy at March 31, 2026 and December 31, 2025:

March 31, 2026

The following tables set forth the Company’s investments and derivatives within the fair value hierarchy at June 30, 2026 and December 31, 2025:

June 30, 2026

($ in thousands) Level 1 Level 2 Level 3 Total

43 unchanged sentences

Total $ 343,624 $ 1,662,092 $ 194,422 $ 2,200,138

The following tables set forth the changes in the fair value of instruments carried at fair value with a Level 3 measurement during the three months ended March 31, 2026 and 2025:

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Fair Value Measurements (continued)

The following tables set forth the changes in the fair value of instruments carried at fair value with a Level 3 measurement during the six months ended June 30, 2026 and 2025:

($ in thousands) Fixed Maturity Securities, Available-For-Sale Mortgage Loans

Balance at December 31, 2025 $ 150,917 $ 9,902

Total losses for the period recognized in net investment gains ( 62 ) ( 814 )

Total losses for the period recognized in net investment (losses) gains ( 62 ) ( 814 )

Purchases 11,266 —

2 unchanged sentences

Balance at March 31, 2026 $ 159,450 $ 9,088

Total (losses) gains for the period recognized in net investment gains ( 161 ) 130

Transfers into Level 3 643 —

Purchases 3,458 —

Sales/Disposals ( 5,518 ) —

Total unrealized gains for the period recognized in accumulated comprehensive income (loss) ( 49 ) —

Balance at June 30, 2026 $ 157,823 $ 9,218

($ in thousands) Fixed Maturity Securities, Available-For-Sale Mortgage Loans

8 unchanged sentences

Total losses for the period recognized in net investment gains attributable to the change in unrealized gains or losses relating to assets held as of period end $ — $ ( 84 )

Total (losses) gains for the period recognized in net investment gains ( 4,081 ) 330

Issuances — 8

Settlements — ( 6,182 )

Transfers into Level 3 6,143 —

Purchases 8,838 —

Sales/Disposals ( 237 ) —

Total unrealized gains for the period recognized in accumulated comprehensive income (loss) 747 —

Balance at June 30, 2025 $ 94,867 $ 10,168

Total gains for the period recognized in net investment gains (losses) attributable to the change in unrealized gains or losses relating to assets held as of period end $ — $ 92

The transfers into Level 3 during the three and six months ended June 30, 2026 were the result of securities that began receiving valuations from asset managers that utilized unobservable inputs at the end of the period.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

2 unchanged sentences

Fair Value Measurements (continued)

The transfers into Level 3 during the three months ended March 31, 2026 were the result of securities that began receiving valuations from asset managers that utilized unobservable inputs at the end of the period.

The Company measures certain assets, including investments in indirect loans and loan collateral, equity method investments and other invested assets, at fair value on a nonrecurring basis only when they are deemed to be impaired.

7 unchanged sentences

Fixed maturity securities, held-to-maturity consists of senior and junior notes with target rates of return.

As of March 31, 2026, the Company determined the fair value of these instruments using the income approach utilizing inputs that are unobservable (Level 3).

As of June 30, 2026, the Company determined the fair value of these instruments using the income approach utilizing inputs that are unobservable (Level 3).

Investment in RedBird Capital Partners:

Included in other long-term investments is an investment in a limited partnership with RedBird Capital Partners, which invests in Bishop Street Underwriters, LLC (“Bishop Street”), a managing general agent (MGA).

The investment had a fair value of $ 47.2 million at March 31, 2026, which was determined using the net asset value.

The investment had a fair value of $ 49.1 million at June 30, 2026, which was determined using the net asset value.

The Company employs procedures to assess the reasonableness of the fair value of the investment including obtaining and reviewing the audited financial statements.

The unfunded commitment related to the investment was $ 18.3 million at March 31, 2026.

The unfunded commitment related to the investment was $ 18.3 million at June 30, 2026.

The Company may sell its interest in the investment with the appropriate prior written notice and approval by the general partner.

6 unchanged sentences

The Company determines the fair value of these instruments using the income approach utilizing inputs that are observable (Level 2).

The following table sets forth the Company’s carrying and fair values of notes payable and subordinated debt as of March 31, 2026 and December 31, 2025:

March 31, 2026 December 31, 2025

The following table sets forth the Company’s carrying and fair values of notes payable and subordinated debt as of June 30, 2026 and December 31, 2025:

June 30, 2026 December 31, 2025

($ in thousands) Carrying

14 unchanged sentences

The Company has invested in Separately Managed Accounts (“SMA1” and “SMA2”).

