LMND.WS / Lemonade, Inc. - Equity Warrant - تصريحات هيئة الأوراق المالية والبورصات، التقرير السنوي، بيان الوكيل

Lemonade, Inc. - ضمان حقوق الملكية
US ˙ NYSEAM

الإحصائيات الأساسية
LEI 5493009BKR06OXXU6853
CIK 1691421
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Lemonade, Inc. - Equity Warrant
SEC Filings (Chronological Order)
توفر هذه الصفحة قائمة كاملة ومرتبة ترتيبًا زمنيًا لتصريحات هيئة الأوراق المالية والبورصات، باستثناء تصريحات الملكية التي نقدمها في مكان آخر.
August 5, 2025 EX-10.3

Whole Account Quota Share Reinsurance Contract issued to Lemonade Insurance Company, Lemonade Insurance N.V. and Metromile Insurance Company by the Subscribing Reinsurer, MAPFRE Re Compania De Reaseguros S.A. (Spain) dated effective July 1, 2025

exhibit103-quotasharerei [***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

August 5, 2025 EX-10.1

Property Per Risk Excess of Loss Reinsurance Contract issued to Lemonade Insurance Company and Metromile Insurance Company by Subscribing Reinsurers effective July 1, 2025

exhibit101-propertyperri [***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

August 5, 2025 EX-99.1

Shareholder Letter Q2 2025 1 $687 $839 $1,083 ($53) ($43) ($41)($67) ($57) ($44) $164 $200 $252 $17 $33 $66 $12 $31 $64 10% 17% 26% ($52) $2 $25 ($50) ($12) $6 1 $402 2,693,107$1,083M IN FORCE PREMIUM (IFP) PREMIUM PER CUSTOMER TOTAL CUSTOMERS ↑29% ↑

lmndshareholderletterq22 Shareholder Letter Q2 2025 1 $687 $839 $1,083 ($53) ($43) ($41)($67) ($57) ($44) $164 $200 $252 $17 $33 $66 $12 $31 $64 10% 17% 26% ($52) $2 $25 ($50) ($12) $6 1 $402 2,693,107$1,083M IN FORCE PREMIUM (IFP) PREMIUM PER CUSTOMER TOTAL CUSTOMERS ↑29% ↑4% ↑24% IN FORCE PREMIUM ($s in m) KEY METRICS ($s in m) Q2 23 Q2 25Q2 24 ADJUSTED EBITDA NET LOSS GEP Q2 23 Q2 25Q2 24 ADJUS

August 5, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 5, 2025 LEMONADE, INC. (Ex

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 5, 2025 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numb

August 5, 2025 EX-10.2

Whole Account Quota Share Reinsurance Contract issued to Lemonade Insurance Company, Lemonade Insurance N.V. and Metromile Insurance Company by the Subscribing Reinsurer, Hannover Ruck SE effective July 1, 2025

exhibit102-quotasharerei [***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

August 5, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

July 2, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): 6/30/2025 LEMONADE, INC. (Exact n

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): 6/30/2025 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Number) (

June 9, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): 6/4/2025 LEMONADE, INC. (Exact na

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): 6/4/2025 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Number) (I

May 6, 2025 EX-99.1

Shareholder Letter Q1 2025 1 $653 $794 $1,008 ($51) ($34) ($47) ($66) ($47) ($62) $154 $188 $234 $21 $37 $46 $17 $35 $39 13% 20% 20% ($49) ($19) ($31) ($46) ($30) ($47) 1 $396 2,545,496$1,008M IN FORCE PREMIUM (IFP) PREMIUM PER CUSTOMER TOTAL CUSTOME

Shareholder Letter Q1 2025 1 $653 $794 $1,008 ($51) ($34) ($47) ($66) ($47) ($62) $154 $188 $234 $21 $37 $46 $17 $35 $39 13% 20% 20% ($49) ($19) ($31) ($46) ($30) ($47) 1 $396 2,545,496$1,008M IN FORCE PREMIUM (IFP) PREMIUM PER CUSTOMER TOTAL CUSTOMERS ↑27% ↑4% ↑21% IN FORCE PREMIUM ($s in m) KEY METRICS ($s in m) Q1 23 Q1 25Q1 24 ADJUSTED EBITDA NET LOSS GEP NET LOSS/GEP Q1 23 Q1 25Q1 24 ADJUSTED

May 6, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

May 6, 2025 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 6, 2025 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Number)

April 23, 2025 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amend

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

April 23, 2025 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amend

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

April 9, 2025 8-K

Termination of a Material Definitive Agreement, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 4, 2025 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numbe

February 26, 2025 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K ☑ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTI

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K ☑ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 for the transition period from to Commission file number: 001-39367 Lemonad

February 26, 2025 S-8

As filed with the Securities and Exchange Commission on February 26, 2025

As filed with the Securities and Exchange Commission on February 26, 2025 Registration No.

