<PAGE>

                                                                     Exhibit 4.2

                           KINGSWAY U.S. FUNDING INC.

                              OFFICERS' CERTIFICATE
                 (pursuant to Section 2.01(b) of the Indenture)

       The undersigned, James R. Zuhlke, President, and Brian K. Williamson,
Chief Financial Officer, of Kingsway U.S. Funding Inc. (the "Company"), being
duly authorized officers, by authority duly delegated by the Board of Directors
of the Company, do hereby certify, pursuant to the resolutions of the Board of
Directors of the Company duly adopted by unanimous written consents dated
February 17, 2003, September __, 2003, and Section 2.01(b) of the Indenture
dated as of ____________, 2003, (the "Indenture"), between the Company, Kingsway
Financial Services Inc., as Guarantor, and BNY Midwest Trust Company as trustee
(the "Trustee"), that with respect to the creation, issuance and sale of up to
US$80,000,000 aggregate principal amount of the Company's ____% Junior
Subordinated Debentures (the "Securities"):

1.     (a)    The Securities shall be designated the "____% Junior
              Subordinated Debentures."

       (b)    The Securities shall be limited to US$80,000,000 aggregate
              principal amount.

       (c)    The Securities shall bear interest at ___% per annum from _______,
              2003, payable quarterly in arrears on March 31, June 30, September
              30 and December 31 of each year (each an "Interest Payment Date"),
              beginning __________, 2003, except as any such Interest Payment
              Date may be adjusted so as to be payable on a Business Day (as
              defined in the Indenture) to the persons in whose names the
              Securities are registered at the close of business on the
              fifteenth day of the last month of the calendar quarter (whether
              or not a Business Day), as the case may be, next preceding such
              Interest Payment Date.

       (d)    Unless previously redeemed or repurchased, the Securities will
              mature on ____________, 2033.

       (e)    Pursuant to Section 2.12 of the Indenture, the Company has the
              right to defer the payment of interest on the Securities at any
              time for a period not exceeding 20 consecutive quarterly periods
              with respect to each deferral period. No Extension Period may
              extend beyond the Stated Maturity.

       (f)    Subject to certain exceptions, the Securities will be redeemable,
              in whole or in part, at the option of the Company at any time
              prior to maturity on or after ___________, 2008 at 100% of the
              principal amount redeemed.

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       (g)    If a Tax Event or Investment Company Event shall occur and be
              continuing, the Company may, at its option and subject to certain
              exceptions, terminate the Trust and distribute the Securities to
              the holders of the Trust Securities at any time within 180 days
              following the occurrence of such Tax Event or an Investment
              Company Event and, if such Tax Event or Investment Company Event
              continues notwithstanding the taking of such actions, prepay the
              Securities in whole (but not in part) at a redemption price equal
              to 100% of the principal amount of such Junior Subordinated
              Debentures plus interest accrued thereon to but excluding the date
              of payment ("the Event Prepayment Price").

       (h)    The Securities will be unsecured obligations of the Company and
              will rank junior and be subordinate in right of payment to all
              Company Senior Debt of the Company and will be effectively
              subordinated to all existing and future liabilities of the
              Company's subsidiaries, all as more fully described in the
              Indenture.

       (i)    The Securities initially will be represented by one certificate
              registered in the name of BNY Midwest Trust Company, as Property
              Trustee to the Trust. Should the Securities be distributed to
              holders of the Trust Securities, beneficial interests in the
              Securities will be held through The Depository Trust Company
              ("DTC").

       (j)    If the Securities are issued in certificated form, the Securities
              shall be issued and transferable only in fully-registered
              certificated form without coupons in denominations of US$25 and
              integral multiples thereof.

       (k)    Any principal and interest, including Additional Interest,
              Additional Amounts and any Additional Sums, if applicable, will be
              payable at the office of the Paying Agent, BNY Midwest Trust
              Company, in the City of New York. The Securities may be presented
              for registration of transfer or exchange, and notices and demands
              to or upon the Company in respect of the Securities may be made,
              at the Corporate Trust Office of the Trustee.

