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Kingsway Financial Services IncInc.Investor Meeting Presentation November 29 and 30, 2011

Forward Looking StatementsThis presentation contains forward-looking statements related to our future growth,trends in our operating companies' businesses and industries and our financial andoperational results and performance that are based on managements' currentexpectations, forecasts and assumptions involving risks and uncertainties that could causeactual outcomes and results to differ materially. A number of factors could cause actualevents, performance or results to differ materially from the events, performance andresults discussed in the forward-lookingstatements.For informationidentifyingStilwell FinancialFund,L.P.important factors that could cause actual results to differ materially from thoseanticipatedi id ini theh fforwardd llookingki statements, see KiKingsway's' securitiesi i filings,filiiincludingl diits 2010 Annual Management's Discussion and Analysis, under the heading Risk Factors.The securities filings can be accessed on the Canadian Securities Administrators' websiteat www.sedar.com,, and on the EDGAR section of the U.S. Securities and ExchangegCommission's website at www.sec.gov or through the Company's website atwww.kingsway-financial.com. Kingsway Financial Services Inc. does not undertake toupdate the forward-looking statements to reflect the impact of circumstances or eventsthat may arise after the date of the forward-lookingfor ard looking statementsstatements.2

What is Kingsway ?Ticker: KFS / KFS.TOExchange: NYSE / TSX Kingsway Financial ServicesInc. (KFS) is a holdingcompany that either owns orP i (asPrice( off 11/22/11):11/22/11)controlsl stakesk ini severall 0.70 NYSEinsuranceStilwell Financial Fund,L.P. industry assetsShares Out: 52.3 mm KFS’s strategy is to manageits existing portfolio andactively pursue newopportunities in order toreturn value to shareholdersMarket Cap: 37 mmNote: Throughoutgthis presentation,pall are in USD.3

Company Timeline1989KFS founded as aspecialty providerof personal andcommercialinsurance in theUS & Canada.Present2007Underwriting resultsbegin to showoperationalchallengesh llKFS now functionsas a merchant bankwith focus on valuecreationStilwell Financial Fund, L.P.1990-2006Acquisitions addseveralcompanies underthe KFSumbrella2008Stilwell Group filesfirst 13-D on KFS;management andboard replaced andmulti-year plan toshed assets andstreamlineoperations begins4

Redefining the Business2009 – 2011Ongoing . . .Transactions:Stilwell Financial Fund, L.P.Use Proceeds to PayYork, Lincoln, Zephyr,Down Debt & RedefineAvalon JEVCO,Avalon,JEVCO AmericanKFSCountry, AmericanService, and Amigo5

What is Kingsway Today ?KINGSWAYFINANCIALSERVICES INC.KINGSWAYAMERICA INC.INSURANCEBUSINESSUNITSMendotaUCCKRe ESTMENTSAtlas FinancialAcadia LPLGIC HoldingsARSAdvantage Auto6INSURANCEADVISORYUNIT1347 Partners

Insurance Business Unit: MendotaSizeGeographyg p yTargetg 70-75mm FL, CA, 20% PreNonTX,, CO,,Tax ReturnStandardNVonStilwell FinancialAuto(largestFund, L.P. StatutoryPremiumstates bySurplusvolume) New leadership is committed to write onlyprofitable premium7

Insurance Business Unit: UCC Managingg g orderlyy runoff of several commercial programsp gandnon-standard auto books Actively writing only non-standardnon standard auto in ILStilwell Financial Fund, L.P. Also writing some non-standard auto in CA, AZ only tocomply with mandatory renewal requirements8

Insurance Business Unit: KRe Barbados Existingg Barbados companyp y with operatingpg historyy No premium currently running through KRe Could be utilized forreinsuranceStilwellFinancialtransactionsFund, L.P.9

