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Item 9A. Controls and Procedures

2025-03-04 compared with 2024-02-29 · 492 added, 483 removed, 2109 unchanged (32% of the section changed)

4 unchanged sentences

Based upon this evaluation, our CEO and CFO concluded that our disclosure controls and procedures were effective as of December 31, 2024.

Remediated Material Weakness

As previously disclosed, the Company became aware that the unaudited consolidated financial statements for the six months ended June 30, 2023 contained material misstatements related to unrecorded reinstatement premium as more fully described in Note 1 to the condensed consolidated financial statements of the 10-Q/A filed with the SEC on November 14, 2023.

Management of the Company concluded that because the controls to evaluate the accounting and disclosure of the reinstatement premium did not operate effectively, and resulted in the failure to detect the misstatement, the deficiencies were a material weakness in the Company's internal control over financial reporting.

A material weakness is a deficiency, or a combination of deficiencies, in internal control over financial reporting, such that there is a reasonable possibility that a material misstatement of the Company’s annual or interim financial statements will not be prevented or detected on a timely basis.

Remedial Actions Implementation

To remediate the material weakness in the Company’s internal control over financial reporting, during the fourth quarter of fiscal year 2023, the Company implemented a remediation plan that included:

(i) additional review procedures within our

accounting department, (ii) additional training of accounting personnel and (iii) enhancing our existing process and internal control documentation and financial statement preparation process, specifically including updates to accounting policies for reinstatement premium, to ensure completion of financial reporting and proper accounting in accordance with U.S.

The implementation of these procedures and controls have remediated the material weakness as of December 31, 2023.

Management’s Annual Report on Internal Control over Financial Reporting

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Changes in Internal Control over Financial Reporting

There were no changes in our internal control over financial reporting (as defined in Rules 13a-15(f) and 15d-15(f) under the Exchange Act) that occurred during our quarter ended December 31, 2023, except for the implementation of the remediation steps described above, that have materially affected, or are reasonably likely to materially affect, our internal control over financial reporting.

There were no changes in our internal control over financial reporting (as defined in Rules 13a-15(f) and 15d-15(f) under the Exchange Act) that occurred during our quarter ended December 31, 2024 that have materially affected, or are reasonably likely to materially affect, our internal control over financial reporting.

The effectiveness of any system of controls and procedures is subject to certain limitations, and, as a result, there can be no assurance that our controls and procedures will detect all errors or fraud.

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Proxy Statement, or alternatively, disclosed in an amendment to this Annual Report on Form 10-K, in either case to be filed with the SEC not later than 120 days after the end of the fiscal year covered by this Annual Report on Form 10-K.

The Company has adopted an insider trading policy which governs transactions in our securities by the Company's directors, officers and employees (including temporary employees) and is designed to promote compliance with insider trading laws, rules and regulations and listing standards applicable to the Company.

A copy of our insider trading policy is filed with this Annual Report on Form 10-K as Exhibit 19.1.

EXECUTIVE COMPENSATION

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333-199958, filed with the Commission on December 9, 2014)

4.2 Certificate of Designations of 7% Series A Perpetual Cumulative Convertible Preferred Shares of James River Group Holdings, Ltd.

dated March 1, 2022 (incorporated by reference to Exhibit 10.3 to the Quarterly Report on Form 10-Q filed on May 10, 2022;

4.2 Amended and Restated Certificate of Designations of 7% Series A Perpetual Cumulative Convertible Preferred Shares of James River Group Holdings, Ltd.

dated November 11, 2024 (incorporated by reference to Exhibit 4.2 of the Current Report on Form 8-K filed on November 13, 2024;

Commission File No.

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4.11 Amended and Restated Declaration of Trust of James River Capital Trust III, dated as of June 15, 2006, by and among James River Group, Inc., as Sponsor, Wilmington Trust Company, as Institutional Trustee and Delaware Trustee, the Administrators (as defined therein) and the holders, from time to time, of undivided beneficial interests in the James River Capital Trust III+

4.12 Guarantee Agreement, dated as of June 15, 2006, by James River Group, Inc., as Guarantor, and Wilmington Trust Company, as Guarantee Trustee, for the benefit of the holders, from time to time, of the capital securities of James River Capital Trust III+

Number Description

4.13 Indenture, dated December 11, 2007, by and between James River Group, Inc.

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as Joint Book Runners and Joint Lead Arrangers, Truist Bank as Syndication Agent, and the lender parties thereto (incorporated by reference to Exhibit 10.1 of the Current Report on Form 8-K filed on July 12, 2023, Commission File No.

10.2 Consent Agreement dated November 8, 2023 to the Third Amended and Restated Credit Agreement dated as of July 7, 2023 by and among James River Group Holdings, Ltd.

10.2 First Amendment dated April 16, 2024 to the Third Amended and Restated Credit Agreement dated as of July 7, 2023 by and among James River Group Holdings, Ltd.

and JRG Reinsurance Company Ltd., as borrowers, KeyBank National Association (“KeyBank”) as Administrative Agent and Letter of Credit Issuer, KeyBank and Truist Securities, Inc.

10.3 Second Amendment dated May 22, 2024 to the Third Amended and Restated Credit Agreement dated as of July 7, 2023 by and among James River Group Holdings, Ltd.

and JRG Reinsurance Company Ltd., as borrowers, KeyBank National Association (“KeyBank”) as Administrative Agent and Letter of Credit Issuer, KeyBank and Truist Securities, Inc.

as Joint Book Runners and Joint Lead Arrangers, Truist Bank as Syndication Agent, and the lender parties thereto (incorporated by reference to Exhibit 10.3 to the Quarterly Report on Form 10-Q filed on August 6, 2024;

Commission File No.

10.4 Continuing Guaranty of Payment, dated as of June 5, 2013, by James River Group, Inc., as Guarantor, pursuant to Credit Agreement, dated as of June 5, 2013, among James River Group Holdings, Ltd.

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and JRG Reinsurance Company Ltd., KeyBank National Association, as Administrative Agent and as Letter of Credit Issuer, and certain Lender parties (incorporated by reference to Exhibit 10.5 to the Annual Report on Form 10-K filed on March 10, 2016, Commission File No.

10.5 Credit Agreement, dated as of August 2, 2017, among James River Group Holdings, Ltd., JRG Reinsurance Company Ltd.

and BMO Harris Bank N.A.

(incorporated by reference to Exhibit 10.1 of the Current Report on Form 8-K filed on August 3, 2017, Commission File No.

10.6 First Amendment to Credit Agreement dated as of November 8, 2019 by and among James River Group Holdings, Ltd.

and JRG Reinsurance Company Ltd., as the borrowers, and BMO Harris Bank, N.A., as the lender (incorporated by reference to Exhibit 10.2 of the Current Report on Form 8-K filed on November 12, 2019, Commission File No.

10.7 Second Amendment to Credit Agreement dated as of February 18, 2022 by and among James River Group Holdings, Ltd.

and JRG Reinsurance Company Ltd.

as the borrowers, and BMO Harris Bank N.A., as the lender (incorporated by reference to Exhibit 10.7 of the Annual Report on Form 10-K filed on March 1, 2022, Commission File No.

Number Description

10.8 Third Amendment to Credit Agreement dated as of January 27, 2023 by and among James River Group Holdings, Ltd.

and JRG Reinsurance Company Ltd.

as the borrowers, and BMO Harris Bank N.A., as the lender (incorporated by reference to Exhibit 10.9 of the Annual Report on Form 10-K filed on February 28, 2023, Commission File No.

10.9 Consent Agreement dated November 8, 2023 to the Credit Agreement dated as of August 2, 2017, as amended, by and among James River Group Holdings, Ltd.

and JRG Reinsurance Company Ltd., as borrowers, and BMO Harris Bank N.A., as the lender (incorporated by reference to Exhibit 10.2 of the Current Report on Form 8-K filed on November 9, 2023, Commission File No.

10.10 Pledge and Security Agreement, dated as of August 2, 2017, by and between JRG Reinsurance Company Ltd., and BMO Harris Bank N.A.

(incorporated by reference to Exhibit 10.2 of the Current Report on Form 8-K filed on August 3, 2017, Commission File No.

10.6 Form of Director and Officer Indemnification Agreement (incorporated by reference to Exhibit 10.7 of Amendment No.

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333-199958, filed with the Commission on November 7, 2014) *

Number Description

10.8 Form of Stock Option Agreement (Amended and Restated James River Group Holdings, Ltd.

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2014 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.1 to the Current Report on Form 8-K filed on October 26, 2022, Commission File No.

10.13 Third Amendment to the James River Group Holdings, Ltd.

2014 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.1 to the Current Report on Form 8-K filed on October 25, 2024;

Commission File No.

10.14 Form of Nonqualified Share Option Agreement (James River Group Holdings, Ltd.

21 unchanged sentences

10.21 Amendment to the 2014 Non-Employee Director Incentive Plan (incorporated by reference to Exhibit 10.1 of the Current Report on Form 8-K filed on May 1, 2019, Commission File No.

10.22 Second Amendment to the James River Group Holdings, Ltd.

2014 Non-Employee Director Incentive Plan (incorporated by reference to Exhibit 10.2 of the Current Report on Form 8-K filed on October 25, 2024 ;

Commission File No.

10.23 Form of Restricted Share Award Agreement (James River Group Holdings, Ltd.

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333-199958, filed with the Commission on November 24, 2014) *

Number Description

10.24 Form of Restricted Share Unit Award Agreement (James River Group Holdings, Ltd., 2014 Non-Employee Director Incentive Plan) (incorporated by reference to Exhibit 10.17 of Amendment No.

1 unchanged sentence

333-199958, filed with the Commission on December 9, 2014) *

10.28 James River Management Company, Inc.

Leadership Recognition Program (incorporated by reference to Exhibit 10.18 of Amendment No.

1 to the Registration Statement on Form S-1, Registration No.

333-199958, filed with the Commission on November 24, 2014)*

10.29 Employment Agreement, dated October 28, 2020, by and among Frank N.

D’Orazio, James River Group Holdings, Ltd., and its subsidiary, James River Group, Inc.

(incorporated by reference to Exhibit 10.1 to the Current Report on Form 8-K filed on November 2, 2020, Commission File No.

10.30 First Amendment to Employment Agreement dated October 28, 2020, by and among Frank N.

D’Orazio, James River Group Holdings, Ltd., and its subsidiary James River Group, Inc.

(incorporated by reference to Exhibit 10.1 to the Current Report on Form 8-K filed on June 8, 2023, Commission File No.

10.25 Form of Retention Award Letter (incorporated by reference to Exhibit 10.1 to the Current Report on Form 8-K filed on July 31, 2024;

Commission File No.

10.26 Amended and Restated Employment Agreement, dated as of July 30, 2024, by and between Frank D’Orazio, James River Group Holdings, Ltd.

and James River Group Inc.

(incorporated by reference to Exhibit 10.2 to the Current Report on Form 8-K filed with on July 31, 2024;

Commission File No.

10.27 Employment Agreement, dated December 19, 2016, by and among James River Group Holdings, Ltd., James River Group, Inc., and Sarah C.

Doran (incorporated by reference to Exhibit 10.1 to the Current Report on Form 8-K filed on December 22, 2016, Commission File No.

Number Description

10.28 Amendment to Employment Agreement dated December 19, 2016, between Sarah C.

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and Richard Schmitzer (incorporated by reference to Exhibit 10.22 to Annual Report on Form 10-K filed on March 1, 2018, Commission File No.

10.34 James River Management Company, Inc.

Leadership Recognition Program Award Letter, dated September 30, 2011 to Richard Schmitzer (incorporated by reference to Exhibit 10.22 of Amendment No.

1 to the Registration Statement on Form S-1, Registration No.

333-199958, filed with the Commission on November 24, 2014)*

10.35 Separation and Release Agreement, dated December 26, 2023, by and among James River Group, Inc., certain subsidiaries of James River Group, Inc.

and Terry McCafferty *

10.36 Amended and Restated Employment Agreement, dated June 7, 2023, by and among James River Group, Inc., certain subsidiaries of James River Group, Inc.

and Terry McCafferty (incorporated by reference to Exhibit 10.2 to the Current Report on Form 8-K filed on June 8, 2023, Commission File No.

10.37 Employment Agreement, dated April 5, 2018, by and among JRG Reinsurance Company, Ltd.

and Daniel Heinlein (incorporated by reference to Exhibit 10.31 to the Annual Report on Form 10-K filed on February 27, 2019, Commission File No.

10.30 Employment Agreement, dated August 19, 2021, by and between Michael J.

Hoffmann and James River Group Holdings, Ltd.

(incorporated by reference to Exhibit 10.44 to Amendment No.

1 to the Annual Report on Form 10-K filed on April 26, 2024, Commission File No.

10.31 Investment Agreement, dated February 24, 2022, by and between James River Group Holdings, Ltd.

5 unchanged sentences

Commission File No.

10.33 First Amendment to Investment Agreement, dated November 11, 2024, by and between James River Group Holdings, Ltd.

and GPC Partners Investments (Thames) LP (incorporated by reference to Exhibit 4.1 of the Current Report on Form 8-K filed on November 13, 2024;

Commission File No.

10.34 Registration Rights Agreement, dated March 1, 2022, by and between James River Group Holdings, Ltd.

1 unchanged sentence

Commission File No.

10.35 First Amendment to the Registration Rights Agreement, dated as of November 11, 2024, by and among James River Group Holdings, Ltd.

and GPC Partners Investments (Thames) LP (incorporated by reference to Exhibit 10.3 of the Current Report on Form 8-K filed on November 13, 2024;

Commission File No.

10.36 Loss Portfolio Transfer Reinsurance Agreement dated September 27, 2021 between James River Insurance Company and James River Casualty Company and Aleka Insurance, Inc.

2 unchanged sentences

(incorporated by reference to Exhibit 10.2 on the Current Report on Form 8-K filed on September 30, 2021, Commission File No.

10.43 Loss Portfolio Transfer Retrocession Agreement entered into on February 23, 2022 by and between JRG Reinsurance Company Ltd.

and Fortitude Reinsurance Company Ltd.

(incorporated by reference to Exhibit 10.2 on the Current Report on Form 8-K filed on February 28, 2022;

10.38 Combined Loss Portfolio Transfer and Adverse Development Cover Reinsurance Contract dated July 2, 2024 between James River Insurance Company and James River Casualty Company and State National Insurance Company, Inc.

(incorporated by reference to Exhibit 10.1 to the Current Report on Form 8-K filed on July 9, 2024;

Commission File No.

10.39 Subscription Agreement, dated November 11, 2024, by and between James River Group Holdings, Ltd.

and Cavello Bay Reinsurance Limited (incorporated by reference to Exhibit 10.1 of the Current Report on Form 8-K filed on November 13, 2024;

Commission File No.

10.40 Registration Rights Agreement, dated December 23, 2024, by and among James River Group Holdings, Ltd.

and Cavello Bay Reinsurance Limited

10.41 Adverse Development Cover Reinsurance Contract, dated November 11, 2024, by and between James River Insurance Company and James River Casualty Company, and Cavello Bay Reinsurance Limited (incorporated by reference to Exhibit 10.2 of the Current Report on Form 8-K filed on November 13, 2024;

Commission File No.

19.1 James River Group Holdings, Ltd.

Insider Trading Policy

Number Description

6 unchanged sentences

97.1 James River Group Holdings, Ltd.

Executive Officer Incentive Compensation Recovery Policy

Executive Officer Incentive Compensation Recovery Policy (incorporated by reference to Exhibit 97.1 to the Annual Report on Form 10-K filed on February 29, 2024;

Commission File No.

101.INS Inline XBRL Instance Document

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* Denotes a management contract or compensatory plan or arrangement.

+ Exhibit not filed with the Securities and Exchange Commission pursuant to Item 601(b)(4)(iii) of Regulation S-K.

The Company will furnish a copy to the SEC upon request.

+ Exhibit or Schedules to Exhibit not filed with the Securities and Exchange Commission pursuant to Item 601(b)(4)(iii) and Regulation 601(a)(5) of Regulation S-K.

The Company will furnish a copy of the omitted Exhibit or Schedules to the SEC upon request.

FORM 10-K SUMMARY

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JAMES RIVER GROUP HOLDINGS, LTD.

February 29, 2024

March 4, 2025

Chief Executive Officer and Director

1 unchanged sentence

NAME TITLE DATE

Chief Executive Officer and Director February 29, 2024

Chief Executive Officer and Director March 4, 2025

D'Orazio (Principal Executive Officer)

Doran Chief Financial Officer February 29, 2024

Doran Chief Financial Officer March 4, 2025

Doran (Principal Financial Officer)

/s/ Michael E.

Crow Principal Accounting Officer February 29, 2024

Director, Non-Executive Chairman of the Board February 29, 2024

Crow Principal Accounting Officer March 4, 2025

/s/ Christine LaSala Director, Non-Executive

Chairperson of the Board March 4, 2025

Christine LaSala

/s/ Matthew B.

Botein Director February 29, 2024

Botein Director March 4, 2025

/s/ Thomas L.

Brown Director February 29, 2024

Brown Director March 4, 2025

/s/ Kirstin M.

Gould Director February 29, 2024

Gould Director March 4, 2025

/s/ Dennis J.

Langwell Director February 29, 2024

Migliorato Director February 29, 2024

/s/ Patricia H.

Roberts Director February 29, 2024

Langwell Director March 4, 2025

Migliorato Director March 4, 2025

Director March 4, 2025

JAMES RIVER GROUP HOLDINGS, LTD.

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Consolidated Balance Sheets as of December 31, 2024 and 2023

Consolidated Statements of Income (Loss) and Comprehensive (Loss) Income for the Years Ended

Consolidated Statements of (Loss) Income and Comprehensive Loss for the Years Ended

December 31, 2024, 2023 and 2022

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generally accepted accounting principles.

We also have audited, in accordance with the standards of the Public Company Accounting Oversight Board (United States) (PCAOB), the Company's internal control over financial reporting as of December 31, 2023, based on criteria established in Internal Control-Integrated Framework issued by the Committee of Sponsoring Organizations of the Treadway Commission (2013 framework), and our report dated February 29, 2024, expressed an unqualified opinion thereon.

