Sean E. Quinn - 15 Feb 2025 Form 4 Insider Report for CIMPRESS plc (CMPR)

Role: EVP, Chief Financial Officer
Signature: /s/ Matthew F. Walsh, as attorney-in-fact for Sean E. Quinn
Issuer symbol: CMPR
Transactions as of: 15 Feb 2025
Net transactions value: -$278,458
Form type: 4
Filing time: 19 Feb 2025, 18:39:20 UTC
Previous filing: 19 Nov 2024
Next filing: 17 Mar 2025
SEC: View on sec.gov

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	CMPR	Ordinary Shares	Options Exercise	$0	+9,977	+281%	$0.000000	13,524	15 Feb 2025	Direct	F1
transaction	CMPR	Ordinary Shares	Options Exercise	$0	+2,300	+17%	$0.000000	15,824	15 Feb 2025	Direct	F1
transaction	CMPR	Ordinary Shares	Options Exercise	$0	+4,571	+29%	$0.000000	20,395	15 Feb 2025	Direct	F2
transaction	CMPR	Ordinary Shares	Tax liability	$278,458	-5,171	-25%	$53.85	15,224	15 Feb 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	-9,977	-100%	$0.000000	0	15 Feb 2025	Ordinary Shares	9,977	$0.000000	Direct	F1, F3
transaction	CMPR	Restricted Share Units (right to acquire)	Options Exercise	$0	-2,300	-14%	$0.000000	13,798	15 Feb 2025	Ordinary Shares	2,300	$0.000000	Direct	F1, F4
transaction	CMPR	Performance Share Units	Options Exercise	$0	-4,571	-9.1%	$0.000000	45,707	15 Feb 2025	Ordinary Shares	4,571	$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 represent the number of shares that automatically vested pursuant to an award of restricted share units (RSUs). Each RSU represents Cimpress' commitment to issue one ordinary share.
F2	The shares acquired represent the number of shares that automatically vested pursuant to an award of performance share units.
F3	These RSUs vest over a three year period: one-third of the original number of shares vest on the Date Exercisable in Table II and one-third vest per year thereafter.
F4	These RSUs vest over a four-year period: 25% of the original number of shares vest on the Date Exercisable in Table II and 6.25% vest at the end of each successive three-month period thereafter.
F5	These performance share units vest over a four year period: 25% of the original number of shares vest on the Date Exercisable in Table II and 6.25% vest per quarter thereafter.