[Form 4] Cimpress PLC Insider Trading Activity

Rhea-AI Filing Summary

Insider transactions at Cimpress plc (CMPR): Robert S. Keane, CEO and Chairman, reported multiple automatic vestings of performance share units (PSUs) and a subsequent open-market sale on 08/15/2025. PSUs converted to ordinary shares at $0 per unit as they vested, increasing his beneficial ownership across several tranches. Following the vestings, Mr. Keane sold 8,455 ordinary shares at a price of $60.16 each, reducing his beneficial ownership to 57,383 shares. The filing shows the structure and vesting schedules for the PSUs, including staggered vesting dates through 08/15/2028 and the initial exercisability dates in 2024 and 2025.

Positive

• Performance share units vested and converted to ordinary shares, reflecting achievement of vesting conditions and executive compensation realization
• Clear vesting schedule disclosed (exercisable dates in 2024 and 2025 with further vesting through 08/15/2028), which aids transparency

Negative

• Insider sale of 8,455 shares at $60.16 reduced reported beneficial ownership from 65,838 to 57,383 ordinary shares
• No information on the proportion of total outstanding shares is provided in this filing, limiting context for the sale's relative size

Insights

Corporate Governance Expert

TL;DR: Routine executive equity vesting with a small open-market sale; limited governance concern absent other context.

This Form 4 documents standard compensation mechanics: multiple performance share units vested and converted into ordinary shares per grant terms, and a portion of the resultant shares were sold at $60.16 each on the filing date. The filing includes vesting schedules through 2028 and shows beneficial ownership changes, not indicative of extraordinary governance events. Materiality is low to moderate for investors because the transactions reflect compensation realization rather than strategic ownership shifts.

Securities Analyst

TL;DR: Compensation-driven share issuance and a modest insider sale; transactional, not transformational.

The report itemizes automatic vesting of PSUs (each representing one ordinary share upon settlement) and the conversion into shares, followed by a disposal of 8,455 shares at $60.16. The aggregate outstanding beneficial ownership after transactions is reported for each security category. From a market-impact perspective, the sale size is small relative to typical public float and represents liquidity/compensation monetization rather than a signal of material change in control or financial condition.

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

OMB APPROVAL

OMB Number:			3235-0287
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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)
08/15/2025

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	08/15/2025		M		9,578	A	$0(1)	51,794	D
Ordinary Shares	08/15/2025		M		145	A	$0(1)	51,939	D
Ordinary Shares	08/15/2025		M		13,551	A	$0(1)	65,490	D
Ordinary Shares	08/15/2025		M		348	A	$0(1)	65,838	D
Ordinary Shares	08/15/2025		F		8,455	D	$60.16	57,383	D

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)	08/15/2025		M			9,578	08/15/2024(2)	08/15/2027	Ordinary Shares	9,578	$0	76,628	D
Performance Share Unit	$0(1)	08/15/2025		M			145	08/15/2024(2)	08/15/2027	Ordinary Shares	145	$0	1,164	D
Performance Share Units	$0(1)	08/15/2025		M			13,551	08/15/2025(2)	08/15/2028	Ordinary Shares	13,551	$0	40,653	D
Performance Share Units	$0(1)	08/15/2025		M			348	08/15/2025(2)	08/15/2028	Ordinary Shares	348	$0	1,042	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. 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	08/15/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What did Robert S. Keane report on Form 4 for CMPR?

He reported automatic vesting of multiple performance share units (PSUs) that converted to ordinary shares and the sale of 8,455 shares at $60.16 on 08/15/2025.

How many ordinary shares did Keane beneficially own after the transactions?

The filing reports 57,383 ordinary shares beneficially owned following the reported sale and vesting transactions.

What were the PSU vesting and exercisability details in the Form 4?

PSUs vested with exercisable dates of 08/15/2024 and 08/15/2025 for different tranches, with full vesting schedules extending through 08/15/2028.

At what price were the sold shares transacted?

The 8,455 ordinary shares were sold at $60.16 per share.

Does the Form 4 indicate these transactions were part of a Rule 10b5-1 plan?

No check box or statement in the provided content indicates these transactions were made pursuant to a Rule 10b5-1 trading plan.