We also have audited, in accordance with the standards of the Public Company Accounting Oversight Board (United States) (PCAOB), the Company's internal control over financial reporting as of December 31, 2024, based on criteria established in Internal Control-Integrated Framework issued by the Committee of Sponsoring Organizations of the Treadway Commission (2013 framework), and our report dated March 4, 2025, expressed an unqualified opinion thereon.

Basis for Opinion

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Valuation of reserves for losses and loss adjustment expenses

Description of the Matter At December 31, 2023, the Company’s reserve for losses and loss adjustment expenses balance was $3.0 billion, $441.7 million of which is reported within liabilities held for sale.

Description of the Matter At December 31, 2024, the Company’s reserve for losses and loss adjustment expenses balance was $3.08 billion.

As described in Notes 1 and 8 of the consolidated financial statements, reserves for losses and loss adjustment expenses reflect the estimated ultimate cost of all incurred unpaid claims including estimates of claims incurred but not reported and loss adjustment expenses as of the balance sheet date.

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Charlotte, North Carolina

February 29, 2024

March 4, 2025

JAMES RIVER GROUP HOLDINGS, LTD.

7 unchanged sentences

and subsidiaries (the Company) maintained, in all material respects, effective internal control over financial reporting as of December 31, 2024, based on the COSO criteria .

We also have audited, in accordance with the standards of the Public Company Accounting Oversight Board (United States) (PCAOB), the consolidated balance sheets of the Company as of December 31, 2023 and 2022, the related consolidated statements of (loss) income and comprehensive loss, changes in shareholders' equity and cash flows for each of the three years in the period ended December 31, 2023, and the related notes and financial statement schedules listed in the Index at Item 15(a) and our report dated February 29, 2024 expressed an unqualified opinion thereon.

We also have audited, in accordance with the standards of the Public Company Accounting Oversight Board (United States) (PCAOB), the consolidated balance sheets of the Company as of December 31, 2024 and 2023, the related consolidated statements of (loss) income and comprehensive loss, changes in shareholders' equity and cash flows for each of the three years in the period ended December 31, 2024, and the related notes and financial statement schedules listed in the Index at Item 15(a) and our report dated March 4, 2025 expressed an unqualified opinion thereon.

Basis for Opinion

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Charlotte, North Carolina

February 29, 2024

March 4, 2025

JAMES RIVER GROUP HOLDINGS, LTD.

44 unchanged sentences

Accrued expenses 53,178 56,722

Income taxes payable — 13,900

Other liabilities 182,524 174,513

3 unchanged sentences

Series A redeemable preferred shares – 2024 and 2023:

$ 0.00125 par value;

165,000 shares authorized;

150,000 shares issued and outstanding

112,500 and 150,000 shares issued and outstanding, respectively

133,115 144,898

4 unchanged sentences

45,644,318 and 37,641,563 shares issued and outstanding, respectively

Preferred Shares – 2024 and 2023:

$ 0.00125 par value;

19,835,000 shares authorized;

no shares issued and outstanding

Additional paid-in capital 933,311 876,240

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Total expenses 778,746 725,095 608,242

Income (loss) from continuing operations before income taxes 86,914 53,272 ( 108,130 )

Income tax expense (benefit) on continuing operations:

(Loss) income from continuing operations before income taxes ( 71,120 ) 86,914 53,272

Income tax (benefit) expense on continuing operations:

Current 3,562 31,677 13,787

1 unchanged sentence

( 7,634 ) 25,705 18,414

Net income (loss) from continuing operations 61,209 34,858 ( 84,895 )

Net (loss) income from continuing operations ( 63,486 ) 61,209 34,858

Discontinued operations (Note 2):

Loss from discontinued operations ( 13,583 ) ( 88,493 ) ( 3,885 )

Loss on held for sale classification of discontinued operations ( 80,400 ) — —

Loss on disposal of discontinued operations ( 4,051 ) ( 80,400 ) —

Total loss from discontinued operations ( 17,634 ) ( 168,893 ) ( 3,885 )

2 unchanged sentences

Net (loss) income available to common shareholders $ ( 118,269 ) $ ( 118,184 ) $ 22,223

Other comprehensive income (loss):

Net unrealized gains (losses), net of taxes of $ 6,384 in 2023, $( 27,041 ) in 2022, and $( 7,135 ) in 2021

Other comprehensive (loss) income:

Net unrealized (losses) gains, net of taxes of $( 1,668 ) in 2024, $ 6,384 in 2023, and $( 27,041 ) in 2022

( 6,276 ) 99,323 ( 193,022 )

Total comprehensive loss $ ( 87,396 ) $ ( 8,361 ) $ ( 162,049 )

Net income (loss) per common share:

Net (loss) income per common share:

Continuing operations $ ( 2.60 ) $ 1.35 $ 0.70

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Outstanding Common

(Par) Additional

Capital Retained (Deficit)

Earnings Accumulated

(Par) Preferred

Shares Additional

Capital Retained Deficit Accumulated

Comprehensive

3 unchanged sentences

Balances at December 31, 2021 37,373,066 $ 7 $ — $ 862,040 $ ( 166,663 ) $ 29,978 $ 725,362

Net loss — — — ( 172,799 ) — ( 172,799 )

Net income — — — — 30,973 — 30,973

Other comprehensive loss — — — — — ( 193,022 ) ( 193,022 )

Issuance of common shares 6,497,500 1 192,106 — — 192,107

Exercise of stock options

93,446 — 1,671 — — 1,671

Vesting of RSUs

2 unchanged sentences

— — — 8,122 — — 8,122

Dividends on Series A preferred shares — — — — ( 8,750 ) — ( 8,750 )

Dividends on common shares — — — — ( 7,615 ) — ( 7,615 )

Balances at December 31, 2022 37,470,237 $ 7 $ — $ 868,858 $ ( 152,055 ) $ ( 163,044 ) $ 553,766

Net income — — — 30,973 — 30,973

Other comprehensive loss — — — — ( 193,022 ) ( 193,022 )

Net loss — — — — ( 107,684 ) — ( 107,684 )

Other comprehensive income — — — — — 99,323 99,323

Vesting of RSUs 171,326 — — ( 1,734 ) — — ( 1,734 )

Compensation expense under share incentive plans

— — — 9,116 — — 9,116

Dividends on Series A preferred shares — — — — ( 10,500 ) — ( 10,500 )

2 unchanged sentences

Net loss — — — — ( 81,120 ) — ( 81,120 )

Other comprehensive income — — — — 99,323 99,323

Other comprehensive loss — — — — — ( 6,276 ) ( 6,276 )

Conversion of Series A Preferred Shares to common shares (Notes 12 and 13) 5,859,375 1 — 38,788 ( 1,289 ) — 37,500

Extinguishment of Series A Preferred Shares - deemed dividend (Note 12) — — — — ( 25,717 ) — ( 25,717 )

Enstar common share investment (Note 13) 1,953,125 1 — 12,499 — — 12,500

Vesting of RSUs 190,255 — — ( 847 ) — — ( 847 )

Compensation expense under share incentive plans

— — — 6,631 — — 6,631

Dividends on Series A preferred shares — — — — ( 10,143 ) — ( 10,143 )

10 unchanged sentences

Net (loss) income $ ( 81,120 ) $ ( 107,684 ) $ 30,973

Adjustments to reconcile net (loss) income to net cash provided by (used in) operating activities:

Adjustments to reconcile net (loss) income to net cash (used in) provided by operating activities:

Deferred policy acquisition costs ( 65,580 ) ( 73,333 ) ( 79,648 )

Amortization of policy acquisition costs 69,261 96,453 88,571

Net realized and unrealized losses (gains) on investments 43,251 28,318 ( 15,564 )

Net realized and unrealized losses on investments 6,985 43,251 28,318

Impairment of intangible assets — 2,500 —

1 unchanged sentence

Income from equity method investments ( 4,133 ) ( 4,881 ) ( 2,458 )

Loss on held-for sale classification of discontinued operations 80,400 — —

Loss on disposal of discontinued operations ( 2,193 ) 80,400 —

Deferred U.S.

11 unchanged sentences

Other 12,423 ( 10,325 ) 83,219

Net cash provided by (used in) operating activities (a) 87,953 222,734 ( 913,546 )

Net cash (used in) provided by operating activities (a) ( 247,085 ) 87,953 222,734

Investing activities

Sale of JRG Re 96,412 — —

Fixed maturity securities:

12 unchanged sentences

Return of capital 1,160 2,793 20,170

Repayments and redemptions 10,133 2,535 3,760

Proceeds from sales and repayments 4,077 10,133 2,535

Securities receivable or payable, net ( 169 ) 3,499 ( 6,684 )

5 unchanged sentences

Issuance of Series A preferred shares (Note 12) — — 144,898

Issuances of common shares - public offering — — 192,107

Issuances of common shares under equity incentive plans — — 1,877

Enstar common share investment (Note 13) 12,500 — —

Payroll taxes withheld and remitted on net settlement of RSUs ( 847 ) ( 1,734 ) ( 1,304 )

3 unchanged sentences

Net cash (used in) provided by financing activities ( 28,846 ) ( 21,115 ) 89,671

Change in cash, cash equivalents, and restricted cash equivalents (b) 83,570 ( 15,749 ) ( 730,052 )

Change in cash, cash equivalents, and restricted cash equivalents 31,101 83,570 ( 15,749 )

Cash, cash equivalents, and restricted cash equivalents at beginning of year 359,949 276,379 292,128

12 unchanged sentences

Change in restricted cash equivalents $ ( 43,744 ) $ ( 30,766 ) $ 1,210

(a) Cash provided by (used in) operating activities for the years ended December 31, 2023, 2022, and 2021 reflects the activity in restricted cash equivalents above.

(a) Cash (used in) provided by operating activities for the years ended December 31, 2024, 2023, and 2022 reflects the activity in restricted cash equivalents above.

As permitted under the agreements establishing the Indemnity Trust and the LPT Trust, we have withdrawn collateral from the Indemnity Trust and the LPT Trust to fund the Loss Fund Trust as required under the Administrative Services Agreement.

1 unchanged sentence

Management’s Discussion and Analysis of Financial Condition and Results of Operations – Amounts Recoverable from an Indemnifying Party and Reinsurer on Legacy Commercial Auto Book ”.

Excluding the restricted cash activity above, cash provided by (used in) operating activities was $ 118.7 million, $ 221.5 million, and $( 155.6 ) million for the years ended December 31, 2023, 2022, and 2021, respectively.

The cash used in operating activities (excluding restricted cash equivalents) in 2021 was largely driven by $ 317.6 million paid to effect a loss portfolio transfer reinsurance transaction.

(b) includes change in cash and cash equivalents classified as held-for-sale (See Note 2).

Excluding the restricted cash activity above, cash (used in) provided by operating activities was $( 203.3 ) million, $ 118.7 million, and $ 221.5 million for the years ended December 31, 2024, 2023, and 2022, respectively.

The $ 203.3 million of cash used in operating activities for the year ended December 31, 2024 primarily reflects the $ 313.2 million and $ 52.8 million of reinsurance premium paid in 2024 related to the E&S ADC and E&S Top Up ADC (See Note 8).

See accompanying notes.

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• James River Insurance Company (“James River Insurance”) is an Ohio domiciled excess and surplus lines insurance company that, with its wholly-owned insurance subsidiary, James River Casualty Company, is authorized to write business in every state and the District of Columbia.

• Falls Lake National Insurance Company (“Falls Lake National”) is an Ohio domiciled insurance company which wholly owns Stonewood Insurance Company (“Stonewood Insurance”), a North Carolina domiciled company, and Falls Lake Fire and Casualty Company, a California domiciled company.

• Falls Lake National Insurance Company (“Falls Lake National”) is an Ohio domiciled insurance company which wholly owns Stonewood Insurance Company (“Stonewood Insurance”), an Ohio domiciled company, and Falls Lake Fire and Casualty Company, a California domiciled company.

Falls Lake National primarily writes specialty admitted fronting and program business and individual risk workers' compensation insurance.

The Company also owns JRG Reinsurance Company Ltd.

(“JRG Re”), a Bermuda domiciled reinsurer, which comprises the remaining operations of the former Casualty Reinsurance segment, and which, prior to the suspension of its underwriting activities in 2023, primarily provided non-catastrophe casualty reinsurance to U.S.

third parties and, through December 31, 2017, to the Company’s U.S.-based insurance subsidiaries.

The Company previously owned JRG Reinsurance Company Ltd.

(“JRG Re”), a Bermuda domiciled reinsurer, which comprised the former Casualty Reinsurance segment, and which, prior to the suspension of its underwriting activities in 2023, primarily provided non-catastrophe casualty reinsurance to U.S.

third parties.

On November 8, 2023, the Company entered into an agreement to sell JRG Re.

The sale is expected to close in the first quarter of 2024 and will result in the Company’s disposition of its casualty reinsurance business and related assets.

The sale closed on April 16, 2024 and resulted in the Company’s disposition of its casualty reinsurance business and related assets.

See Held-for-Sale and Discontinued Operations below and Note 2 for additional disclosure.

7 unchanged sentences

The results of operations of a component of the Company are reported in discontinued operations when certain criteria are met as of the date of disposal, or earlier if classified as held-for-sale.

The Company has determined that the definitive agreement to sell JRG Re meets the criteria for JRG Re to be classified as held for sale and that the sale represents a strategic shift that will have a major effect on the Company's operations.

The Company has determined that the definitive agreement to sell JRG Re met the criteria for JRG Re to be classified as held for sale and that the sale represented a strategic shift that will have a major effect on the Company's operations.

Accordingly, the results of JRG Re's operations have been presented as discontinued operations, and the assets and liabilities of JRG Re have been classified as held-for-sale and segregated for all periods presented in this Annual Report on Form 10-K.

61 unchanged sentences

The allowance for credit losses was $ 22.3 million and $ 17.9 million at December 31, 2024 and 2023, respectively.

Credit loss expense was $ 2.8 million for the year ended December 31, 2023, $ 1.1 million for the year ended December 31, 2022, and $ 9.4 million for the year ended December 31, 2021 ($ 7.1 million of which was deducted from amounts due to our reinsurers).

Credit loss expense was $ 6.9 million for the year ended December 31, 2024, $ 2.8 million for the year ended December 31, 2023, and $ 1.1 million for the year ended December 31, 2022.

Receivables written off against the allowance for credit losses totaled $ 2.5 million for the year ended December 31, 2024, $ 1.2 million for the year ended December 31, 2023, and $ 1.5 million for the year ended December 31, 2022.

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The Company also considers the expected impact of current and future expected economic conditions and adjusts estimates if needed based on an evaluation of these factors.

The allowance for credit losses on reinsurance recoverables at December 31, 2023 and 2022 was $ 660,000 and $ 580,000 , respectively.

The allowance for credit losses on reinsurance recoverables at December 31, 2024 and 2023 was $ 1.2 million and $ 660,000 , respectively.

Other amounts payable to reinsurers or receivable from reinsurers are netted where the right of offset exists.

12 unchanged sentences

Premiums written and earned, as well as related acquisition expenses, are recorded based upon the projected loss experience under the contracts.

Other income is principally comprised of fee income earned on policies for which the Company has no exposure to underwriting risk.

Other income is principally comprised of fee income in the Specialty Admitted Insurance segment earned on policies for which the segment has no exposure to underwriting risk and broker incentive income in the Excess and Surplus Lines segment.

Fee income of $ 4.6 million, $ 5.3 million, and $ 3.8 million is included in other income for the years ended December 31, 2024, 2023, and 2022, respectively.

1 unchanged sentence

Policies are accounted for on an individual basis, with no aggregation by counterparty.

Broker incentive income in the Excess and Surplus Lines segment was $ 5.4 million, $ 1.3 million, and $ 471,000 for the years ended December 31, 2024, 2023, and 2022, respectively.

Deferred tax assets and deferred tax liabilities are provided for the future tax consequences attributable to temporary differences between the financial statement carrying amounts of assets and liabilities and their respective U.S.

21 unchanged sentences

In evaluating whether there has been impairment to the intangible asset, management determines the fair value of the intangible asset and compares the resulting fair value to the carrying value of the intangible asset.

If the carrying value exceeds the fair value, the intangible asset is written down to fair value, and the impairment is reported through earnings.

The Company evaluates intangible assets with definite lives for impairment when impairment indicators are noted.

If the carrying value exceeds the fair value, the intangible asset

James River Group Holdings, Ltd.

2 unchanged sentences

Years ended December 31, 2024, 2023, and 2022

is written down to fair value, and the impairment is reported through earnings.

The Company evaluates intangible assets with definite lives for impairment when impairment indicators are noted.

Impairment of Long-Lived Assets

1 unchanged sentence

If indicators of impairment are present, fair value is calculated using estimated future cash flows expected to be generated from the use of those assets.

In the fourth quarter of 2023, the Company determined that the sustained decrease in the share price of the Company’s common stock was an indication of impairment, and accordingly, the Company performed impairment testing on its goodwill and other intangible assets using a December 31, 2023 valuation date.

In the fourth quarter of 2024, the Company determined that the decrease in the share price of the Company’s common stock during the quarter was an indication of impairment, and accordingly, the Company performed impairment testing on its goodwill and other intangible assets using a December 31, 2024 valuation date.

As a result of this testing, the Company concluded that no impairment of the intangible assets had occurred.

15 unchanged sentences

Management uses this information and its judgment to make decisions on the final recorded reserve for losses and loss adjustment expenses.

Management believes that the use of judgment is necessary to arrive at a best estimate for the reserve for losses and loss adjustment expenses given the long-tailed nature of the business generally written by the Company and the limited operating experience of the fronting and program business in the Specialty Admitted Insurance segment and the commercial auto business in the Excess and Surplus Lines segment.

Judgment is also required to make actuarial adjustments, if needed, for changes in claims processing and case reserving that could cause current reported loss and paid loss development patterns to deviate from historical patterns.

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This turnover and change in underlying mix of exposures can cause actuarial estimates based on prior experience to be less reliable than estimates for more stable, admitted books of business.

Catastrophes of significant magnitude, including hurricanes and earthquakes, involve complex coverage issues.

Catastrophes of significant magnitude, including hurricanes, earthquakes, and wildfires, involve complex coverage issues.

In estimating the reserve for losses and loss adjustment expenses for these catastrophes, management uses case reserve estimates based on information obtained from site inspections by the Company’s adjustors and the terms of coverage provided in the policies.