February 26, 2025 EX-10.33

Amended and Restated Customer Investment Agreement dated February 3, 2025, between Lemonade, Inc. and GC Customer Value Arranger LLC, as Arranger on behalf of the Investors

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

February 26, 2025 EX-19.1

nsider Tra

EXHIBIT 19.1 Lemonade, Inc. Insider Trading Compliance Policy Lemonade, Inc. (the “Company”) seeks to promote a culture that encourages ethical conduct and a commitment to compliance with the law. We require our personnel to comply at all times with federal laws and regulations governing insider trading. This policy sets forth procedures designed to help comply with these laws and regulations. Per

February 26, 2025 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-8 (Form Type) LEMONADE, INC. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered (1) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Common Stock, par value $0.00001

February 25, 2025 EX-99.1

Shareholder Letter Q4 2024 2 Dear Shareholders, Our fourth quarter saw accelerating topline growth, expense stability, significantly narrowing Adj. EBITDA losses, and $27 million of Adjusted Free Cash Flow (“Adj. FCF”)1. By any standard, it was our b

Shareholder Letter Q4 2024 2 Dear Shareholders, Our fourth quarter saw accelerating topline growth, expense stability, significantly narrowing Adj.

February 25, 2025 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 25, 2025 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File N

February 7, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 3, 2025 LEMONADE, INC. (

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 3, 2025 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Nu

January 6, 2025 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): January 2, 2025 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Num

October 31, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

October 30, 2024 EX-99.1

Shareholder Letter Q3 2024 Dear Shareholders, Our third quarter results were very strong, headlined by accelerating topline growth, relative stability in expenses, and $48 million of net cash flow (“NCF”). Here’s a look at the key metrics: • Cash Flo

lmndq32024shlfinal103024 Shareholder Letter Q3 2024 Dear Shareholders, Our third quarter results were very strong, headlined by accelerating topline growth, relative stability in expenses, and $48 million of net cash flow (“NCF”).

October 30, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 30, 2024 LEMONADE, INC. (

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 30, 2024 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Nu

July 31, 2024 EX-10.5

Whole Quota Share Reinsurance Contract issued to Lemonade Insurance Company and Metromile Insurance Company by the Subscribing Reinsurer, Swiss Reinsurance America Corporation effective July 1, 2024

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

July 31, 2024 EX-10.3

Whole Quota Share Reinsurance Contract issued to Lemonade Insurance Company, Lemonade Insurance N.V. and Metromile Insurance Company by the Subscribing Reinsurer, Hannover Ruck SE effective July 1, 2024

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

July 31, 2024 EX-10.2

Property Per Risk Excess of Loss Contract issued to Lemonade Insurance Company and Metromile Insurance Company by Subscribing Reinsurers effective July 1, 2024

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

July 31, 2024 EX-10.1

Amended and Restated Customer Investment Agreement dated June 27, 2024 between Lemonade, Inc. and GC Customer Value Arranger LLC as Arranger on behalf of the Investors

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

July 31, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

July 31, 2024 EX-10.4

Whole Quota Share Reinsurance Contract issued to Lemonade Insurance Company, Lemonade Insurance N.V. and Metromile Insurance Company by the Subscribing Reinsurer, MAPFRE Re (Spain) dated effective July 1, 2024

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

July 30, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 30, 2024 LEMONADE, INC. (Exa

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 30, 2024 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numbe

July 30, 2024 EX-99.1

Shareholder Letter Q2 2024 2 Dear Shareholders, Our second quarter results were excellent, headlined by robust topline growth, relative stability in expenses, and we were net cash flow ("NCF") positive. We also wanted to highlight our upcoming Invest

lmndshlq22024final Shareholder Letter Q2 2024 2 Dear Shareholders, Our second quarter results were excellent, headlined by robust topline growth, relative stability in expenses, and we were net cash flow ("NCF") positive.

