A Growing International Specialty InsurerAnnual Meeting of Shareholders

June 17, 2020

1

• Anchored by Canadian specialty lines franchise operating profitably for 14 years

• Fee-based U.S. hybrid fronting platform with accelerating premium growth and profitability

• Offshore reinsurance subsidiary provides flexibility, capital support and internal reinsurance

• $253 million of book value (approximately $24.61 in BVPS as at May 15, 2020)

• Debt-to-capital ratio of 12% (internal target of 20%)

• Well capitalized, with 233% MCT ratio in Canada at Q1 2020, excess capital in U.S.

• 5-year average 88% combined ratio in Canada, with a 19% trailing 12 month ROE at Q1 2020

• 5-year average 15% growth in GPW in Canada

• U.S. platform launched in 2018 is largest contributor to premiums and demonstrating increased profitability

• Access to capital and international reinsurance relationships to fund growth

• Management team with a diversity of skills, and strong relationships with rating agencies, regulators and distribution partners

• Board of Directors comprised of seasoned executives with strong experience across financial services

• Lead shareholder Partners Value Investments LP with 18% ownership and a strong balance sheet

• Senior management group directly owns 6% of shares outstanding

• Strong access to capital, supportive institutional shareholders, and financial strength to pursue growth opportunities

Diversified Specialty Insurance Platform

A Growing International Specialty Insurer

International Specialty Insurer Targeting Mid-teens ROEs and Growth in Book Value

Strong FinancialProfile

Growth Opportunities Across the Platform

Globally Experienced Management Team &

Board of Directors

Strong Shareholders & Significant Management

Ownership

2

• Safety and support of employees and partners is Trisura’s top priority

• Work from home initiated beginning of March with negligible operational interruption

• Surety claims yet to be impacted by the shutdown, majority of bonded projects deemed essential; ultimate experience dependent on overall strength of construction supply chain

• Risk Solutions premium growth slowed by shutdown and consumer spending, profitability impact minimal

• Corporate Insurance insulated from business interruption-related claims to date, topline growth remains positive

• Premium growth impacted by economic shutdown, although remains in line with Q1 average through May

• Profitability continues to improve, supported by maturation of programs and earning of deferred fee income

• Strong and diverse panel of reinsurers continue to provide capacity through renewal, submission flow is healthy

• Portfolios rebounded following March sell-off, in line with public equity, preferred share and debt markets

• Capitalized on opportunities to enhance yield while maintaining stable risk profile

Employees &Partners

Canada

United States

Investments

COVID-19 Update

Conservative Underwriting, Operational Resilience and Long-Term Mindset Help Navigate COVID-19 Volatility

3

$170

$534

$153

$537

100

200

300

400

500

600

Q1 '18 Q2 '18 Q3 '18 Q4 '18 Q1 '19 Q2 '19 Q3 '19 Q4 '19 Q1 '20 Current

Market Capitalization Consolidated LTM GPW

2019: A Transformational Year

Key Achievements

June - December 2017: Completed spin-off from Brookfield, developed public company infrastructure and U.S.’s capabilities

January - December 2019: Grew gross premiums written by 12% in Canada with an 87.8% combined ratio

May - December 2018: Enhanced corporate governance and risk management functions through dedicated board committees and personnel

January - December 2019: Grew gross premium written in the U.S. to $264 million, with net income of $3.8 million in its second year of operation

May 2020: Completed $68 million equity raise and increased capacity on revolving credit facility to $50 million

December 2018: Completed internalization of investment function across all three subsidiaries

November 2019: Completed the acquisition of 21st Century Preferred Insurance Company (Trisura Insurance Company) providing access to admitted markets in the U.S.

September 2019: Completed inaugural equity raise of $58 million

Market Capitalization and Consolidated Gross Premium Written ($ millions)

Note: ‘Current’ market capitalization as at May 29, 2020.

