Clarke Inc. — Capital/Financing Update 2021

Sep 30, 2021

FIRST SUPPLEMENTAL TRUST INDENTURE

This First Supplemental Trust Indenture is entered into as of the 30[th] day of September, 2021,

BETWEEN:

CLARKE INC. , a corporation existing under the laws of Canada and having its head office in the City of Halifax, in the Province of Nova Scotia (hereinafter called the " Corporation ")

AND

COMPUTERSHARE TRUST COMPANY OF CANADA , a trust company incorporated under the federal laws of Canada having an office in the City of Toronto, in the Province of Ontario, in its capacity as trustee under a fourth amended and restated trust indenture dated September 30, 2019 (hereinafter called the " Indenture Trustee ")

WITNESSETH THAT:

WHEREAS the Corporation and the Indenture Trustee entered into a fourth amended and restated trust indenture dated September 30, 2019 (the " Indenture ");

AND WHEREAS there is one series of debentures outstanding under the Indenture, being the Series B 6.25% convertible unsecured subordinated debentures due February 28, 2023 (the " Series B Debentures ");

AND WHEREAS Article 16 of the Indenture permits the Corporation and the Indenture Trustee to execute, acknowledge and deliver a supplemental indenture for the purpose of giving effect to any Extraordinary Resolution (as defined in the Indenture) passed as provided in Article 13 of the Indenture;

AND WHEREAS the holders of the Series B Debentures have approved an Extraordinary Resolution to provide for certain amendments to the Series B Debentures and to enter into this first supplemental trust indenture (this " First Supplemental Indenture ") with the Indenture Trustee to provide for such amendments, which First Supplemental Indenture and Indenture will govern the terms of the Series B Debentures;

AND WHEREAS all necessary acts and proceedings have been done and taken and all necessary resolutions have been passed, including an Extraordinary Resolution to authorize the execution and delivery of this First Supplemental Indenture, to make the same effective and binding upon the Corporation, and to make the amendments to the Series B Debentures, when authenticated by the Indenture Trustee as provided in this First Supplemental Indenture, valid, binding and legal obligations of the Corporation with the benefit and subject to the terms of the Indenture and this First Supplemental Indenture;

AND WHEREAS the foregoing recitals are made as representations and statements of fact by the Corporation and not by the Indenture Trustee;

NOW THEREFORE it is hereby covenanted, agreed and declared as follows:

ARTICLE 1 DEFINITIONS AND AMENDMENTS TO INDENTURE

1.1 Definitions

All capitalized terms not defined herein shall have the meanings given to them in the Indenture.

1.2 Amendments to Indenture

This First Supplemental Indenture is supplemental to the Indenture and shall hereafter be read together and shall have effect, so far as practicable, with respect to the Debentures as if all the provisions of the Indenture and this First Supplemental Indenture were contained in one instrument. The Indenture is and shall remain in full force and effect with regards to all matters governing the Debentures, except as the Indenture is amended, superseded, modified or

supplemented by this First Supplemental Indenture. Any references in the text of this First Supplemental Indenture to section numbers, article numbers, "hereto", "herein", "hereby", "hereunder", "hereof" and similar expressions refer to the Indenture unless otherwise qualified.

ARTICLE 2 THE SERIES B DEBENTURES

2.1 Amendments to Series B Debentures

The provisions of the Series B Debentures as set forth in the Indenture are amended as follows:

• (a) Section 2.4(b) of the Indenture is hereby deleted in its entirety and replaced with the following:

"The Series B Debentures issued as of October 20, 2005, shall mature on January 1, 2028, and shall bear interest (subject to the provisions of Section 2.18) from April 30, 2014 to and including April 29, 2023 at a rate of 6.25% per annum and from April 30, 2023 to January 1, 2028 at a rate of 5.50% per annum, in each case payable in arrears in equal semi-annual installments on April 30 and October 31 in each year, the last such payment to be pro rata and fall due on January 1, 2028, payable after as well as before maturity and after as well as before default, with interest on amounts in default at the same rate, compounded, semi-annually."

• (b) Section 2.4(e) of the Indenture is hereby amended by deleting the reference to "February 28, 2023" in the first paragraph of that section and replacing it with "January 1, 2028".