1 unchanged sentence

Although management believes that the reserve for losses and loss adjustment expenses is reasonable, it is possible that the Company’s actual incurred losses and loss adjustment expenses will not develop in a manner consistent with the assumptions inherent in the determination of these reserves.

Specifically, the Company’s actual ultimate loss ratio could differ from management’s initial expected loss ratio and/or the Company’s actual reporting patterns for losses could differ from the expected reporting patterns.

Accordingly, the ultimate settlement of losses and the related loss adjustment expenses may vary significantly from the estimates included in the Company’s consolidated financial statements.

These estimates are reviewed

Specifically, the Company’s actual ultimate loss ratio could differ from management’s initial expected loss ratio and/or the Company’s actual reporting patterns for losses could differ from the

James River Group Holdings, Ltd.

2 unchanged sentences

Years ended December 31, 2024, 2023, and 2022

continually by management and are adjusted as necessary as experience develops or new information becomes known;

expected reporting patterns.

Accordingly, the ultimate settlement of losses and the related loss adjustment expenses may vary significantly from the estimates included in the Company’s consolidated financial statements.

These estimates are reviewed continually by management and are adjusted as necessary as experience develops or new information becomes known;

such adjustments are included in current operations.

Retroactive Reinsurance Accounting

Loss portfolio transfers and adverse development covers are forms of reinsurance utilized by the Company to transfer losses and loss adjustment expenses and associated risk of adverse development on covered subject business, as defined in the respective agreements, to an assuming reinsurer in exchange for a reinsurance premium.

The Company periodically reevaluates the remaining reserves subject to loss portfolio transfers and adverse development covers, and when recognized adverse prior year development on the subject business causes the cumulative amounts ceded under the agreements to exceed the consideration paid, the agreements move into a gain position subject to retroactive reinsurance accounting under GAAP.

Gains are deferred under retroactive reinsurance accounting and recognized in earnings in proportion to actual paid recoveries under the agreements using the recovery method.

Share Based Compensation

22 unchanged sentences

Years ended December 31, 2024, 2023, and 2022

The following represents a reconciliation of the numerator and denominator of the basic and diluted earnings (loss) per common share computations contained in the consolidated financial statements.

The following represents a reconciliation of the numerator and denominator of the basic and diluted (loss) earnings per common share computations contained in the consolidated financial statements.

Year Ended December 31,

1 unchanged sentence

(in thousands, except share and per share amounts)

Net income (loss) from continuing operations $ 61,209 $ 34,858 $ ( 84,895 )

Net (loss) income from continuing operations $ ( 63,486 ) $ 61,209 $ 34,858

Dividends on Series A preferred shares ( 37,149 ) ( 10,500 ) ( 8,750 )

Income (loss) from continuing operations available to common shareholders $ 50,709 $ 26,108 $ ( 84,895 )

(Loss) income from continuing operations available to common shareholders $ ( 100,635 ) $ 50,709 $ 26,108

Loss from discontinued operations ( 17,634 ) ( 168,893 ) ( 3,885 )

4 unchanged sentences

Diluted 38,685,003 37,810,440 37,650,969

Net income (loss) per common share:

Net (loss) income per common share:

Continuing operations $ ( 2.60 ) $ 1.35 $ 0.70

4 unchanged sentences

$ ( 3.06 ) $ ( 3.13 ) $ 0.59

For the years ended December 31, 2023, 2022, and 2021, potential common shares of 5,722,915 , 4,728,461 , and 95,219 , respectively, were excluded from the calculation of diluted earnings (loss) per common share as their effects were anti-dilutive.

For the years ended December 31, 2024, 2023, and 2022, potential common shares of 7,886,906 , 5,722,915 , and 4,728,461 , respectively, were excluded from the calculation of diluted (loss) earnings per common share as their effects were anti-dilutive.

Adopted Accounting Standards

The guidance in ASU 2023-07 —Segment Reporting (Topic 280):

Improvements to Reportable Segment Disclosures was designed to improve reportable segment disclosure requirements, primarily through enhanced disclosures about significant segment expenses.

This ASU is effective for fiscal years beginning after December 15, 2023, and interim periods within fiscal years beginning after December 15, 2024.

The Company adopted the new standard effective with this Form 10-K by providing additional segment disclosures in Note 20.

The new standard did not have a material impact on the Company's financial statements.

No accounting standards were adopted during the year ended December 31, 2024 that had a material impact on our financial statements.

Prospective Accounting Standards

There are no prospective accounting standards which are expected to have a material impact on our financial statements subsequent to December 31, 2023 .

The guidance in ASU 2023-09 —Income Taxes (Topic 740):

Improvements to Income Tax Disclosures was designed to increase transparency about income tax information through improvements to the rate reconciliation and disclosure of income taxes paid.

This ASU is effective for fiscal years beginning after December 15, 2024.

Although the Company continues to evaluate the impact of adopting this new accounting standard, the amendments are disclosure-related and are not expected to have a material impact on the Company's financial statements.

The guidance in ASU 2024-03 , Income Statement - Reporting Comprehensive Income - Expense Disaggregation Disclosures (Subtopic 220-40):

Disaggregation of Income Statement Expenses requires additional, disaggregated disclosure around certain income statement expense line items.

This ASU is effective for fiscal years beginning after December 15, 2026

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2024, 2023, and 2022

and interim periods beginning after December 15, 2027, although early adoption is permitted.

The Company is in the process of evaluating the impact of this new guidance on the disclosures in its financial statements.

There are no other prospective accounting standards which are expected to have a material impact on our financial statements subsequent to December 31, 2024 .

Discontinued Operations

On November 8, 2023, the Company entered into a Stock Purchase Agreement (the “Stock Purchase Agreement”) with Fleming Intermediate Holdings LLC, a Cayman Islands limited liability company (the “Buyer”).

Pursuant to the Stock Purchase Agreement, and on the terms and subject to the conditions therein, the Buyer agreed to purchase from the Company all of the common shares of JRG Re (the “Transaction”).

JRG Re comprises the remaining operations of the former Casualty Reinsurance segment, and the Transaction, which is expected to close in the first quarter of 2024, will result in the Company’s disposition of its casualty reinsurance business and related assets.

Total consideration to the Company for the sale of JRG Re includes (A) $ 277 million (the “Purchase Price”), which is comprised of (i) $ 138 million payable by the Buyer to the Company on the closing date in cash, subject to final closing adjustments based on changes in JRG Re’s adjusted net worth between March 31, 2023 and the closing date, and (ii) a $ 139 million dividend or return of capital or surplus by JRG Re to the Company prior to the closing date, which dividend or return of capital or surplus is subject to the availability of unencumbered assets on the closing date, and (B) $ 2.5 million to be

Pursuant to the Stock Purchase Agreement, and on the terms and subject to the conditions therein, the Buyer agreed to purchase from the Company all of the common shares of JRG Re.

JRG Re comprised the remaining operations of the former Casualty Reinsurance segment, and the sale of JRG Re, which closed on April 16, 2024, resulted in the Company’s disposition of its casualty reinsurance business and related assets.

Pursuant to the terms of the Stock Purchase Agreement, the aggregate purchase price received by the Company, after giving effect to estimated adjustments based on changes in JRG Re’s adjusted net worth between March 31, 2023 and the closing, totaled approximately $ 291.4 million (the “Closing Date Purchase Price”).

The aggregate Closing Date Purchase Price was comprised of (i) $ 152.4 million paid in cash by the Buyer and (ii) an aggregate $ 139.0 million dividend and distribution from contributed surplus by JRG Re to the Company.

In accordance with the Stock Purchase Agreement, the cash portion of the purchase price was calculated based on an estimated balance sheet of JRG Re as of the date of closing.

The estimated balance sheet is subject to final post-closing adjustments, which resulted in the downward adjustment to the purchase price discussed below.

The Buyer delivered a closing statement to the Company, and pursuant to the procedures in the Stock Purchase Agreement, the Company has given its notice of disagreement with the Buyer’s closing statement.

In its notice of disagreement, the Company (i) agreed with an $ 11.4 million downward adjustment to the Closing Date Purchase Price due to losses from JRG Re’s operations between the date of the balance sheet used to produce the estimated closing statement and the Closing Date, which downward adjustment was paid to the Buyer on October 18, 2024, and (ii) disputed $ 54.1 million in aggregate downward adjustments to the Closing Date Purchase Price claimed by the Buyer, which the Company believes are unsupported by the facts known to the Company and the terms of the Stock Purchase Agreement.

The Stock Purchase Agreement provides procedures for resolving disputes between the parties regarding the closing statement and it is possible that the resolution of these disputes could result in a significant reduction to the amount of the purchase price.

The Company determined that the sale of JRG Re met the criteria to be classified as held for sale at December 31, 2023 and that the sale represented a strategic shift that will have a major effect on its operations.

Accordingly, the results of JRG Re's operations have been presented as discontinued operations, and the assets and liabilities of JRG Re at December 31, 2023 have been classified as held for sale and segregated for all periods presented in this Annual Report on Form 10-K.

The $ 139.0 million pre-closing dividend includes the forgiveness of $ 133.2 million owed from JRGH to JRG Re and $ 5.8 million which was paid in cash to JRGH.

In the fourth quarter of 2023, after giving effect to the pre-closing dividend, the Company recorded an estimated loss on sale of $ 80.4 million to write down the carrying value of JRG Re to its estimated fair value based upon the estimated sales price of the transaction less costs to sell and other adjustments in accordance with the Stock Purchase Agreement.

At December 31, 2024, the estimated loss on the sale was revised to $ 78.3 million.

The loss on disposal for the year ended December 31, 2024 of $ 4.1 million includes the $ 2.1 million gain for the change in the estimated loss on sale and selling costs incurred of $ 6.2 million.

The $ 5.8 million cash portion of the pre-closing dividend is included in other liabilities at December 31, 2023.

The Company also recognized losses of $ 53.2 million for the year ended December 31, 2023 associated with JRG Re's fixed maturity securities as the Company no longer had the intent or ability to hold securities in an unrealized loss position until a recovery of their fair value could occur.

The losses are included in net realized and unrealized (losses) gains on investments in the operating results presented below.

James River Group Holdings, Ltd.

2 unchanged sentences

Years ended December 31, 2024, 2023, and 2022

paid by the Buyer to the Company in the event that certain conditions outlined in the Stock Purchase Agreement are met on the date that is nine months following the closing date.

The Purchase Price is subject to adjustment based on changes in JRG Re’s adjusted net worth between March 31, 2023 and the closing date.

The Company has determined that the sale of JRG Re meets the criteria to be classified as held for sale and that the sale represents a strategic shift that will have a major effect on our operations.

Accordingly, the results of JRG Re's operations have been presented as discontinued operations, and the assets and liabilities of JRG Re have been classified as held for sale and segregated for all periods presented in this Annual Report on Form 10-K.

The $ 139 million pre-closing dividend includes the forgiveness of $ 133.2 million owed from JRGH to JRG Re and $ 5.8 million to be paid in cash to JRGH.

In the fourth quarter of 2023, after giving effect to the pre-closing dividend, we recorded an estimated loss on sale of $ 80.4 million to write down the carrying value of JRG Re to its estimated fair value based upon the estimated sales price of the transaction less costs to sell and other adjustments in accordance with the Stock Purchase Agreement.

The $ 5.8 million cash portion of the pre-closing dividend is included in other liabilities presented below.

The Company also recognized losses of $ 53.2 million for the year ended December 31, 2023 associated with JRG Re's fixed maturity securities as the Company no longer has the intent or ability to hold securities in an unrealized loss position until a recovery of their fair value could occur.

The losses are included in net realized and unrealized (losses) gains on investments in the operating results presented below.

JRG Re's assets and liabilities held for sale were comprised of the following:

JRG Re's assets and liabilities held for sale at December 31, 2023 were comprised of the following:

(in thousands)

2 unchanged sentences

Equity securities, at fair value 2,779

Bank loan participations, at fair value — 100,710

Short-term investments — 12,461

Total invested assets 535,021

3 unchanged sentences

Reinsurance recoverable on unpaid and paid losses, net 234,615

Prepaid reinsurance premiums — 4,723

Deferred policy acquisition costs 4,986

32 unchanged sentences

Loss from discontinued operations ( 13,583 ) ( 88,493 ) ( 3,885 )

Loss on held for sale classification of discontinued operations ( 80,400 ) — —

Loss on disposal of discontinued operations ( 4,051 ) ( 80,400 ) —

Total loss from discontinued operations ( 17,634 ) ( 168,893 ) ( 3,885 )

5 unchanged sentences

Net cash provided by investing activities of discontinued operations 63,104 115,145 8,497

Net cash (used in) provided by discontinued operations $ ( 762 ) $ ( 16,625 ) $ 6,439

Net cash provided by (used in) discontinued operations $ 37,989 $ ( 762 ) $ ( 16,625 )

Interest paid by discontinued operations $ 1,388 $ 3,951 $ 2,578

JRG Re Commitments and Contingent Liabilities

JRG Re has entered into three letter of credit facilities with banks as security to third-party reinsureds on reinsurance assumed by JRG Re.

JRG Re has established custodial accounts to secure these letters of credit.

Under a $ 75.0 million facility, $ 4.7 million of letters of credit were issued through December 31, 2023 which were secured by deposits of $ 3.2 million.

Under the 2013 Facility, $ 42.7 million of letters of credit were issued through December 31, 2023 which were secured by deposits of $ 51.1 million.

Under the 2017 Facility (as defined in Note 10), $ 25.5 million of letters of credit were issued through December 31, 2023 which were secured by deposits of $ 35.6 million.

JRG Re has also established trust accounts to secure its obligations to selected reinsureds.

The total amount deposited in the trust accounts for the benefit of third-party reinsureds was $ 444.8 million at December 31, 2023.

Casualty Re Loss Portfolio Transfer

On February 23, 2022, JRG Re entered into a loss portfolio transfer retrocession agreement (the “Casualty Re LPT”) with Fortitude Reinsurance Company Ltd.

(“FRL”) under which FRL reinsures the majority of JRG Re's reserves.

Under the terms of the transaction, which closed on March 31, 2022 (the “Retrocession Closing Date”), JRG Re (a) ceded to FRL all existing

James River Group Holdings, Ltd.

2 unchanged sentences

Years ended December 31, 2024, 2023, and 2022

and future claims for losses arising under certain casualty reinsurance agreements with underlying insurance companies with treaty inception dates ranging from 2011 to 2020 (the “Subject Business”), in each case net of third-party reinsurance and other recoveries, up to an aggregate limit of $ 400.0 million;

(b) continues to manage and retain the benefit of other third-party reinsurance on the Subject Business;

(c) paid FRL a reinsurance premium of $ 335.0 million, $ 310.0 million of which JRG Re credited to a notional funds withheld account (the “Funds Withheld Account”) and $ 25.0 million of which was paid in cash to FRL;

and (d) pays FRL a 2 % per annum crediting rate on the Funds Withheld Account balance on a quarterly basis.

The total premium, initial Funds Withheld Account credit, and aggregate limit were adjusted for claims paid from October 1, 2021 to the Retrocession Closing Date.

JRG Re incurred $ 6.8 million of net adverse reserve development in the three months ended March 31, 2022 associated with the Casualty Re LPT.

At December 31, 2023, the balance of the Funds Withheld Account was $ 137.8 million and reinsurance recoverables from FRL under the Casualty Re LPT were $ 221.7 million.

Retroactive Reinsurance Accounting

The Company periodically reevaluates the remaining reserves subject to the Casualty Re LPT.

For the years ended December 31, 2023 and 2022, due to adverse paid and reported loss trends, JRG Re recognized adverse prior year development of $ 52.9 million and $ 6.1 million, respectively, on the reserves subject to the Casualty Re LPT, resulting in corresponding additional amounts ceded under the loss portfolio transfer.

The Casualty Re LPT is in a gain position as the cumulative amounts ceded under the loss portfolio transfer exceeds the consideration paid, requiring the application of retroactive reinsurance accounting under GAAP.

Under retroactive reinsurance accounting, gains are deferred and recognized in earnings in proportion to actual paid recoveries under the loss portfolio transfer using the recovery method.

Over the life of the contract, we would expect no economic impact to JRG Re as long as any additional losses are within the limit of the loss portfolio transfer and the counterparty performs under the contract.

In periods where JRG Re recognizes a change in the estimate of the reserves subject to the loss portfolio transfer that increases or decreases the amounts ceded under the loss portfolio transfer, the proportion of actual paid recoveries to total ceded losses is affected and the change in deferred gain is recognized in earnings as if the revised estimate of ceded losses was available at the effective date of the loss portfolio transfer.

The effect of the deferred retroactive reinsurance benefit is recorded in losses and loss adjustment expenses for the discontinued operations of JRG Re and reported within loss from discontinued operations on the Consolidated Statements of (Loss) Income and Comprehensive Loss.

For the years ended December 31, 2023 and 2022, retroactive reinsurance benefits totaling $ 24.0 million and $ 1.7 million, respectively, were recorded in losses and loss adjustment expenses using the recovery method.

As of December 31, 2023 and 2022, the cumulative amounts ceded under the Casualty Re LPT was $ 393.9 million and $ 341.1 million, respectively.

The total deferred retroactive reinsurance gain of $ 33.2 million at December 31, 2023 and $ 4.4 million at December 31, 2022 under the loss portfolio transfer is presented within the liabilities held for sale of JRG Re on the Company's Consolidated Balance Sheets.

The Company has $ 6.1 million of aggregate limit remaining under the Casualty Re LPT at December 31, 2023.

Bermuda Statutory Matters

Under the Bermuda Insurance Act 1978 and related regulations, an insurer must maintain minimum statutory capital and surplus at the greater of a minimum solvency margin (“MSM”) and the Enhanced Capital Requirement (“ECR”), which is the higher of the MSM and capital calculated by the Bermuda Solvency Capital Requirement (“BSCR”) model or an approved internal model.

The estimated minimum statutory solvency margin required at December 31, 2023 for JRG Re was approximately $ 31.1 million.

Actual statutory capital and surplus at December 31, 2023 was $ 361.3 million.

The statutory net loss was $ 36.1 million for the year ended December 31, 2023.

The ECR for the year ended December 31, 2022 was $ 106.4 million.

The BSCR models for the year ended December 31, 2023 will not be filed with the Bermuda Monetary Authority until April 30, 2024.

The Company believes that the minimum statutory capital and surplus requirements will be met.