       (l)    The Company shall reimburse the Trust for any expenses incurred by
              or imposed upon the Trust and other governmental charges imposed
              thereon; and if the Trust is required to pay additional taxes,
              duties, or other governmental charges (including Additional
              Taxes), the Company will pay as additional amounts on the
              Securities such amounts as shall be required so that the
              Distributions payable by the Trust shall not be reduced as a
              result of such additional taxes, duties and other governmental
              charges, including payment of all Additional Amounts and
              Additional Sums as set forth in the Indenture.

       (m)    The Securities shall have the benefit of the Guarantee of Kingsway
              Financial Services Inc., as set forth in Article XIV of the
              Indenture.

                                       2

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       (n)    All references in the Indenture and the Securities to the date the
              Securities were originally issued shall refer in the case of the
              Securities to the date hereof.

       (o)    The Securities shall not be subject to any sinking fund.

       (p)    The Securities shall not be defeasible.

       (q)    The Stated Maturity of the Securities shall not be subject to
              extension.

2.     The Securities shall be in the form of the certificate attached hereto as
       Exhibit A, and such form of certificate is hereby approved and provides
       for all of the terms specified in item (1) above.

3.     The certificate representing the Securities shall be executed, by manual
       or facsimile signature, by the President or Chief Financial Officer of
       the Company, in the name of, and for and on behalf of, the Company, in
       substantially the form hereinabove approved with such changes therein or
       additions thereto as may be approved by such officer, such approval to be
       conclusively evidenced by his execution and delivery thereof. The
       certificate shall be attested, by manual or facsimile signature, by the
       Secretary or Assistant Secretary of the Company. The manual or facsimile
       signatures of all such officers shall signify due execution by the
       Company of the certificate representing the Securities notwithstanding
       that, at the time of authentication and delivery thereof by the Trustee,
       any of such persons shall have ceased to be an officer of the Company.
       The proper officers are directed to take and perform all such other
       actions which, in their judgment, are necessary or advisable in
       connection with the foregoing.

4.     The date of issuance and delivery of the Securities shall be ___________,
       2003 or such later date as may be provided for in the Underwriting
       Agreement dated as of __________, 2003, among the Trust, the Company, the
       Guarantor, Kingsway America Inc. and the Underwriters named therein.

5.     Capitalized terms not defined herein shall have the meanings set forth in
       the Indenture.

       IN WITNESS WHEREOF, the undersigned have executed this Certificate this
___ day of _________, 2003.

                                           _____________________________________
                                           James R. Zuhlke
                                           President and Chief Executive Officer


                                           _____________________________________
                                           Brian K. Williamson

                                       3

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                                                   Chief Financial Officer

                                       4

<PAGE>

                           [Form of Face of Security]

                        __% Junior Subordinated Debenture
                                    Due 2033

                     Guaranteed as to Payment of Principal,
                        Premium, if any, and Interest by
                        Kingsway Financial Services Inc.

                                                          CUSIP  No. 496859 AA 7
  No. R -                                                         US$___________

       Kingsway U.S. Funding Inc., a corporation duly organized and existing
under the laws of the state of Delaware (hereinafter called the "Company", which
term includes any successor Person under the Indenture dated as of ________,
2003 (herein called the "Indenture"), between the Company, Kingsway Financial
Services Inc., as Guarantor (herein called the "Guarantor") and BNY Midwest
Trust Company, as Trustee (herein called the "Trustee", which term includes any
successor trustee under the Indenture)), for value received, hereby promises to
pay to _____________________, or registered assigns, the principal sum of
US$_________ on ______________, 2033, and to pay interest thereon from
__________, 2003, or from the most recent Interest Payment Date to which
interest has been paid or duly provided for, quarterly in arrears on March 31,
June 30, September 30 and December 31 in each year, commencing __________, 2003,
at the rate of ___% per annum, including any Additional Amounts and any
Additional Sums, if applicable, until the principal hereof is paid or made
available for payment, and at the rate of ___% per annum on any overdue
principal and premium and on any overdue installment of interest, Additional
Interest, Additional Amounts, and Additional Sums, if applicable. The interest
so payable, and punctually paid or duly provided for, on any Interest Payment
Date will, as provided in the Indenture, be paid to the Person in whose name
this Security (or one or more Predecessor Securities) is registered at the close
of business on the Regular Record Date for such interest, which will be the
fifteenth day of the last month of the calendar quarter (whether or not a
Business Day), as the case may be, next preceding such Interest Payment Date.
Any such interest not so punctually paid or duly provided for will forthwith
cease to be payable to the Holder on such Regular Record Date and may either be
paid to the Person in whose name this Security (or one or more Predecessor
Securities) is registered at the close of business on a Special Record Date for
the payment of such Defaulted Interest to be fixed by the Trustee, notice
whereof will be given to Holders of Securities of this series not less than 10
calendar days prior to such Special Record Date, or be paid at any time in any
other lawful manner not inconsistent with the requirements of any securities
exchange on which the Securities of this series may be listed, and upon such
notice as may be required by such exchange, all as more fully provided in said
Indenture.