4

• Gain Admitted state licenses and write Admitted business

• Support trajectory of growth and profitability in Canada

• Evaluate strategic partnerships, licensing, and bolt-on and transformational M&A

• Build fronting model in U.S. Admitted and E&S markets

• Expand North American primary insurance market share

• Expand distribution and capacity relationships

• Maintain underwriting focus and expertise to achieve low 90s combined ratio

• Leverage technology infrastructure to drive scalability and partnerships with capacity providers

• Demonstrate value of specialty / niche focus through underwriting margin outperformance

• Achieve operational leverage

• Gain scale, demonstrating a sustainable mid-teens ROE

• Synchronize risk management through regional platforms

• Integrate captive reinsurance

• Gain corporate and preferred share ratings

• Maintain current ratings and appropriate regulatory capital

• Optimize capital allocation across investments, reinsurance and underwriting

• Increase allocation to alternatives, including commercial real estate, private loans and infrastructure debt

• Develop track record of execution, expand shareholders and distribution partners

• Enhance yield while maintaining stable risk profile and improving diversification

• Strengthen access to capital

Growth

Strategic Priorities

Profitability

Risk & Capital Management

Investments / Capital Markets

Centralized Corporate Function Providing Support for Operating Subsidiaries to Grow

Near Term Long Term

5

62.6%

95.0%

10.0%

72.5%

101.0%

8.5%

--

20.0%

40.0%

60.0%

80.0%

100.0%

120.0%

Loss / LAE Ratio Combined Ratio Pre-tax ROE

Non-admitted Surplus Line Insurers U.S. P&C Industry

1 Source: MSA Research, SNL Financial, A.M. Best.2 Industry looks at 50%+ non-admitted as appropriate; excludes E&S premiums written at Lloyd’s. 3 Represents U.S. domiciled insurers that primarily write surplus and / or specialty admitted business as defined by A.M. Best.

Favorable Profitability

2009 – 2018 Average

3

North American Specialty Insurance

2018 2019

$678.0 $707.1

--

$20.0

$40.0

$60.0

$80.0

$100.0

$120.0

$140.0

$160.0

$180.0

$200.0

2018 2019

$34.8 $40.4

U.S. Market (US$ billions)

E&S Market P&C Industry

U.S. - Admitted vs. E&S

Trisura’s North American Specialty Lines Business has Attractive Profitability with Growth Capacity

Admitted E&S (Non-Admitted)

Pricing Rates and form need to be approved

Well developed risks (standard auto, etc.)

Product Freedom of rate and form

Unique and emergingrisks

Licensing Carrier needs approval from each state to conduct business

U.S. carrier only needs a license in one state; non-U.S. carrier regulated through the NAIC (Lloyd’s)

TrisuraFootprint

19 states All U.S. jurisdictions

2

• Commercial products/services not provided by most insurers

• Focused underwriting knowledge, financial and structuring expertise

• Claims are less frequent but can be higher in severity

• Severity can be mitigated through use of reinsurance

• Improved pricing power relative to standard insurance, supporting strong underwriting performance and operational ROEs

• Outsized growth relative to P&C industry over the past 5 years

• Trisura has a 14 year history of profitable underwriting in Canada and 2 year history in the U.S.

$ 0. 0

$ 20 .0

$ 40 .0

$ 60 .0

$ 80 .0

$ 10 0 .0

$ 12 0 .0

2018 2019

$67.0 $67.0

$ 0. 0

$ 10 .0

$ 20 .0

$ 30 .0

$ 40 .0

$ 50 .0

$ 60 .0

$ 70 .0

$ 80 .0

2018 2019

$5.4 $6.1

Canadian Market ($ billions)

Specialty Market P&C Industry

11.0% YoY Growth 0.1% YoY Growth

7.8% CAGR (’15–’19) 3.7% CAGR (’15–’19)

DWP Growth1 DWP Growth1

7.8% CAGR (’15–’19) 4.6% CAGR (’15–’19)

16.1% YoY Growth 4.3% YoY Growth

U.S. Market1

6

1,2947,585

17,658

27,194

41,886

55,467

71,187

95,371

120,682

6

595

965

1,540

2,352

3,103

4,099

0

1,000

2,000

3,000

4,000

5,000

6,000

0

20,000

40,000

60,000

80,000

100,000

120,000

140,000

Q1 '18 Q2 '18 Q3 '18 Q4 '18 Q1 '19 Q2 '19 Q3 '19 Q4 '19 Q1 '20

Gross Premium Written Fee Income Earned

• Fee-based model retains up to 10% of premiums, ceding remainder to reinsurance partners in exchange for a fee

• Participate in Excess and Surplus (50 state licenses) and Admitted (19 state licenses) markets

• In 2019, wrote $264 million in premiums, generating $8 million in earned fees

• First quarter of 2020 produced $121 million in premiums and $4 million in earned fees across 35 programs

• Aggregates premiums from program administrators and other distribution partners to act as a conduit to reinsurance markets and capacity providers

• Trisura addresses the lack of supply of effective insurance arrangements for program administrators focused on specialty insurance in the U.S.