• (c) The first sentence of the second paragraph of Section 2.4(e) of the Indenture is hereby deleted in its entirety and replaced with the following:

"The Conversion Price in effect as of September 30, 2021 for each Common Share to be issued upon conversion of the Series B Debentures shall be equal to $13.74, such that approximately 72.78 Common Shares shall be issued for each $1,000 principal amount of Series B Debentures so converted."

• (d) Schedules B.1 and B.2 of the Indenture are hereby deleted in their entirety and replaced with Schedules B.1 and B.2 to this First Supplemental Indenture.

ARTICLE 3 ADDITIONAL MATTERS

3.1 Confirmation of Indenture

The Indenture, as amended and supplemented by this First Supplemental Indenture, is in all respects confirmed.

3.2 Acceptance of Trust

The Indenture Trustee hereby accepts the trusts in this First Supplemental Indenture declared and provided for and agrees to perform the same upon the terms and conditions herein set forth and to hold all rights, privileges and benefits conferred hereby and by law in trust for the various Persons who shall from time to time be Debentureholders, subject to the provisions set forth in the Indenture.

3.3 Governing Law

This First Supplemental Indenture and the Debentures shall be governed by and construed in accordance with the laws of the Province of Nova Scotia and the laws of Canada applicable therein and shall be treated, in all respects, as a Nova Scotia contract.

3.4 Further Assurances

The parties shall, with reasonable diligence, do all such things and provide all such reasonable assurances as may be required to consummate the transactions contemplated by this First Supplemental Indenture, and each party shall provide such further documents or instruments required by the other party as may be reasonably necessary or desirable to effect the purpose of this First Supplemental Indenture and carry out its provisions.

3.5 Conflicts

If a provision of this First Supplemental Indenture is inconsistent or conflicts with any provision of the Indenture, the relevant provision of this First Supplemental Indenture shall prevail and be paramount.

3.6 Counterparts

This First Supplemental Indenture may be executed by the parties in separate counterparts, each of which when so executed and delivered shall be an original, but all such counterparts shall together constitute one and the same instrument.

[Remainder of page intentionally left blank.]

IN WITNESS WHEREOF the parties hereto have executed these presents under their respective corporate seals and the hands of their proper officers in that behalf.

CLARKE INC.

Per: (signed) "Tom Casey" Name: Tom Casey Title: Chief Financial Officer

COMPUTERSHARE TRUST COMPANY OF CANADA

Per: (signed) "Bianca Kara" Name: Bianca Kara Title: Corporate Trust Officer Per: (signed) "Jeremie Bruton" Name: Jeremie Bruton Title: Associate Trust Officer

[ Signature Page – First Supplemental Indenture ]

SCHEDULE "B.1"

to the Fourth Amended and Restated Trust Indenture between Clarke Inc. and Computershare Trust Company of Canada

FORM OF DEBENTURE

This Debenture is a global Debenture within the meaning of the Indenture herein referred to and is registered in the name of a Depository or a nominee thereof. This Debenture may not be transferred to or exchanged for Debentures registered in the name of any person other than the Depository or a nominee thereof and no such transfer may be registered except in the limited circumstances described in the Indenture. Every Debenture authenticated and delivered upon registration of, transfer of, or in exchange for, or in lieu of, this Debenture shall be a global Debenture subject to the foregoing, except in such limited circumstances described in the Indenture.

Unless this Debenture is presented by an authorized representative of CDS Clearing and Depository Services Inc. ("CDS") to Clarke Inc. or its agent for registration of transfer, exchange or payment, and any Debenture issued in respect thereof is registered in the name of CDS & CO., or in such other name as is requested by an authorized representative of CDS (and any payment is made to CDS & CO. or to such other entity as is requested by an authorized representative of CDS), ANY TRANSFER, PLEDGE OR OTHER USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL since the registered holder hereof, CDS & CO. has a property interest in the securities represented by this certificate herein and it is a violation of its rights for another person to hold, transfer or deal with this certificate. This certificate is issued pursuant to a Master Letter of Representations of Clarke Inc. to CDS, as such letter may be replaced or amended from time to time.

No. […]

CUSIP 181901AC3 $ […]

CLARKE INC.