June 11, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 5, 2024 LEMONADE, INC. (Exac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 5, 2024 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Number

May 1, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

April 30, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 30, 2024 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numb

April 30, 2024 EX-99.1

Shareholder Letter Q1 2024 2 Dear Shareholders, Our first quarter results were excellent, and we’re pleased to note that we now expect cash flow breakeven by year-end 2024. Here’s a quick look at our operating metrics for Q1: • Top line: At $794 mill

shareholderletterq12024f Shareholder Letter Q1 2024 2 Dear Shareholders, Our first quarter results were excellent, and we’re pleased to note that we now expect cash flow breakeven by year-end 2024.

April 24, 2024 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amend

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

April 24, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amend

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

February 29, 2024 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-8 (Form Type) LEMONADE, INC. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered (1) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Common Stock, par value $0.00001

February 29, 2024 S-8

As filed with the Securities and Exchange Commission on February 28, 2024

As filed with the Securities and Exchange Commission on February 28, 2024 Registration No.

February 28, 2024 EX-10.32

Agreement by and between

1 Severance Agreement THIS SEVERANCE AGREEMENT (the “Severance Agreement”) is entered into as of the Effective Date (as defined below) between Lemonade, Inc.

February 28, 2024 EX-97.1

Policy Relating to Recovery of Erroneously Awarded Compensation

LEMONADE, INC. POLICY FOR RECOVERY OF ERRONEOUSLY AWARDED COMPENSATION Lemonade, Inc. (the “Company”) has adopted this Policy for Recovery of Erroneously Awarded Compensation (the “Policy”), effective as of October 25, 2023 (the “Effective Date”). Capitalized terms used in this Policy but not otherwise defined herein are defined in Section 11. 1. Persons Subject to Policy This Policy shall apply t

February 28, 2024 EX-4.3

Description of Securi

Exhibit 4.3 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934, AS AMENDED Lemonade, Inc. has one class of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”): our common stock, par value $0.00001 per share. References herein to, “we,” “us,” “our”, and “our company” refer to

February 28, 2024 EX-10.26

Amended and Restated Customer Investment Agreement dated January 8, 2024, between Lemonade, Inc. and GC Customer Value Arranger LLC, as Arranger on behalf of the Investors

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

February 28, 2024 EX-21.1

List of Subsidiaries of Lemonade, Inc.

EXHIBIT 21.1 Subsidiaries of Lemonade, Inc. Name State or Other Jurisdiction of Incorporation or Organization Lemonade Agency B.V. Netherlands Lemonade B.V. Netherlands Lemonade E&S Insurance Agency, LLC Delaware Lemonade Insurance Agency, LLC New York Lemonade Insurance Company New York Lemonade Insurance N.V. Netherlands Lemonade Life Insurance Agency, LLC Delaware Lemonade Ltd. Israel Lemonade

February 28, 2024 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K ☑ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTI

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K ☑ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 for the transition period from to Commission file number: 001-39367 Lemonad

February 27, 2024 EX-99.1

\ Shareholder Letter Q4 2023 2 Dear Shareholders, We’re happy to report on a strong fourth quarter and an upbeat outlook for 2024. • Top line: At $747 million, in-force premium (IFP) grew by 20% year on year, while revenue grew 31%. • Loss Ratio: At

\ Shareholder Letter Q4 2023 2 Dear Shareholders, We’re happy to report on a strong fourth quarter and an upbeat outlook for 2024.

February 27, 2024 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 27, 2024 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File N

February 14, 2024 SC 13G/A

LMND / Lemonade, Inc. / Schreiber Daniel A. - SC 13G/A Passive Investment

SC 13G/A 1 danielschreiberschedule13g.htm SC 13G/A United States Securities and Exchange Commission Washington, D.C. 20549 Schedule 13G (Rule 13d-102) Information to be Included in Statements Filed Pursuant to § 240.13d-1(b), (c) and (d) and Amendments Thereto Filed Pursuant to § 240.13d-2 UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 2)* Lemonade, Inc. (Name of Issuer) Common Stock, pa

February 14, 2024 SC 13G/A

LMND / Lemonade, Inc. / Wininger Shai - SC 13G/A Passive Investment

SC 13G/A 1 shaiwiningerschedule13g2024.htm SC 13G/A United States Securities and Exchange Commission Washington, D.C. 20549 Schedule 13G (Rule 13d-102) Information to be Included in Statements Filed Pursuant to § 240.13d-1(b), (c) and (d) and Amendments Thereto Filed Pursuant to § 240.13d-2 UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 3)* Lemonade, Inc. (Name of Issuer) Common Stock, p