Fee-based Business Model

Focus on Providing Program Services

Emerging Fee-Based Platform with Significant Growth Potential

U.S. Specialty Insurance: Operating Metrics

Gross Premium Written & Fee Income ($000s)

U.S. platform began writing business in February 2018.

Business Segmentation (Net Basis)

Commercial Auto36.6%

Commercial Multiple - Peril 28.4%

Primary and Excess Casualty 24.7%

Homeow ners Multiple Peril , 3.9%

Farmow ners Multiple Peril , 3.3%

Other3.1%

7

88.7% 87.7%

85.7% 85.3%

91.7%88.8%

86.3%87.8%

50.0%

55.0%

60.0%

65.0%

70.0%

75.0%

80.0%

85.0%

90.0%

95.0%

0

50,000

100,000

150,000

200,000

250,000

2012 2013 2014 2015 2016 2017 2018 2019

Surety Risk Solutions Corporate Insurance Combined Ratio

Canadian Specialty Insurance: Operating Metrics

Segmented Gross Premiums Written, Fees & Combined Ratio ($ millions)

$68

$81

(Unaudited)

$94

$107

$128

$150

$169

Strong Track Record of Growth and Underwriting Profitability Drives Consistent Mid-teens ROEs

ROE 10.9% 12.4% 14.3% 14.6% 8.4% 13.7% 19.1% 19.1%

Book Value $49.7 $54.3 $60.7 $63.0 $67.9 $73.1 $74.6 $90.3

$188

81 USDCAD exchange rate of 1.4187 at 3/31/2020 used to convert USD reserves to CAD..

Reinsurance

• Trisura Group has $94 million1 in reinsurance reserves across 10 in-force contracts

− Ceased writing new business in 2008

• In 2019, adopted a better duration matched portfolio of assets to minimize volatility

− Introduced specialized annuity asset manager for legacy policies in Q2 2020

• Provided over US$25 million in capital to Trisura Group, redeployed to launch U.S. platform

• Providing reinsurance support to Trisura Group’s onshore subsidiaries

Reserves & # of In-force Reinsurance Contracts ($000s) Net Claim Reserves ($000s)

Life$75,874

91%

P&C$7,125

9%

As at Q4/2019

Life$87,077

92%

P&C$7,387

8%

As at Q1/2020

34

21

1513 12

10 10

$150,263

$122,077

$96,505

$88,373$79,088 $82,999

$94,464

0

5

10

15

20

25

30

35

40

0

20

40

60

80

100

120

140

160

2014 2015 2016 2017 2018 2019 Q1 2020

# of In-force Reinsurance Contracts Total Reserves

9

(000s)

Trisura

Guarantee

Trisura

International

Trisura

Specialty Corporate Total

Assets 420.2 116.3 596.2 75.9 1,208.6Liabilities 342.2 97.8 480.9 34.9 955.8Book Value 77.9 18.5 115.3 40.9 252.8Book Value Per Share 7.59 1.80 11.23 3.99 24.61

Note: The financial data listed above is unaudited summary pro forma financial data for Trisura Group for the periods indicated. The results of operations for the periods reflected herein are not necessarily indicative of results that may be expected for future periods, and actual results may differ materially from those listed above. Cash from equity raise is gross of related offering expenses, net of underwriters’ fees.

Balance Sheet (Pro-forma May equity raise)

Conservative balance sheet and investment portfolio

Balance Sheet ($ millions)

Segmented Book Value

AssetsCash and Cash Equivalents 149.9Investments 394.5Other Assets 664.2Total Assets 1,208.6

Liabilities & Shareholder's EquityUnearned Premiums 401.6Unpaid Claims & Loss Adjustment Provisions 311.5Other Liabilities 242.7Total Liabilities 955.8Shareholder's Equity 252.8Total Liabilities & Shareholder's Equity 1,208.6

Shares Outstanding 10.3Book Value Per Share 24.61

10

Investments

Portfolio by Asset Class

Fixed Income Portfolio by Rating

Fixed Income Portfolio by Term

Investment Yield

Investment portfolio categorization as at March 31, 2020. U.S. and International portfolios converted to CAD at quarter-end exchange rate. Cash excluded from Rating and Term segmentation.