(a corporation incorporated under the Canada Business Corporations Act )

SERIES B CONVERTIBLE UNSECURED SUBORDINATED DEBENTURE

Due January 1, 2028

CLARKE INC. (the " Corporation ") for value received hereby acknowledges itself indebted and, subject to the provisions of the Fourth Amended and Restated Trust Indenture (the " Indenture ") dated as of September 30, 2019 between the Corporation and Computershare Trust Company of Canada (the " Indenture Trustee "), as supplemented by the First Supplemental Indenture dated September 30, 2021, promises to pay to the registered holder hereof on January 1, 2028 (the " Maturity Date ") or on such earlier date as the principal amount hereof may become due in accordance with the provisions of the Indenture the principal sum of ______ Dollars ($______) in lawful money of Canada on presentation and surrender of this Debenture at the main branch of the Indenture Trustee in Toronto, Ontario in accordance with the terms of the Indenture and to pay interest on the principal amount hereof from the date hereof, or from the last interest payment date to which interest shall have been paid or made available for payment on the outstanding Series B Debentures (as hereinafter defined), whichever is later, at the rate of 6.25% per annum until and including April 29, 2023 and thereafter at a rate of 5.50% from April 30, 2023 to January 1, 2028, in like money, in arrears in equal semi-annual installments (less any tax required by law to be deducted) on April 30 and October 31 in each year commencing on April 30, 2014 and, should the Corporation at any time make default in the payment of any principal or interest, to pay interest on the amount in default at the same rate, in like money.

Interest hereon shall be payable by electronic funds transfer or by cheque mailed to the registered holder hereof and, subject to the provisions of the Indenture, the electronic funds transfer or mailing of such cheque shall, to the extent of the sum represented thereby (plus the amount of any tax withheld), satisfy and discharge all liability for interest on this Series B Debenture. Subject to applicable law and applicable regulatory approval, the Corporation shall have the right, at its option upon not more than 60 days' and not less than 15 days' prior written notice, to elect to satisfy its obligation to pay interest on the Series B Debentures, in whole or in part, in each case, by issuing and delivering Freely Tradeable Common Shares to Debentureholders in accordance with the terms of the Indenture.

This Series B Debenture is one of the Series B Convertible Unsecured Subordinated Debentures due on the Maturity Date of the Corporation issued or issuable under the provisions of the Indenture (referred to herein as the " Series B Debentures "). The Series B Debentures are limited to an aggregate principal amount of $120,000,000 in lawful money of Canada. Reference is hereby expressly made to the Indenture for a description of the terms and conditions upon which the Series B Debentures are or are to be issued and held and the rights and remedies of the holders of the Series B Debentures and of the Corporation and of the Indenture Trustee, all to the same effect as if the provisions of the Indenture were herein set forth, to all of which provisions the holder of this Series B Debenture by acceptance hereof assents.

The Series B Debentures are issuable only in denominations of $1,000 and integral multiples thereof. Upon compliance with the provisions of the Indenture, Series B Debentures of any denomination may be exchanged for an equal aggregate principal amount of Series B Debentures in any other authorized denomination or denominations.

The whole, or if this Series B Debenture is in a denomination in excess of $1,000, any part of which is $1,000 or an integral multiple thereof, or the principle of this Series B Debenture is convertible, at the option of the holder hereof, upon surrender of this Series B Debenture at the principal office of the Indenture Trustee in Toronto, Ontario, at any time prior to the close of business on the Business Day immediately preceding the Maturity Date, into Common Shares (without adjustment for interest accrued hereon or for dividends or distributions on Common Shares issuable upon conversion) at a conversion price of $13.74 (the " Conversion Price "), being a rate of approximately 72.78 Common Shares for each $1,000 principal amount of the Series B Debentures, all subject to the terms and conditions and in the manner set forth in the Indenture. The indenture makes provision for the adjustment of the Conversion Price in the events therein specified. No fractional Common Shares will be issued on any conversion but in lieu thereof, the Corporation will satisfy such fractional interests by a cash payment equal to the market price of such fractional interest determined in accordance with the Indenture. Holders converting their Series B Debentures will receive accrued and unpaid interest thereon.

On and after June 1, 2020, but prior to the Maturity Date, the Series B Debentures will be redeemable, in whole or in part, at a price equal to the principal amount thereof, plus accrued and unpaid interest, at the Corporation's sole option on not more than 60 days' and not less than 15 days' prior notice. In the case of redemption of less than all of the Debentures, the Series B Debentures to be redeemed will be selected by the Indenture Trustee on a pro rata basis or in such other manner as the Indenture Trustee deems equitable, subject to the consent of the Toronto Stock Exchange.

