X0508 4 2025-12-11 0 0001691421 Lemonade, Inc. LMND 0001874702 Eckstein Adina C/O LEMONADE, INC. 5 CROSBY STREET, 3RD FLOOR NEW YORK NY 10013 0 1 0 0 Chief Operating Officer 1 COMMON STOCK 2025-12-11 4 S 0 7919 84.15 D 188391 D Represents sale pursuant to a Rule 10b5-1 trading plan adopted on September 8, 2025. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price. /s/ Timothy Bixby, Attorney-in-Fact for Adina Eckstein 2025-12-15