Maarten Wensveen - 15 Aug 2025 Form 4 Insider Report for CIMPRESS plc (CMPR)

Role: EVP & Chief Technology Officer
Signature: /s/ Matthew F. Walsh, as attorney-in-fact for Maarten Wensveen
Issuer symbol: CMPR
Transactions as of: 15 Aug 2025
Net transactions value: -$342,611
Form type: 4
Filing time: 15 Aug 2025, 20:38:02 UTC
Previous filing: 11 Aug 2025
Next filing: 05 Nov 2025
SEC: View on sec.gov

Reporting Owners (1)

Name	Relationship	Address	Signature	Signature date	CIK
Wensveen Maarten	EVP & Chief Technology Officer	CIMPRESS PLC, FIRST FLOOR BUILDING 3, FINNABAIR BUSINESS & TECHNOLOGY PARK, DUNDALK, COUNTY LOUTH, IRELAND	/s/ Matthew F. Walsh, as attorney-in-fact for Maarten Wensveen	15 Aug 2025	0001766117

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	CMPR	Ordinary Shares	Options Exercise	$0	+2,337	+6.5%	$0.000000	38,343	15 Aug 2025	Direct	F1
transaction	CMPR	Ordinary Shares	Options Exercise	$0	+1,860	+4.9%	$0.000000	40,203	15 Aug 2025	Direct	F1
transaction	CMPR	Ordinary Shares	Options Exercise	$0	+3,697	+9.2%	$0.000000	43,900	15 Aug 2025	Direct	F2
transaction	CMPR	Ordinary Shares	Options Exercise	$0	+5,212	+12%	$0.000000	49,112	15 Aug 2025	Direct	F2
transaction	CMPR	Ordinary Shares	Tax liability	$342,611	-5,695	-12%	$60.16	43,417	15 Aug 2025	Direct

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	CMPR	Restricted Share Units (right to acquire)	Options Exercise	$0	-2,337	-100%	$0.000000	0	15 Aug 2025	Ordinary Shares	2,337	$0.000000	Direct	F1, F3
transaction	CMPR	Restricted Share Units (right to acquire)	Options Exercise	$0	-1,860	-20%	$0.000000	7,440	15 Aug 2025	Ordinary Shares	1,860	$0.000000	Direct	F1, F4
transaction	CMPR	Performance Share Units	Options Exercise	$0	-3,697	-11%	$0.000000	29,575	15 Aug 2025	Ordinary Shares	3,697	$0.000000	Direct	F2, F5
transaction	CMPR	Performance Share Units	Options Exercise	$0	-5,212	-25%	$0.000000	15,636	15 Aug 2025	Ordinary Shares	5,212	$0.000000	Direct	F2, F5

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	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.
F2	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.
F3	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.
F4	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.
F5	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.