If a takeover bid for the Series B Debentures, within the meaning of the Securities Act (Nova Scotia), is made and 90% or more of the principal amount of all the Series B Debentures (other than the Series B Debentures held at the date of the takeover bid by or on behalf of the Offeror, Associates or Affiliates of the Offeror or anyone acting jointly or in concert with the Offeror) are taken up and paid for by the Offeror, the Offeror will be entitled to acquire the Series B Debentures of those holders who did not accept the offer on the same terms as the Offeror acquired the first 90% of the principal amount of the Series B Debentures.

The Corporation may, on notice as provided in the Indenture, at its option (subject to any applicable regulatory approval), elect to satisfy the obligation to repay the principal amount of this Series B Debenture due on the Maturity Date by the issue of that number of Common Shares obtained by dividing the principal amount of the Series B Debentures then outstanding by 95% of the weighted average trading price of the Common Shares on the Toronto Stock Exchange for the 20 consecutive trading days ending on the fifth trading day preceding the Maturity Date.

The indebtedness evidenced by this Series B Debenture, and by all other Series B Debentures now or hereafter certified and delivered under the Indenture, is a direct unsecured obligation of the Corporation, and is subordinated in right of payment, to the extent and in the manner provided in the Indenture, to the prior payment of all Senior Indebtedness, whether outstanding at the date of the Indenture or thereafter created, incurred, assumed or guaranteed.

The principal hereof may become or be declared due and payable before the stated maturity in the events, in the manner, with the effect and at the times provided in the Indenture.

The Indenture contains provisions making binding upon all holders of Debentures outstanding thereunder (or in certain circumstances, specific series of Debentures) resolutions passed at meetings of such holders held in accordance with such provisions and instruments signed by the holders of a specified majority of Debentures outstanding (or specific series), which resolutions or instruments may have the effect of amending the terms of this Series B Debenture or the Indenture.

The Indenture contains provisions disclaiming any personal liability on the part of holders of Common Shares or the directors, officers or agents of the Corporation in respect of any obligation or claim arising out of the Indenture or this Series B Debenture.

This Series B Debenture may only be transferred, upon compliance with the conditions prescribed in the Indenture, in one of the registers to be kept at the principal offices of the Indenture Trustee in Toronto, Ontario and in such other place or places and/or by such other registrars (if any) as the Corporation with the approval of the Indenture Trustee may designate. No transfer of this Series B Debenture shall be valid unless made to the register by the registered holder hereof or his executors or administrators or other legal representatives, or his or their attorney duly appointed by an instrument in form and substance satisfactory to the Indenture Trustee or other registrar, and upon compliance with such reasonable requirements as the Indenture Trustee and/or other registrar may prescribe and upon surrender of this Series B Debenture for cancellation.

This Series B Debenture shall not become obligatory for any purpose until it shall have been certified by the Indenture Trustee under the Indenture.

Capitalized words or expressions used in this Series B Debenture shall, unless otherwise defined herein, have the meaning ascribed thereto in the Indenture.

IN WITNESS WHEREOF CLARKE INC. has caused this Series B Debenture to be signed by its authorized representative as of the ● day of ●, 20●.

CLARKE INC.

By: […] […]

TRUSTEE'S CERTIFICATE

This Series B Debenture is one of the Series B Convertible Unsecured Subordinated Debentures due January 1, 2028 referred to in the Indenture within mentioned.

COMPUTERSHARE TRUST COMPANY OF CANADA

By: (Authorized Officer)

THIS CERTIFICATE OF THE INDENTURE TRUSTEE SIGNED ON THE SECURITIES WILL NOT BE CONSTRUED AS A REPRESENTATION OR WARRANTY BY THE INDENTURE TRUSTEE AS TO THE VALIDITY OF THE INDENTURE OR OF THE SECURITIES OR OF THEIR ISSUANCE AND THE INDENTURE TRUSTEE WILL IN NO RESPECT BE LIABLE OR ANSWERABLE FOR THE USE MADE OF SUCH SECURITIES OR ANY OF THEM OR THE PROCEEDS THEREOF. THIS CERTIFICATE OF THE INDENTURE TRUSTEE SIGNED ON THE SECURITIES WILL, HOWEVER, BE A REPRESENTATION AND WARRANTY BY THE INDENTURE TRUSTEE THAT THE SECURITIES HAVE BEEN DULY CERTIFIED BY OR ON BEHALF OF THE INDENTURE TRUSTEE PURSUANT TO THE PROVISIONS OF THE INDENTURE.

