[Form 4] Cimpress PLC Insider Trading Activity

Rhea-AI Filing Summary

Maarten Wensveen, EVP & Chief Technology Officer of Cimpress plc (CMPR), reported multiple equity award vestings and one open-market sale on 08/15/2025. Several restricted share units (RSUs) and performance share units (PSUs) vested, resulting in automatic acquisitions of ordinary shares at $0 per share: 2,337 RSUs, 1,860 RSUs, 3,697 PSUs and 5,212 PSUs were recorded as acquired. On the same date he sold 5,695 ordinary shares at $60.16 each. Following these transactions, Wensveen beneficially owns 43,417 ordinary shares and holds vested and unvested derivative awards reflected in Table II. The filings note standard multi-year vesting schedules for RSUs and PSUs.

Positive

• Multiple RSUs and PSUs vested, increasing the reporting person's beneficial stake through automatic award settlements at $0 per share
• Vesting schedules disclosed (25% initial vesting with subsequent quarterly or annual vesting), providing clarity on future share releases
• Filing appears complete and timely, including signature by attorney-in-fact and detailed transaction entries

Negative

• Disposition of 5,695 shares at $60.16 reduced direct holdings to 43,417 ordinary shares
• No indication of purpose for the sale is provided in the filing (e.g., tax withholding or diversification), so motivation is not disclosed

Insights

Securities Analyst

TL;DR: Insider received multiple vested RSUs/PSUs and executed a small sale, resulting in modest net share change; no new compensation terms disclosed.

The report documents automatic vesting of both restricted share units and performance share units, increasing the reporting person’s beneficial ownership through award settlements at $0 exercise price. The single reported disposition of 5,695 shares at $60.16 appears to be a routine sale rather than a large, dilutive event relative to company equity. Vesting schedules disclosed are multi-year with standard 25% first-tranche vesting and subsequent quarterly or annual vesting.

Corporate Governance Expert

TL;DR: Transactions are standard compensation vesting and a contemporaneous open-market sale; governance disclosures appear complete and timely.

The Form 4 cites automatic vesting mechanics and performance-based settlement for PSUs, with explicit vesting timelines. The filing is signed by an attorney-in-fact and includes price and amounts for the sale, meeting disclosure requirements for Section 16 reporting. There are no new grants, plan amendments, or unusual transfer vehicles disclosed.

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^*

Wensveen Maarten

(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)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	EVP & Chief Technology Officer

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		2,337	A	$0(1)	38,343	D
Ordinary Shares	08/15/2025		M		1,860	A	$0(1)	40,203	D
Ordinary Shares	08/15/2025		M		3,697	A	$0(2)	43,900	D
Ordinary Shares	08/15/2025		M		5,212	A	$0(2)	49,112	D
Ordinary Shares	08/15/2025		F		5,695	D	$60.16	43,417	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
Restricted Share Units (right to acquire)	$0(1)	08/15/2025		M			2,337	08/15/2022(3)	08/15/2025	Ordinary Shares	2,337	$0	0	D
Restricted Share Units (right to acquire)	$0(1)	08/15/2025		M			1,860	08/15/2023(4)	08/15/2026	Ordinary Shares	1,860	$0	7,440	D
Performance Share Units	$0(2)	08/15/2025		M			3,697	08/15/2024(5)	08/15/2027	Ordinary Shares	3,697	$0	29,575	D
Performance Share Units	$0(2)	08/15/2025		M			5,212	08/15/2025(5)	08/15/2028	Ordinary Shares	5,212	$0	15,636	D

Explanation of Responses:

1. The shares acquired automatically vested pursuant to an award of restricted share units (RSUs), with each RSU representing Cimpress' commitment to issue one ordinary share.

2. 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.

3. These RSUs vest over the following four-year period: 25% of the original number of RSUs granted vest on the Date Exercisable in Table II and 25% of such number of RSUs vest yearly thereafter.

4. These RSUs vest over the following four-year period: 25% of the original number of RSUs granted vest on the Date Exercisable in Table II and 6.25% of such number of RSUs vest quarterly thereafter.

5. 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 Maarten Wensveen	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.
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FAQ

What did Maarten Wensveen report on the Form 4 for CMPR?

He reported the automatic vesting and acquisition of RSUs and PSUs totaling 12, (2,337+1,860+3,697+5,212) awards on 08/15/2025 and an open-market sale of 5,695 shares at $60.16.

How many Cimpress (CMPR) shares does Wensveen beneficially own after these transactions?

The Form 4 reports beneficial ownership of 43,417 ordinary shares following the transactions.

Were any new equity grants reported for CMPR in this Form 4?

No new grants are reported; the Form 4 documents the vesting/settlement of existing RSUs and PSUs and a sale.

What vesting schedules are disclosed for the RSUs and PSUs?

RSUs and PSUs generally vest over four years with 25% vesting on the first exercisable date and the remainder vesting annually or quarterly as specified.

At what price were the sold Cimpress shares executed?

The reported sale of 5,695 shares was executed at a price of $60.16 per share.