James River : Third Quarter 2025

3Q 2025

Investor Presentation

November 2025

A Leading Specialty Insurer with a Diversified E&S Platform

James River's positioning creates profitable opportunities in today's market

Key Investment Highlights

A focus on profitable growth within an attractive small to medium enterprise E&S market

Reinvigorated underwriting culture with significant focus on active performance monitoring and enterprise risk management

20+ year wholesale-only distribution model creates deep alignment and loyalty with wholesale network

Strong balance sheet with significant reinsurance and legacy protection for 2023 and prior accident years

Refreshed management team with extensive industry experience

Active focus on lasting expense efficiencies, including benefits of recent redomicile to the U.S.

$1.3 Billion

Gross Written Premium(1)

$5.0 Billion

Total Assets

$504 Million

Total Shareholders'

Equity

"A-" (Excellent)

A.M. Best Rating

Upgraded technology platform that continues to create and improve underwriting efficiencies

1. Gross Written Premiums reflect LTM information as of September 30, 2025. All other information as of September 30, 2025 unless otherwise noted. 3

Prioritizing Balance Sheet and Aligning Leadership Energy

Management has focused the Company on its core strengths: Risk Management, Performance Monitoring, and Underwriting

Recent Company Milestones

Nov/Dec

2020

Frank D'Orazio

joins James River

$75 MM Uber reserve additions during 4Q20

Sept

2021

Raiser / Uber Unlimited Loss Portfolio Transfer ("LPT")

$200 MM

Uber reserve additions YTD

Feb

2022

Casualty Re LPT Purchase

$115 MM

Casualty Re reserve additions during 4Q21

Sept

2023

Renewal Rights

of Workers'

Comp Sale

April

2024

Casualty Re Sale

2H

2024

$122 MM E&S

reserve additions during 2H24

Completion

of Strategic Review; Finalized Core E&S LPT / ADC for an aggregate $235 MM, validating capital from sophisticated industry investor

Feb

2025

Non-Executive Chairman of the Board Ollie Sherman announces he will retire. Christine LaSala appointed as

next Non-Executive Chairperson

May

2025

E&S segment leadership transition.

Todd Sutherland announced as President, succeeding Richard Schmitzer

2H

2025

New Leadership Appointments Announced: Board of Directors - Joel Cavaness

Chief Information Officer - Val Langenburg and Group Chief Claims Officer - Justin Zaharris; President of Falls Lake - Lisa Binnie

Redomicile to U.S.

Completed

4

3Q 2025 Results Evidence Momentum in Niche Casualty Classes

Annualized Adjusted Net Operating Return on Tangible Common Equity(1)

19.3%

Adjusted Net Operating Income(1)

$17.4 Million

E&S Combined Ratio

88.3%

Average Renewal Premium Shift to Smaller Accounts

Reduced 12.7% YTD

Attractive Renewal Rate Environment

+10% Overall YTD +11% Casualty YTD +19% Excess Casualty YTD

Submission Volume Increase

+5% YTD

Group Expense Ratio

28.3%

Expense Savings(2)

18%

Redomicile Enables Greater Expense Efficiencies

November 7

Profitability Focused - Enabled by Positioning, People, and Technology

• U.S. Small and Medium Company Focus with Limited Property & Auto

• Wholesale Only Distribution Creates Loyalty and Drives Strong Submission Growth

• New Energy and Leadership Appointments Across E&S and Group

• Durable Expense Management

  Initiatives Create Efficient Path

• E&S Retention Increasing in Strong Rate Environment

• De-risked Fronting Business with Deliberately Low Retention

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1. Adjusted net operating return on tangible common equity and adjusted net operating income and are non-GAAP financial measures. See "Non-GAAP Financial Measures" and "Reconciliation of Non-GAAP Measure" on the Disclosure page.

2. Expense savings reflect percentage decline of G&A expenses quarter over quarter for E&S (13%), Specialty Admitted (37%), and Corporate (14%) on an aggregate basis.

E&S Market: Significant Long-Term Growth and Pricing Tailwinds

The E&S market - with its flexibility and niche focus - has shown itself to be a permanent force in aligning capital and need, with an outlook poised for continued profitable growth

U.S. Excess & Surplus Lines DWP ($BN) (1)

2013 - 2017

Average Growth Rate

4%

2017 - 2020

Average Growth Rate

12%

2020 - 2024

Average Growth Rate

20%

$75.5

$62.9

$86.5

$98.2

$27.3

$28.9 $29.8 $29.9 $31.5 $34.6

$40.3

$47.6

2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024

E&S industry DWP has grown at double digit rates the past 6 years driven by rising renewal rates and changes in risk appetite within the admitted market.

