Sean E. Quinn - Aug 15, 2022 Form 4 Insider Report for CIMPRESS plc (CMPR)

Role: EVP, Chief Financial Officer
Signature: /s/Kathryn L. Leach, as attorney-in-fact for Sean E. Quinn
Stock symbol: CMPR
Transactions as of: Aug 15, 2022
Transactions value $: -$55,629
Form type: 4
Date filed: 8/17/2022, 01:16 PM
Previous filing: Jul 6, 2022
Next filing: Feb 16, 2023

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	CMPR	Ordinary Shares	Options Exercise	$0	+2.81K	+99.57%	$0.00	5.62K	Aug 15, 2022	Direct	F1
transaction	CMPR	Ordinary Shares	Options Exercise	$0	+1.49K	+26.49%	$0.00	7.11K	Aug 15, 2022	Direct	F1
transaction	CMPR	Ordinary Shares	Tax liability	-$55.6K	-1.26K	-17.75%	$44.08	5.85K	Aug 15, 2022	Direct
holding	CMPR	Ordinary Shares						9.38K	Aug 15, 2022	By Ashley E. Quinn Trust DTD 11/26/2014

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	-2.81K	-25%	$0.00	8.41K	Aug 15, 2022	Ordinary Shares	2.81K	$0.00	Direct	F1, F2
transaction	CMPR	Restricted Share Unit (right to acquire)	Options Exercise	$0	-1.49K	-33.33%	$0.00	2.98K	Aug 15, 2022	Ordinary Shares	1.49K	$0.00	Direct	F1, F2
transaction	CMPR	Restricted Share Units (right to acquire)	Award	$0	+36.8K		$0.00	36.8K	Aug 15, 2022	Ordinary Shares	36.8K	$0.00	Direct	F1, F3
transaction	CMPR	Option (right to buy)	Award	$0	+74.2K		$0.00	74.2K	Aug 15, 2022	Ordinary Shares	74.2K	$46.20	Direct	F4

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

Explanation of Responses:

Id	Content
F1	Each restricted stock unit (RSU) represents Cimpress' commitment to issue one ordinary share.
F2	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.
F3	These RSUs vest over a four-year period: 25% of the original number of shares vest on the Exercisable Date shown in Table II and 6.25% vest at the end of each successive three-month period thereafter.
F4	This option becomes exercisable as to 25% of the original number of shares on the Exercisable Date shown on Table II, and as to an additional 6.25% of the original number of shares on the last day of each successive fiscal quarter thereafter.