                                       5

<PAGE>

       So long as no Event of Default has occurred and is continuing, the
Company shall have the right at any time during the term of this Security, from
time to time, to defer payment of interest on such Security for up to 20
consecutive quarterly interest payment periods with respect to each deferral
period (each an "Extension Period"), during which Extension Periods the Company
shall have the right to make partial payments of interest on any Interest
Payment Date, and at the end of which the Company shall pay all interest
(compounded quarterly) then accrued and unpaid, including Additional Interest,
any Additional Amounts, and any Additional Sums, if applicable; provided,
however, that no Extension Period may extend beyond the Maturity of this
Security. During any such Extension Period, the Company and the Guarantor will
not (a) declare or pay any dividends or distributions on, or redeem, purchase,
acquire or make a liquidation payment with respect to, any of its capital stock
(which includes common and preferred stock) or (b) make, or permit any
Subsidiary to make, any payment of principal, interest or premium, if any (other
than payments under the Subordinated Notes), on or repay, repurchase or redeem
any debt security that ranks pari passu with or junior in interest to this
Security, the Guarantee, the Guarantee Agreement or the Subordinated Notes, as
the case may be, or (c) make, or permit any Subsidiary to make, any guarantee
payments with respect to any guarantee of any debt security (other than payments
under the Guarantee or the Guarantee Agreement), if such guarantee ranks pari
passu with or junior in interest to this Security, the Guarantee, the Guarantee
Agreement, or the Subordinated Notes, as the case may be. Notwithstanding the
foregoing, the following shall not be prohibited: (i) repurchases, redemptions
or other acquisitions of shares of capital stock of the Guarantor in connection
with any employment contract, benefit plan or other similar arrangement with or
for the benefit of one or more employees, officers, directors or consultants, in
connection with a dividend reinvestment or stockholder stock purchase plan or in
connection with the issuance of capital stock of the Guarantor (or securities
convertible into or exercisable for such capital stock) as consideration in an
acquisition transaction entered into prior to the occurrence of the Event of
Default or selection of an Extension Period by the Company, as applicable, (ii)
any transactions described in (a) or (b) above resulting from any
reclassification of the Guarantor's capital stock, or the exchange or conversion
of any class or series of the Guarantor's capital stock for any other class or
series of the Guarantor's capital stock, or the exchange or conversion of any
class or series of the Guarantor's Indebtedness for any class or series of the
Guarantor's capital stock, (iii) the purchase of fractional interests in shares
of the Guarantor's capital stock pursuant to the conversion or exchange
provisions of such capital stock or the security being converted or exchanged,
or (iv) any declaration of a dividend in connection with any stockholders'
rights plan, or the issuance of rights, stock or other property under any
stockholders' rights plan, or the redemption or repurchase of rights pursuant
thereto. Prior to the termination of any such Extension Period, but provided
that no Event of Default has occurred and is continuing, the Company may further
extend such Extension Period; provided, however, that such extension does not
cause such Extension Period to exceed 20 consecutive quarterly interest payment
periods or extend beyond the Maturity of this Security. Upon the termination of
any Extension Period and the payment of all accrued and unpaid interest
(compounded quarterly), including Additional Interest, any Additional Amounts,
and any Additional Sums, if applicable, and then due, the Company may elect to
begin a new Extension Period, subject to the above requirements. No interest
shall be due and payable during an Extension Period except at the end thereof.
The Company shall give the Holder of this Security and the Trustee notice of its