Under the Bermuda Insurance Act 1978, an insurer must maintain a minimum liquidity ratio in which the value of its relevant assets is not less than 75.0 % of the amount of its relevant liabilities for general business.

Relevant assets include cash and cash equivalents, fixed maturities, quoted alternative investments, accrued interest income, premiums receivable, losses recoverable from reinsurers, and funds withheld.

The relevant liabilities include total insurance provisions and other liabilities less deferred income taxes and letters of credit, guarantees and other instruments.

As of December 31, 2023, the minimum liquidity ratio requirements were met.

Dividend Restrictions

The Bermuda Insurance Act of 1978 prohibits an insurer from declaring or paying a dividend if it is in breach of its minimum solvency margin, its enhanced capital requirement, or its minimum liquidity ratio, or if the declaration or payment of such dividend would cause such a breach.

An insurer can declare or pay dividends without prior regulatory approval up to 25%

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2023, 2022, and 2021

of the total statutory capital and surplus (as shown on its previous financial year's statutory balance sheet).

The maximum combined amount of dividends and return of capital that can be paid without prior regulatory approval from JRG Re at December 31, 2023 is calculated to be approximately $ 90.3 million.

However, this dividend amount is subject to annual enhanced solvency requirement calculations.

All necessary approvals have been obtained by JRG Re to facilitate the $ 139 million pre-closing dividend pursuant to the SPA covering the sale of JRG Re.

The Company’s available-for-sale fixed maturity securities are summarized as follows:

62 unchanged sentences

At December 31, 2024, 100.0 % of the Company’s fixed maturity security portfolio was rated “BBB-” or better (“investment grade”) by Standard & Poor’s or received an equivalent rating from another nationally recognized rating agency.

Fixed maturity securities with ratings below investment grade by Standard & Poor's or another nationally recognized rating agency at December 31, 2023 had a fair value of $ 1.3 million.

At December 31, 2024 there were no fixed maturity securities with ratings below investment grade by Standard & Poor's or another nationally recognized rating agency.

The Company periodically reviews its available-for-sale fixed maturities to determine whether any unrealized losses exist that are due to credit-related factors.

7 unchanged sentences

Management may conclude that a qualitative analysis is sufficient to support its conclusion that the present value of expected cash flows equals or exceeds a security's amortized cost.

As a result of this review, management concluded that there were no credit-related impairments of fixed maturities at December 31, 2023, 2022, or 2021.

Management does not intend to sell the securities in an unrealized loss position, and it is not "more likely than not" that the Company will be required to sell these securities before a recovery in their value to their amortized cost basis occurs.

The Company elected the fair value option to account for bank loan participations.

Under the fair value option, bank loan participations are measured at fair value, and changes in unrealized gains and losses in bank loan participations are reported in

As a result of this review, management concluded that there were no credit-related impairments of fixed maturities at December 31, 2024 or December 31, 2023.

During the year ended December 31, 2024, management recognized an impairment loss of $ 207,000 for one fixed maturity security due to the Company's inability to hold the security until a recovery in its value to the amortized cost basis.

For the remainder of securities in an unrealized loss position, management does not intend to sell the securities and it is not "more likely than not" that the Company will be required to sell these securities before a recovery in their value to their amortized cost basis occurs.

James River Group Holdings, Ltd.

2 unchanged sentences

Years ended December 31, 2024, 2023, and 2022

our income statement as net realized and unrealized gains (losses) on investments.

The Company elected the fair value option to account for bank loan participations.

Under the fair value option, bank loan participations are measured at fair value, and changes in unrealized gains and losses in bank loan participations are reported in our income statement as net realized and unrealized gains (losses) on investments.

Applying the fair value option to the bank loan portfolio increases volatility in the Company's financial statements, but management believes it is less subjective and less burdensome to implement and maintain than ASU 2016-13, which would have otherwise been required.

1 unchanged sentence

Investment income on bank loan participations included in net investment income was $ 17.0 million, $ 12.0 million, $ 4.3 million during the years ended December 31, 2024, 2023, and 2022, respectively.

Net realized and unrealized gains (losses) on investments includes gains of $ 9.0 million, losses of $ 5.4 million, and gains of $ 2.3 million related to changes in unrealized gains and losses on bank loan participations for the years ended December 31, 2023, 2022, and 2021, respectively.

Management concluded that $ 946,000 and $ 592,000 of the unrealized losses were due to credit-related impairments for the years ended December 31, 2023 and 2022.

Management concluded that none of the unrealized losses were due to credit-related impairments for the year ended December 31, 2021 .

Net realized and unrealized gains (losses) on investments includes losses of $ 620,000 , gains of $ 9.0 million, and losses of $ 5.4 million related to changes in unrealized gains and losses on bank loan participations for the years ended December 31, 2024, 2023, and 2022, respectively.

Management concluded that $ 3.3 million, $ 397,000 , and $ 574,000 of the net realized and unrealized gains (losses) were due to credit-related impairments for the years ended December 31, 2024, 2023, and 2022, respectively.

Losses due to credit-related impairments were determined based upon consultations and advice from the Company's specialized investment manager and consideration of any adverse situations that could affect the borrower's ability to repay, the estimated value of underlying collateral, and other relevant factors.

51 unchanged sentences

Total $ 3,625 $ 10,441 $ ( 15,720 )

The change in the Company’s available-for-sale fixed maturity gross unrealized net losses was $ 30.4 million for the year ended December 31, 2023.

The change in the Company's available-for-sale fixed maturity gross unrealized net (losses) gains was $( 131.4 ) million and $( 34.2 ) million for the years ended December 31, 2022 and 2021, respectively.

The change in the Company’s available-for-sale fixed maturity gross unrealized net losses was $( 7.9 ) million, $ 30.4 million and $( 131.4 ) million for the years ended December 31, 2024, 2023, and 2022, respectively.

James River Group Holdings, Ltd.

34 unchanged sentences

Expenses for the LLCs are not significant and are comprised of administrative and interest expenses.

During the fourth quarter of 2022, the underlying projects in two of our LLCs were sold at the manager's discretion.The Company received proceeds of $ 20.2 million, comprised of $ 17.2 million in the Excess and Surplus Lines segment and $ 3.0 million in the Corporate and Other segment.

During the fourth quarter of 2022, the underlying projects in two of our LLCs were sold at the manager's discretion.

The Company received proceeds of $ 20.2 million, comprised of $ 17.2 million in the Excess and Surplus Lines segment and $ 3.0 million in the Corporate and Other segment.

During the year ended December 31, 2023, the Company received additional proceeds from the sales of $ 3.1 million in the Excess and Surplus Lines segment and $ 524,000 in the Corporate and Other segment.

The Company could receive additional contingent payments in the future according to terms of the transaction.

The Company received cash distributions from all renewable energy investments totaling $ 3.7 million and $ 21.6 million for the years ended December 31, 2023 and 2022, respectively.

During the year ended December 31, 2024, the Company received additional proceeds from the sales of $ 1.7 million in the Excess and Surplus Lines segment and $ 293,000 in the Corporate and Other segment.

The Company received cash distributions from all renewable energy investments totaling $ 439,000 and $ 3.7 million for the years ended December 31, 2024 and 2023, respectively.

(b) The Company's Excess and Surplus Lines and Corporate and Other segments have invested in two notes receivable for renewable energy projects.

1 unchanged sentence

During the year ended December 31, 2024 , the Company received principal repayments of $ 608,000 and $ 761,000 on the notes receivable in the Company's Excess and Surplus Lines segment and Corporate and Other segment, respectively.

During the year ended December 31, 2022 , the Company received principal repayments of $ 1.1 million and $ 1.4 million on the notes receivable in the Company's Excess and Surplus Lines segment and Corporate and Other segment, respectively.

During the year ended December 31, 2023 , the Company received principal repayments of $ 593,000 and $ 742,000 on the notes receivable in the Company's Excess and Surplus Lines segment and Corporate and Other segment, respectively.

James River Group Holdings, Ltd.

5 unchanged sentences

During the year ended December 31, 2022, the Company recognized an impairment loss of $ 538,000 on one limited partnership in the Corporate & Other segment.

At December 31, 2023, the Company’s Excess and Surplus Lines segment has outstanding commitments to invest another $ 6.3 million in these limited partnerships.

At December 31, 2024, the Company’s Excess and Surplus Lines segment has outstanding commitments to invest another $ 4.7 million in these limited partnerships and a $ 20.0 million commitment to invest in a new limited partnership.

(d) The Company's Excess and Surplus Lines segment holds two notes receivable for structured private specialty credit.

94 unchanged sentences

Property and equipment, net $ 19,773 $ 16,995

The Company has entered into operating leases for office space in Bermuda, North Carolina, Virginia, Arizona, and Georgia.

The Company has entered into operating leases for office space in North Carolina, Virginia, Arizona, and Georgia.

The present value of future lease payments for the Company’s leases with terms greater than 12 months are included on the consolidated balance sheets as lease liabilities and right-of-use lease assets.

13 unchanged sentences

Years ending December 31, (in thousands)

Thereafter 158

Total lease payments 5,956

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The following table provides a reconciliation of the beginning and ending reserve balances for losses and loss adjustment expenses, net of reinsurance, to the gross amounts reported in the consolidated balance sheets.

Reinsurance recoverables on unpaid losses and loss adjustment expenses are presented gross of an allowance for credit losses on reinsurance balances of $ 660,000 , $ 580,000 , and $ 607,000 at December 31, 2023, 2022, and 2021, respectively.

Reinsurance recoverables on unpaid losses and loss adjustment expenses are presented gross of an allowance for credit losses on reinsurance balances of $ 1.2 million, $ 660,000 , and $ 580,000 at December 31, 2024, 2023, and 2022, respectively.

Year Ended December 31,

12 unchanged sentences

Change in deferred reinsurance gain - retroactive reinsurance 37,237 4,991 15,742

Loss reserves ceded in loss portfolio transfer — — 256,452

Loss reserves ceded in E&S ADC 313,242 — —

Reserve for losses and loss adjustment expenses net of reinsurance recoverables at end of period 1,086,278 1,246,973 1,080,766

1 unchanged sentence

Reserve for losses and loss adjustment expenses gross of reinsurance recoverables on unpaid losses and loss adjustment expenses at end of period $ 3,084,406 $ 2,606,107 $ 2,340,963

The foregoing reconciliation shows that $ 31.6 million of net adverse development was experienced in 2023 on the reserve for losses and loss adjustment expenses held at December 31, 2022 (excluding adverse prior year development on the commercial auto loss portfolio transfer subject to retroactive reinsurance accounting - see Loss Portfolio Transfer below).

The foregoing reconciliation shows that $ 76.1 million of net adverse development was experienced in 2024 on the reserve for losses and loss adjustment expenses held at December 31, 2023 (excluding adverse prior year development subject to retroactive reinsurance accounting - see Loss Portfolio Transfers and Adverse Development Covers below).

This net adverse reserve development included $ 76.7 million of net adverse development in the Excess and Surplus Lines segment, including a $ 52.2 million reserve charge upon execution of the E&S ADC (consideration paid in excess of initial reserves), and $ 607,000 of net favorable development in the Specialty Admitted Insurance segment.

The foregoing reconciliation shows that $ 31.6 million of net adverse development was experienced in 2023 on the reserve for losses and loss adjustment expenses held at December 31, 2022 (excluding adverse prior year development subject to retroactive reinsurance accounting - see Loss Portfolio Transfers and Adverse Development Covers below).

This net adverse reserve development included $ 32.6 million of net adverse development in the Excess and Surplus Lines segment, with adverse development in accident years 2020 and prior exceeding favorable development on accident years 2022 and 2021, and $ 972,000 of net favorable development in the Specialty Admitted Insurance segment.

The foregoing reconciliation shows that $ 4.4 million of net favorable development was experienced in 2022 on the reserve for losses and loss adjustment expenses held at December 31, 2021 (excluding adverse prior year development on the commercial auto loss portfolio transfer subject to retroactive reinsurance accounting - see Loss Portfolio Transfer below).

This net favorable reserve development included $ 210,000 of net favorable development in the Excess and Surplus Lines segment and $ 4.2 million of net favorable development in the Specialty Admitted Insurance segment.

The Company also experienced $ 5.0 million of net catastrophe losses in the current accident year in 2022 related to Hurricane Ian.

The foregoing reconciliation shows that $ 188.2 million of net adverse development was experienced in 2021 on the reserve for losses and loss adjustment expenses held at December 31, 2020.

This net adverse reserve development included $ 190.7 million of net adverse development in the Excess and Surplus Lines segment including $ 200.1 million of net adverse

The foregoing reconciliation shows that $ 4.4 million of net favorable development was experienced in 2022 on the reserve for losses and loss adjustment expenses held at December 31, 2021 (excluding adverse prior year development subject to retroactive reinsurance accounting - see Loss Portfolio Transfers and Adverse Development Covers below).

This net favorable

James River Group Holdings, Ltd.

2 unchanged sentences

Years ended December 31, 2024, 2023, and 2022

development in the commercial auto line of business that was primarily related to the 2019 and prior accident years with Rasier.

The adverse development for commercial auto was partially offset by $ 9.4 million of net favorable development in the Core E&S underwriting divisions.

The Company also experienced $ 2.5 million of net favorable development on prior accident years in the Specialty Admitted Insurance segment, as losses on our workers’ compensation business written prior to 2020 continued to develop more favorably than we had anticipated.

The Company also experienced $ 5.0 million of net catastrophe losses in the current accident year in 2021 related to Hurricane Ida.

Loss Portfolio Transfers

Loss portfolio transfers are a form of reinsurance utilized by the Company to transfer losses and loss adjustment expenses and associated risk of adverse development on covered subject business, as defined in the respective agreements, to an assuming reinsurer in exchange for a reinsurance premium.

Loss portfolio transfers can bring economic finality on the subject risks when they no longer meet the Company's appetite or are no longer aligned with the Company's risk management guidelines.

reserve development included $ 210,000 of net favorable development in the Excess and Surplus Lines segment and $ 4.2 million of net favorable development in the Specialty Admitted Insurance segment.

The Company also experienced $ 5.0 million of net catastrophe losses in 2022 related to Hurricane Ian.

Loss Portfolio Transfers and Adverse Development Covers

Loss portfolio transfers and adverse development covers are forms of retroactive reinsurance utilized by the Company to transfer losses and loss adjustment expenses and associated risk of adverse development on covered subject business, as defined in the respective agreements, to an assuming reinsurer in exchange for a reinsurance premium.

This reinsurance can bring economic finality (up to the limit of such agreements, if applicable) on the subject risks when they no longer meet the Company's risk appetite or are no longer aligned with the Company's risk management guidelines.

Commercial Auto Loss Portfolio Transfer

On September 27, 2021, James River Insurance Company and James River Casualty Company (together, “James River”) entered into a loss portfolio transfer transaction (the “Commercial Auto LPT”) with Aleka Insurance, Inc.

On September 27, 2021, James River Insurance and James River Casualty Company (together, “James River”) entered into a loss portfolio transfer transaction (the “Commercial Auto LPT”) with Aleka Insurance, Inc.

(“Aleka”), a captive insurance company affiliate of Rasier LLC, to reinsure substantially all of the Excess and Surplus Lines segment's legacy portfolio of commercial auto policies previously issued to Rasier LLC and its affiliates (collectively, “Rasier”) for which James River is not otherwise indemnified by Rasier.

Under the terms of the transaction, effective as of July 1, 2021, James River ceded to Aleka approximately $ 345.1 million of commercial auto liabilities relating to Rasier policies written in the years 2013-2019, which amount constituted the reinsurance premium.

The reinsurance coverage is structured to be fully collateralized, is not subject to an aggregate limit, and is subject to certain exclusions.

A pre-tax loss of $ 29.6 million was recognized as adverse loss and loss adjustment reserve development in the Excess and Surplus Lines segment for the third quarter of 2021 associated with the loss portfolio transfer.

The cumulative amounts ceded under the loss portfolio transfer were $ 459.3 million, $ 456.2 million and $ 391.8 million as of December 31, 2024, 2023, and 2022, respectively.

Combined Loss Portfolio Transfer and Adverse Development Cover

On July 2, 2024, James River entered into a Combined Loss Portfolio Transfer and Adverse Development Cover Reinsurance Contract (the “E&S ADC”) with State National Insurance Company, Inc.

(“State National”).

The transaction closed upon signing.

The E&S ADC was effective January 1, 2024 (the “Effective Date”) and applies to James River’s Excess & Surplus Lines segment casualty portfolio losses attaching to premium earned during 2010-2023 (both years inclusive), excluding, among others, losses related to commercial auto policies issued to a former large insured or its affiliates (the “Subject Business”).

Pursuant to the E&S ADC, (a) State National reinsures 85 % of losses paid on and after the Effective Date in respect of the Subject Business in excess of $ 716.6 million up to an aggregate limit of $ 467.1 million (with State National’s share of the aggregate limit being $ 397.0 million) in exchange for a reinsurance premium paid by James River equal to $ 313.2 million, (b) James River continues to manage claims and to manage and collect the benefit of other existing third-party reinsurance on the Subject Business, which third-party reinsurance inures to the benefit of the E&S ADC, and (c) James River is entitled to a profit commission of 50 % of any favorable development on the business ceded to State National below 104.5 % of carried reserves, which profit commission shall not exceed $ 87.0 million in total.

The Company has $ 41.2 million of aggregate limit remaining on the E&S ADC at December 31, 2024.

Adverse Development Cover

On November 11, 2024, Enstar Group Limited ("Enstar"), through its subsidiary Cavello Bay Reinsurance Limited, entered into an adverse development cover agreement with James River ("E&S Top Up ADC"), pursuant to which, in exchange for a premium of $ 52.8 million (less an amount equal to the federal excise tax payable on the premium), Cavello Bay reinsures, effective January 1, 2024, 100 % of the losses associated with James River’s Excess & Surplus Lines segment casualty portfolio losses attaching to premium earned during 2010-2023 (both years inclusive).

The E&S Top Up ADC excludes losses related to commercial auto policies issued to a former large insured or its affiliates and is subject to a retention by James River of $ 1,183.7 million (the limit of the E&S ADC executed on July 2, 2024) and up to an aggregate limit of $ 75.0 million.

The E&S Top Up ADC closed on December 23, 2024.

The Company recognized a $ 52.8 million reduction in pre-tax income in connection with the adverse development cover upon closing.