REGISTRATION PANEL

(No writing hereon except by Indenture Trustee or other registrar)

Date of Registration	In Whose Name Registered	Signature of Indenture Trustee or Registrar

ASSIGNMENT

FOR VALUE RECEIVED, the undersigned hereby sells, assigns and transfers unto ____, whose address and social insurance number, if applicable, are set forth below, this Series B Debenture (or $_______ principal amount hereof*) of CLARKE INC. standing in the name(s) of the undersigned in the register maintained by the Corporation with respect to such Series B Debenture and does hereby irrevocably authorize and direct the Indenture Trustee to transfer such Series B Debenture in such register, with full power of substitution in the premises.

Dated:

Address of Transferee:

(Street Address, City, Province and Postal Code)

Social Insurance Number of Transferee, if applicable:

*If less than the full principal amount of the within Series B Debenture is to be transferred, indicate in the space provided the principal amount (which must be $1,000 or an integral multiple thereof, unless you hold a Series B Debenture in a non-integral multiple of $1,000, in which case such Series B Debenture is transferable only in its entirety) to be transferred.

The signature(s) to this assignment must correspond with the name(s) as written upon the face of this Series B Debenture in every particular without alteration or any change whatsoever. The signature(s) must be guaranteed by a Canadian chartered bank or trust company or by a member of an acceptable Medallion Guarantee Program. Notarized or witnessed signatures are not acceptable as guaranteed signatures. The Guarantor must affix a stamp bearing the actual words: "SIGNATURE GUARANTEED".

The registered holder of this Series B Debenture is responsible for the payment of any documentary, stamp or other transfer taxes that may be payable in respect of the transfer of this Series B Debenture.

Signature of Guarantor:

Authorized Officer Signature of transferring registered holder

Name of Institution

EXHIBIT "1"

TO CDS GLOBAL DEBENTURE

CLARKE INC.

SERIES B CONVERTIBLE UNSECURED SUBORDINATED DEBENTURES

DUE JANUARY 1, 2028

Initial Principal Amount: _____

CUSIP: […] ISIN: […]

Authorization: ___________

ADJUSTMENTS

DATE	AMOUNT OF INCREASE	AMOUNT OF DECREASE	NEW PRINCIPAL AMOUNT	AUTHORIZATION

SCHEDULE "B.2"

CLARKE INC.

SERIES B CONVERTIBLE UNSECURED SUBORDINATED DEBENTURES

DUE JANUARY 1, 2028

MATURITY NOTICE

To: Holders of Series B Convertible Unsecured Subordinated Debentures due January 1, 2028 (the " Debentures ") of Clarke Inc. (the " Corporation ")

Note: All capitalized terms used herein have the meaning ascribed thereto in the Fourth Amended and Restated Trust Indenture mentioned below, unless otherwise indicated.

Notice is hereby given pursuant to section 2.4(f) of the Fourth Amended and Restated Trust Indenture dated as of September 30, 2019 (the " Indenture ") between the Corporation and Computershare Trust Company of Canada, as trustee (the " Indenture Trustee "), that the Debentures will become due and payable as of January 1, 2028 (the " Maturity Date ").

[Pursuant to section 4.10 of the Indenture, the Corporation hereby advises the holders of the Series B Debentures that it is exercising the Common Share Repayment Right and that it will satisfy its obligations to pay the principal amount of the Series B Debentures by delivering to the Series B Debenture holders (subject to withholding or deduction on account of applicable taxes) that number of Freely Tradeable Common Shares equal to the number obtained by dividing the principal amount of such Series B Debentures by 95% of the Current Market Price of Common Shares on the Maturity Date. Upon presentation and surrender of the Series B Debentures, the Corporation shall pay or cause to be paid in cash to the holder all accrued and unpaid interest to the Maturity Date, together with the case equivalent representing fractional Common Shares, and shall, on the Maturity Date, send to the Indenture Trustee certificates representing the Common Shares to which the holder is entitled.]

DATED:

CLARKE INC.

(Authorized Officer)