Cash & Equivalents, 18%

Government Bonds, 26%

Corporate Bonds and Other Fixed

Income, 40%

Alternatives, 1%

Preferred Shares , 7%

Structural Insurance Asset, 2%

Common Shares & Other, 6%

AAA15%

AA28%

A28%

BBB20%

High-Yield9%

< 1 Year,

12%

1-3 Years,

34%

3-5 Years,

23%

5-10 Years,

5%

> 10 Years,

26%

3.1%

4.0%

4.9%

3.1%

3.7% 3.7%

1.5% 1.5% 1.5%

0%

1%

2%

3%

4%

5%

6%

Q1 '18 Q1 '19 Q1 '20

Canada U.S. Reinsurance

11

Board of Directors & Management

• Trisura Group has a robust management team and board of directors consisting of insurance executives with significant Canadian, U.S. and international experience

Board of Directors

Management

George Myhal President and CEO, Windermere Investment Corporation; former CEO, Partners Value Investments LP

Paul Gallagher Vice President, Investments, Carfin Inc., former CFO, Wittington Investments

Barton Hedges Former CEO, Greenlight Re (NASDAQ: GLRE)

Greg Morrison Former CEO, Trisura Group, former CEO, Platinum Underwriters (NSYE: PTP1)

Robert Taylor Former CEO, Trisura Guarantee Insurance Company

David Clare CEO, Trisura Group

David Clare CEO, Trisura Group

David Scotland CFO, Trisura Group

Jimmy Doyle CRO, Trisura Group, CEO, Reinsurance

Chris Sekine CEO, Canada

Michael Beasley CEO, United States

1 Prior to the acquisition of Platinum Underwriters by Renaissance Holdings Ltd. On March 3, 2015.

12

• Anchored by Canadian specialty lines franchise operating profitably for 14 years

• Fee-based U.S. hybrid fronting platform with accelerating premium growth and profitability

• Offshore reinsurance subsidiary provides flexibility, capital support and internal reinsurance

• $253 million of book value (approximately $24.61 in BVPS as at May 15, 2020)

• Debt-to-capital ratio of 12% (internal target of 20%)

• Well capitalized, with 233% MCT ratio in Canada at Q1 2020, excess capital in U.S.

• 5-year average 88% combined ratio in Canada, with a 19% trailing 12 month ROE at Q1 2020

• 5-year average 15% growth in GPW in Canada

• U.S. platform launched in 2018 is largest contributor to premiums and demonstrating increased profitability

• Access to capital and international reinsurance relationships to fund growth

• Management team with a diversity of skills, and strong relationships with rating agencies, regulators and distribution partners

• Board of Directors comprised of seasoned executives with strong experience across financial services

• Lead shareholder Partners Value Investments LP with 18% ownership and a strong balance sheet

• Senior management group directly owns 6% of shares outstanding

• Strong access to capital, supportive institutional shareholders, and financial strength to pursue growth opportunities

Diversified Specialty Insurance Platform

A Growing International Specialty Insurer

International Specialty Insurer Targeting Mid-teens ROEs and Growth in Book Value

Strong FinancialProfile

Growth Opportunities Across the Platform

Globally Experienced Management Team &

Board of Directors

Strong Shareholders & Significant Management

Ownership

13

Questions?

14

Business Overview

• International specialty insurance provider operating in the Surety, Risk Solutions, Corporate Insurance, Fronting and Reinsurance segments of the market

− Canada - Successful 14 year operating history in the Canadian specialty insurance market

− United States – Growing fee-based fronting platform in the U.S. Excess & Surplus and Admitted markets

− Reinsurance – International reinsurer with run-off book providing captive reinsurance for onshore premium

• Dedicated and specialized in-house investment management team

• Traded on the TSX under the symbol TSU and supported by a diverse group of shareholders

Trisura Group

Canada ReinsuranceUnited States

OSFI Oklahoma DOI FSC (Barbados)Regulator

Corporate Structure Ownership

Partners Value Investments

18%

Trisura Management

6%

Top 5 Institutions

20%

Other Institutional & Retail

56%

Ownership summary data as at May 23rd, 2020.