As of March 31, 2026 and December 31, 2025, the Company held direct investments in mortgage loans from various creditors through SMA1 and SMA2.

As of June 30, 2026 and December 31, 2025, the Company held direct investments in mortgage loans from various creditors through SMA1 and SMA2.

The Company’s mortgage loan portfolios are primarily senior loans on real estate across the U.S.

1 unchanged sentence

The principal amounts of the loans are approximately 64 % of the property’s appraised value at the time the loans were made.

The following table sets forth the carrying value of the Company’s mortgage loans as of March 31, 2026 and 2025:

($ in thousands) March 31, 2026 December 31, 2025

The following table sets forth the carrying value of the Company’s mortgage loans as of June 30, 2026 and 2025:

($ in thousands) June 30, 2026 December 31, 2025

Commercial $ 2,598 $ 3,334

1 unchanged sentence

$ 9,218 $ 9,902

The following table sets forth the Company’s gross investment income for mortgage loans for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

The following table sets forth the Company’s gross investment income for mortgage loans for the three and six months ended June 30, 2026 and 2025:

Three months ended June 30, Six months ended June 30,

($ in thousands) 2026 2025 2026 2025

Commercial $ 130 $ 109 $ ( 694 ) $ 217

Retail — — — 304

Hospitality 161 161 320 410

2 unchanged sentences

The Company writes off the uncollectible amount in the period it was determined to be uncollectible.

There was no write-off for uncollectible amounts during the three months ended March 31, 2026 and 2025, respectively.

As of March 31, 2026 and as of December 31, 2025, $ 2.5 million mortgage loans were in the process of foreclosure and there was 1 mortgage loan that was not producing income for the previous 12 months.

There was no write-off for uncollectible amounts during the three and six months ended June 30, 2026 and 2025, respectively.

As of June 30, 2026 and as of December 31, 2025, $ 2.6 million mortgage loans were in the process of foreclosure and there was 1 mortgage loan that was not producing income for the previous 12 months.

Equity Method Investments and Other

The following table sets forth the carrying value and ownership percentage of the Company’s equity method investments as of March 31, 2026 and 2025:

($ in thousands) March 31, 2026 December 31, 2025

The following table sets forth the carrying value and ownership percentage of the Company’s equity method investments as of June 30, 2026 and 2025:

($ in thousands) June 30, 2026 December 31, 2025

Carrying Value Ownership % Carrying Value Ownership %

11 unchanged sentences

Equity Method Investments and Other (continued)

The following table sets forth the components of net investment income (loss) from equity method investments for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

The following table sets forth the components of net investment income (loss) from equity method investments for the three and six months ended June 30, 2026 and 2025:

Three months ended June 30, Six months ended June 30,

($ in thousands) 2026 2025 2026 2025

7 unchanged sentences

$ ( 1,057 ) $ ( 898 ) $ ( 2,354 ) $ ( 2,886 )

The following table sets forth the unfunded commitment of equity method investments as of March 31, 2026 and December 31, 2025:

($ in thousands) March 31, 2026 December 31, 2025

The following table sets forth the unfunded commitment of equity method investments as of June 30, 2026 and December 31, 2025:

($ in thousands) June 30, 2026 December 31, 2025

Brewer Lane Ventures Fund II LP units $ 2,368 $ 3,237

6 unchanged sentences

The Company amortizes this difference over a 15 -year useful life.

The following table sets forth the Company’s recorded investment in RISCOM compared to its share of underlying equity as of March 31, 2026 and December 31, 2025:

($ in thousands) March 31, 2026 December 31, 2025

The following table sets forth the Company’s recorded investment in RISCOM compared to its share of underlying equity as of June 30, 2026 and December 31, 2025:

($ in thousands) June 30, 2026 December 31, 2025

Investment in RISCOM:

2 unchanged sentences

Recorded investment balance $ 2,952 $ 3,307

The following table sets forth the Company’s recorded investment in JVM Funds LLC compared to its share of underlying equity as of March 31, 2026 and December 31, 2025:

($ in thousands) March 31, 2026 December 31, 2025

The following table sets forth the Company’s recorded investment in JVM Funds LLC compared to its share of underlying equity as of June 30, 2026 and December 31, 2025:

($ in thousands) June 30, 2026 December 31, 2025

Investment in JVM Funds LLC:

3 unchanged sentences

Investment in Indirect Loans and Loan Collateral

As of March 31, 2026 and December 31, 2025, the Company held indirect investments in collateralized loans and loan collateral through SMA1 and SMA2.