February 13, 2024 SC 13G/A

LMND / Lemonade, Inc. / SoftBank Group Capital Ltd Passive Investment

SC 13G/A 1 formsc13ga.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A* Under the Securities Exchange Act of 1934 (Amendment No. 1)* Lemonade, Inc. (Name of Issuer) Common Stock, $0.00001 par value per share (Title of Class of Securities) 52567D 107 (CUSIP Number) December 31, 2023 (Date of Event which Requires Filing of this Statement) Check the appropria

February 13, 2024 SC 13G/A

LMND / Lemonade, Inc. / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SC 13G/A 1 tv01327-lemonadeinc.htm SCHEDULE 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 2)* Name of issuer: Lemonade Inc Title of Class of Securities: Common Stock CUSIP Number: 52567D107 Date of Event Which Requires Filing of this Statement: December 29, 2023 Check the appropriate box to designate the rule

January 29, 2024 SC 13G

LMND / Lemonade, Inc. / BlackRock Inc. Passive Investment

SC 13G 1 us52567d1072012924.txt us52567d1072012924.txt SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No: ) Lemonade, Inc - (Name of Issuer) Common Stock - (Title of Class of Securities) 52567D107 - (CUSIP Number) December 31, 2023 - (Date of Event Which Requires Filing of this Statement) Check the appropriate box to desi

January 11, 2024 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): January 8, 2024 LEMONADE, INC. (E

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): January 8, 2024 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Num

December 20, 2023 EX-3.1

Amended and Restated By-laws of Lemonade, Inc.

Amended and Restated Bylaws of Lemonade, Inc. (a Delaware Public Benefit Corporation) Dated as of December 14, 2023 i Table of Contents Page Article I - Corporate Offices ......................................................................................................................... 1 1.1 Registered Office ...................................................................................

December 20, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 14, 2023 LEMONADE, INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 14, 2023 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File N

November 21, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 17, 2023 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File N

November 9, 2023 EX-4.3

Form of Indenture.

Exhibit 4.3 LEMONADE, INC. INDENTURE Dated as of , 20 [] Trustee TABLE OF CONTENTS Page ARTICLE I. DEFINITIONS AND INCORPORATION BY REFERENCE 1 Section 1.1. Definitions. 1 Section 1.2. Other Definitions. 4 Section 1.3. Incorporation by Reference of Trust Indenture Act. 5 Section 1.4. Rules of Construction. 5 ARTICLE II. THE SECURITIES 6 Section 2.1. Issuable in Series. 6 Section 2.2. Establishment

November 9, 2023 EX-FILING FEES

Filing Fee Table

Exhibit 107 CALCULATION OF FILING FEE TABLE S-3ASR (Form Type) Lemonade, Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Newly Registered Securities Fees to Be Paid Eq

November 9, 2023 S-3ASR

As filed with the Securities and Exchange Commission on November 9, 2023

As filed with the Securities and Exchange Commission on November 9, 2023 Registration No.

November 3, 2023 EX-10.1

Transition Letter Agreement by and between John Peters and Lemonade, Inc. dated November 1, 2023

Exhibit 10.1 November 1, 2023 John Peters via email Dear John: This letter memorializes the understanding between you and Lemonade, Inc. (the “Company”) regarding a reduction in your duties and the corresponding reduction to your annual base salary. You have agreed that, in connection with a reduction of your duties to thirty hours per week of service to the Company, your annual base salary will b

November 3, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

November 3, 2023 EX-33.3

Certification of Chief Financial Officer pursuant to 18 U.S.C. Section 1350.

Exhibit 32.3 CERTIFICATION PURSUANT TO 18 U.S.C. SECTION 1350, AS ADOPTED PURSUANT TO SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002 In connection with the Quarterly Report on Form 10-Q of Lemonade, Inc. (the “Company”) for the period ended September 30, 2023, as filed with the Securities and Exchange Commission on the date hereof (the “Report”), I, Tim Bixby, Chief Financial Officer of the Company

November 1, 2023 EX-99.1

Shareholder Letter Q3 2023 2 Dear Shareholders, We’re happy to report that our third quarter delivered strong results across our key metrics versus Q3 2022. • Top line: At $719 million, in-force premium (IFP) grew 18%. • Operating Expense: At $98 mil

Shareholder Letter Q3 2023 2 Dear Shareholders, We’re happy to report that our third quarter delivered strong results across our key metrics versus Q3 2022.

