Cimpress : Lender Presentation

CIMPRESS PLC

LENDER PRESENTATION

APRIL 2021

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SAFE HARBOR STATEMENT

This presentation, as well as the question and answer session that follows, contains statements about our future expectations, plans, and prospects of our business that constitute forward-looking statements for purposes of the safe harbor provisions under the Private Securities Litigation Reform Act of 1995, including our expectations for the growth and development of our businesses, our planned redemption of our senior secured notes, our plans with respect to our financial policy and capital allocation, the size of our market and anticipated changes to our markets and opportunities post-pandemic, and our expectations with respect to 99designs and design services. Forward-looking projections and expectations are inherently uncertain, are based on assumptions and judgments by management, and may turn out to be wrong. Our actual results may differ materially from those indicated by our forward-looking statements as a result of various important factors, including but not limited to flaws in the assumptions and judgments upon which our forecasts are based; our failure to execute our strategy; the development, duration, and severity of the COVID-19 pandemic; our failure to anticipate and react to the effects of the pandemic on our customers, supply chain, markets, team members, and business; our inability to make the investments in our business that we plan to make or the failure of those investments to achieve the results we expect; loss or unavailability of key personnel; unanticipated changes in our markets, customers, or business; our failure to attract new customers and retain our current customers; competitive pressures; our failure to manage the growth and complexity of our business; the failure of the businesses we acquire or invest in to perform as expected; changes in the laws and regulations, or in the interpretations of laws and regulations, that affect our businesses; our failure to maintain compliance with the covenants in our debt documents or to pay our debts when due; general economic conditions; and other factors described in our Form 10-K for the fiscal year ended June 30, 2020 and the other documents we periodically file with the U.S. Securities and Exchange Commission.

In addition, our statements and projections represent our expectations and beliefs as of the date of this presentation, and subsequent events and developments may cause these expectations, beliefs, and projections to change. We specifically disclaim any obligation to update any forward- looking statements. These forward-looking statements should not be relied upon as representing our expectations or beliefs as of any date subsequent to the date of this presentation.

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DISCLAIMERS

Special notice regarding borrower names

For the purposes of this document, All RC Borrowers, collectively the "RCF Borrowers" will be defined collectively as the following:

• Cimpress plc
• Vistaprint Limited
• Cimpress Schweiz GmbH
• Vistaprint B.V.
• Cimpress USA Incorporated
• Vistaprint Netherlands B.V.

TLB Borrowers, collectively the "TLB Borrowers" will be defined collectively as the following and when combined with the RCF Borrowers, as "Cimpress" or the "Borrower"

• Cimpress USA Incorporated
• Vistaprint Netherlands B.V.

SPECIAL NOTICE FOR PUBLIC-SIDERS

THE BORROWER OR THE TARGET HAS REPRESENTED AND WARRANTED TO THE ARRANGER EITHER THAT:

1. THE INFORMATION IN THIS DOCUMENT DOES NOT CONSTITUTE OR CONTAIN ANY MATERIAL NON-PUBLIC INFORMATION WITH RESPECT TO THE BORROWER OR THE TARGET OR ANY PARTY RELATED THERETO (COLLECTIVELY, "PARTIES") OR THEIR RESPECTIVE SECURITIES FOR PURPOSES OF UNITED STATES FEDERAL AND STATE SECURITIES LAWS;

However, the information contained in this document is subject to, and must be kept confidential in accordance with, the Notice to and Undertaking by Recipients accompanying this document.

Notice to and undertaking by recipients dated April 2021

The information and documents following this Notice (the "Confidential Materials") have been prepared from information supplied by or on behalf of Cimpress plc ("Borrower"), and is being furnished by JPMorgan Chase Bank, N.A. through its agent J.P. Morgan Securities LLC ("Lead Left Arranger") to you and the financial institution that you represent as a potential lender (collectively, "Recipient") in the proposed amendment to the Credit Facilities described herein (the "Amendment").

By accepting the Confidential Materials for review, Recipient agrees to be bound by the terms of this notice and the undertakings set forth herein. If Recipient is unwilling to accept such undertakings, do not open the Confidential Materials or, if Confidential Materials are provided in hard copy, return the Confidential Materials to the Lead Left Arranger immediately without reviewing them or making any copies, extracts or use of them and, if applicable, immediately terminate access to the related SyndTrak site.

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DISCLAIMERS (CONTINUED)

I. Confidentiality

As used herein: (a) "Evaluation Materials" means the Confidential Materials and any other information regarding Borrower or the Amendment furnished or communicated to Recipient by or on behalf of Borrower in connection with the Amendment (whether prepared or communicated by the Lead Left Arranger or Borrower, their respective advisors or otherwise) and (b) "Internal Evaluation Materials" means all memoranda, notes, and other documents and analyses developed by Recipient embodying any Evaluation Materials.