As of June 30, 2026 and December 31, 2025, the Company held indirect investments in collateralized loans and loan collateral through SMA1 and SMA2.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

2 unchanged sentences

Equity Method Investments and Other (continued)

The carrying value of the SMA1 and SMA2 as of March 31, 2026 and December 31, 2025 were as follows:

($ in thousands) March 31, 2026 December 31, 2025

The carrying value of the SMA1 and SMA2 as of June 30, 2026 and December 31, 2025 were as follows:

($ in thousands) June 30, 2026 December 31, 2025

SMA1 $ 10,045 $ 15,418

4 unchanged sentences

(“Mangrove”).

HSIC-01 is a VIE for which the Company is the primary beneficiary.

HSIC-01 is a variable interest entity (“VIE”) for which the Company is the primary beneficiary.

The purpose of the VIE is to hedge price volatility risks of certain insurance products by investing in dairy and livestock commodities.

4 unchanged sentences

In addition, there is no recourse to the assets of HSIC-01 other than to satisfy associated liabilities.

The following table presents the assets of HSIC-01, included in the condensed consolidated balance sheet as of March 31, 2026.

The assets presented below only include third-party net assets and exclude any intercompany balances, which were eliminated upon consolidation.

($ in thousands) March 31, 2026

The following table presents the assets of HSIC-01, included in the condensed consolidated balance sheet as of June 30, 2026.

The assets presented below only include third-party net assets and exclude any intercompany balances, which were eliminated in consolidation.

($ in thousands) June 30, 2026

Cash and cash equivalents $ 10,564

9 unchanged sentences

The Company has not elected hedge accounting for these derivatives.

The following table presents the notional amounts and fair value of derivative assets in the condensed consolidated balance sheets at March 31, 2026:

The following table presents the notional amounts and fair value of derivative assets in the condensed consolidated balance sheets at June 30, 2026:

($ in thousands) Derivative Assets

2 unchanged sentences

The Company presents the net gain (loss) recognized on derivative instruments in economic hedging relationships in “losses and loss adjustment expenses” on the condensed consolidated statements of operations.

For the three months ended March 31, 2026, the Company recognized $ 31.3 million, respectively, of pre-tax net losses in losses and loss adjustment expenses.

For the three and six months ended June 30, 2026, the Company recognized a pre-tax gain of $ 9.6 million and a pre-tax loss of $ 21.7 million, respectively, in losses and loss adjustment expenses.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

10 unchanged sentences

During the fourth quarter of 2025, the Company entered into a Term Loan Credit Agreement (the “Term Loan Facility”) with a syndicate of participating banks.

The Term Loan Facility includes (a) an unsecured senior delayed draw term loan facility (“DDTL”) in the aggregate principal amount of $ 150.0 million (the “Tranche A DDTL”) and (b) an additional unsecured senior DDTL in the aggregate principal of $ 150.0 million (the “Tranche B DDTL” and together with the Tranche A DDTL, the “Term Loan Facility”).

The Term Loan Facility includes (a) an unsecured senior delayed draw term loan facility (“DDTL”) in the aggregate principal amount of $ 150.0 million (the “Tranche A DDTL”) and (b) an additional unsecured senior DDTL in the aggregate principal amount of $ 150.0 million (the “Tranche B DDTL” and together with the Tranche A DDTL, the “Term Loan Facility”).

The Term Loan Facility was used by the Company to fund a portion of the consideration of the Company’s acquisition of Apollo Group Holdings Limited (“Apollo”) and related transaction fees and expenses.

5 unchanged sentences

On December 30, 2025, the Company drew $ 150.0 million of the Tranche A DDTL and $ 150.0 million of the Tranche B DDTL for the acquisition of Apollo on January 1, 2026.

On June 26, 2026, the Company repaid $ 50.0 million of outstanding principal under the Tranche A DDTL.

