CIMPRESS plc

On September 9, 2024, Robert Keane, our Founder, Chairman and Chief Executive Officer, adopted a plan for the sale of Cimpress ordinary shares that is intended to satisfy the affirmative defense conditions of Exchange Act Rule 10b5-1(c) (the "Original Plan"). The Original Plan provided for the sales, on the dates and at the prices set forth in the Original Plan, of up to 35,000 ordinary shares held by Mr. Keane as of the date of the Original Plan adoption. The Original Plan was scheduled to expire on August 1, 2025.

On December 12, 2024, Mr. Keane adopted an amendment to the Original Plan that is intended to satisfy the affirmative defense conditions of Exchange Act Rule 10b5-1(c) (the "Amended Plan"). The Amended Plan provides for the sales, on the dates and at the prices set forth in the Amended Plan, of up to 102,000 ordinary shares held by Mr. Keane as of the date of the Amended Plan adoption. The Amended Plan expires on November 1, 2025.

On September 9, 2024, Maarten Wensveen, our Executive Vice President and Chief Technology Officer, adopted a plan for the sale of Cimpress ordinary shares that is intended to satisfy the affirmative defense conditions of Exchange Act Rule 10b5-1(c). The plan provides for the sales, on the dates and at the prices set forth in the plan, of up to 22,830 ordinary shares held by Mr. Wensveen as of the date of the plan adoption. Mr. Wensveen's plan expires on September 9, 2025.