The Company has $ 75.0 million of aggregate limit remaining on the E&S Top Up ADC at December 31, 2024.

Retroactive Reinsurance Accounting

The Company periodically reevaluates the remaining reserves subject to the Commercial Auto LPT, and when recognized adverse prior year development on the subject business causes the cumulative amounts ceded under the loss portfolio transfer to exceed the consideration paid, the loss portfolio transfer moves into a gain position subject to retroactive reinsurance accounting under GAAP.

Gains are deferred under retroactive reinsurance accounting and recognized in earnings in proportion to actual paid recoveries under the loss portfolio transfer using the recovery method.

While the deferral of gains can introduce volatility in our results in the short-term, over the life of the contract, we would expect no economic impact to the Company as long as the counterparty performs under the contract.

The Company periodically reevaluates the remaining reserves subject to the Commercial Auto LPT, the E&S ADC, and the E&S Top Up ADC, and when recognized adverse prior year development on the subject business causes the cumulative amounts ceded under the agreements to exceed the consideration paid, the agreements move into a gain position subject to retroactive reinsurance accounting under GAAP.

Gains are deferred under retroactive reinsurance accounting and recognized in earnings in proportion to actual paid recoveries under the agreements using the recovery method.

While the deferral of gains can introduce volatility in our results in the short-term, over the life of the contract, we would expect no economic impact to the

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2024, 2023, and 2022

Company as long as the counterparty performs under the contract.

The impact of retroactive reinsurance accounting is not indicative of our current and ongoing operations.

For the years ended December 31, 2023 and 2022, due to adverse paid and reported loss trends on the legacy Rasier business, the Company recognized adverse prior year development of $ 64.4 million and $ 46.7 million, respectively, on the net reserves subject to the Commercial Auto LPT, resulting in corresponding additional amounts ceded under the Commercial Auto LPT.

As a result, the cumulative amounts ceded under the Commercial Auto LPT exceed the consideration paid, moving the Commercial Auto LPT into a gain position.

The Company has applied retroactive reinsurance accounting to the loss portfolio transfer.

Retroactive reinsurance benefits of $ 59.4 million and $ 31.0 million, respectively, were recorded in losses and loss adjustment expenses on the Consolidated Statements of (Loss) Income and Comprehensive Loss for the years ended December 31, 2023 and 2022 using the recovery method.

The cumulative amounts ceded under the loss portfolio transfer were $ 456.2 million and $ 391.8 million as of December 31, 2023 and 2022, respectively.

The deferred retroactive reinsurance gain related to the Commercial Auto LPT separately presented on the Company's Consolidated Balance Sheets was $ 20.7 million and $ 15.7 million at December 31, 2023 and 2022, respectively.

The following tables summarize the retroactive reinsurance accounting for the Commercial Auto LPT and the E&S ADC for the years ended December 31, 2024, 2023, and 2022.

Year Ended December 31,

2024 2023 2022

(in thousands)

Commercial Auto LPT

Deferred retroactive reinsurance gain at beginning of period $ 20,733 $ 15,742 $ —

Adverse prior year development on subject business 3,051 64,403 46,697

Retroactive reinsurance benefits under the recovery method ( 14,562 ) ( 59,412 ) ( 30,955 )

Deferred retroactive reinsurance gain at end of period $ 9,222 $ 20,733 $ 15,742

Deferred retroactive reinsurance gain at beginning of period $ — $ — $ —

Adverse prior year development ceded on subject business 48,748 — —

Retroactive reinsurance benefits under the recovery method — — —

Deferred retroactive reinsurance gain at end of period $ 48,748 $ — $ —

Deferred retroactive reinsurance gain at beginning of period $ 20,733 $ 15,742 $ —

Adverse prior year development on subject business 51,799 64,403 46,697

Retroactive reinsurance benefits under the recovery method ( 14,562 ) ( 59,412 ) ( 30,955 )

Deferred retroactive reinsurance gain at end of period $ 57,970 $ 20,733 $ 15,742

James River Group Holdings, Ltd.

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Total $ 1,175,562

Total outstanding losses and loss adjustment expenses, net of reinsurance before E&S ADC $ 1,243,864

Reinsurance recoverable for E&S ADC $ 349,337

All outstanding losses and loss adjustment expenses prior to 2015, net of reinsurance ( 81 claims outstanding)

29 unchanged sentences

Total $ 1,389,554

Total outstanding losses and loss adjustment expenses, net of reinsurance before Rasier LPT $ 127,866

Reinsurance recoverable for Rasier LPT $ 78,065

Total outstanding losses and loss adjustment expenses, net of reinsurance before Commercial Auto LPT $ 85,047

Reinsurance recoverable for Commercial Auto LPT $ 35,315

Reinsurance recoverable for E&S ADC $ 12,653

All outstanding losses and loss adjustment expenses prior to 2015, net of reinsurance ( 0 claims outstanding)

Total outstanding losses and loss adjustment expenses, net of reinsurance $ 37,104

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2023 21,095 19,218

Total $ 147,462

Cumulative paid losses and loss adjustment expenses, net of reinsurance (in thousands)

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Total $ 209,613

All outstanding losses and loss adjustment expenses, net of reinsurance $ 107,982

All outstanding losses and loss adjustment expenses prior to 2015, net of reinsurance ( 1 claim outstanding)

Outstanding losses and loss adjustment expenses, assumed from involuntary pools $ 1,125

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Net reserve for losses and loss adjustment expenses 1,086,278

Reinsurance recoverables on unpaid losses (gross of $ 660,000 allowance for credit losses on reinsurance recoverables)

Reinsurance recoverables on unpaid losses (gross of $ 1.2 million allowance for credit losses on reinsurance recoverables)

Gross reserve for losses and loss adjustment expenses $ 3,084,406

6 unchanged sentences

In determining the cumulative number of reported claims, the Company measures claim counts by individual claimant for individual risk workers’ compensation policies in the Specialty Admitted Insurance segment.

In the Excess and Surplus Lines insurance segment and for fronting and programs in the Specialty Admitted Insurance segment, the Company measures claim counts by claim event.

In the Excess and Surplus Lines segment and for fronting and programs in the Specialty Admitted Insurance segment, the Company measures claim counts by claim event.

The claim counts include all claims reported, even if the Company does not establish a liability for the claim (i.e.

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Accident Year Incurred Losses

Expenses IBNR Cumulative # of

Expenses IBNR before E&S ADC IBNR net of E&S ADC Cumulative # of

Reported Claims

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Accident Year Incurred Losses

Expenses IBNR before Rasier LPT IBNR net of Rasier LPT Cumulative # of

Expenses IBNR before Commercial Auto LPT& E&S ADC IBNR net of Commercial Auto LPT & E&S ADC Cumulative # of

Reported Claims

82 unchanged sentences

The 2013 Facility is comprised of the following at December 31, 2024:

• A $ 102.5 million secured revolving facility utilized by JRG Re to issue letters of credit for the benefit of third-party reinsureds.

This portion of our credit facility is secured by our investment securities.

At December 31, 2023, the Company had $ 42.7 million of letters of credit issued under the secured facility.

• A $ 212.5 million unsecured revolving facility to meet the working capital needs of the Company.

2 unchanged sentences

At December 31, 2024 and 2023, the Company had a drawn balance of $ 185.8 million outstanding on the unsecured revolver.

James River Group Holdings, Ltd.

and JRG Re are borrowers on the 2013 Facility.

The 2013 Facility has been amended from time to time since its inception in 2013.

On November 8, 2019, the Company entered into a Second Amended and Restated Credit Agreement for the 2013 Facility which, among other things, extended the maturity date of the 2013 Facility until November 8, 2024, increased the amount available under the unsecured revolving credit facility to $ 212.5 million, lowered the applicable interest rate and letter of credit fees, and modified certain negative covenants to be less restrictive.

On July 7, 2023, the Company entered into a Third Amended and Restated Credit Agreement for its $ 315.0 million senior revolving credit facility which, among other things, extended the maturity date of such facility until July 7, 2026 and increased the applicable interest rate and letter of credit fees.

A subsidiary of the bank holding company for which the former Non-Executive Chairman of the Company was previously Lead Independent Director is one of the lenders for the 2013 Facility, with a $ 50.0 million commitment allocation on the total $ 315.0 million 2013 Facility.

The 2013 Facility contains certain financial and other covenants (including minimum net worth, maximum ratio of total adjusted debt outstanding to total capitalization, and financial strength ratings) with which the Company was in compliance at December 31, 2023, with the exception of a default of the financial strength rating covenant due to the downgrade of JRG Re by A.M.

Best on December 20, 2023 from “A-” (Excellent) to “B++” (good).

The financial strength rating covenant requires

• A $ 45.0 million secured revolving facility to issue letters of credit for the benefit of third-party reinsureds.

At December 31, 2024, the Company had $ 7.5 million of letters of credit issued under the secured facility, all of which are collateralized by a back-to-back letter of credit issued by Comerica Bank on behalf of JRG Re.

On July 7, 2023, the Company entered into a Third Amended and Restated Credit Agreement for the 2013 Facility which, among other things, extended the maturity date of such facility until July 7, 2026 and increased the applicable interest rate and letter of credit fees.

The 2013 Facility has been amended from time to time, including on April 16, 2024 when the 2013 Facility was amended in connection with the closing of the sale of JRG Re by the Company to (i) release JRG Re as a borrower and release all collateral pledged by JRG Re thereunder, and (ii) decrease the secured revolving facility commitment from $ 102.5 million to $ 45.0 million.

Additionally, the Third Amended and Restated Credit Agreement provides for an accordion feature that permits the Company to request that one or more lenders (without the consent of the other lenders) or one or more financial institutions which were not previously party to the Third Amended and Restated Credit Agreement (with the consent of the administrative agent) provide it with increases in the secured or unsecured revolving credit facilities of up to an aggregate of $ 100.0 million, which is unchanged from the accordion feature set forth in the Second Amended and Restated Credit Agreement.

The Company’s ability to request such increases in the revolving credit facility is subject to its compliance with customary conditions set forth in the Third Amended and Restated Credit Agreement.

James River Group Holdings, Ltd.

2 unchanged sentences

Years ended December 31, 2024, 2023, and 2022

that each of our regulated insurance subsidiaries maintain an A.M.

Best rating not lower than “A- ” (Excellent).

Our lenders have waived this default through March 1, 2025, and in any event, we expect it to be cured upon the closing of the sale of JRG Re, at which time we expect JRG Re to be removed as a borrower under the 2017 Facility.

On August 2, 2017, the Company and its wholly-owned subsidiary, JRG Re, together as borrowers, entered into a credit agreement (the "2017 Facility") that provides the Company with a revolving line of credit of up to $ 100.0 million, which may be used for loans and letters of credit made or issued, at the borrowers' option, on a secured or unsecured basis.

The loans and letters of credit made or issued under the revolving line of credit may be used to finance the Borrowers’ general corporate purposes.

The 2017 Facility has been amended from time to time since its inception in 2017.

On November 8, 2019, the Company entered into a First Amendment to Credit Agreement which, among other things, lowered the applicable interest rate and modified certain negative covenants to be less restrictive.

Obligations under the 2017 Facility carry a variable rate of interest subject to terms in the credit agreement which is currently at 1-month SOFR (the Company, per the terms of the credit agreement, can elect between one, two, three, or six month interest periods) plus a 0.1 % SOFR index adjustment and a SOFR margin ( 1.50 % at December 31, 2023) and will mature 30 days after notice of termination from the lender.

Interest accrues quarterly and is payable in arrears at variable rates which are subject to change according to terms in the credit agreement.

At December 31, 2023, unsecured loans of $ 21.5 million and secured letters of credit totaling $ 25.5 million were outstanding under the facility.

The Company repaid $ 40.0 million of loans in 2022.

In order to secure borrowings and letters of credit made or issued under the secured portion of the 2017 Facility, JRG Re entered into a pledge and security agreement on August 2, 2017 with the lender, pursuant to which JRG Re pledged certain investment securities.

In the event the Company elects to pledge investment securities as collateral for the secured portion of the revolving credit facility, the Company will enter into a similar pledge and security agreement.

A subsidiary of the bank holding company for which the former Non-Executive Chairman of the Company was previously Lead Independent Director is one of the lenders for the 2013 Facility, with a $ 40.9 million commitment allocation on the total $ 257.5 million 2013 Facility.

On August 2, 2017, the Company and its wholly-owned subsidiary, JRG Re, together as borrowers, entered into a credit agreement (the "2017 Facility") that provided the Company with a revolving line of credit of up to $ 100.0 million, which was used for loans and letters of credit made or issued, at the borrowers' option, on a secured or unsecured basis.

The loans and letters of credit made or issued under the revolving line of credit were used to finance the Borrowers’ general corporate purposes.

Obligations under the 2017 Facility carried a variable rate of interest subject to terms in the credit agreement.

The 2017 Facility was amended from time to time since its inception in 2017, including on April 16, 2024 in connection with the closing of the sale of JRG Re by the Company to (i) release JRG Re as a borrower and release all collateral pledged by JRG Re thereunder, (ii) increase the applicable interest rates, (iii) eliminate the letter of credit portion of the facility, and (iv) to build in an automatic decrease of the facility amount by the amount of each letter of credit outstanding under the 2017 Facility as of the date of the amendment with effect from the date each such letter of credit is cancelled.

The 2017 Facility was terminated in November 2024.

An affiliate of the lender under the 2017 Facility was an underwriter in the December 2014 initial public offering of the Company’s common shares and a joint lead book-running manager in the Company’s May 2021 public offering of the Company’s common shares.

The 2017 Facility contains certain financial and other covenants with which we are in compliance at December 31, 2023, with the exception of a default of the financial strength rating covenant due to the downgrade of JRG Re by A.M.

Best on December 20, 2023 from “A-” (Excellent) to “B++” (good).

The financial strength rating covenant requires that each of our regulated insurance subsidiaries maintain an A.M.

Best rating not lower than “A-” (Excellent).

On May 26, 2004, James River Group issued $ 15.0 million of unsecured, floating rate senior debentures (the “Senior Debt”), due April 29, 2034 unless accelerated earlier, through an indenture.

13 unchanged sentences

Each Trust was created solely for the purpose of issuing the Trust Preferred Securities.

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2023, 2022, and 2021

Each Trust used proceeds from the sale of its Trust Preferred Securities to purchase the Company’s floating rate junior subordinated debentures (the “Junior Subordinated Debt”) issued to the Trust under an indenture (each, an “Indenture”;

2 unchanged sentences

The Company purchased all of the outstanding common stock of the Trusts, and the investment in the Trusts is included in “other assets” in the accompanying consolidated balance sheets.

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2024, 2023, and 2022

The following table summarizes the nature and terms of the junior subordinated debt and trust preferred securities outstanding at December 31, 2024 (including the Company’s repurchases of a portion of these trust preferred securities):

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Series A Preferred Shares

On February 24, 2022, we entered into an Investment Agreement with GPC Partners Investments (Thames) LP (“GPC Partners”), an affiliate of Gallatin Point Capital LLC, relating to the issuance and sale of 150,000 7 % Series A Perpetual Cumulative Convertible Preferred Shares, par value $ 0.00125 per share (the “Series A Preferred Shares”), for an aggregate purchase price of $ 150.0 million, or $ 1,000 per share, in a private placement.

Initial Issuance and Terms

On February 24, 2022, the Company entered into an Investment Agreement with GPC Partners Investments (Thames) LP (“GPC Partners”), an affiliate of Gallatin Point Capital LLC, relating to the issuance and sale of 150,000 7 % Series A Perpetual Cumulative Convertible Preferred Shares, par value $ 0.00125 per share (the “Series A Preferred Shares”), for an aggregate purchase price of $ 150.0 million, or $ 1,000 per share, in a private placement.

The transaction closed on March 1, 2022 (the “Series A Closing Date”).

The Series A Preferred Shares rank senior to our common shares with respect to dividend rights and rights on the distribution of assets on any liquidation, dissolution or winding up of the affairs of the Company, upon which the holders of Series A Preferred Shares would receive the greater of the $ 1,000 liquidation preference per share (the “Liquidation Preference”) plus accrued and unpaid dividends, or the amount they would have received if they had converted all of their Series A Preferred Shares to common shares immediately before such liquidation, dissolution or winding up.

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2023, 2022, and 2021

The Series A Preferred Shares rank senior to the Company's common shares with respect to dividend rights and rights on the distribution of assets on any liquidation, dissolution or winding up of the affairs of the Company, upon which the holders of Series A Preferred Shares would receive the greater of the $ 1,000 liquidation preference per share (the “Liquidation Preference”) plus accrued and unpaid dividends, or the amount they would have received if they had converted all of their Series A Preferred Shares to common shares immediately before such liquidation, dissolution or winding up.

Holders of the Series A Preferred Shares are entitled to a dividend at the initial rate of 7 % of the Liquidation Preference per annum, paid in cash, in-kind in common shares or in Series A Preferred Shares, at the Company's election.

On the five-year anniversary of the Series A Closing Date, and each five-year anniversary thereafter, the dividend rate will reset to a rate equal to the five-year U.S.

Prior to the amendment on November 11, 2024 (as discussed below), on the five-year anniversary of the Series A Closing Date, and each five-year anniversary thereafter, the dividend rate would reset to a rate equal to the five-year U.S.

treasury rate plus 5.2 %.

Dividends accrue and are payable quarterly.

Prior to the amendment on November 11, 2024 (disclosed below), cash dividends of $ 10.5 million were paid in the nine months ended September 30, 2024, including cash dividends paid in January, April, July, and September for the three month periods ended December 31, 2023, March 31, 2024, June 30, 2024, and September 30, 2024.

For the years ended December 31, 2023 and 2022, cash dividends of $ 10.5 million and $ 8.8 million were declared, respectively, of which $ 2.6 million was payable at December 31 of both years.

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2024, 2023, and 2022

The Series A Preferred Shares are convertible at the option of the holders thereof at any time into common shares at an initial conversion price of $ 26.5950 , making the Series A Preferred Shares initially convertible into 5,640,158 common shares.

1 unchanged sentence

The measurement period for the adverse reserve development anti-dilution adjustment commenced with the quarter beginning January 1, 2022 and ends with the quarter ending December 31, 2025.

As of December 31, 2023, net adverse reserve development exceeded the threshold.

