[Form 4] CIMPRESS plc Insider Trading Activity

Rhea-AI Filing Summary

Cimpress plc CEO, Chairman and Director Robert S. Keane reported equity award activity involving performance share units (PSUs). On 11/15/2025, three PSU awards vested and were settled in ordinary shares, delivering 9,579, 146 and 3,388 ordinary shares at an exercise price of $0 per share. To cover related obligations, 5,404 ordinary shares were disposed of at $66.59 per share. Following these transactions, he directly owned 65,092 ordinary shares. He also reported substantial indirect holdings through several entities, including 220,503 shares via the Keane Family Foundation and 986,785 shares via Third Delaware 2011, LLC.

SEC Form 4

FORM 4

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
or Section 30(h) of the Investment Company Act of 1940

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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Keane Robert S

(Last) (First) (Middle)

CIMPRESS PLC, FIRST FLOOR BUILDING 3

FINNABAIR BUSINESS & TECHNOLOGY PARK

(Street)

DUNDALK, COUNTY LOUTH, IRELAND

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
CIMPRESS plc [ CMPR ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	CEO, Chairman

3. Date of Earliest Transaction (Month/Day/Year)
11/15/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	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	11/15/2025		M		9,579	A	$0(1)	66,962	D
Ordinary Shares	11/15/2025		M		146	A	$0(1)	67,108	D
Ordinary Shares	11/15/2025		M		3,388	A	$0(1)	70,496	D
Ordinary Shares	11/15/2025		F		5,404	D	$66.59	65,092	D
Ordinary Shares								220,503	I	By Keane Family Foundation
Ordinary Shares								28,375	I	By RHS Delaware Holdings LLC
Ordinary Shares								43,128(2)	I	By Eastern Irrevocable, LLC
Ordinary Shares								47,088(2)	I	By Western Irrevocable, LLC
Ordinary Shares								51,900	I	By Delaware 2001 Investment Trust
Ordinary Shares								780,000	I	By Second Delaware 2003, LLC
Ordinary Shares								986,785	I	By Third Delaware 2011, LLC

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 (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	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 (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (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: 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
Performance Share Units	$0(1)	11/15/2025		M			9,579	08/15/2024(3)	08/15/2027	Ordinary Shares	9,579	$0	67,049	D
Performance Share Unit	$0(1)	11/15/2025		M			146	08/15/2024(3)	08/15/2027	Ordinary Shares	146	$0	1,018	D
Performance Share Units	$0(1)	11/15/2025		M			3,388	08/15/2025(3)	08/15/2028	Ordinary Shares	3,388	$0	37,265	D

Explanation of Responses:

1. 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.

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

3. 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.

Remarks:

	/s/ Matthew F. Walsh, as attorney-in-fact for Robert S. Keane	11/18/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
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