                                       5

<PAGE>

election to begin any Extension Period at least five Business Days prior to the
Interest Payment Date, or prior to the earlier of (i) the date the Distributions
on the Preferred Securities to which this Security relates would have been
payable except for the election to begin or extend such Extension Period or (ii)
the date the Administrative Trustees of Kingsway Financial Capital Trust I are
required to give notice to any exchange or automated quotation system or to
holders of such Preferred Securities of the record date or the date such
Distributions are payable, but in any event not less than five Business Days
prior to such record date. There is no limitation on the number of times the
Company may elect to begin an Extension Period.

       Payment of the principal of (and premium, if any) and any such interest,
including any Additional Interest, any Additional Amounts, and any Additional
Sums, if applicable, on this Security will be made at the office or agency of
the Company maintained for the purpose in New York, NY, in such coin or currency
of the United States of America as at the time of payment is legal tender for
payment of public and private debts; provided, however, that at the option of
the Company, payment of interest may be made by check mailed to the address of
the Person entitled thereto as such address appears in the Security Register.

       This Security has the benefit of the Guarantee as contained and described
in the Indenture.

       REFERENCE IS HEREBY MADE TO THE FURTHER PROVISIONS SET FORTH ON THE
REVERSE HEREOF. SUCH PROVISIONS WILL FOR ALL PURPOSES HAVE THE SAME EFFECT AS
THOUGH FULLY SET FORTH IN THIS PLACE.

       This Security will not be valid or become obligatory for any purpose
until the certificate of authentication herein has been signed manually by the
Trustee under the Indenture referred to on the reverse side hereof.

       IN WITNESS WHEREOF, this instrument has been duly executed in accordance
with the Indenture.

                                                   KINGSWAY U.S. FUNDING INC.


                                                   By:__________________________
                                                        Name:
                                                        Title:

Attest:


By:____________________

                                       7

<PAGE>

                          [Form of Reverse of Security]

       This Security is one of a duly authorized issue of securities of the
Company (herein called the "Securities") under the Indenture, to which Indenture
and all indentures supplemental thereto reference is hereby made for a statement
of the respective rights, limitations of rights, duties, and immunities
thereunder of the Company, the Guarantor, the Trustee, and the Holders of the
Securities of this series and of the terms upon which the Securities are, and
are to be, authenticated and delivered. This Security is one of the series
designated on the face hereof limited in aggregate principal amount to
US$80,000,000.

       The Securities of this series are subject to redemption at the election
of the Company: (a) in whole or in part, on or after _________, 2008 and up to
90 days prior to _____, 2033 upon not less than 30 calendar days' notice by
mail, (b) in whole but not in part at any time within 180 days following the
occurrence of a Tax Event or an Investment Company Event, or (c) as otherwise
provided in the Indenture.

       In the event of redemption of this Security in part only, a new Security
or Securities of this series and of like tenor for the unredeemed portion hereof
will be issued in the name of the Holder hereof upon the cancellation hereof.

       The indebtedness evidenced by this Security is, to the extent and in the
manner provided in the Indenture, subordinate and junior in right of payment to
the prior payment in full of all amounts due and payable with respect to all
Company Senior Debt and all Guarantor Senior Debt as defined in the Indenture,
and this Security is issued subject to the provisions of the Indenture with
respect thereto. Each Holder of this Security, by accepting the same, (a) agrees
to and shall be bound by such provisions, (b) authorizes and directs the Trustee
on his, her or its behalf to take such action as may be necessary or appropriate
to acknowledge or effectuate the subordination so provided, and (c) appoints the
Trustee his, her or its attorney-in-fact for any and all such purposes.