Insurance Services Business Unit: ARS Managesg approximatelyppy 80 million of commercial andpersonal assigned risk business through its significant marketshare of the assigned risk and take-out market Partners with BerkshireHathawaysubsidiaryStilwellFinancial Fund,L.P. National Liability& Fire Insurance Company (NL&F) Pre-tax earnings could increase if assigned risk pools expand orARS leveragesg its distribution to pursuepnew opportunitiespp10

Insurance Services Business Unit: ARS“Standard”StandardInsurance Co.Standard insurancecompanies engage ARS Stilwell Financial Fund, L.P.to handle their assignedrisk pool businessARS(TPA/MGA)State assigned risk poolsassign a quota of assignedrisk business to standardinsurance companiesAssigned RiskPoolARS services all of the policy and claims administrationfor NL&F which assumes the underwriting risk of thestandard insurance companies11

Insurance Services Business Unit: Advantage AutoSizeGeographGeographyTarget 20-25mm Metro 20%NonChicagoEBITDAStandard Stilwell FinancialMarketFund, L.P.Auto(IL, IN)Premium Managing general underwriter Currently organized to begin writing onpaperpMendakota p12

Insurance Investments: Atlas & AcadiaAtlAtlasA diAcadia Atlas is the combination of former KFS unitsAmerican Countryy and American ServiceInsurance Acadia Acquisition Partners, L.P. boughtformer KFS sub Hamilton Risk Managementgincluding Kingsway Amigo InsuranceCompany in March of 2011Financial Fund, L.P. Atlas going public transaction wasStilwellcompletedin 2010 and KFS received consideration of KFS acts as the general partner to Acadia and 57mm broken out as follows:holds a limited partnership investment Cash: 7.9mm Preferred shares: 18.0mm Common Shares: 31.1mm KFS receives a management fee of 300 400k per year KFS holds a 10mm senior Hamilton noteand a 5mm junior note Atlas is publicly traded in Canada under thesymbol “AFH” Acadia represents potential future liquidity Atlas book value per Atlas common share is 2.21 per share as of June 30, 201113

Insurance Investment: LGIC Holdings KFS owns a 49% minorityy investment in a holdingg companyp ywhich acquired Walshire Assurance Company and its whollyowned subsidiary Lincoln General Tawa plc owns a 51% majority investment and has significantoperational involvementStilwell Financial Fund,, L.P. KFS received a release and settlement related to its pastownershipp14

Insurance Advisory Unit: 1347 Partners1347 Partners is the trade name KFS uses for its merchant bankingactivities to pursue opportunistic insurance industry-relatedtransactions as an advisor, an investor and a financier of capitalAdvisorInvestorStilwell Financial Fund, L.P.FinancierExample:Example:Example:Recent agreementPartnership with a realWill seek to becomewith United Insuranceestate assetthe GP ofHoldings Corp.management ventureopportunisticannounced in Augustinsurance industry-2011related transactions15

Managerial Balance SheetManagerial AssetsInvestment in AcadiaInvestment in UCCInvestment in MendotaInvestment in ARSInvestment in BarbadosDebt Liabilities & Shareholders’ Equity11,705FMV 2012 Senior Notes, due 7/11/20121,6089,821FMV 2014 Senior Notes, due 2/1/201426,02233 36633,366FMV Trust Preferreds, due 2032‐2034Stilwell26,783FinancialFund, L.P.8 8298,82917,2184,196Atlas Common Stock30,554Atlas Preferred Stock18,000Other Assets, net45,763Total AssetsFMV 2015 KLROCs,KLROCs due 6/30/2015180,188Total Debt Liabilities53,677Shareholders’ Equity126,511Total Debt Liabilities & Shareholders' Equity180,188Source: Internal non-audited managerial company balance sheet as of 9/30/201116