The Term Loan Facility includes customary covenants, including certain limitations on the incurrence by the Company of additional indebtedness exceeding $ 10.0 million and on the Company’s ability to make distributions to its stockholders, or redeem, repurchase or retire shares of stock, upon the occurrence of certain events and certain financial covenants, including financial covenants relating to our minimum consolidated net worth, maximum total debt to capitalization, minimum A.M.

Best rating and minimum liquidity, as well as customary events of default.

As of March 31, 2026, the Company was in compliance with all covenants.

As of June 30, 2026, the Company was in compliance with all covenants.

The Term Loan Facility is unsecured.

In connection with the Revolving Credit Facility (defined below), during the fourth quarter of 2025, the Company and the subsidiary guarantors party thereto, entered into a guaranty agreement, pursuant to which the Company’s obligations under the Term Loan Facility are guaranteed by the Company and its existing wholly-owned subsidiaries and subsequently acquired or organized subsidiaries, excluding insurance company subsidiaries and subject to certain other exceptions.

The Company reports debt related to the Term Loan Facility in its March 31, 2026 Condensed Consolidated Balance Sheet, net of debt issuance costs of approximately $ 5.1 million.

The Company reports debt related to the Term Loan Facility in its June 30, 2026 condensed consolidated balance sheet, net of debt issuance costs of approximately $ 3.9 million.

These deferred financing costs are presented as a direct deduction from the carrying amount of the debt.

1 unchanged sentence

During the fourth quarter of 2025, the Company entered into a Credit Agreement (the “Revolving Credit Facility”) with a syndicate of participating banks.

The Revolving Credit Facility is unsecured and provided the Company with up to a initial maximum principal amount of $ 150.0 million which was increased to $ 250.0 million on the closing date of the Company’s acquisition of Apollo.

The Revolving Credit Facility is unsecured and provided the Company with up to an initial maximum principal amount of $ 150.0 million which was increased to $ 250.0 million on the closing date of the Company’s acquisition of Apollo.

The Company initially drew $ 43.0 million, which was used to redeem the Company’s prior revolving credit facility (described below).

1 unchanged sentence

The proceeds were used for the acquisition of Apollo on January 1, 2026.

Interest on the Revolving Credit Facility is payable quarterly.

Amounts drawn under the Facility bear interest at either term SOFR plus a margin, which ranges from 150 and 190 basis points, or the base rate plus a margin, which ranges from

SKYWARD SPECIALTY INSURANCE GROUP, INC.

2 unchanged sentences

Notes Payable & Subordinated Debt (continued)

50 basis points to 90 basis points, each depending on the Company’s debt to capitalization ratio.

Interest on the Revolving Credit Facility is payable quarterly.

Amounts drawn under the Facility bear interest at either term SOFR plus a margin, which ranges from 150 and 190 basis points, or the base rate plus a margin, which ranges from 50 basis points to 90 basis points, each depending on the Company’s debt to capitalization ratio.

SOFR is calculated using a SOFR floor of 0.00 % and a credit spread adjustment of 0.10 %.

4 unchanged sentences

Best Rating and minimum liquidity, as well as customary events of default.

As of March 31, 2026, the Company was in compliance with all covenants.

As of June 30, 2026, the Company was in compliance with all covenants.

In May 2019, the Company entered into an agreement to issue unsecured subordinated notes (the “Notes”) with an aggregate principal amount of $ 20.0 million.

3 unchanged sentences

The Notes have junior priority to all previously issued debt.

The Company reports debt related to the Notes in its March 31, 2026 Condensed Consolidated Balance Sheet and its December 31, 2025 Consolidated Balance Sheet, net of debt issuance costs of approximately $ 0.4 million.

The Company reports debt related to the Notes in its June 30, 2026 Condensed Consolidated Balance Sheet and its December 31, 2025 Consolidated Balance Sheet, net of debt issuance costs of approximately $ 0.4 million.

These deferred financing costs are presented as a direct deduction from the carrying amount of the subordinated debt.

The Company has two reportable segments, the Skyward Specialty segment and the Apollo segment, through which it offers a broad array of commercial property and casualty products and solutions on a non-admitted (or E&S) and admitted basis, predominantly in the United States.

Stockholders' Equity

Share Repurchase Program

In October 2024, the Company’s Board of Directors (the “Board”) approved a share repurchase program authorizing the repurchase of up to $ 50.0 million of the Company’s common stock.