November 1, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 1, 2023 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Nu

August 4, 2023 EX-10.6

Contract issued to Lemonade Insurance Company and Lemonade Insurance N.V. by the Subscribing Reinsurer Swiss Re, dated July 1, 2023

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

August 4, 2023 EX-10.2

Property Per Risk Excess of Loss Reinsurance Contract issued to Lemonade Insurance Company and Lemonade Insurance N.V. by the Subscribing Reinsurers, dated July 1,

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

August 4, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

August 4, 2023 EX-10.5

Contract issued to Lemonade Insurance Company and Lemonade Insurance N.V. by the Subscribing Reinsurer MAPFRE Re (Spain), dated July 1, 2023

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

August 4, 2023 EX-10.1

Customer Investment Agreement, dated June 28, 2023, between Lemonade, Inc. and GC Customer Value Arranger, LLC, as Arranger on behalf of the Investors

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

August 4, 2023 EX-10.4

Contract issued to Lemonade Insurance Company and Lemonade Insurance N.V. by the Subscribing Reinsurer Hannover Ruck SE, dated July 1, 2023

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

August 4, 2023 EX-10.3

Automatic Facultative Property Per Risk Excess of Loss Reinsurance Contract issued to Lemonade Insurance Company by the Subscribing Reinsurer Arch Reinsurance Company, dated July 1, 2023

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private and confidential.

August 2, 2023 EX-99.1

Shareholder Letter Q2 2023 2 Dear Shareholders, 2023’s second quarter delivered better than expected top and bottom lines, as well as reinsurance and growth financing programs which herald a step function improvement in our capital efficiency, enabli

lmndshareholderletterq22 Shareholder Letter Q2 2023 2 Dear Shareholders, 2023’s second quarter delivered better than expected top and bottom lines, as well as reinsurance and growth financing programs which herald a step function improvement in our capital efficiency, enabling both faster growth and deeper cash reserves: • Top line: At $687 million, in-force premium (IFP) grew by 50% year over year.

August 2, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 2, 2023 LEMONADE, INC. (Ex

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 2, 2023 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numb

June 29, 2023 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 28, 2023 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numbe

June 27, 2023 8-K

Entry into a Material Definitive Agreement

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 21, 2023 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numbe

June 9, 2023 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 7, 2023 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Number

June 9, 2023 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-3 (Form Type) LEMONADE, INC. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered(1) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Carry

June 9, 2023 S-3ASR

As filed with the Securities and Exchange Commission on June 9, 2023

As filed with the Securities and Exchange Commission on June 9, 2023 Registration No.

May 5, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

May 3, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 3, 2023 LEMONADE, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 3, 2023 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Number)

May 3, 2023 EX-99.1

Shareholder Letter Q1 2023 2 Dear Shareholders, The first quarter of 2023 was strong, clocking solid performance across our key metrics. Notwithstanding persistent inflation and heightened frequency of severe weather events, the primary dials with wh

lmndshareholderletterq12 Shareholder Letter Q1 2023 2 Dear Shareholders, The first quarter of 2023 was strong, clocking solid performance across our key metrics.

April 28, 2023 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amend

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

April 28, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amend

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

April 5, 2023 SC 13G/A

LMND / Lemonade Inc / Clavel Alex - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A* Under the Securities Exchange Act of 1934 (Amendment No. 1)* Lemonade, Inc. (Name of Issuer) Common Stock, $0.00001 par value per share (Title of Class of Securities) 52567D 107 (CUSIP Number) March 31, 2023 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule

March 10, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 10, 2023 LEMONADE, INC. (Ex

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 10, 2023 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numb

March 3, 2023 S-8

As filed with the Securities and Exchange Commission on March 3, 2023

As filed with the Securities and Exchange Commission on March 3, 2023 Registration No.

March 3, 2023 EX-21.1

List of Subsidiaries of Lemonade, Inc.

EXHIBIT 21.1 Subsidiaries of Lemonade, Inc. Name State or Other Jurisdiction of Incorporation or Organization Lemonade Agency B.V. Netherlands Lemonade B.V. Netherlands Lemonade E&S Insurance Agency, LLC Delaware Lemonade Insurance Agency, LLC New York Lemonade Insurance Company New York Lemonade Insurance N.V. Netherlands Lemonade Life Insurance Agency, LLC Delaware Lemonade Ltd. Israel Lemonade

March 3, 2023 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K ☑ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTI

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K ☑ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 for the transition period from to Commission file number: 001-39367 Lemonad

March 3, 2023 EX-10.37

Personal Automobile Quota Share Reinsurance Contract issued to Metromile Insurance Company by Swiss Re America Corporation, dated February 24, 2023

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10), because it is both not material and the type of information that the registrant treats as private or confidential.

