of this Report (including Exhibit 99.1 attached hereto) shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly provided by specific reference in such a filing.

CFO — Tim Bixby: Tim Bixby is transitioning from CFO to a Board member, and Nick Stead has been appointed as the new CFO.

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 $1…

SIGNATURES Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized. LEMONADE, INC. Date: June 24, 2026 By: /s/ Daniel Schreiber Daniel Schreiber Chief Executive Officer

of this Report (including Exhibit 99.1 attached hereto) shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly provided by specific reference in such a filing.

of this Report (including Exhibit 99.1 attached hereto) shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly provided by specific reference in such a filing.

of this Report (including Exhibit 99.1 attached hereto) shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly provided by specific reference in such a filing.

Director — Mr. Prashant Ratanchandani: Appointment of a new director to the Board.

Director — Mr. Geoff Seeley: Appointment of Mr. Geoff Seeley to the Board as a Class I director.

of this Report (including Exhibit 99.1 attached hereto) shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly provided by specific reference in such a filing.

Entry into a Material Definitive Agreement. As of June 30, 2025, Lemonade, Inc. (the “Company”), together with certain of its wholly-owned subsidiaries, agreed to the terms of its reinsurance program, effective July 1, 2025, and expiring June 30, 2026 (the “Reinsurance Program”). The Reinsurance Program includes Whole Account Quota Share Reinsurance Contracts by and among the Company, Lemonade Insurance Company ("LIC"), Metromile Insurance Company (“MIC”) and Lemonade Insurance N.V. (“Lemonad…

of this Report (including Exhibit 99.1 attached hereto) shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly provided by specific reference in such a filing.

Termination of a Material Definitive Agreement. On April 4, 2025, pursuant to its terms and conditions, Lemonade, Inc. (the “Company”) terminated the Warrant Agreement, dated October 14, 2022 with Chewy Insurance Services, LLC ( the “Warrantholder” or "Chewy"). The Warrantholder previously vested and exercised 181,191 warrant shares and the Company will cancel the remaining 3,170,834 shares. The Company and Chewy also terminated the Omnibus Agreement, dated October 14, 2022. The agency agreem…

of this Report (including Exhibit 99.1 attached hereto) shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly provided by specific reference in such a filing.

Entry into a Material Definitive Agreement. On February 3, 2025, Lemonade, Inc. (the “Company”) entered into a Fourth Amended and Restated Customer Investment Agreement (the “Agreement”), with GC Customer Value Arranger, LLC, as Arranger on behalf of the Investors (the “Investors”). Unless otherwise specified, capitalized terms used but not defined herein have the meanings given to them in the Agreement. Under the original customer investment agreement dated June 28, 2023, as amended in Janua…

SIGNATURES Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized. LEMONADE, INC. Date: February 7, 2025 By: /s/ Tim Bixby Tim Bixby Chief Financial Officer

of this Report (including Exhibit 99.1 attached hereto) shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly provided by specific reference in such a filing.

of this Report (including Exhibit 99.1 attached hereto) shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly provided by specific reference in such a filing.

of this Report (including Exhibit 99.1 attached hereto) shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly provided by specific reference in such a filing.

Results of Operations and Financial Condition. On February 27, 2024, Lemonade, Inc. (the "Company") announced its financial results for the quarter and year ended December 31, 2023 by issuing a letter to shareholders. The full text of the letter to shareholders is furnished as Exhibit 99.1 to this Current Report on Form 8-K (the "Report").

SIGNATURES Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized. LEMONADE, INC. Date: January 11, 2024 By: /s/ Tim Bixby Tim Bixby Chief Financial Officer

Entry into a Material Definitive Agreement. On January 8, 2024, Lemonade, Inc. (the “Company”) entered into an Amended and Restated Customer Investment Agreement (the “Agreement”), with GC Customer Value Arranger, LLC, as Arranger on behalf of the Investors (the “Investors”). Unless otherwise specified, capitalized terms used but not defined herein have the meanings given to them in the Agreement. Under the Agreement, the Investors will provide the Company up to $150 million from June 28, 202…

President and CEO — Shai Wininger and Daniel Schreiber: Co-CEOs Shai Wininger and Daniel Schreiber return to their previous roles as President and CEO, respectively.

Director — Irina Novoselsky, Silvija Martincevic: Two directors resigned and were replaced by new appointees.

of this Report (including Exhibit 99.1 attached hereto) shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly provided by specific reference in such a filing.