On July 15, 2026, the Board authorized an increase to the share repurchase program authorizing the repurchase of up to an additional $ 50.0 million of the Company's common stock.

As a result, the total amount authorized under the share repurchase program increased to $ 100.0 million.

The shares may be repurchased from time to time in open market purchases, privately-negotiated transactions, block purchases, accelerated share repurchase agreements or a combination of methods, including through Rule 10b5-1 trading plans.

The timing, manner, price and amount of any repurchases under the share repurchase program will be determined by the Company’s discretion.

The share repurchase program does not require the Company to repurchase any specific number of shares, and may be modified, suspended or terminated at any time.

During the three and six months ended June 30, 2026, the Company repurchased 222,635 shares for approximately $ 9.7 million under this plan.

These shares represent the total repurchased under the plan as of June 30, 2026.

The Company has two reportable segments, the Skyward Specialty segment and the Apollo segment, through which it offers a broad array of commercial property and casualty products and reinsurance solutions on a non-admitted (or E&S) and admitted basis, predominantly in the United States.

The Company defines its segment on the basis of the way in which internally reported financial information is regularly reviewed by the Chief Operating Decision Maker (“CODM”) to analyze financial performance, make decisions and allocate resources.

5 unchanged sentences

Apollo operates within the Lloyd’s of London market, leveraging Lloyd’s global licensing, centralized underwriting infrastructure, and long‑standing distribution networks to access niche and emerging specialty classes across international markets.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Segments (continued)

The accounting policies of the segments are the same as those described in Note 1 “Summary of Significant Accounting Policies” of the Company’s Annual Report on Form 10-K for the year ended December 31, 2025.

5 unchanged sentences

The competitive analysis along with the monitoring of budgeted versus actual results are used in assessing performance of the segments and in establishing management’s compensation.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Segments (continued)

The following table presents gross written premiums by underwriting division for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

The following table presents gross written premiums by underwriting division for the three and six months ended June 30, 2026 and 2025:

Three months ended June 30, Six months ended June 30,

($ in thousands) 2026 2025 2026 2025

17 unchanged sentences

Total gross written premiums $ 740,554 $ 584,914 $ 1,408,258 $ 1,120,240

The following table sets forth the Apollo segment’s managed premiums for the three months ended March 31, 2026:

Three months ended March 31,

The following table sets forth the Apollo segment’s managed premiums for the three and six months ended June 30, 2026:

Three months ended June 30, Six months ended June 30,

Aligned Syndicates $ 217,196 $ 427,745

1 unchanged sentence

Total managed premiums $ 318,121 $ 618,126

The following table presents information about reported segment net underwriting income, significant segment expenses and a reconciliation of net underwriting income to net income for the three and six months ended June 30, 2026 and 2025:

SKYWARD SPECIALTY INSURANCE GROUP, INC.

2 unchanged sentences

Segments (continued)

Three months ended March 31, 2026 2025

Three months ended June 30, 2026 2025

($ in thousands) Skyward Specialty Apollo Total Skyward Specialty Total

14 unchanged sentences

Net investment income 30,727 18,704

Net investment (losses) gains ( 601 ) 3,090

Other income 13 7

Interest expense 8,812 1,876

Amortization expense 8,843 372

Other expenses 3,737 1,002

Income before income taxes 63,557 49,795

Income tax expense 14,519 10,956

Net income $ 49,038 $ 38,839

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Segments (continued)

Six months ended June 30, 2026 2025

($ in thousands) Skyward Specialty Apollo Total Skyward Specialty Total

Underwriting income

Net earned premiums $ 742,289 $ 136,190 $ 878,479 $ 595,908 $ 595,908

Underwriting fee income — 22,666 22,666 — —

Commission and fee income 3,861 — 3,861 4,536 4,536

Total underwriting revenues 746,150 158,856 905,006 600,444 600,444

Losses and LAE 465,198 76,766 541,964 368,571 368,571

Amortization of policy acquisition costs 103,986 26,784 130,770 89,126 89,126

Other operating and general expenses 87,108 20,736 107,844 75,878 75,878

Corporate expenses — — 9,281 — 7,143

Fee‑based service expenses — 8,732 8,732 — —

Total underwriting expenses 656,292 133,018 798,591 533,575 540,718

Underwriting income $ 89,858 $ 25,838 $ 106,415 $ 66,869 $ 59,726

Reconciliation of underwriting income to net income:

Underwriting income $ 106,415 $ 59,726

Net investment income 57,782 38,126

Net investment gains 2,584 9,840

9 unchanged sentences

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

The following table sets forth the Company’s income tax expense and effective tax rates for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

The following table sets forth the Company’s income tax expense and effective tax rates for the three and six months ended June 30, 2026 and 2025:

Three months ended June 30, Six months ended June 30,

($ in thousands) 2026 2025 2026 2025

3 unchanged sentences

The effect of foreign operations is primarily related to income of our foreign operations taxed at statutory tax rates of 15 % in Bermuda and 25 % in UK.