March 3, 2023 EX-10.36

Automobile Quota Share Reinsurance Contract issued to Metromile Insurance Company by the Subscribing Reinsurer MAPFRE Re (Spain), dated March 23, 2023

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

March 3, 2023 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-8 (Form Type) LEMONADE, INC. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title (1) Fee Calculation Rule Amount Registered (2) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Common Stock, par value $0.0

March 3, 2023 EX-4.2

Amended and Restated Investors' Rights Agreement by and between Lemonade, Inc. and certain security holders of Lemonade, Inc., dated October 14, 2022.

Execution copy AMENDED AND RESTATED INVESTORS’ RIGHTS AGREEMENT This AMENDED AND RESTATED INVESTORS’ RIGHTS AGREEMENT (the “Agreement”) is made as of October 14, 2022 (the “Effective Date”), by and among Lemonade, Inc.

March 2, 2023 NT 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING SEC File Number: 001-39367 CUSIP Number: 52567D 107 (Check one): ⌧ Form 10-K □ Form 20-F □ Form 11-K □ Form 10-Q □ Form 10-D □ Form N-SAR □ Form N-CSR For Period Ended: December 31, 2022 □ Transition Report on Form 10-K □ Transition Report on Form 20-F □ Transition Report on Form 11-K □

March 2, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 24, 2023 LEMONADE, INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 24, 2023 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File N

February 22, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 22, 2023 LEMONADE, INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 22, 2023 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File N

February 22, 2023 EX-99.1

Shareholder Letter Q4 2022 2 Dear Shareholders, In Short • Top line: Our fourth quarter saw 64% top line growth, with IFP of $625 million. • Loss Ratio: Steady and significant improvement in loss ratios across the book. Gross Loss Ratio was 89% for t

shareholderletterq420222 Shareholder Letter Q4 2022 2 Dear Shareholders, In Short • Top line: Our fourth quarter saw 64% top line growth, with IFP of $625 million.

February 14, 2023 SC 13G

LMND / Lemonade Inc / Schreiber Daniel A. - SC 13G Passive Investment

United States Securities and Exchange Commission Washington, D.C. 20549 Schedule 13G (Rule 13d-102) Information to be Included in Statements Filed Pursuant to § 240.13d-1(b), (c) and (d) and Amendments Thereto Filed Pursuant to § 240.13d-2 UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1)* Lemonade, Inc. (Name of Issuer) Common Stock, par value $0.00001 (Title of Class of Securities) 525

February 14, 2023 SC 13G

LMND / Lemonade Inc / Wininger Shai - SC 13G Passive Investment

United States Securities and Exchange Commission Washington, D.C. 20549 Schedule 13G (Rule 13d-102) Information to be Included in Statements Filed Pursuant to § 240.13d-1(b), (c) and (d) and Amendments Thereto Filed Pursuant to § 240.13d-2 UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 2)* Lemonade, Inc. (Name of Issuer) Common Stock, par value $0.00001 (Title of Class of Securities) 525

February 9, 2023 SC 13G/A

LMND / Lemonade Inc / VANGUARD GROUP INC - SCHEDULE 13G/A Passive Investment

SC 13G/A 1 tv01289-lemonadeinc.htm SCHEDULE 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No.: 1)* Name of issuer: Lemonade Inc. Title of Class of Securities: Common Stock CUSIP Number: 52567D107 Date of Event Which Requires Filing of this Statement: December 30, 2022 Check the appropriate box to designate the rule

December 8, 2022 8-A12B

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 LEMONADE, INC. (Exact Name of Registrant as S

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 LEMONADE, INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or other jurisdiction of Incorporation or Organization) 32-0469673 (I.R.S. Employer Identification No.) 5 Cro

December 7, 2022 RW

December 6, 2022

December 6, 2022 Via EDGAR United States Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.

December 7, 2022 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-3 (Form Type) LEMONADE, INC. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered(1) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Carry

December 7, 2022 EX-99.1

Metromile, Inc. June 30, 2022 unaudited consolidated financial statements

METROMILE, INC. CONSOLIDATED BALANCE SHEETS (In thousands, except share and per share amounts) June 30, 2022 December 31, 2021 (unaudited) Assets Investments Marketable securities - restricted (amortized cost of $63,833 and $62,741) $ 63,256 $ 62,625 Total investments 63,256 62,625 Cash and cash equivalents 69,576 120,940 Restricted cash and cash equivalents 33,031 42,881 Receivable for securities

December 7, 2022 S-3ASR

As filed with the Securities and Exchange Commission on December 6, 2022

As filed with the Securities and Exchange Commission on December 6, 2022 Registration No.