Cash UsesAs of September 30, 2011MaturityPrincipal (mm)Annually 6 (Estimated)2012 1 6 1.6Stilwell Financial Fund, L.P.2014 27.0LROC Preferred Units2015 18.8Subordinated Trust Preferred Interest (1)2016 24 (Estimated)2032-2034 90.5Operations (not including interest expense)6 0% Senior Unsecured6.0%7.5% Senior NotesSubordinated Trust Preferred( ) Pursuant to the contractual terms of its outstandingg Trust Preferred indentures, which permit(1)pinterest deferral,the Company gave notice on February 28, 2011 to its Trust Preferred trustees of its intention to exercise itsvoluntary right to defer interest payments for up to 20 quarters17

Cash SourcesPotential Sources of Cash from OperationsHolding Company CashA di IInvestmentAcadiaStilwell Financial Fund, L.P.Atlas InvestmentARS Earnings1347 Partners – New Ventures18

Shareholder ListHolderPercentage (%)The Stilwell Group (1)16.8Bruce Mitchell10.7Oakmont Capital (2)676.7American Physicians2.8Dimensional Fund2.3KBW Inc1.6Larry Swets, Jr. (3)1.4DiDirectors&MManagement as a GGroup 25.0025 00(1) Board Member Joseph Stilwell is affiliated with The Stilwell Group((2)) Board Members Terryy Kavanaghg and Gregg Hannon are affiliated with Oakmont Capitalp(3) President & CEO19

Board of DirectorsBoard MemberDirector SinceShares OwnedGregory Hannon (1)20093.5mm(1)Terence Kavanagh (1)20093.5mm(1)Spencer Schneider200926kJoseph Stilwell20098.8mm(1) BBoardd MembersM b TTerry KKavanaghh anddGGreg HHannon are affiliatedffili d withi h OakmontO kCapitalC i l anddhave a combined ownership of 3.5 mm shares20

Looking Forward DeDe-emphasizeemphasize capital-intensivecapital intensive insurance underwriting andemphasize fee-generating services Leverage existing core competencies and skill sets across theinsurance industry Stilwell Financial Fund, L.P. Focus on 1347 Partners activities – the “merchant banking”approach21

1347 Partners – the Merchant Banking Approach Allows KFS to leverage its existing skill set (and correspondingoverhead) to projects outside of the existing balance sheet Example: Acting as a General Partner in the acquisition ofa companyStilwellourFinancialFund, L.P. Opportunity: Apply“solution-focused”KFS experienceto other troubled companiespin exchangeg for a fee and pprofitparticipation Use of vehicles such as Special Purpose Acquisition Companies,CompaniesCapital Pool Companies and other unconventional financingoptions as advisor, investor or financier of other insuranceenterprises22

Summary Points & Future Objectives KFS offers the opportunity to invest across a diverse pool ofinsurance assets and insurance-related businesses Insurance investments and existing liquidity provide ability toStilwell Financial Fund, L.P.meet future obligations KFS will leverage its relationships and assets to opportunisticallyseek new sources of revenue and earnings in order to returnvalue to shareholders23

Management BiosLarryy G. Swets,, Jr.,J , CFAPresident and CEO, Kingsway Financial Services Inc.Mr. Swets is the President and CEO of Kingsway Financial Services Inc. Before joining Kingswayin JJanuaryy 2010,, Larryy founded Itasca Financial LLC,, an advisoryy and investment firm specializingpgin the insurance industry. Prior to his work at Itasca Financial, Larry served as an insurancecompany executive and advisor, including the role of Director of Investments and Fixed IncomeStilwell Financial Fund, L.P.Portfolio Manager for Kemper Insurance. At Kemper he also evaluated business units, executedcorporateptransactions and divestitures, and developedp financial pprojectionsjand analysisy for thecompany during its runoff stage. He began his career in insurance as an intern in the KemperScholar program in 1994.Larryy graduatedgfrom ValparaisopUniversityy and earned a Masters degreeg in Finance from DePaulUniversity; he also holds the Chartered Financial Analyst designation. He is also a member ofYoung Presidents’ Organization (YPO).24