The effective tax rate for three months ended March 31, 2026 was impacted by certain discrete tax items, primarily tax benefits from stock-based compensation, which reduced the effective tax rate by 3.1 %.

The Company paid income taxes of $ 2.9 million during the three months ended March 31, 2026.

The increase in the effective tax rate for the three months ended June 30, 2026, was primarily driven by state taxes.

The increase in the effective tax rate for the six months ended June 30, 2026 was primarily attributable to foreign taxes associated with the Apollo acquisition, partially offset by discrete tax benefits, primarily from stock-based compensation.

The Company paid income taxes of $ 27.4 million and $ 30.3 million during the three and six months ended June 30, 2026, respectively, and paid $ 20.3 million during the three and six months ended 2025.

Losses and Loss Adjustment Expenses

The following table sets forth the reconciliation of unpaid losses and loss adjustment expenses (“LAE”) as reported in the condensed consolidated balance sheets as of and for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

Six months ended June 30,

($ in thousands) 2026 2025

20 unchanged sentences

Commission and fee income is primarily generated from SUA for the placement of insurance policies on either a third-party insurance or reinsurance company.

The following table sets forth the Company’s disaggregated revenues from contracts with customers for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

The following table sets forth the Company’s disaggregated revenues from contracts with customers for the three and six months ended June 30, 2026 and 2025:

Three months ended June 30, Six months ended June 30,

($ in thousands) 2026 2025 2026 2025

1 unchanged sentence

SUA fee income 342 608 797 1,785

Other 1,461 397 2,054 407

Total commission and fee revenue 4,581 4,095 7,910 7,119

1 unchanged sentence

Net commission and fee income $ 2,334 $ 2,560 $ 3,861 $ 4,536

The Company’s contract assets from commission and fee income as of March 31, 2026 and December 31, 2025 were $ 0.7 million and $ 1.0 million, respectively.

The Company’s contract assets from commission and fee income as of June 30, 2026 and December 31, 2025 were $ 1.0 million.

Through its Apollo subsidiary ASML, the Company earns revenue for services performed in its capacity as managing agent to both its wholly owned and third‑party capitalized Lloyd’s syndicates.

These revenues primarily consist of managing agency fees, which compensate the Company for underwriting oversight, operational administration, and regulatory and compliance support, as well as profit commission, which is contingent upon the underwriting performance of certain syndicates.

ASML receives managing agency fees from managed syndicates, including 1969, 1971 and 1972 (collectively the “Managed Syndicates”) at a rate of 0.9 % of the managed stamp capacity and for SPA1925 at 1.0 %, which is fully recognized over the period the services are rendered.

ASML receives profit commission at a rate of 17.5 % for Syndicate 1969 and 20.0 % for Syndicate 1971, subject to a two-year deficit clause.

No profit commission has been recognized for SPA1925 or Syndicate 1972.

ASML also receives a share of the leader’s fee for managing consortium arrangements.

These revenues primarily consist of managing agency fees, which compensate the Company for underwriting oversight, operational administration, and regulatory and compliance support, as well as profit commissions, which is contingent upon the underwriting and investment performance of certain syndicates.

ASML receives (i) managing agency fees from managed syndicates, including 1969, 1971 and 1972 (collectively the “Managed Syndicates”) at a rate of 0.9 % of the managed stamp capacity and for SPA1925 at 1.0 %, which is fully recognized over the period the services are rendered, (ii) profit commissions from certain syndicates, subject to a two-year deficit clause, and (iii) a share of the leader’s fee for managing consortium arrangements.

Managing agency fees and services revenue are recognized over time as services are rendered, while profit commission is recognized only when it becomes probable that no significant reversal will occur.

This revenue is disclosed in underwriting fee income.