December 2, 2022 8-A12B

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 LEMONADE, INC. (Exact Name of Registrant as S

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 LEMONADE, INC. (Exact Name of Registrant as Specified in Its Charter) Delaware (State or other jurisdiction of Incorporation or Organization) 32-0469673 (I.R.S. Employer Identification No.) 5 Cro

November 30, 2022 S-3

As filed with the Securities and Exchange Commission on November 30, 2022

As filed with the Securities and Exchange Commission on November 30, 2022 Registration No.

November 30, 2022 EX-99.1

Metromile, Inc. June 30, 2022 unaudited consolidated financial statements

METROMILE, INC. CONSOLIDATED BALANCE SHEETS (In thousands, except share and per share amounts) June 30, 2022 December 31, 2021 (unaudited) Assets Investments Marketable securities - restricted (amortized cost of $63,833 and $62,741) $ 63,256 $ 62,625 Total investments 63,256 62,625 Cash and cash equivalents 69,576 120,940 Restricted cash and cash equivalents 33,031 42,881 Receivable for securities

November 30, 2022 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-3 (Form Type) LEMONADE, INC. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered(1) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Carry

November 9, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2022 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

November 9, 2022 EX-4.4

Amendment No. 1 to Warrant Agreement, dated June 17, 2022 between Metromile, Inc., Continental Stock Transfer & Trust Company, as warrant agent, an American Stock Transfer & Trust Company, as successor warrant agent

AMENDMENT NO. 1 TO WARRANT AGREEMENT THIS AMENDMENT NO. 1 TO WARRANT AGREEMENT (this ?Amendment?), is made and entered into as of June 17, 2022, by and among Metromile, Inc., a Delaware corporation (f/k/a ?INSU Acquisition Corp. II?, the ?Company?), Continental Stock Transfer & Trust Company, a New York limited purpose trust company, as warrant agent (?Continental?), and American Stock Transfer &

November 8, 2022 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 8, 2022 LEMONADE, INC. (

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 8, 2022 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Nu

November 8, 2022 EX-99.1

Shareholder Letter Q3 2022 2 Dear Shareholders, We're very happy to report on another strong quarter, with both top and bottom lines coming in ahead of our expectations. Our third quarter saw 76% top line growth, with IFP of $609 million, and at $66

shareholderletterq320221 Shareholder Letter Q3 2022 2 Dear Shareholders, We're very happy to report on another strong quarter, with both top and bottom lines coming in ahead of our expectations.

October 20, 2022 EX-10.2

Warrant Agreement, dated as of October 14, 2022, by and between Lemonade, Inc. and Chewy Insurance Services, LLC

Exhibit 10.2 Certain identified information has been excluded from this exhibit because it is both not material and is the type that the registrant treats as private or confidential. Information that was omitted has been noted in this document with a placeholder identified by the mark ?[***]?. WARRANT TO PURCHASE COMMON STOCK THE SECURITIES REPRESENTED BY THIS INSTRUMENT HAVE NOT BEEN REGISTERED U

October 20, 2022 EX-10.1

Omnibus Agreement, dated as of October 14, 2022, by and between Lemonade, Inc. and Chewy Insurance Services, LLC

Exhibit 10.1 Certain identified information has been excluded from this exhibit because it is both not material and is the type that the registrant treats as private or confidential. Information that was omitted has been noted in this document with a placeholder identified by the mark ?[***]?. OMNIBUS AGREEMENT Dated as of October 14, 2022 by and between LEMONADE, INC. and CHEWY INSURANCE SERVICES

October 20, 2022 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 14, 2022 LEMONADE, INC. (

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 14, 2022 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Nu

October 11, 2022 8-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 7, 2022 (July 28, 2022)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 7, 2022 (July 28, 2022) LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (C

October 11, 2022 EX-99.3

UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION

UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION The following unaudited pro forma condensed combined financial statements combine the separate historical financial information of Lemonade, Inc.