       As provided in and subject to the provisions of the Indenture, if an
Event of Default with respect to the Securities of this series at the time
Outstanding occurs and is continuing, then and in every such case the Trustee or
the Holders of not less than 25% in principal amount of the Outstanding
Securities of this series may declare the principal amount of all the Securities
of this series to be due and payable immediately, by a notice in writing to the
Company and the Guarantor (and to the Trustee if given by Holders); provided,
however, that if, upon an Event of Default, the Trustee or the Holders of not
less than 25% in principal amount of the Outstanding Securities of this series
fails to declare the principal of all the Securities of this series to be
immediately due and payable, the holders of at least 25% in aggregate
Liquidation Amount of the corresponding series of Preferred Securities then
outstanding shall have such right by a notice in writing to the Company, the
Guarantor, the Trustee and the Property Trustee. The Holders of a majority in
aggregate principal amount of the Outstanding Securities of this series may
annul such declaration and waive the default if the default (other than the
non-payment of the principal of, any premium and interest on, and any Additional
Amounts with respect to, these

                                       8

<PAGE>

Securities which has become due solely by such acceleration) has been cured or
waived as provided in the Indenture, and a sum sufficient to pay all overdue
interest (including any Additional Interest and Additional Amounts) and
principal due otherwise than by acceleration has been deposited with the
Trustee. Should the Holders of these Securities fail to annul such declaration
and waive such default, the holders of a majority in aggregate Liquidation
Amount of the Preferred Securities shall have such right. Upon any such
declaration such specified amount of principal and the accrued interest
(including any Additional Interest and Additional Amounts) on all the Securities
of this series shall become immediately due and payable, provided that the
payment of principal and interest on such Securities shall remain subordinated
to the extent provided in the Indenture.

       The Indenture permits, with certain exceptions as therein provided, the
amendment thereof and the modification of the rights and obligations of the
Company, the Guarantor and the rights of the Holders of the Securities of this
series at any time by the Company, the Guarantor and the Trustee with the
consent of the Holders of a majority in principal amount of the Securities of
this series at the time Outstanding. The Indenture also contains provisions
permitting the Holders of specified percentages in principal amount of the
Securities of this series at the time Outstanding, on behalf of the Holders of
all Securities of this series, to waive compliance by the Company or the
Guarantor, as the case may be, with certain provisions of the Indenture and
certain past defaults under the Indenture and their consequences. Any such
consent or waiver by the Holder of this Security will be conclusive and binding
upon such Holder and upon all future Holders of this Security and of any
Security issued upon the registration of transfer hereof or in exchange herefor
or in lieu hereof, whether or not notation of such consent or waiver is made
upon this Security.

       As provided in and subject to the provisions of the Indenture, the Holder
of this Security will not have the right to institute any proceeding with
respect to the Indenture or for the appointment of a receiver or trustee or for
any other remedy thereunder, unless such Holder shall have previously given the
Trustee written notice of a continuing Event of Default with respect to the
Securities of this series, the Holders of not less than 25% in principal amount
of the Securities of this series at the time Outstanding shall have made written
request to the Trustee to institute proceedings in respect of such Event of
Default as Trustee and offered the Trustee indemnity reasonably satisfactory to
it, and the Trustee shall not have received from the Holders of a majority in
principal amount of Securities of this series at the time Outstanding a
direction inconsistent with such request and shall have failed to institute such
proceeding for 60 calendar days after receipt of such notice, request, and offer
of indemnity; provided that, if upon an Event of Default, the Trustee or the
Holders of not less than 25% in principal amount of the Outstanding Securities
of this series fails to declare the principal of all the Securities of this
series to be immediately due and payable, the holders of at least 25% in
aggregate Liquidation Amount of the corresponding series of Preferred Securities
then outstanding shall have such right by a notice in writing to the Company,
the Guarantor and the Trustee. The foregoing will apply to any suit instituted
by the Holder of this Security for the enforcement of any payment of principal
hereof or any premium or interest hereon on or after the respective due dates
expressed herein.

                                       9

<PAGE>

       No reference herein to the Indenture and no provision of this Security or
of the Indenture will alter or impair the obligation of the Company or the
Guarantor, as the case may be, which is absolute and unconditional, to pay the
principal of and any premium and interest (including Additional Interest, any
Additional Amounts, any Gross Up Amounts, and any Additional Sums, if
applicable) on this Security or the Guarantee, as the case may be, at the times,
place, and rate, and in the coin or currency, herein prescribed.

