Sec Form 3 Filing - Baumgartner Florian @ CIMPRESS plc - 2023-02-01

FORM 3 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person Baumgartner Florian 2. Issuer Name and Ticker or Trading Symbol CIMPRESS plc [ CMPR] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) _____ Director _____ 10% Owner X __ Officer (give title below) _____ Other (specify below) EVP and CEO, Vista (Last) (First) (Middle) C/O CIMPRESS PLC, BUILDING D, XEROX TECHNOLOGY PARK 3. Date of Earliest Transaction (MM/DD/YY) 02/01/2023 (Street) DUNDALK, CO. LOUTH, IRELAND 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price Ordinary Shares 10,347 D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares Share Option (right to buy) $ 46.2 06/30/2023( 1 ) 08/15/2032 Ordinary Shares 54,557 D Restricted Share Units (right to acquire) $ 0 ( 3 ) 07/01/2021( 2 ) 07/01/2024 Ordinary Shares 2,658 D Restricted Share Units (right to acquire) $ 0 ( 3 ) 05/15/2021( 4 ) 02/15/2025 Ordinary Shares 16,488 D Restricted Share Units (right to acquire) $ 0 ( 3 ) 08/15/2021( 2 ) 08/15/2024 Ordinary Shares 1,668 D Restricted Share Units (right to acquire) $ 0 ( 3 ) 08/15/2022( 2 ) 08/15/2025 Ordinary Shares 2,804 D Restricted Share Units (right to acquire) $ 0 ( 3 ) 02/15/2023( 5 ) 02/15/2025 Ordinary Shares 12,685 D Restricted Share Units (right to acquire) $ 0 ( 3 ) 04/15/2023( 2 ) 04/15/2026 Ordinary Shares 33,054 D Restricted Share Units (right to acquire) $ 0 ( 3 ) 08/15/2023( 6 ) 08/15/2026 Ordinary Shares 27,056 D Restricted Share Units (right to acquire) $ 0 ( 3 ) 01/15/2024( 6 ) 01/15/2027 Ordinary Shares 16,409 D Performance Share Units $ 111.7 ( 8 ) ( 7 ) 11/21/2027 Ordinary Shares 10,743 D Performance Share Units $ 95.46 ( 10 ) ( 9 ) 02/15/2029 Ordinary Shares 10,999 D Performance Share Units $ 100.46 ( 8 ) ( 11 ) 08/15/2029 Ordinary Shares 10,451 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Baumgartner Florian C/O CIMPRESS PLC BUILDING D, XEROX TECHNOLOGY PARK DUNDALK, CO. LOUTH, IRELAND EVP and CEO, Vista Signatures /s/Kathryn L. Leach, as attorney-in-fact for Florian Baumgartner 02/07/2023 Signature of Reporting Person Date

Explanation of Responses:

( 1 )This option vests over a four year period: 25% of the original number of shares subject to the option vest on the Date Exercisable shown on Table II and 6.25% of the shares vest per quarter thereafter. ( 2 )These RSUs vest over a four year period: 25% of the original number of shares vest on the Date Exercisable in Table II and 25% vest per year thereafter. ( 3 )Each restricted share unit (RSU) represents Cimpress' commitment to issue one ordinary share. ( 4 )These RSUs vest over a four year period: 6.25% of the original number of shares vest on the Exercisable Date show in Table II and 6.25% vest per quarter thereafter. ( 5 )These RSUs vest over a three year period: 33.3% of the original number of shares vest on the Date Exercisable in Table II and 33.3% vest per year thereafter. ( 6 )These RSUs vest over a four year period: 25% of the original number of shares vest on the Exercisable Date show in Table II and 6.25% vest per quarter thereafter. ( 7 )Each of these performance share units (PSU) represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the compound annual growth rate (CAGR) of the three-year moving average of Cimpress' daily share price (3YMA). The service-based vesting condition is that 25% of the original number of PSUs vest on each October 6 of 2020 through 2023 so long as the reporting person continues to be an eligible participant under Cimpress' 2016 Performance Incentive Plan on such vesting date. If the 3YMA CAGR equals or exceeds (i) 9% on any of the fourth through seventh anniversaries of the grant date or (ii) 7% on the eighth anniversary of the grant date, then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance. ( 8 )This dollar amount is the 3YMA on the date of grant, which is the baseline against which the CAGR of the 3YMA will be measured. ( 9 )Each of these PSUs represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the CAGR of the 3YMA. The service-based vesting condition is that 25% of the original number of PSUs vest on each June 30 of 2021 through 2024 so long as the reporting person continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan on such vesting date. If the 3YMA CAGR equals or exceeds (i) 9% on any of the fourth through seventh anniversaries of the grant date or (ii) 7% on the eighth anniversary of the grant date, then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance. ( 10 )This dollar amount is the two-year moving average of Cimpress' daily share price on the date of grant, which is the baseline against which the CAGR of the 3YMA will be measured. ( 11 )Each of these PSUs represents a right to receive between 0 and 2.5 Cimpress ordinary shares upon the satisfaction of both (A) service-based vesting and (B) performance conditions relating to the CAGR of the 3YMA. The service-based vesting condition is that 25% of the original number of PSUs vest on each June 30 of 2022 through 2025 so long as the reporting person continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan on such vesting date. If the 3YMA CAGR equals or exceeds (i) 9% on any of the fourth through seventh anniversaries of the grant date or (ii) 7% on the eighth anniversary of the grant date, then the reporting person is entitled to receive a distribution of up to 2.5 Cimpress ordinary shares for each vested PSU on a sliding scale based on the actual CAGR performance.

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).

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