Robert S. Keane - 15 Nov 2025 Form 4 Insider Report for CIMPRESS plc (CMPR)

Role: CEO, Chairman, Director
Signature: /s/ Matthew F. Walsh, as attorney-in-fact for Robert S. Keane
Issuer symbol: CMPR
Transactions as of: 15 Nov 2025
Net transactions value: -$359,852
Form type: 4
Filing time: 18 Nov 2025, 16:14:36 UTC
Previous filing: 28 Aug 2025
Next filing: 17 Feb 2026
SEC: View on sec.gov

Reporting Owners (1)

Name	Relationship	Address	Signature	Signature date	CIK
Keane Robert S	CEO, Chairman, Director	CIMPRESS PLC, FIRST FLOOR BUILDING 3, FINNABAIR BUSINESS & TECHNOLOGY PARK, DUNDALK, COUNTY LOUTH, IRELAND	/s/ Matthew F. Walsh, as attorney-in-fact for Robert S. Keane	18 Nov 2025	0001337084

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	CMPR	Ordinary Shares	Options Exercise	$0	+9,579	+17%	$0.000000	66,962	15 Nov 2025	Direct	F1
transaction	CMPR	Ordinary Shares	Options Exercise	$0	+146	+0.22%	$0.000000	67,108	15 Nov 2025	Direct	F1
transaction	CMPR	Ordinary Shares	Options Exercise	$0	+3,388	+5%	$0.000000	70,496	15 Nov 2025	Direct	F1
transaction	CMPR	Ordinary Shares	Tax liability	$359,852	-5,404	-7.7%	$66.59	65,092	15 Nov 2025	Direct
holding	CMPR	Ordinary Shares						220,503	15 Nov 2025	By Keane Family Foundation
holding	CMPR	Ordinary Shares						28,375	15 Nov 2025	By RHS Delaware Holdings LLC
holding	CMPR	Ordinary Shares						43,128	15 Nov 2025	By Eastern Irrevocable, LLC	F2
holding	CMPR	Ordinary Shares						47,088	15 Nov 2025	By Western Irrevocable, LLC	F2
holding	CMPR	Ordinary Shares						51,900	15 Nov 2025	By Delaware 2001 Investment Trust
holding	CMPR	Ordinary Shares						780,000	15 Nov 2025	By Second Delaware 2003, LLC
holding	CMPR	Ordinary Shares						986,785	15 Nov 2025	By Third Delaware 2011, LLC

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	Performance Share Units	Options Exercise	$0	-9,579	-13%	$0.000000	67,049	15 Nov 2025	Ordinary Shares	9,579	$0.000000	Direct	F1, F3
transaction	CMPR	Performance Share Unit	Options Exercise	$0	-146	-13%	$0.000000	1,018	15 Nov 2025	Ordinary Shares	146	$0.000000	Direct	F1, F3
transaction	CMPR	Performance Share Units	Options Exercise	$0	-3,388	-8.3%	$0.000000	37,265	15 Nov 2025	Ordinary Shares	3,388	$0.000000	Direct	F1, F3

* 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 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.
F2	Includes 28,375 shares held by RHS Holdings Incorporated, of which The Eastern Irrevocable Trust and The Western Irrevocable Trust are the sole shareholders.
F3	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.