       As provided in the Indenture and subject to certain limitations therein
set forth, the transfer of this Security is registerable in the Security
Register, upon surrender of this Security for registration of transfer at the
office or agency of the Company in any place where the principal of and any
premium and interest on this Security are payable, duly endorsed by, or
accompanied by a written instrument of transfer in form satisfactory to the
Company and the Security Registrar duly executed by, the Holder hereof or his
attorney duly authorized in writing, and thereupon one or more new Securities of
this series and of like tenor, of authorized denominations and for the same
aggregate principal amount, will be issued to the designated transferee or
transferees.

       The Securities of this series are issuable only in registered form
without coupons in denominations of US$25 and integral multiples thereof. As
provided in the Indenture and subject to certain limitations therein set forth,
Securities of this series are exchangeable for a like aggregate principal amount
of Securities of this series and of like tenor of a different authorized
denomination, as requested by the Holder surrendering the same.

       No service charge will be made for any such registration of transfer or
exchange, but the Company may require payment of a sum sufficient to cover any
tax or other governmental charge payable in connection therewith.

       Prior to due presentment of this Security for registration of transfer,
the Company, the Guarantor, the Trustee, and any agent of the Company, the
Guarantor or the Trustee may treat the Person in whose name this Security is
registered as the owner hereof for all purposes, whether or not this Security
shall be overdue, and neither the Company, the Guarantor, the Trustee, nor any
such agent will be affected by notice to the contrary.

       All terms used in this Security that are defined in the Indenture will
have the respective meanings assigned to them in the Indenture.

       This Security shall be governed by, and construed in accordance with, the
laws of the State of New York, without regard to conflicts of laws principles
thereof.

                                    GUARANTEE

                                       10

<PAGE>

       For value received, the undersigned has unconditionally guaranteed, to
the extent set forth in the Indenture and subject to the provisions in the
Indenture (including, without limitation, the provisions relating to
subordination of the Guarantee pursuant to Article XV of the Indenture), the due
and punctual payment by the Company of all Guaranteed Obligations (as defined in
Section 14.01 of the Indenture) with respect to this Security, whether at
maturity, by acceleration, redemption or otherwise, all in accordance with the
terms of the Indenture. The obligations of the undersigned to the Holders of
this Security and to the Trustee pursuant to this Guarantee and the Indenture
are expressly set forth in Article XIV of the Indenture and reference is hereby
made to the Indenture for the precise terms of this Guarantee. Each Holder of a
Security, by accepting the same, agrees to and shall be bound by such
provisions.

                                       11

<PAGE>

            IN WITNESS WHEREOF, the Guarantor has duly executed this Guarantee.

                                               KINGSWAY FINANCIAL SERVICES INC.

                                               By_______________________________
                                                   Name:
                                                   Title:


                                               By_______________________________
                                                   Name:
                                                   Title:

                     Trustee's Certificate of Authentication

       This is one of the Securities of the series designated therein referred
to in the within mentioned Indenture.

                                               BNY Midwest Trust Company,
                                               as Trustee

Dated:_____________                            By:_______________________
                                                   Authorized Signatory

                     [Form of Legend for Global Securities]

       THIS SECURITY IS A GLOBAL SECURITY WITHIN THE MEANING OF THE INDENTURE
HEREINAFTER REFERRED TO AND IS REGISTERED IN THE NAME OF A DEPOSITARY OR A
NOMINEE THEREOF. THIS SECURITY MAY NOT BE TRANSFERRED TO, OR REGISTERED OR
EXCHANGED FOR SECURITIES REGISTERED IN THE NAME OF, ANY PERSON OTHER THAN THE
DEPOSITARY OR A NOMINEE THEREOF, AND NO SUCH TRANSFER MAY BE REGISTERED, EXCEPT
IN THE LIMITED CIRCUMSTANCES DESCRIBED IN THE INDENTURE. EVERY SECURITY
AUTHENTICATED AND DELIVERED UPON REGISTRATION OF TRANSFER OF, OR IN EXCHANGE
FOR, OR IN LIEU OF, THIS SECURITY WILL BE A GLOBAL SECURITY SUBJECT TO THE
FOREGOING, EXCEPT IN SUCH LIMITED CIRCUMSTANCES.

                                       12