If net adverse reserve development exceeds the threshold at the conclusion of the measurement period (or upon a mandatory or optional conversion, if earlier), the conversion price will be adjusted pursuant to the Certificate of Designations and the adjusted conversion price will become effective after the filing of the Company's financial statements for the period ending December 31, 2025 (or immediately after the close of business on the date of the public filing of the Company's financial statements for the most recent quarterly period preceding a mandatory or optional conversion, if earlier).

None of the other triggers that would result in additional adjustments to the conversion price have been met at December 31, 2023.

The Certificate of Designations setting forth the terms of the Series A Preferred Shares limits our ability to pay dividends to our common shareholders.

If we pay cash dividends of more than $ 0.05 per common share per quarter, without the consent of at least the majority of the Series A Preferred Shares then outstanding, we will be required to reduce the conversion price of the Series A Preferred Shares.

Additionally, the payment of cash dividends in excess of $ 0.10 per common share per quarter is not permitted if the dividends on the Series A Preferred Shares for that quarter are not paid in cash, unless the Company’s U.S.-based insurance subsidiaries and direct Bermuda-based insurance subsidiary satisfy certain capital requirements.

Prior to the amendment on November 11, 2024 (disclosed below), net adverse reserve development exceeded the threshold.

If net adverse reserve development exceeded the threshold at the conclusion of the measurement period (or upon a mandatory or optional conversion, if earlier), the conversion price would be adjusted pursuant to the Certificate of Designations, subject to a floor conversion price of $ 21.902 , and the adjusted conversion price would become effective after the filing of the Company's financial statements for the period ending December 31, 2025 (or immediately after the close of business on the date of the public filing of the Company's financial statements for the most recent quarterly period preceding a mandatory or optional conversion, if earlier).

None of the other triggers that would result in additional adjustments to the conversion price had been met prior to the amendment on November 11, 2024.

The Certificate of Designations setting forth the terms of the Series A Preferred Shares (the “Certificate of Designations”) limits the Company's ability to pay dividends to its common shareholders.

If the Company pays cash dividends of more than $ 0.05 per common share per quarter, without the consent of at least the majority of the Series A Preferred Shares then outstanding, the Company will be required to reduce the conversion price of the Series A Preferred Shares.

Share dividends payable on the common shares to our shareholders also trigger a reduction of the conversion price applicable to the Series A Preferred Shares.

5 unchanged sentences

The repurchase price will be payable in cash.

Because the Company may be required to repurchase all or a portion of the Series A Preferred Shares at the option of the holder upon the occurrence of certain change of control events, the Series A Preferred Shares were classified as mezzanine equity in the Company's consolidated balance sheets and recognized at their fair value of $ 150.0 million (the proceeds on the date of issuance) less issuance costs of $ 5.1 million, resulting in a carrying value of $ 144.9 million.

Under the terms of the Investment Agreement, GPC Partners has the right to designate one member of the Board (the “Series A Designee”).

GPC Partners initially designated Matthew Botein as the Series A Designee, and Mr.

Botein was approved by the Board as a Class I director with a term that expired at the 2024 annual general meeting of the Company’s

James River Group Holdings, Ltd.

2 unchanged sentences

Years ended December 31, 2024, 2023, and 2022

Because the Company may be required to repurchase all or a portion of the Series A Preferred Shares at the option of the holder upon the occurrence of certain change of control events, the Series A Preferred Shares have been classified as mezzanine equity in the Company's consolidated balance sheets and are recognized at fair value of $ 150.0 million (the proceeds on the date of issuance) less issuance costs of $ 5.1 million, resulting in a carrying value of $ 144.9 million.

Under the terms of the Investment Agreement, GPC Partners has the right to designate one member of the Board (the “Series A Designee”).

GPC Partners has designated Matthew Botein as the Series A Designee and, accordingly, the Board approved the appointment of Mr.

Botein to serve as a Class I director with a term expiring at the 2024 annual meeting of the Company’s shareholders.

shareholders.

Botein was re-elected as a director at the 2024 annual general meeting for a term ending at the 2025 annual general meeting.

2024 Amendment and Revised Terms

On November 11, 2024, the Company amended the Certificate of Designations held by GPC Partners to, among other things, (i) convert $ 37.5 million of the outstanding Series A Preferred Shares to common stock at a per share price of $ 6.40 (the “Minimum Price”), (ii) increase the voluntary conversion price from 127.5 % to 130 % of the Minimum Price, (iv) increase the mandatory conversion price from 130 % to 200 % of the voluntary conversion price, (v) delay the first date on which the dividend rate re-sets from March 1, 2027 to October 1, 2029, (vi) cap the dividend rate at 8 %, (vii) eliminate the adverse development anti-dilution adjustment provision, and (viii) limit transfers of the Series A Preferred Shares without the Company’s consent if, after the transfer, the transferee would hold 9.9 % or more of the voting equity of the Company or, in the event of an A.M.

Best downgrade of James River Insurance Company below A- (Excellent), 19.9 % of the voting equity.

The Company accounted for the amendment as an extinguishment of the pre-amendment Series A Preferred Shares due to the significance of quantitative and qualitative changes to the shares.

The Company estimated the fair value of the new Series A Preferred Shares to be $ 133.1 million on the date of issuance and classified the new Series A Preferred Shares as mezzanine equity.

The redemption feature, which could require the Company to repurchase all or a portion of the Series A Preferred Shares at the option of the holder upon the occurrence of certain change of control events, was not impacted by the amendment.

The Company recorded a deemed dividend of $ 25.7 million within retained deficit for the difference between the $ 144.9 million carrying value of the extinguished pre-amendment Series A preferred shares and the combined $ 133.1 million estimated fair value of the new Series A Preferred Shares and $ 37.5 million of new common shares issued through conversion of Series A Preferred Shares in the amendment.

Cash dividends of $ 2.3 million were paid on the Series A Preferred Shares in the three months ended December 31, 2024 including a $ 299,000 stub period dividend on the 37,500 Series A Preferred Shares converted to common shares with the amendment and a $ 2.0 million dividend on the 112,500 Series A Preferred Shares that remain outstanding post-amendment.

The new Series A Preferred Shares were valued at the time of the amendment using a lattice method commonly applied to value preferred shares.

The new Series A Preferred Shares are classified as level 3 in the valuation hierarchy due to the presence of significant unobservable inputs.

Shareholders' Equity

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Issued and outstanding common shares, beginning of year 37,641,563 37,470,237

Conversion of Series A Preferred Shares to common shares 5,859,375 —

Enstar common share investment 1,953,125 —

Vesting of RSU awards 190,255 171,326

Issued and outstanding common shares, end of year 45,644,318 37,641,563

On May 10, 2021, the Company closed the offering and public sale (the “Offering”) of an aggregate of 6,497,500 of the Company’s common shares at a public offering price of $ 31.00 per share.

The Company received net proceeds (before expenses) from the Offering of $ 192.1 million, which were used for general corporate purposes.

The common shares were offered and sold pursuant to an underwriting agreement entered into by the Company, Barclays Capital, Inc., and Keefe, Bruyette & Woods, Inc., as representatives of the several underwriters named therein.

On November 11, 2024, the Company amended the Certificate of Designations to, among other things, convert 37,500 outstanding Series A Preferred Shares with a liquidation value of $ 37.5 million to common shares at a per share price of $ 6.40 , resulting in the issuance of 5,859,375 common shares.

The difference between the $ 6.40 share price per the amended Certificate of Designations and the $ 6.62 closing price of the Company's shares on November 11, 2024 is considered a deemed dividend for accounting purposes, resulting in a $ 1.3 million charge to retained deficit.

On November 11, 2024, Enstar Group Limited ("Enstar"), through its subsidiary Cavello Bay Reinsurance Limited, entered into a subscription agreement to purchase $ 12.5 million of the Company’s common shares at a share price of $ 6.40 .

The Enstar investment closed on December 23, 2024, resulting in the issuance of 1,953,125 common shares.

The difference between the $ 6.40 share price per the subscription agreement and the $ 4.66 closing price of the Company's shares on December 23, 2024 is considered a deemed contribution for accounting purposes, resulting in a $ 3.4 million increase in additional paid-in-capital.

The Company has 5,757,650 common shares reserved for future issuance upon exercise or vesting of equity awards, as applicable, and 13,521,635 common shares reserved for issuance upon conversion of the Series A Preferred Shares.

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July 25, 2024 $ 0.05 September 16, 2024 September 30, 2024 $ 1,938

October 26, 2023 $ 0.05 December 11, 2023 December 29, 2023 $ 1,919

November 9, 2024 $ 0.01 December 16, 2024 December 31, 2024 $ 446

Total $ 0.16 $ 6,263

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Awards under the LTI Plan are made in the form of performance restricted share units (a “PRSU”) and service based restricted share units (RSUs).

Initial awards were granted in the first quarter of 2023.

Each PRSU will represent a contingent right to receive one Company common share based upon the level of achievement of certain performance metrics during the performance period, with payout for achievement of threshold, target and maximum performance levels to be set at 50 %, 100 % and 200 % of the target number of PRSUs, respectively.

The initial PRSU awards have a performance period of January 1, 2023 through December 31, 2025.

Each PRSU represents a contingent right to receive one Company common share based upon the level of achievement of certain performance metrics during the performance period, with payout for achievement of threshold, target and maximum performance levels set at 50 %, 100 % and 200 % of the target number of PRSUs, respectively.

The PRSUs awarded in the first quarter of 2023 have a performance period of January 1, 2023 through December 31, 2025.

The PRSUs awarded in the first quarter of 2024 have a performance period of January 1, 2024 through December 31, 2026.

Non-employee directors of the Company are eligible to receive non-qualified stock options, share appreciation rights, performance shares, restricted shares, RSUs, and other awards under the 2014 Director Plan.

The maximum number of shares available for issuance under the 2014 Director Plan is 150,000 , and at December 31, 2023, 66,999 shares are available for grant.

The 2014 Director Plan was amended on October 24, 2024, increasing the number of shares available for issuance under the 2014 LTIP by 100,000 shares.

James River Group Holdings, Ltd.

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Years ended December 31, 2024, 2023, and 2022

Following the amendment, the maximum number of shares available for issuance under the 2014 Director Plan is 250,000 , and at December 31, 2024, 131,927 shares are available for grant.

Generally, awards issued under the 2014 LTIP and 2014 Director Plan vest immediately in the event that an award recipient is terminated without Cause (as defined), and in the case of the 2014 LTIP for Good Reason (as defined), at any time following a Change in Control (as defined in the applicable plans).

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Exercisable, end of year — $ — 74,390 $ 42.17 287,974 $ 35.26

All of the outstanding options are fully vested (vesting period of three years from date of grant) and have a contractual life of seven years from the original date of grant.

All of the outstanding options have an exercise price equal to the fair value of the underlying shares at the date of grant.

The intrinsic value of each option is determined based on the difference between the fair value of the underlying share and the exercise price of the underlying option.

The total intrinsic value of options exercised during 2023, 2022 and 2021 was $ 0 , $ 0 and $ 1.3 million, respectively.

There were no options granted in 2024, 2023, or 2022.

The value of the options granted prior to 2022 was estimated at the date of grant using the Black-Scholes-Merton option pricing model.

The options outstanding at December 31, 2023 lapsed in the year ended December 31, 2024.

At December 31, 2024, no options remain outstanding.

The options outstanding at December 31, 2023 and 2022 were fully vested (vesting period of three years from date of grant) and had a contractual life of seven years from the original date of grant.

All options had an exercise price equal to the fair value of the underlying shares at the date of grant.

The intrinsic value of each option was determined based on the difference between the fair value of the underlying share and the exercise price of the underlying option.

No options were exercised during 2024, 2023 or 2022.

The aggregate intrinsic value of options outstanding and options exercisable was $ 0 at December 31, 2023 and 2022.

The fair value used for calculating intrinsic values was $ 9.24 and $ 20.91 at December 31, 2023 and 2022, respectively.

The weighted-average remaining contractual life of the options outstanding and exercisable at December 31, 2023 is 0.1 years.

There were no options granted in 2023, 2022, or 2021.

The value of the options granted was estimated at the date of grant using the Black-Scholes-Merton option pricing model.

The following table summarizes RSU activity:

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Forfeited ( 101,494 ) $ 17.55 ( 51,928 ) $ 24.08 ( 39,827 ) $ 25.41

PRSU performance adjustment ( 29,679 ) $ 24.83 — $ — — $ —

Unvested, end of year 885,173 $ 15.30 751,254 $ 23.48 665,458 $ 25.98

3 unchanged sentences

The holders of RSUs are entitled to dividend equivalents.

The dividend equivalents are settled in cash at the same time that the underlying RSUs vest and are subject to the same risk of

James River Group Holdings, Ltd.

2 unchanged sentences

Years ended December 31, 2024, 2023, and 2022

forfeiture as the underlying shares.

dividend equivalents are settled in cash at the same time that the underlying RSUs vest and are subject to the same risk of forfeiture as the underlying shares.

The fair value of the RSUs granted is based on the market price of the underlying shares at the date of grant.

The RSUs granted in 2023 include 91,818 PRSU awards.

The RSUs granted in 2024 and 2023 include 231,492 and 91,818 PRSU awards, respectively.

Initial PRSU awards are granted at the 100 % target performance level.

The Company projects the level of achievement for each award during the performance period and periodically adjusts the number of outstanding awards to reflect the number of awards expected to vest.

In 2024, a downward performance adjustment was made to the outstanding PRSUs granted in 2023.

Compensation Expense

Share based compensation expense is recognized on a straight-line basis over the vesting period.

Compensation cost for PRSUs is based upon the probable outcome of performance conditions.

The amount of expense and related tax benefit is summarized below:

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tax benefit on share based compensation expense $ 1,214 $ 1,690 $ 1,526

Compensation cost for PRSUs is based upon the probable outcome of performance conditions.

In 2024, the Company adjusted the probable outcome of performance conditions for the 2023 PRSUs which resulted in a cumulative adjustment to reduce the compensation expense recognized for the awards of $ 451,000 .

At December 31, 2024, the Company had $ 6.3 million of unrecognized share based compensation expense expected to be charged to earnings over a weighted-average period of 1.6 years.

Currently, James River Group Holdings, Ltd.

and its Bermuda-based subsidiary, JRG Re, are not subject to income or capital tax.

is not (and its former Bermuda-based subsidiary, JRG Re, prior to its disposition was not) subject to income or capital tax.

The Companies have obtained from the Bermuda Minister of Finance an assurance that, in the event Bermuda enacts legislation imposing tax, the imposition of any such tax shall not be applicable to the Company until March 31, 2035 (the “EUTP Act”).

Effective for tax years beginning on or after January 1, 2025, Bermuda has introduced the Corporate Income Tax Act 2023 ("CIT Act") where a Bermuda Constituent Entity group (BCE) that is part of an “in scope Multi-National Enterprise group” (MNE) will be subject to a 15% corporate income tax.

The CIT Act will supersede the assurance received from the Bermuda Minister of Finance under the EUTP Act.

The CIT Act supersedes the assurance received from the Bermuda Minister of Finance under the EUTP Act.

A MNE group with a limited international footprint is not an in scope MNE, thus not subject to CIT.

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The expected income tax provision computed from pre-tax income at the weighted-average tax rate has been calculated as the sum of the pre-tax income in each jurisdiction multiplied by that jurisdiction’s applicable Federal statutory tax rate.

Federal statutory tax rates of 0% and 21% have been used in 2023, 2022 and 2021 for Bermuda and the U.S., respectively.

income (loss) before Federal income taxes was $ 119.9 million, $ 85.9 million, and $( 89.3 ) million for the years ending December 31, 2023, 2022, and 2021, respectively.

The Tax Act base-erosion and anti-abuse tax (“BEAT”) provisions impose a minimum tax on applicable taxpayers that make certain payments to related foreign persons.

BEAT subjects the modified taxable income of an applicable taxpayer to a specified tax rate (10% in 2023).

Modified taxable income is generally calculated by adding back certain payments to related foreign persons to regular taxable income.

A reconciliation of the difference

James River Group Holdings, Ltd.

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Years ended December 31, 2024, 2023, and 2022

between the Company’s Federal income tax provision on U.S.

statutory tax rates of 0% and 21% have been used in 2024, 2023 and 2022 for Bermuda and the U.S., respectively.

income (loss) before Federal income taxes was $( 40.0 ) million, $ 119.9 million, and $ 85.9 million for the years ending December 31, 2024, 2023, and 2022, respectively.

The Tax Act base-erosion and anti-abuse tax (“BEAT”) provisions impose a minimum tax on applicable taxpayers that make certain payments to related foreign persons.

BEAT subjects the modified taxable income of an applicable taxpayer to a specified tax rate (10% in 2024).

Modified taxable income is generally calculated by adding back certain payments to related foreign persons to regular taxable income.

A reconciliation of the difference between the Company’s Federal income tax provision on U.S.

income and the expected Federal tax provision on U.S.

21 unchanged sentences

Allowance for credit losses 4,496 3,240

Other invested assets 3,552 998

Net unrealized losses 18,595 16,613

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Deferred income taxes have not been accrued with respect to certain undistributed earnings of foreign subsidiaries.

If the earnings were to be distributed, as dividends or otherwise, such amounts may be subject to withholding taxation in the jurisdiction of the paying entity.

If the earnings were to be distributed, as dividends or otherwise, such amounts may be subject to withholding taxation in the

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2024, 2023, and 2022

jurisdiction of the paying entity.

The Company asserts that U.S.

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The carryforward period for non-insurance companies is unlimited but limited to 80% of the current year taxable income.

At December 31, 2023, the Company has no net operating loss carryforwards.

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2023, 2022, and 2021

At December 31, 2024, the Company has $ 984,000 of net operating loss carryforwards that were generated in 2024 and do not expire.

The Company had no reserve for future tax contingencies or liabilities (“unrecognized tax benefits”) at December 31, 2024 or 2023.

2 unchanged sentences

The rates of tax are established based on the nature of the risk, unless reduced by an applicable U.S.

For the years ended December 31, 2023, 2022, and 2021, the Company paid $ 0 , $ 0 , and $ 338,000 , respectively, of federal excise taxes on its intercompany reinsurance transactions.

The Company also paid excise taxes of $ 194,000 , $ 842,000 , and $ 1.5 million for the years ended December 31, 2023, 2022, and 2021, respectively, on written premiums assumed from third-party insurers with respect to risks located in the U.S.