The following table sets forth the Apollo’s revenues from contracts with customers for the three months ended March 31, 2026:

Three months ended March 31,

The following table sets forth Apollo’s revenues from contracts with customers for the three and six months ended June 30, 2026:

Three months ended June 30, Six months ended June 30,

($ in thousands) 2026 2026

1 unchanged sentence

Profit commission & consortium overrider charged to Managed Syndicates 8,072 14,623

Miscellaneous fee income 1,008 1,008

Underwriting fee income $ 12,588 $ 22,666

3 unchanged sentences

Underwriting, Acquisition and Insurance Expenses

The following table sets forth the components of underwriting, acquisition and insurance expenses for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

The following table sets forth the components of underwriting, acquisition and insurance expenses for the three and six months ended June 30, 2026 and 2025:

Three months ended June 30, Six months ended June 30,

($ in thousands) 2026 2025 2026 2025

4 unchanged sentences

Certain premiums and benefits are assumed from and ceded to other insurance companies under various reinsurance agreements.

The reinsurance agreements provide the Company with increased capacity to write larger risks and maintain its exposure to loss within its capital resources.

The reinsurance agreements provide the Company with increased capacity to write larger risks and maintain its exposure to loss within its risk tolerance.

The Company remains obligated for amounts ceded in the event that the reinsurers do not meet their obligations.

The following tables set forth the effects of reinsurance on written and earned premiums and losses and loss adjustment expenses for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

The following tables set forth the effects of reinsurance on written and earned premiums and losses and loss adjustment expenses for the three and six months ended June 30, 2026 and 2025:

Three months ended June 30,

($ in thousands) Written Earned Written Earned

4 unchanged sentences

Ceded losses and LAE incurred $ 183,466 $ 138,438

The following table sets forth the components of reinsurance recoverables and ceded unearned premium as of March 31, 2026 and December 31, 2025:

($ in thousands) March 31, 2026 December 31, 2025

Six months ended June 30,

($ in thousands) Written Earned Written Earned

Direct premiums $ 1,065,509 $ 1,044,752 $ 869,391 $ 778,215

Assumed premiums 342,749 294,293 250,849 165,147

Ceded premiums ( 489,759 ) ( 460,566 ) ( 437,756 ) ( 347,454 )

Net premiums $ 918,499 $ 878,479 $ 682,484 $ 595,908

Ceded losses and LAE incurred $ 336,039 $ 273,905

The following table sets forth the components of reinsurance recoverables and ceded unearned premium as of June 30, 2026 and December 31, 2025:

($ in thousands) June 30, 2026 December 31, 2025

Ceded unpaid losses and LAE $ 1,162,484 $ 921,165

3 unchanged sentences

Ceded unearned premium $ 337,180 $ 238,948

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Reinsurance (continued)

The Company entered into agreements with several of its reinsurers, whereby the reinsurer established funded trust accounts with the Company as the sole beneficiary.

These trust accounts provide the Company additional security to collect claim recoverables under reinsurance contracts and the Company does not carry these on the balance sheet because the Company will only have custody over these accounts upon the failure of the reinsurer to pay amounts due.

At March 31, 2026, the market value of these accounts was approximately $ 250.7 million.

At June 30, 2026, the market value of these accounts was approximately $ 224.0 million.

The trust amount will be adjusted periodically, by mutual agreement, based on claim payments and loss reserve recoverables.

Certain ceded reinsurance contracts that transfer only significant timing risk and do not transfer sufficient underwriting risk are accounted for using the deposit method of accounting.

The Company’s deposit asset at March 31, 2026 and December 31, 2025 was $ 18.2 million and $ 22.7 million, respectively, and was included in other assets on the condensed consolidated balance sheets.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

The Company’s deposit asset at June 30, 2026 and December 31, 2025 was $ 30.7 million and $ 22.7 million, respectively, and was included in other assets on the condensed consolidated balance sheets.