15

Contract Surety

Commercial Surety

Developer Surety

Gross Premiums Written and Fees Combined Ratio

2012 to 2019 CAGR: 10.6%

Canadian Specialty Insurance: Surety

Operating Results ($000s)

84.2%

History of Strong Underwriting and

Growth

Leading and Proprietary

E-Commerce Platform(Trisura OnLine)

Strong Brand and Market Expertise with In-House Execution

Capabilities

#4 in Canadian Surety Market (~$650 million

industry1)

1 Management estimates based on Surety Association of Canada data.

Operating Lines

Surety Represented 32% of 2019 Gross Premiums Written

Longstanding Relationships with Broker Community

31,19437,226 40,696 42,994 47,088

53,075 55,33763,269

2012 2013 2014 2015 2016 2017 2018 2019

81.6% 78.7% 82.8% 71.8% 80.8% 72.6% 85.1%

16

Warranty Programs

Fronting Solutions

Associations and Groups

Canadian Specialty Insurance: Risk Solutions

Innovative & CustomizedInsurance Structures

Caters to a DiverseSet of Clients

Top 10 in Canadian Warranty & Risk Solutions

Gross Premiums Written and Fees Combined Ratio

Operating Results ($000s)

Focus Area

Risk Solutions Represented 42% of 2019 Gross Premiums Written

2012 to 2019 CAGR: 27.5%

14,21721,448

27,57635,840

49,305

64,20574,624 77,843

2012 2013 2014 2015 2016 2017 2018 2019

81.0% 90.3% 110.8% 86.6% 139.3% 92.8% 90.6% 90.1%

17

Directors’ & Officers’ (D&O) Liability

Professional Liability

Technology & Cyber Liability

Multimedia Liability

Fidelity

Comprehensive General Liability and Property

Canadian Specialty Insurance: Corporate Insurance

Longstanding Relationships with Broker Community

Leading Professional Liability Underwriter in

Canada

Market Leading Claims Management Capabilities

Top 13 D&O and E&O and Top 10 Fidelity Insurer in

Canada

Gross Premiums Written and Fees Combined Ratio

Operating Results ($000s)

Operating Lines

Corporate Insurance Represented 26% of 2019 Gross Premiums Written

2012 to 2019 CAGR: 11.5%

95.4% 94.6% 78.9% 87.7% 78.1% 96.0% 100.6% 88.8%

22,144 22,720 25,224 28,456 31,760 32,71939,073

47,373

2012 2013 2014 2015 2016 2017 2018 2019

18

Hybrid Fronting Model

Distribution Partners(e.g. Managing General

Agents - “MGAs”)

Capacity Providers(e.g. Reinsurers)

Premiums Premiums

Claims Payment Claims Payment

Fronting Fee

(% of Ceded Premium)

• Profitability driven by recurring fronting fee, calculated on ceded premiums written (90% - 100%)

• Exposure to underwriting results on retained premiums (0% - 10%)

• Premiums to capital leverage potential of ~4 - 5x at current retention and A.M. Best rating

• Yield on investment portfolio to compliment fee income and underwriting profitability

19

Notice to Recipients

Trisura Group Ltd. (“Trisura”) is not making any offer or invitation of any kind by communication of this document to the recipient and under no circumstances is it to be construed as a prospectus or anadvertisement.

Except where otherwise indicated herein, the information provided herein is based on matters as they exist as of the date of preparation and not as of any future date, is subject to change, and will not be updated orotherwise revised to reflect information that subsequently becomes available or circumstances existing or changes occurring after the date hereof. Unless otherwise noted, all references to “$” or “Dollars” are toCanadian Dollars.

