CIMPRESS plc

On May 8, 2026, Maarten Wensveen, our Executive Vice President & Chief Technology and MCP Operations 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) and that expires on August 31, 2027. The plan provides for sales, on dates and at prices set forth in the plan, of up to 69,687 ordinary shares held by Mr. Wensveen as of the date of the plan adoption.

On May 26, 2026, Sean Quinn, our Executive Vice President and Chief Financial Officer, terminated a Rule 10b5-1(c) trading arrangement previously adopted on February 25, 2026. The terminated arrangement was originally scheduled to expire on July 30, 2027, and authorized the potential sale of up to 121,057 ordinary shares held by Mr. Quinn as of the date of the plan adoption plus additional ordinary shares that became, or could have become, eligible for sale under the arrangement during its originally scheduled term upon the vesting and settlement of equity awards.

On June 5, 2026, Robert Keane, our 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) and that expires on February 26, 2027. The plan provides for sales, on dates and at prices set forth in the plan, of up to 126,900 ordinary shares held by Mr. Keane as of the date of the plan adoption.