Lemonade, Inc.

Item 1.01 Entry into a Material Definitive Agreement. On June 22, 2026, Lemonade, Inc. (the "Company") and Hannover Re (Ireland) DAC ("Hannover"), entered into a New Business Financing Agreement (the “Agreement”) under which Hannover will provide up to $250 million of outstanding capital related to the financing of the Company’s sales and marketing growth efforts ("Growth Spend") from January 1, 2027 ("Funding Begin Date") through December 31, 2028, subject to a maximum outstanding capital amount of $150 million from Funding Begin Date through December 31, 2027, and up to $250 million at any time during the period from January 1, 2028 through December 31, 2028. Unless otherwise specified, capitalized terms used but not defined herein have the meanings given to them in the Agreement. Under the Agreement, subject to certain terms and conditions, at the start of each monthly Growth Period, Hannover shall provide financing of the Company's Growth Spend of up to 80% but not to exceed $20 million per Reference Cohort. During each monthly Growth Period, the Company will repay each amount previously financed based on a specific percentage of premiums collected for assigned customer cohorts associated with the funded Growth Spend ("Reference Premium"), which includes the Funding Amount plus a rate of return in accordance with the Counterparty Cap Amount, defined as the sum of (a) the greater of (i) 0% or (ii) the three-year U.S. Treasury Bill rate, plus (b) 5.8%. Once fully repaid, the Company will retain all future Reference Premium related to each Reference Cohort. The Agreement also includes certain financial covenants, cancellation and commitment termination provisions. The Agreement contains standard customary representations, warranties and covenants by the parties, and will continue to be in effect unless terminated by either party pursuant to its terms. The foregoing description of the Agreement does not purport to be complete and is qualified in its entirety by reference to the full text of the Agreement, which the Company expects to file as an exhibit to its Quarterly Report on Form 10-Q for the quarter ended June 30, 2026.

Item 2.03 Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant. The disclosure set forth above under Item 1.01 of this Current Report on Form 8-K is incorporated by reference into this Item 2.03.