Recipient acknowledges that Borrower considers the Evaluation Materials to include confidential, sensitive or proprietary information and agrees to use reasonable precautions in accordance with its established procedures to keep the Evaluation Materials confidential; provided that (i) it may disclose such information to which Borrower gives its prior written consent and (ii) such information may be disclosed to it, its affiliates and their respective partners, directors, officers, employees, agents, advisors and other representatives (collectively, "Representatives") (such Representatives shall be informed by Recipient of the confidential nature of such information and shall be directed to treat such information in accordance with the terms hereof). Recipient agrees to be responsible for any breach of this Notice and Undertaking by its Representatives.

The foregoing confidentiality requirements do not apply to (i) any information that is or becomes generally available to the public by or on behalf of the Borrower, (ii) any information available to Recipient from a source other than Borrower, provided that such source is not known to Recipient to be subject to any confidentiality obligations to Borrower or its agents, (iii) any disclosure required by law, regulation or administrative or other legal process or requested by regulatory or governmental authorities, (iv) any disclosure consented to by Borrower or (v) any information independently developed by Recipient without use of the Evaluation Materials.

If Recipient decides not to participate in the Amendment, then upon request of the Lead Left Arranger, Recipient shall as soon as practicable return all Evaluation Materials (other than Internal Evaluation Materials) to the Lead Left Arranger or represent in writing to the Lead Left Arranger that Recipient has destroyed all copies of the Evaluation Materials (other than Internal Evaluation Materials), unless prohibited from doing so by law, regulation or Recipient's internal policies and procedures.

Recipient agrees that money damages would not be a sufficient remedy for breach of this Notice and Undertaking, and that in addition to all other remedies available at law or in equity, Borrower and the Lead Left Arranger shall each be entitled to equitable relief, including injunction and specific performance, without proof of actual damages.

The terms and conditions of Part I of this Notice and Undertaking shall apply until you become a party to the definitive agreements evidencing the Amendment and thereafter the provisions relating to confidentiality contained in such agreements shall govern. If you do not enter into the Amendment, this Notice and Undertaking shall terminate on the date falling one year after the date hereof.

II. Information, etc.

Recipient acknowledges and agrees that (i) the Lead Left Arranger received the Evaluation Materials from third party sources (including Borrower) and it is provided to Recipient for informational purposes only, (ii) the Lead Left Arranger and its affiliates have no responsibility, and shall not be liable, for the accuracy or completeness or lack thereof of the Evaluation Materials or any information contained therein, (iii) no representation regarding the Evaluation Materials is made by the Lead Left Arranger or its affiliates, (iv) neither the Lead Left Arranger nor its affiliates has made any independent verification as to the accuracy or completeness of the Evaluation Materials and (v) the Lead Left Arranger and its affiliates shall have no obligation to update or supplement any Evaluation Materials or otherwise provide additional information.

The Evaluation Materials has been prepared to assist potential lenders in making their own evaluation of Borrower and the Amendment and does not purport to be all-inclusive or to contain all of the information that a potential lender may consider material or desirable in making its decision to become a lender. Each Recipient of the information contained herein should take such steps as it deems necessary to assure that it has the information it considers material or desirable in making its decision to become a lender and should perform its own independent investigation and analysis of the Amendment or the transactions contemplated thereby and the Borrower (including its creditworthiness). Recipient represents that it is sophisticated and experienced in extending credit to entities similar to Borrower. The information contained herein is not a substitute for Recipient's independent evaluation and analysis and should not be considered as a recommendation by the Lead Left Arranger or any of its affiliates that any Recipient enter into the Amendment.

The Evaluation Materials may include certain forward looking statements and projections provided by Borrower. Any such statements and projections reflect various estimates and assumptions by Borrower concerning anticipated results. No representations or warranties are made by Borrower or any of its affiliates as to the accuracy of any such statements or projections. Whether or not any such forward looking statements or projections are in fact achieved will depend upon future events some of which are not within the control of Borrower. Accordingly, actual results may vary from the projected results and such variations may be material. Statements contained herein describing documents and agreements are summaries only and such summaries are qualified in their entirety by reference to such documents and agreements.

This Notice and Undertaking shall be governed by and construed in accordance with the law of the State of New York.

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WE ARE TAKING STEPS TO

STRENGTHEN OUR CAPITAL STRUCTURE

• Proactively implement a flexible capital structure to
• • Facilitate investment in our business
  • Withstand potential future temporary COVID-related impacts
• Lower weighted average cost of debt by repaying expensive 12% 2nd lien debt
• Extend maturity profile
• Increase liquidity relative to current structure
• Diversify and expand lender base by accessing the institutional loan market in both the U.S. and Europe
• Transaction will be net leverage neutral while maintaining significant amount of pre-payable debt available for de-levering
• We are committed to maintaining our prudent financial policy

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