The Company paid excise taxes of $ 204,000 , $ 194,000 , and $ 842,000 for the years ended December 31, 2024, 2023, and 2022, respectively, on written premiums assumed from third-party insurers with respect to risks located in the U.S.

These excise taxes are reflected as “other operating expenses” in the Company’s Consolidated Statements of (Loss) Income and Comprehensive Loss.

8 unchanged sentences

Total $ 193,198 $ 193,656 $ 152,570

Other expenses of $ 3.8 million, $ 795,000 , and $ 2.6 million for the years ended December 31, 2023, 2022, and 2021, respectively, primarily consist of certain nonoperating expenses including legal fees related to a class action lawsuit, legal and other professional fees related to the Company's May 2021 common share offering, legal and other professional fees and other expenses related to various strategic initiatives including loss portfolio transfers accounted for as retroactive reinsurance, and employee severance costs.

Other expenses of $ 6.1 million, $ 3.8 million, and $ 795,000 for the years ended December 31, 2024, 2023, and 2022, respectively, primarily consist of certain nonoperating expenses including legal fees related to a class action lawsuit, and legal and other professional fees and other expenses related to various strategic initiatives.

Employee Benefits

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Commitments and Contingent Liabilities

The Company is involved in various legal proceedings, including commercial matters and litigation regarding insurance claims which arise in the ordinary course of business, as well as an alleged class action lawsuit.

The Company is involved in various legal proceedings, including commercial matters and litigation regarding insurance claims which arise in the ordinary course of business.

In addition, the Company is involved from time to time in legal actions which seek extra-contractual damages, punitive damages or penalties, including claims alleging bad faith in the handling of insurance claims.

The Company believes that the outcome of such matters, individually and in the aggregate, is not reasonably likely to have a material adverse effect on the Company's consolidated financial position, results of operations or cash flows.

On July 9, 2021 a purported class action lawsuit was filed in the U.S.

District Court, Eastern District of Virginia (the “Court”) by Employees’ Retirement Fund of the City of Fort Worth against James River Group Holdings, Ltd.

and certain of its present and former officers (together, “Defendants”).

On September 22, 2021, the Court entered an order appointing Employees’ Retirement Fund of the City of Fort Worth and the City of Miami General Employees’ and Sanitation Employees’ Retirement Trust as co-lead plaintiffs (together, “Plaintiffs”).

Plaintiffs’ consolidated amended complaint was filed on November 19, 2021 (the “First Amended Complaint”).

The Defendants filed a motion to dismiss the First Amended Complaint on January 18, 2022, Plaintiffs’ opposition thereto was filed on March 4, 2022, and the Defendants’ reply to the Plaintiffs’ opposition was filed on April 4, 2022.

On August 25, 2022, Plaintiffs filed a motion for leave to file a second amended class action complaint (the “Second Amended Complaint”).

On September 8 , 2022, the Defendants consented to the Plaintiffs’ motion to file the Second Amended Complaint, and filed a motion to dismiss the Second Amended Complaint on October 24, 2022 (the “Second MTD”).

The Plaintiffs’ opposition to the Second MTD was filed on November 7, 2022, and the Defendant’s reply to the Plaintiffs’ opposition was filed on November 14, 2022.

On August 28, 2023, the Court denied the Second MTD.

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2023, 2022, and 2021

The Second Amended Complaint asserts claims under Sections 10(b) and 20(a) of the Securities Exchange Act of 1934 on behalf of a putative class of persons and entities that purchased the Company’s stock between February 22, 2019 and October 25, 2021, alleges that Defendants failed to make appropriate disclosures concerning the adequacy of reserves for policies that covered Rasier LLC, a subsidiary of Uber Technologies, Inc., and seeks unspecified damages, costs, attorneys’ fees and such other relief as the court may deem proper.

We engaged in mediation in the fourth quarter of 2023 and on December 7, 2023, in connection with the mediation, we reached an agreement in principle to settle the action.

On December 22, 2023, the parties submitted the stipulation of settlement to the Court for approval.

The settlement provides for a full release of all defendants in connection with the allegations made and a settlement payment to the class of $ 30 million, inclusive of all Plaintiffs’ attorneys fees and expenses and settlement costs, all of which will be paid by the Company’s insurance carriers.

On January 26, 2024 the Court issued an order granting preliminary approval of the settlement and scheduled a final settlement hearing for May 24, 2024.

On November 13, 2023, a purported class action lawsuit was filed in the U.S.

1 unchanged sentence

and certain of its officers, asserting claims under Sections 10(b) and 20(a) of the Securities Exchange Act of 1934.

Glantz alleges that he purchased James River common stock between August 7, 2023 and November 7, 2023, inclusive, that the Company failed to disclose that it lacked effective internal controls regarding the recognition of reinstatement premiums for reinsurance and as a result the Company overstated its net income, and that, as a result, Mr.

Glantz suffered unspecified damages.

On January 12, 2024, both Mr.

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Ghimire's competing motion for appointment as lead plaintiff.

The court's appointment of Lead Plaintiff is pending.

The Company believes that the claims are without merit and intends to vigorously defend this lawsuit.

On March 25, 2024 the court entered an order appointing Mr.

Ghimire as lead plaintiff.

On May 24, 2024, plaintiff filed its consolidated amended complaint alleging that he acquired the Company’s common stock at artificially inflated pricing between May 2, 2023 and November 7, 2023, inclusive, that the Company knew and/or recklessly disregarded that it had improperly accounted for

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2024, 2023, and 2022

reinsurance premiums and did not have effective internal control over financial reporting, and that as a result, he suffered unspecified damages, and seeking unspecified damages, costs, attorneys' fees and such other relief as the court may deem proper.

On July 23, 2024 the Company filed a motion to dismiss the consolidated amended complaint.

On September 6, 2024, the plaintiff filed its Opposition to Motion to Dismiss and on October 8, 2024, the Company filed its Reply to the plaintiff's Opposition to Motion to Dismiss.

On January 23, 2025 the court granted the Company's Motion to Dismiss with prejudice.

On March 11, 2024, the Company filed a complaint (the “Complaint”) in the Supreme Court of the State of New York, New York County, Commercial Division against Fleming Intermediate Holdings LLC (“Fleming”), a Cayman Islands limited liability company, relating to the previously announced Stock Purchase Agreement, dated as of November 8, 2023 (the “Stock Purchase Agreement”), pursuant to which Fleming agreed to purchase all of the outstanding common shares of JRG Re (the “Transaction”).

The complaint alleges that Fleming breached the Stock Purchase Agreement by its refusal to close the Transaction on March 1, 2024 as required under the terms of the Stock Purchase Agreement, and seeks specific performance of Fleming’s obligation to complete the Transaction and an award of damages.

The Company subsequently filed a motion for preliminary injunction to require Fleming to fulfill its contractual obligation to close the Transaction, and on April 6, 2024 the Court granted the Company’s motion and ordered Fleming to complete the Transaction on or prior to April 16, 2024.

On April 8, 2024, Fleming filed a notice of appeal of the preliminary injunction, which Fleming withdrew on October 9, 2024.

The Transaction closed on April 16, 2024.

On April 19, 2024, Fleming filed a motion to dismiss the Complaint.

On May 9, 2024, the Company filed an amended complaint seeking, among other things, specific performance and damages suffered as a result of Fleming's breach of the Stock Purchase Agreement.

On June 6, 2024, Fleming filed a motion to dismiss the amended complaint, on July 3, 2024 the Company filed an opposition to the motion to dismiss, on July 24, 2024 Fleming filed its reply to the opposition, and on October 29, 2024 the court heard oral argument on the motion to dismiss.

On July 15, 2024, Fleming filed a lawsuit in the U.S.

District Court, Southern District of New York against James River Group Holdings, Ltd.

and certain of its officers, asserting claims under Sections 10(b) and 20(a) of the Securities Exchange Act of 1934, common law fraud, and breaches of contract, and seeking unspecified monetary damages, including compensatory, consequential and punitive damages, all associated with Fleming's purchase of JRG Re pursuant to the Stock Purchase Agreement.

On July 31, 2024, Fleming filed an amended complaint, on September 13, 2024 the Company filed a motion to dismiss the amended complaint, and on October 18, 2024 Fleming filed a second amended complaint.

On November 15, 2024, the Company filed a motion to dismiss the second amended complaint, on December 23, 2024 Fleming filed an opposition to the motion to dismiss, and on January 17, 2025 the Company filed its reply to Fleming's opposition.

The Company believes that it has substantial defenses and intends to vigorously defend this lawsuit.

Amounts Recoverable from an Indemnifying Party and Reinsurer on Legacy Commercial Auto Book

James River previously issued a set of commercial auto insurance contracts to Rasier (the “Rasier Commercial Auto Policies”) under which James River pays losses and loss adjustment expenses on the contracts.

James River previously issued a set of commercial auto insurance contracts (the “Rasier Commercial Auto Policies”) to Rasier under which James River pays losses and loss adjustment expenses on the contracts.

James River has indemnity agreements with Rasier (non-insurance entities) (collectively, the “Indemnity Agreements”) and is contractually entitled to reimbursement for the portion of the losses and loss adjustment expenses paid on behalf of Rasier under the Rasier Commercial Auto Policies and other expenses incurred by James River.

1 unchanged sentence

Under the terms of the Commercial Auto LPT, effective as of July 1, 2021, James River ceded to Aleka approximately $ 345.1 million of commercial auto liabilities relating to Rasier Commercial Auto Policies written in the years 2013-2019, which amount constituted the reinsurance premium.

For the years ended December 31, 2023 and 2022, due to adverse paid and reported loss trends on the legacy Rasier business, the Company recognized adverse prior year development of $ 64.4 million and $ 46.7 million, respectively, on the reserves subject to the Commercial Auto LPT, bringing the cumulative amount ceded under the Commercial Auto LPT to $ 456.2 million at December 31, 2023.

Since inception, due to adverse paid and reported loss trends on the legacy Rasier business, the Company has recognized adverse prior year development of $ 114.2 million on the reserves subject to the Commercial Auto LPT, bringing the cumulative amount ceded under the Commercial Auto LPT to $ 459.3 million at December 31, 2024.

Each of Rasier and Aleka are required to post collateral under the Indemnity Agreements and the Commercial Auto LPT:

2 unchanged sentences

In connection with the execution of the Commercial Auto LPT, James River returned $ 691.3 million to the Indemnity Trust, representing the remaining balance of the amount withdrawn in October 2019, as was permitted under the indemnification agreements with Rasier and the associated trust agreement.

At December 31, 2023, the balance in the Indemnity Trust was $ 138.4 million, and, together with the balance of the Loss Fund Trust (as defined below) attributable to the Indemnity Agreements as described below, the total balance of collateral securing Rasier’s obligations under the Indemnity Agreements was $ 183.6 million.

• Pursuant to the Commercial Auto LPT, Aleka is required to post collateral equal to 102 % of James River's estimate of Aleka's obligations under the Commercial Auto LPT, calculated in accordance with standard actuarial principles and based on reserves recorded in the Company's statutory financial statements.

The collateral is provided through a collateral trust arrangement (the “LPT Trust”) established in favor of James River by Aleka.

At December 31, 2023, the balance in the LPT Trust was $ 63.7 million, and, together with the balance of the Loss Fund Trust (as defined below) attributable to the Commercial Auto LPT as described below, the total balance of collateral securing Aleka’s obligations under the Commercial

At December 31, 2024, the balance in the Indemnity Trust was $ 64.7 million, and, together with the balance of the Loss Fund Trust (as defined below) attributable to the

James River Group Holdings, Ltd.

2 unchanged sentences

Years ended December 31, 2024, 2023, and 2022

Auto LPT was $ 83.8 million.

At December 31, 2023, the total reinsurance recoverables under the Commercial Auto LPT was $ 84.5 million (including $ 78.1 million of unpaid recoverables and $ 6.4 million of paid recoverables).

Indemnity Agreements as described below, the total balance of collateral securing Rasier’s obligations under the Indemnity Agreements was $ 82.1 million.

The collateral is provided through a collateral trust arrangement (the “LPT Trust”) established in favor of James River by Aleka.

At December 31, 2024, the balance in the LPT Trust was $ 30.1 million, and, together with the balance of the Loss Fund Trust (as defined below) attributable to the Commercial Auto LPT as described below, the total balance of collateral securing Aleka’s obligations under the Commercial Auto LPT was $ 37.8 million.

At December 31, 2024, the total reinsurance recoverables under the Commercial Auto LPT was $ 36.6 million.

In connection with the execution of the Commercial Auto LPT, James River and Aleka entered into an administrative services agreement (the “Administrative Services Agreement”) with a third party claims administrator (the “Administrator”) pursuant to which the Administrator handles the claims on the Rasier Commercial Auto Policies for the remaining life of those claims.

7 unchanged sentences

To mitigate these risks, the Company closely and frequently monitors exposure compared to collateral held, and requests additional collateral in accordance with the terms of the Commercial Auto LPT and Indemnity Agreements when its analysis indicates that the Company has uncollateralized exposure.

Other Comprehensive Income (Loss)

Other Comprehensive (Loss) Income

The following table summarizes the components of other comprehensive income (loss):

2 unchanged sentences

(in thousands)

Unrealized gains (losses) arising during the period, before U.S.

Unrealized (losses) gains arising during the period, before U.S.

income taxes $ ( 9,222 ) $ 105,368 $ ( 219,788 )

income taxes 1,937 ( 6,313 ) 26,780

Unrealized gains (losses) arising during the period, net of U.S.

Unrealized (losses) gains arising during the period, net of U.S.

income taxes ( 7,285 ) 99,055 ( 193,008 )

3 unchanged sentences

Reclassification adjustment for investment (losses) gains realized in net income ( 1,009 ) ( 268 ) 14

Other comprehensive income (loss) $ 99,323 $ ( 193,022 ) $ ( 51,921 )

In addition to the net realized investment (losses) gains of $( 339,000 ), $ 275,000 , and $ 4.9 million on available-for-sale fixed maturity securities for the years ended December 31, 2023, 2022, and 2021, the Company recognized net realized and unrealized investment gains (losses) in the respective years of $ 5.5 million, $( 5.7 ) million, and $ 2.0 million on its investments in bank loan participations and $ 5.2 million, $( 11.1 ) million, and $ 4.3 million on its investments in equity securities.

Other comprehensive (loss) income $ ( 6,276 ) $ 99,323 $ ( 193,022 )

In addition to the net realized investment (losses) gains of $( 1.3 ) million, $( 339,000 ), and $ 275,000 on available-for-sale fixed maturity securities for the years ended December 31, 2024, 2023, and 2022, the Company recognized net realized and unrealized investment (losses) gains in the respective years of $( 3.8 ) million, $ 5.5 million, and $( 5.7 ) million on its investments in bank loan participations and $ 8.7 million, $ 5.2 million, and $( 11.1 ) million on its investments in equity securities.

James River Group Holdings, Ltd.

5 unchanged sentences

The Excess and Surplus Lines segment primarily offers commercial excess and surplus lines liability and excess property insurance products.

The Specialty Admitted Insurance segment offers specialty admitted fronting and program business and workers’ compensation insurance coverage.

The Specialty Admitted Insurance segment offers specialty admitted fronting and program business and, prior to the sale of the Company's renewal rights in 2023, workers’ compensation insurance coverage.

The Corporate and Other segment consists of certain management and treasury activities of James River Group, James River UK, and JRG Holdings as well as interest expense associated with senior debt and Junior Subordinated Debt, and investment income.

3 unchanged sentences

The segment information below excludes discontinued operations for all periods presented.

Segment revenues for each reportable segment consist of net earned premiums, net investment income, and realized and unrealized (losses) gains on investments.

Segment profit (loss) is measured by underwriting profit (loss), which is generally defined as net earned premiums and gross fee income (in specific instances when the Company is not retaining insurance risk) in “other income” in the Consolidated Statements of (Loss) Income and Comprehensive Loss less loss and loss adjustment expenses on business not subject to retroactive reinsurance accounting for loss portfolio transfers (see Loss Portfolio Transfer in Note 8 - Reserve for Losses and Loss Adjustment Expenses ) and other operating expenses of the operating segments.

Gross fee income of $ 5.3 million, $ 3.8 million, and $ 4.5 million from the Specialty Admitted Insurance segment for the years ended December 31, 2023, 2022, and 2021, respectively, was included in other income and in underwriting profit (loss).

Segment profit (loss) is measured by underwriting profit (loss), which is generally defined as net earned premiums and gross fee income (in specific instances when the Company is not retaining insurance risk) in “other income” in the Consolidated Statements of (Loss) Income and Comprehensive Loss less loss and loss adjustment expenses on business not subject to retroactive reinsurance accounting (see Retroactive Reinsurance Accounting in Note 8 - Reserve for Losses and Loss Adjustment Expenses ) and other operating expenses.

Other operating expenses include the underwriting, acquisition, and insurance expenses of the operating segments and, for consolidated underwriting profit, the expenses of the Corporate and Other segment.

Other operating expenses for the Corporate and Other segment include personnel costs associated with the Bermuda and U.S.

holding companies, professional fees, share-based compensation for the full Company, and various other corporate expenses that were not reimbursed by our subsidiaries, including costs associated with rating agencies and strategic initiatives.

Net commissions in the table below are net of amounts deferred as deferred policy acquisition costs.

Employee compensation includes both cash and share-based compensation, as well as employer expenses related to payroll taxes and benefits, and is net of amounts allocated to losses and loss adjustment expenses and amounts deferred.

All other operating expenses include, amongst other expenses, costs for insurance, outside professional fees including legal, audit, and consulting, office rent, bad debt expense, and taxes, licenses and fees on business written.

Segment results are reported prior to the effects of intercompany pooling agreements and intercompany reinsurance agreements.

1 unchanged sentence

based insureds.

Segment revenues for each reportable segment consist of net earned premiums, net investment income, and realized and unrealized (losses) gains on investments.

The Company's Chief Executive Officer ("CEO") has final authority over segment resource allocation decisions and performance assessment, and consequently, is identified as the Chief Operating Decision Maker ("CODM").

The CEO considers segment underwriting profit (loss) in the annual budget and forecasting process, and in monthly financial reviews of actual segment results compared to budget and prior year periods in order to assess segment performance and make strategic operating decisions regarding the business written by the segments, the allocation of capital and personnel to the segments, and compensation for segment employees.

