Kingsway Financial Services Investor Presentation — February 2018

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Kingsway Financial Services Inc.

This presentation includes “forward -looking statements” within themeaning ofSection 27AoftheSecurities Act

of1933 andSection 21EoftheSecurities Exchange Actof1934 thatarenothistorical facts, andinvolve risks and

uncertainties thatcould cause actual results todiffer materially from those expected andprojected .Words such as

“expects,” “believes,” “anticipates,” “intends,” “estimates,” “seeks,” andvariations andsimilar words andexpressions

areintended toidentify such forward -looking statements .Such forward -looking statements relate tofuture events or

future performance, butreflect Kingsway management’s current beliefs, based oninformation currently available .A

number offactors could cause actual events, performance orresults todiffer materially from theevents,

performance andresults discussed intheforward -looking statements .Forinformation identifying important factors

thatcould cause actual results todiffer materially from those anticipated intheforward -looking statements, please

refer tothesection entitled “Risk Factors” intheCompany’s 2016 Annual Report onForm 10-K.Except as

expressly required byapplicable securities laws, theCompany disclaims anyintention orobligation toupdate or

revise anyforward -looking statements whether asaresult ofnewinformation, future events orotherwise .

Alldollar amounts setforth inthispresentation areinU.S.dollars unless stated otherwise .Kingsway Forward -looking Statements

2Kingsway Representatives

Larry G. Swets, Jr., CEO and Board Member (Co -Chief

John T. Fitzgerald, President, COO and Board Member

(Co-Chief Capital Allocator)

William A. Hickey, Jr., Executive Vice President, CFO

Hassan R. Baqar, Vice President

Steve Harrison, President of Mendota Insurance Company

Peter Dikeos, President of Trinity Warranty Services

Gale Sommers, President of Professional Warranty

Services CorporationAgenda ( 10:30 am –1:30 pm ET / lunch to

2.2017 Operating Results

3.Sum of the Parts Discussion

3Representatives and AgendaOpening Remarks: Kingsway Philosophy

we do the right thing

Intellectual Curiosity

we strive to be lifelong learners

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