Earnings Per Share

The following table sets forth the computation of basic and diluted net earnings per share for the three months ended March 31, 2026 and 2025:

Three months ended March 31,

The following table sets forth the computation of basic and diluted net earnings per share for the three and six months ended June 30, 2026 and 2025:

Three months ended June 30, Six months ended June 30,

($ in thousands, except for share and per share amounts) 2026 2025 2026 2025

6 unchanged sentences

Diluted earnings per share $ 1.07 $ 0.93 $ 2.17 $ 1.94

The following table presents anti-dilutive instruments that were excluded from the calculation of diluted weighted-average common share equivalents during the three months ended March 31, 2026 and 2025:

Three months ended March 31,

The following table presents anti-dilutive instruments that were excluded from the calculation of diluted weighted-average common share equivalents during the three and six months ended June 30, 2026 and 2025:

Three months ended June 30, Six months ended June 30,

2026 2025 2026 2025

Stock units 348,788 49,540 344,753 109,359

4 unchanged sentences

The Company holds a 20 % ownership interest in RISCOM.

Net earned premium and gross commission expense related to these agreements for the three months ended March 31, 2026 and 2025 were as follows:

Three months ended March 31,

Net earned premium and gross commission expense related to these agreements for the three and six months ended June 30, 2026 and 2025 were as follows:

Three months ended June 30, Six months ended June 30,

($ in thousands) 2026 2025 2026 2025

1 unchanged sentence

Commissions 7,647 7,533 15,835 15,165

Premiums receivable as of March 31, 2026 and December 31, 2025 were $ 18.4 million and $ 13.9 million, respectively.

Advisory and professional services fees and expense reimbursements paid to various affiliated stockholders and directors for the three months ended March 31, 2026 and 2025 were $ 0.2 million.

Premiums receivable as of June 30, 2026 and December 31, 2025 were $ 17.2 million and $ 13.9 million, respectively.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Related Party Transactions (continued)

See Note 6 for investments involving affiliated companies and additional related party transactions.

2 unchanged sentences

Apollo underwrites a multi-class specialty insurance portfolio and offers products across Property, Casualty, Marine, Energy & Transportation, Specialty and Reinsurance, as well as digital and embedded risk programs.

The Company acquired Apollo

SKYWARD SPECIALTY INSURANCE GROUP, INC.

AND SUBSIDIARIES

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED)

Acquisitions (continued)

to broaden its specialty insurance platform, expand into additional specialty niches, enhance its innovation and technology capabilities, and strengthen its market position.

The Company acquired Apollo to broaden its specialty insurance platform, expand into additional specialty niches, enhance its innovation and technology capabilities, and strengthen its market position.

The fair value of the consideration transferred, or the purchase price, is approximately $ 559.1 million.

64 unchanged sentences

VOBA is aggregated with deferred policy acquisition costs and included within deferred policy acquisition costs and VOBA on the consolidated balance sheets.

For the three months ended March 31, 2026 the Company recognized $ 7.3 million and $ 6.7 million in underwriting, acquisition and insurance expenses and amortization expense, respectively, on the consolidated statements of operations related to the amortization of VOBA .

For the three and six months ended June 30, 2026 the Company recognized $ 7.3 million and $ 14.6 million, respectively, in underwriting, acquisition and insurance expenses, and $ 6.7 million and $ 13.4 million, respectively, in amortization expense on the consolidated statements of operations related to the amortization of VOBA.

Estimated fair values of assets acquired and liabilities assumed from Apollo are subject to change as additional information is obtained, and will be updated and finalized within the measurement period that will not extend beyond 12 months from the Acquisition Date.

Any measurement period adjustments will be recorded in the period in which the adjustments are identified, as if they had been recognized as of the acquisition date.

The results of operations for Apollo of $ 80.1 million of revenue and $ 22.2 million of net income from the date of the acquisition to the period ended March 31, 2026, have been included within the accompanying consolidated statements of operations and comprehensive loss.

The results of operations for Apollo of $ 78.7 million and $ 158.9 million of revenue for the three and six months ended June 30, 2026, respectively, and $ 15.4 million and $ 37.6 million of net income for the three and six months ended June 30, 2026, respectively, have been included within the accompanying consolidated statements of operations and comprehensive loss.

All transaction expenses incurred by the Company were expensed as incurred and reflected in the Company’s results of operations for the period ended December 31, 2025 in accordance with ASC 805.

No material transaction expenses were incurred for the period ended March 31, 2026.

No material transaction expenses were incurred for the period ended June 30, 2026.

The Company has not presented the unaudited supplemental pro forma financial information required by ASC 805-10-50-2(h) as it is impractical to do so, as Apollo did not historically prepare quarterly financial statements and its historical financial information was prepared under U.K.

13 unchanged sentences

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-Q

Item 1. Financial Statements