1. Source: S&P Global Market Intelligence - P&C Market Share Report 2024 sourced from Capital IQ Pro for 262 total participants and excluding US territories. 6

Our Core Competency in E&S Aligns With Attractive Market

We are one of the largest and most concentrated public companies in E&S exposure

100%

Most Concentrated E&S Companies(1) - 2024 Direct Written Premium

85%

76% (2)

42%

29% 25% 24%

16%

9% 8%

$1.9 BN $332 MM $1.1 BN $848 MM $4.1 BN $3.8 BN $2.2 BN $5.6 BN $8.5 BN $1.6 BN

Significant focus on small and medium sized accounts which have historically been more profitable

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1. Statutory E&S direct written premium as defined and calculated by S&P Global Market Intelligence. Represents statutory E&S direct written premium divided by GAAP consolidated gross written premium for 2024.

2. GAAP E&S segment GWP of $1.0 Bn. 18% of Specialty Admitted segment business was non-admitted in 2024.

DIVERSIFIED E&S PLATFORM

Enables Opportunistic Growth and Prudent Risk Selection

Key Drivers

Specialty (2)

13%

Property

4%

33%

Primary Casualty (3)

• Material changes to underwriting and performance monitoring since 2023 allow us to nimbly address opportunities in changing markets

• 5 primary divisions with designated leaders empowered to achieve growth and profitability objectives across 15 distinct underwriting disciplines

• Active portfolio management approach drives opportunistic underwriting

• Limited natural catastrophe and tariff risk given business mix

• Exclusive focus on U.S. small and medium enterprise casualty

Manufacturers

& Contractors

17%

E&S GWP(1)

$1.0 Billion

33%

Excess Casualty

1. Gross Written Premiums reflect LTM information as of September 30, 2025.

2. Includes the following underlying divisions, Allied Health & Medical, Energy, Environmental, Life Sciences, Management Liability, and Professional Liability.

3. Includes the following underlying divisions, General Casualty, Sports &

Entertainment, Commercial Auto, Small Business, Contract Binding. 8

Attractive Rate and Strong E&S Submissions Create Opportunities

Rate and submission opportunities have enabled us to better target attractive lower premium accounts

Casualty focused accounts

for over 96% of E&S GWP

3Q25 casualty E&S renewal

rate change of 6.1%

10%

YTD '25 Renewal

Rate Change

5%

YTD '25

Submission Growth

(13%)

Average Renewal Premium Per Policy

7%

YTD '25

New Quote Growth

E&S submissions are growing and retention and hit ratios are within historical ranges despite underwriting repositioning

Focus on small and medium accounts have historically been more profitable and less vulnerable to turnover.

Strength of the current casualty market provides robust tailwinds and a strong foundation for continued growth across our diverse underwriting divisions

E&S ex. Uber GWP ($ MM) Compounded Rate Change

53%

67%

95%

82%

$921

$1,004

$1,017

$1,007

38%

$834

23%

$699

1. Figures presented on an LTM basis as of September 30, 2025 unless otherwise noted.

   2020 2021 2022 2023 2024 LTM 3Q25

   34 consecutive quarters of increased renewal rate changes, compounded

   to 95%(2) for the quarter ending September 30, 2025

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2. Compounded rate change differs from previously published compounded rate change of 108% at 2Q25 due to updated actuarial methodologies.

Selective Growth Driven by Strong ERM & Underwriting Discipline

Stable 3Q25 E&S segment accident year loss ratio of 63.5% due to nimble shifts in business mix, significant changes to

underwriting appetite and meaningful rate gained

Initial E&S Segment Accident Year Loss Ratio Has Been Stable

1,000,000

800,000

600,000

400,000

200,000

-

62% 64% 64%

2023 2024 LTM 3Q25

E&S Accident Year Loss Ratio JRVR E&S Gross Written Premium

Increased retention at mid-year E&S reinsurance treaty renewal reflecting confidence in underwriting actions

Material bifurcation in performance between pre 2023 and more recent accident years reflecting the positive impact of our material underwriting changes throughout the portfolio

Collaboration across underwriting, pricing, and claims creates continual performance feedback loop and is a result of material underwriting actions established by management over several years

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