The segment information presented below aligns with the information that is presented regularly to the CEO.

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2024, 2023, and 2022

Surplus Lines Specialty

5 unchanged sentences

Net earned premiums 512,237 87,959 — 600,196

Fee income — 4,585 — 4,585

Losses and loss adjustment expenses 485,951 68,423 — 554,374

losses and loss adjustment expense - retroactive reinsurance 37,237 — — 37,237

Losses and loss adjustment expenses excluding retroactive reinsurance 448,714 68,423 — 517,137

Other operating expenses:

Net commissions 56,186 ( 11,243 ) — 44,943

Employee compensation 62,176 14,115 23,804 100,095

All other operating expenses 22,616 14,376 11,168 48,160

140,978 17,248 34,972 193,198

Underwriting (loss) profit ( 77,455 ) 6,873 ( 34,972 ) ( 105,554 )

Segment revenues 594,433 109,472 3,721 707,626

1 unchanged sentence

Interest expense — — 24,666 24,666

Underwriting profit of operating segments 54,347 4,077 — 58,424

Segment goodwill 181,831 — — 181,831

Segment assets 3,516,399 1,390,894 99,783 5,007,076

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2024, 2023, and 2022

Surplus Lines Specialty

Insurance Corporate

(in thousands)

As of and for the Year Ended

2 unchanged sentences

Net earned premiums 609,566 98,439 — 708,005

Fee income — 5,301 — 5,301

Losses and loss adjustment expenses 425,035 75,122 — 500,157

losses and loss adjustment expense - retroactive reinsurance 4,991 — — 4,991

Losses and loss adjustment expenses excluding retroactive reinsurance 420,044 75,122 — 495,166

Other operating expenses:

Net commissions 61,542 ( 12,809 ) — 48,733

Employee compensation 57,436 18,492 22,502 98,430

All other operating expenses 16,197 18,858 11,438 46,493

135,175 24,541 33,940 193,656

Underwriting profit 54,347 4,077 ( 33,940 ) 24,484

Segment revenues 690,388 119,777 1,844 812,009

1 unchanged sentence

Interest expense — — 24,627 24,627

Underwriting profit of operating segments 83,051 4,234 — 87,285

Segment goodwill 181,831 — — 181,831

4 unchanged sentences

Years ended December 31, 2024, 2023, and 2022

Surplus Lines Specialty

Insurance Corporate

(in thousands)

As of and for the Year Ended

2 unchanged sentences

Net earned premiums 555,597 74,137 — 629,734

Fee income — 3,761 — 3,761

Losses and loss adjustment expenses 382,094 58,548 — 440,642

losses and loss adjustment expense - retroactive reinsurance 15,742 — — 15,742

Losses and loss adjustment expenses excluding retroactive reinsurance 366,352 58,548 — 424,900

Other operating expenses:

Net commissions 47,006 ( 18,411 ) — 28,595

Employee compensation 47,898 17,823 20,857 86,578

All other operating expenses 11,290 15,704 10,403 37,397

106,194 15,116 31,260 152,570

Underwriting profit 83,051 4,234 ( 31,260 ) 56,025

Segment revenues 570,087 81,593 9,834 661,514

1 unchanged sentence

Interest expense — — 13,872 13,872

Underwriting (loss) profit of operating segments ( 121,478 ) 9,667 — ( 111,811 )

Segment goodwill 181,831 — — 181,831

Segment assets 2,627,956 1,277,988 85,332 3,991,276

The following table reconciles the underwriting profit (loss) of operating segments by individual segment to consolidated income (loss) from continuing operations before income taxes:

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2024, 2023, and 2022

The following table reconciles the underwriting (loss) profit of operating segments by individual segment to consolidated (loss) income from continuing operations before income taxes:

Year Ended December 31,

1 unchanged sentence

(in thousands)

Underwriting profit (loss) of the operating segments:

Underwriting (loss) profit of the operating segments:

Excess and Surplus Lines $ ( 77,455 ) $ 54,347 $ 83,051

Specialty Admitted Insurance 6,873 4,077 4,234

Total underwriting profit (loss) of operating segments 58,424 87,285 ( 111,811 )

Total underwriting (loss) profit of operating segments ( 70,582 ) 58,424 87,285

Other operating expenses of the Corporate and Other segment ( 34,972 ) ( 33,940 ) ( 31,260 )

Underwriting profit (loss) 24,484 56,025 ( 139,420 )

Underwriting (loss) profit ( 105,554 ) 24,484 56,025

Losses and loss adjustment expenses - retroactive reinsurance ( 37,237 ) ( 4,991 ) ( 15,742 )

6 unchanged sentences

Impairment of intangible assets — ( 2,500 ) —

Income (loss) from continuing operations before income taxes $ 86,914 $ 53,272 $ ( 108,130 )

(Loss) income from continuing operations before income taxes $ ( 71,120 ) $ 86,914 $ 53,272

The Company currently has 15 underwriting divisions, including 14 in the Excess and Surplus Lines segment, and one in the Specialty Admitted Insurance segment.

Each underwriting division focuses on a specific industry group or coverage.

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2023, 2022, and 2021

Gross written premiums by segment and underwriting division are presented below:

19 unchanged sentences

Total $ 1,431,772 $ 1,508,660 $ 1,411,372

The Company does business with three brokers that generated $ 324.7 million, $ 246.4 million and $ 145.2 million of gross written premiums for the Excess and Surplus Lines segment for the year ended December 31, 2023, representing 21.5 %, 16.3 % and 9.6 % of consolidated gross written premiums and 32.2 %, 24.5 % and 14.4 % of the Excess and Surplus Lines segment’s gross written premiums, respectively.

The Company does business with three brokers that generated $ 345.1 million, $ 245.5 million and $ 134.1 million of gross written premiums for the Excess and Surplus Lines segment for the year ended December 31, 2024, representing 24.1 %, 17.1 %

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2024, 2023, and 2022

and 9.4 % of consolidated gross written premiums and 33.9 %, 24.1 % and 13.2 % of the Excess and Surplus Lines segment’s gross written premiums, respectively.

The Company has agency contracts with various branches within the aforementioned brokers.

1 unchanged sentence

No individual insured generated 10.0% or more of the gross written premiums for the Excess and Surplus Lines segment for the year ended December 31, 2024.

The Specialty Admitted Insurance segment accepts applications for insurance from a variety of sources, including independent retail agents, program administrators and managing general agents (“MGAs”).

The Specialty Admitted Insurance segment accepts applications for insurance from a variety of sources, including program administrators and managing general agents (“MGAs”).

The Company does business with two agencies that generated $ 175.7 million and $ 63.7 million of gross written premiums for the Specialty Admitted Insurance segment for the year ended December 31, 2024, representing 12.3 % and 4.5 % of consolidated gross written premiums and 42.4 % and 15.4 % of the Specialty Admitted Insurance segment’s gross written premiums, respectively.

11 unchanged sentences

Treasury and publicly-traded equity securities are generally based on Level 1 inputs which use the market approach valuation technique.

The values for all other fixed maturity securities (including state and municipal securities and obligations

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2023, 2022, and 2021

The values for all other fixed maturity securities (including state and municipal securities and obligations of U.S.

government corporations and agencies) and bank loan participations generally incorporate significant Level 2 inputs, and in some cases, Level 3 inputs, using the market approach and income approach valuation techniques.

5 unchanged sentences

The Company’s control process includes, but is not limited to, initial and ongoing evaluation of the methodologies used, a review of specific securities and an assessment for proper classification within the fair value hierarchy, and obtaining and reviewing internal control reports for the investment manager that obtains fair values from independent pricing services.

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2024, 2023, and 2022

Assets measured at fair value on a recurring basis as of December 31, 2024 are summarized below:

20 unchanged sentences

Short-term investments $ — $ 97,074 $ — $ 97,074

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2023, 2022, and 2021

Assets measured at fair value on a recurring basis as of December 31, 2023 are summarized below:

20 unchanged sentences

Short-term investments $ — $ 72,137 $ — $ 72,137

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2024, 2023, and 2022

A reconciliation of the beginning and ending balances of available-for-sale fixed maturity securities, equity securities, and bank loan participations measured at fair value on a recurring basis using significant unobservable inputs (Level 3) is shown below:

18 unchanged sentences

The Company held one equity security at December 31, 2022 for which the fair value was determined using significant unobservable inputs (Level 3).

The fair value of $ 39,000 for the equity security was based on expected proceeds from its sale.

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2023, 2022, and 2021

During 2021, one equity security was transferred from Level 2 to Level 3 as the security was no longer actively traded.

This security was exchanged for an equity security that was publicly traded and it was transferred from Level 3 to Level 1.

The fair value of $ 7,000 for the equity security was obtained from our asset manager and was derived from an internal model.

Transfers out of Level 3 occur when the Company is able to obtain reliable prices from pricing vendors for which the Company was previously unable to obtain reliable prices.

10 unchanged sentences

There were no investments for which external sources were unavailable to determine fair value as of December 31, 2024 and 2023.

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2024, 2023, and 2022

The carrying values and fair values of financial instruments are summarized below:

13 unchanged sentences

The fair values of other invested assets-notes receivable, senior debt, and junior subordinated debt at December 31, 2024 and 2023 were determined by calculating the present value of expected future cash flows under the terms of the note agreements or debt agreements, as applicable, discounted at an estimated market rate of interest at December 31, 2024 and 2023, respectively.

The Company also utilized an internally developed valuation model based on the spread of a comparable market index to determine the fair value of certain other invested assets-notes receivable at December 31, 2023.

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2023, 2022, and 2021

The fair values of senior debt and junior subordinated debt at December 31, 2024 and 2023 were determined using inputs to the valuation methodology that are unobservable (Level 3).

4 unchanged sentences

The principal differences between SAP and GAAP as they relate to the financial statements of the Company’s insurance subsidiaries are (a) policy acquisition costs are expensed as incurred under SAP, whereas they are deferred and amortized under GAAP, (b) certain assets are not admitted for purposes of determining surplus under SAP, (c) the classification and carrying amounts of investments in certain securities are different under SAP and GAAP, and (d) the criteria for providing asset valuation allowances and the methodologies used to determine the amount thereof are different under SAP and GAAP.

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2024, 2023, and 2022

Combined net income, statutory capital and surplus and minimum required statutory capital and surplus, as determined in accordance with statutory accounting practices, for the U.S.

24 unchanged sentences

Operating costs under the lease were $ 2.1 million for each of the years ended December 31, 2024, 2023, and 2022, respectively.

Upon retiring effective July 31, 2021, the Company’s former President and Chief Operating Officer entered into a consulting agreement with the Company to provide consulting services as requested by the Company’s Chief Executive Officer during the period August 1, 2021 through December 31, 2021.

The Company incurred expenses of $ 146,000 in 2021 as compensation for rendering these consulting services.

James River Group Holdings, Ltd.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2023, 2022, and 2021

Subsequent Events

On January 27, 2025, the Company borrowed $ 25.0 million on the unsecured revolver of the 2013 Facility, increasing the outstanding drawn balance to $ 210.8 million.

The Company remains in compliance with financial and other covenants (including minimum net worth, maximum ratio of total adjusted debt outstanding to total capitalization, and financial strength ratings) under the 2013 Facility after giving effect to this borrowing.

On February 20, 2025, the Board of Directors declared a cash dividend of $ 0.01 per common share.

1 unchanged sentence

On February 20, 2025, the Board of Directors declared a quarterly dividend on the Series A Preferred Shares.

The dividend of $ 2.6 million will be payable in cash on April 1, 2024 to shareholders of record on March 15, 2024 .

The dividend of $ 2.0 million will be payable in cash on March 31, 2025 to shareholders of record on March 15, 2025 .

On February 20, 2025, the Board of Directors approved awards under the 2014 LTIP and the 2014 Director Plan to the Company’s employees and directors with an aggregate fair value of $ 9.1 million and a grant date of March 5, 2025.

The 2013 Facility and 2017 Facility contain certain financial and other covenants with which we are in compliance at December 31, 2023, with the exception of a default of the financial strength rating covenant due to the downgrade of JRG Re by A.M.

Best on December 20, 2023 from “A-” (Excellent) to “B++” (good).

The financial strength rating covenant requires that each of our regulated insurance subsidiaries maintain an A.M.

Best rating not lower than “A-” (Excellent).

On February 26, 2024, our lenders waived this default through March 1, 2025, which, in any event, we expect to be cured upon the closing of the sale of JRG Re, at which time we expect JRG Re to be removed as a borrower under the 2013 Facility and 2017 Facility.

On February 26, 2024, JRGH received $ 5.8 million from JRG Re representing the cash portion of the pre-closing dividend pursuant to the Stock Purchase Agreement covering the sale of JRG Re.

See Note 2 - Discontinued Operations.

Unaudited Selected Quarterly Financial Data

The following is a summary of the unaudited quarterly results of operations:

2023 Quarter 2023

First Second Third Fourth Year

(in thousands except per share data)

Gross written premiums $ 353,454 $ 423,050 $ 342,851 $ 389,305 $ 1,508,660

Total revenues 188,804 194,782 210,319 218,104 812,009

Underwriting profit 7,314 1,878 11,827 3,465 24,484

Income from continuing operations 5,302 12,129 23,722 20,056 61,209

Income (loss) from discontinued operations 1,704 3,785 ( 4,171 ) ( 170,211 ) ( 168,893 )

Net income (loss) 7,006 15,914 19,551 ( 150,155 ) ( 107,684 )

Net income (loss) available to common shareholders 4,381 13,289 16,926 ( 152,780 ) ( 118,184 )

Comprehensive income (loss) 37,908 ( 543 ) ( 20,675 ) ( 25,051 ) ( 8,361 )

Net income (loss) per common share:

Continuing operations $ 0.07 $ 0.25 $ 0.56 $ 0.46 $ 1.35

Discontinued operations $ 0.05 $ 0.10 $ ( 0.11 ) $ ( 4.52 ) $ ( 4.49 )

$ 0.12 $ 0.35 $ 0.45 $ ( 4.06 ) $ ( 3.14 )

Continuing operations $ 0.07 $ 0.25 $ 0.55 $ 0.46 $ 1.34

Discontinued operations $ 0.05 $ 0.10 $ ( 0.10 ) $ ( 3.89 ) $ ( 4.47 )

$ 0.12 $ 0.35 $ 0.45 $ ( 3.43 ) $ ( 3.13 )

JAMES RIVER GROUP HOLDINGS, LTD.

and Subsidiaries

Notes to Consolidated Financial Statements

Years ended December 31, 2023, 2022, and 2021

2022 Quarter 2022

First Second Third Fourth Year

(in thousands except per share data)

Gross written premiums $ 329,992 $ 391,602 $ 328,174 $ 361,604 $ 1,411,372

Total revenues 157,625 154,856 162,228 186,805 661,514

Underwriting profit 13,792 14,698 8,240 19,295 56,025

Income (loss) from continuing operations 13,939 7,219 ( 12,161 ) 25,861 34,858

(Loss) income from discontinued operations ( 3,734 ) 445 7,540 ( 8,136 ) ( 3,885 )

Net income (loss) 10,205 7,664 ( 4,621 ) 17,725 30,973

Net income (loss) available to common shareholders 9,330 5,039 ( 7,246 ) 15,100 22,223

Comprehensive (loss) income ( 75,766 ) ( 50,936 ) ( 65,277 ) 29,930 ( 162,049 )

Net income (loss) per common share:

Continuing operations $ 0.35 $ 0.12 $ ( 0.39 ) $ 0.62 $ 0.70

Discontinued operations $ ( 0.10 ) $ 0.01 $ 0.20 $ ( 0.22 ) $ ( 0.11 )

$ 0.25 $ 0.13 $ ( 0.19 ) $ 0.40 $ 0.59

Continuing operations $ 0.35 $ 0.12 $ ( 0.39 ) $ 0.60 $ 0.69

Discontinued operations $ ( 0.10 ) $ 0.01 $ 0.20 $ ( 0.20 ) $ ( 0.10 )

$ 0.25 $ 0.13 $ ( 0.19 ) $ 0.40 $ 0.59

JAMES RIVER GROUP HOLDINGS, LTD.

Summary of Investments—Other than Investments in Related Parties

55 unchanged sentences

(in thousands)

Net investment income $ 1,860 $ — $ —

Other income 90 88 55

4 unchanged sentences

Total expenses 39,245 34,423 22,216

Loss before equity in net income of subsidiaries ( 34,335 ) ( 22,161 ) ( 17,594 )

Loss before equity in net (loss) income of subsidiaries ( 37,295 ) ( 34,335 ) ( 22,161 )

Equity in net (loss) income of subsidiaries (1)

1 unchanged sentence

Net (loss) income $ ( 81,120 ) $ ( 107,684 ) $ 30,973

Other comprehensive income (loss):

Equity in other comprehensive earnings (losses) of subsidiaries 99,323 ( 193,022 ) ( 51,921 )

Other comprehensive (loss) income:

Equity in other comprehensive (losses) earnings of subsidiaries ( 6,276 ) 99,323 ( 193,022 )

Total comprehensive loss $ ( 87,396 ) $ ( 8,361 ) $ ( 162,049 )

(1) Includes amounts for JRG Re which is classified as held for sale on our Consolidated Balance Sheets.

(1) Includes amounts for JRG Re which was classified as held for sale on our Consolidated Balance Sheets as of December 31, 2023.

The sale of JRG Re closed on April 16, 2024.

Operating results of JRG Re are included in discontinued operations in our Consolidated Statements of (Loss) Income and Comprehensive Loss.

17 unchanged sentences

Investing activities

Sale of JRG Re 136,213 — —

Dividends from subsidiaries 5,755 — —

Net cash provided by investing activities 141,968 — —

1 unchanged sentence

Senior debt repayments ( 21,500 ) — ( 40,000 )

Subsidiary note repayments — — ( 70,000 )

Contribution to subsidiary ( 23,364 ) — ( 144,000 )

1 unchanged sentence

Issuance of Series A preferred shares — — 144,898

Issuances of common shares - public offering — — 192,107

Issuances of common shares under equity incentive plans — — 1,877

Enstar common share investment 12,500 — —

Payroll taxes withheld and remitted on net settlement of RSUs ( 847 ) ( 1,734 ) ( 1,304 )

102 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-K

Item 9A. Controls and Procedures