Sec Form 4 Filing - Baumgartner Florian @ CIMPRESS plc - 2025-08-15

FORM 4 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, FIRST FLOOR BUILDING 3, FINNABAIR BUSINESS & TECHNOLOGY PARK 3. Date of Earliest Transaction (MM/DD/YY) 08/15/2025 (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 08/15/2025 M 934 A $ 0 ( 1 ) 50,848 D Ordinary Shares 08/15/2025 M 1,691 A $ 0 ( 1 ) 52,539 D Ordinary Shares 08/15/2025 M 3,550 A $ 0 ( 2 ) 56,089 D Ordinary Shares 08/15/2025 M 5,212 A $ 0 ( 2 ) 61,301 D Ordinary Shares 08/15/2025 F 5,408 D $ 60.16 55,893 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 Restricted Share Units (right to acquire) $ 0 ( 1 ) 08/15/2025 M 934 08/15/2022( 3 ) 08/15/2025 Ordinary Shares 934 $ 0 0 D Restricted Share Units (right to acquire) $ 0 ( 1 ) 08/15/2025 M 1,691 08/15/2023( 4 ) 08/15/2026 Ordinary Shares 1,691 $ 0 6,764 D Performance Share Units $ 0 ( 2 ) 08/15/2025 M 3,550 08/15/2024( 5 ) 08/15/2027 Ordinary Shares 3,550 $ 0 28,400 D Performance Share Units $ 0 ( 2 ) 08/15/2025 M 5,212 08/15/2025( 5 ) 08/15/2028 Ordinary Shares 5,212 $ 0 15,636 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Baumgartner Florian C/O CIMPRESS PLC, FIRST FLOOR BUILDING 3 FINNABAIR BUSINESS & TECHNOLOGY PARK DUNDALK, CO. LOUTH, IRELAND EVP and CEO, Vista Signatures /s/ Matthew F. Walsh, as attorney-in-fact for Florian Baumgartner 08/15/2025 Signature of Reporting Person Date

Explanation of Responses:

( 1 )The shares acquired automatically vested pursuant to an award of restricted share units (RSUs), with each RSU representing Cimpress' commitment to issue one ordinary share. ( 2 )The shares acquired automatically vested pursuant to an award of performance share units (PSUs), with each PSU representing Cimpress' commitment to issue one ordinary share following the determination of the number of shares issuable pursuant to the award based on the level of achievement against the performance conditions. ( 3 )These RSUs vest over the following four-year period: 25% of the original number of RSUs granted vest on the Date Exercisable in Table II and 25% of such number of RSUs vest yearly thereafter. ( 4 )These RSUs vest over the following four-year period: 25% of the original number of RSUs granted vest on the Date Exercisable in Table II and 6.25% of such number of RSUs vest quarterly thereafter. ( 5 )These PSUs vest over the following four-year period: 25% of the number of shares determined to be issuable pursuant to the award based on the level of achievement against the performance conditions vest on the Date Exercisable shown in Table II and 6.25% of such number of shares vest quarterly thereafter.

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).

** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).

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