CAUTIONARY STATEMENTS REGARDING FORWARD-LOOKING STATEMENTS AND INFORMATION

This presentation contains “forward-looking information” within the meaning of Canadian securities laws. Forward-looking statements include statements that are predictive in nature, depend upon or refer to futureevents or conditions, and include statements regarding our and our subsidiaries’ operations, business, financial condition, expected financial results, performance, prospects, opportunities, priorities, targets, goals,ongoing objectives, strategies and outlook, as well as the outlook for North American and international economies for the current fiscal year and subsequent periods, and include, but are not limited to, statementsregarding our asset management. In some cases, forward-looking statements can be identified by terms such as “expects,” “anticipates,” “plans,” “believes,” “estimates,” “seeks,” “intends,” “targets,” “projects,”“forecasts” or negative versions thereof and other similar expressions or future or conditional verbs such as “may,” “will,” “should,” “would” and “could.” In particular, the forward-looking statements contained in thispresentation include statements referring to the impact of current market or economic conditions on our businesses and the impact of COVID-19 on the market, economic conditions, or our businesses.

Although we believe that our anticipated future results, performance or achievements expressed or implied by the forward-looking statements and information are based upon reasonable assumptions andexpectations, the reader should not place undue reliance on forward- looking statements and information because they involve known and unknown risks, uncertainties and other factors, many of which are beyondour control, which may cause our and our subsidiaries’ actual results, performance or achievements to differ materially from anticipated future results, performance or achievements expressed or implied by suchforward-looking statements and information.

Factors that could cause actual results to differ materially from those contemplated or implied by forward-looking statements include, but are not limited to: (i) investment returns that are lower than target; (ii) theimpact or unanticipated impact of general economic, political and market factors in the countries in which we do business including as a result of Covid-19; (iii) the behavior of financial markets, including fluctuationsin interest and foreign exchange rates; (iv) global equity and capital markets and the availability of equity and debt financing and refinancing within these markets; (v) strategic actions including dispositions; the abilityto complete and effectively integrate acquisitions into existing operations and the ability to attain expected benefits; (vi) changes in accounting policies and methods used to report financial condition (includinguncertainties associated with critical accounting assumptions and estimates); (vii) the ability to appropriately manage human capital; (viii) the effect of applying future accounting changes; (ix) business competition;(x) operational and reputational risks; (xi) technological change; (xii) changes in government regulation and legislation within the countries in which we operate; (xiii) governmental investigations; (xiv) litigation;(xv) changes in tax laws; (xvi) ability to collect amounts owed; (xvii) catastrophic events, such as earthquakes, hurricanes and epidemics/pandemics; (xviii) the possible impact of international conflicts and otherdevelopments including terrorist acts and cyberterrorism; (xix) the introduction, withdrawal, success and timing of business initiatives and strategies; (xx) the failure of effective disclosure controls and procedures andinternal controls over financial reporting and other risks; (xxi) health, safety and environmental risks; (xxii) the maintenance of adequate insurance coverage;(xxiii) the existence of information barriers between certainbusinesses within our operations; (xxiv) risks specific to our business segments; and (xxv) and factors detailed from time to time in our documents filed with the securities regulators in Canada, including in ourAnnual Report available on SEDAR at www.sedar.com.

We caution that the foregoing list of important factors that may affect future results is not exhaustive. When relying on our forward-looking statements, investors and others should carefully consider the foregoingfactors and other uncertainties and potential events. Except as required by law, we undertake no obligation to publicly update or revise any forward-looking statements or information in this presentation, whether as aresult of new information, future events or otherwise.

Past performance is not necessarily indicative of future results and there can be no assurance that comparable results will be achieved, that an investment will be similar to the historic investments presented herein(because of economic conditions, the availability of investment opportunities or otherwise), that targeted returns, diversification or asset allocations will be met or that an investment strategy or investment objectiveswill be achieved.

OTHER CAUTIONARY STATEMENTS

Certain of the information contained herein is based on or derived from information provided by independent third-party sources. While Trisura believes that such information is accurate as of the date it was producedand that the sources from which such information has been obtained are reliable, Trisura does not guarantee the accuracy or completeness of such information and has not independently verified such information orthe assumptions on which such information is based. This document is subject to the assumptions (if any) and notes contained herein.

The information in this document does not take into account your investment objectives, financial situation or particular needs and nothing contained herein should be construed as legal, business or tax advice. Eachprospective investor should consult its own attorney, business adviser and tax advisor as to legal, business, tax and related matters concerning the information contained herein.