August 30, 2022 SC 13G

LMND / Lemonade Inc / Clavel Alex - SC 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G* Under the Securities Exchange Act of 1934 Lemonade, Inc. (Name of Issuer) Common Stock, $0.00001 par value per share (Title of Class of Securities) 52567D 107 (CUSIP Number) August 24, 2022 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which th

August 30, 2022 SC 13G/A

LMND / Lemonade Inc / Nyatta Mwashuma Kamata - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G* Under the Securities Exchange Act of 1934 (Amendment No. 1) Lemonade, Inc. (Name of Issuer) Common Stock, $0.00001 par value per share (Title of Class of Securities) 52567D 107 (CUSIP Number) August 24, 2022 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pu

August 9, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2022 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

August 9, 2022 EX-10.1

Property Per Risk Excess of Loss Reinsurance Contract Issued to Lemonade Insurance Company and Lemonade Insurance N.V. by the Subscribing Issuers

PROPERTY PER RISK EXCESS OF LOSS REINSURANCE CONTRACT issued to LEMONADE INSURANCE COMPANY New York, New York and LEMONADE INSURANCE N.

August 9, 2022 EX-10.2

Automatic Facultative Property Per Risk Excess of Loss Reinsurance Contract issued to Lemonade Insurance Company by the Subscribing Reinsurer

AUTOMATIC FACULTATIVE PROPERTY PER RISK EXCESS OF LOSS REINSURANCE CONTRACT issued to LEMONADE INSURANCE COMPANY New York, New York including any and/or all companies that are or may hereafter become affiliated therewith 1 AUTOMATIC FACULTATIVE PROPERTY PER RISK EXCESS OF LOSS REINSURANCE CONTRACT Article TABLE OF CONTENTS Page Preamble .

August 8, 2022 EX-99.1

Shareholder Letter Q2 2022 2 Dear Shareholders, In Short: • Second quarter was strong: Both top and bottom lines came in ahead of expectations, with IFP at $458m, Net Loss at $68m and Adjusted EBITDA loss at $50m. • Cross-Sells trended up: 23% of sal

shareholderletterq220228 Shareholder Letter Q2 2022 2 Dear Shareholders, In Short: • Second quarter was strong: Both top and bottom lines came in ahead of expectations, with IFP at $458m, Net Loss at $68m and Adjusted EBITDA loss at $50m.

August 8, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 8, 2022 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numb

July 28, 2022 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-8 (Form Type) LEMONADE, INC. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title (1) Fee Calculation Rule Amount Registered (2) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Common Stock, par value $0.0

July 28, 2022 EX-99.1

Lemonade Completes Acquisition of Metromile In return for under $145 million in stock, Lemonade receives over $155 million in cash, over $110 million in car premiums, an insurance entity with 49 state licenses, and precision data from half a billion

Exhibit 99.1 Lemonade Completes Acquisition of Metromile In return for under $145 million in stock, Lemonade receives over $155 million in cash, over $110 million in car premiums, an insurance entity with 49 state licenses, and precision data from half a billion auto trips July 28, 2022?Lemonade (NYSE: LMND), the insurance company powered by AI and social impact, today announced the closing of the

July 28, 2022 S-8

As filed with the Securities and Exchange Commission on July 28, 2022

As filed with the Securities and Exchange Commission on July 28, 2022 Registration No.

July 28, 2022 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 28, 2022 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numbe

June 14, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Other Events, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 8, 2022 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Number

May 10, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amend

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

May 10, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

May 9, 2022 EX-99.1

Shareholder Letter Q1 2022 2 Dear Shareholders, We're happy to report that the year kicked off with a strong first quarter. Notwithstanding the turbulent market forces and macroeconomic environment, both our top line and our bottom line came in ahead

Shareholder Letter Q1 2022 2 Dear Shareholders, We're happy to report that the year kicked off with a strong first quarter.

May 9, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 9, 2022 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Number)

April 29, 2022 DEF 14A

definitive proxy statement on Schedule 14A, filed with the Commission on April 29, 2022

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

April 29, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amend

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

April 14, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 14, 2022 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numb

March 9, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 9, 2022 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numbe

March 1, 2022 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K ☑ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 ☐ TRANSITION REPORT PURSUANT TO SECTI

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 for the transition period from to Commission file number: 001-39367 Lemonad

February 23, 2022 EX-99.1

Shareholder Letter Q4 2021 2 Dear Shareholders, 2021 was a very productive year for us, and we ended it materially larger, more diversified, and strategically stronger than ever. The year kicked off with a substantial capital raise that we expect wil

Shareholder Letter Q4 2021 2 Dear Shareholders, 2021 was a very productive year for us, and we ended it materially larger, more diversified, and strategically stronger than ever.

February 23, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 23, 2022 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File N

February 15, 2022 SC 13G/A

LMND / Lemonade Inc / Wininger Shai - SC 13G/A Passive Investment

United States Securities and Exchange Commission Washington, D.C. 20549 Schedule 13G (Rule 13d-102) Information to be Included in Statements Filed Pursuant to ? 240.13d-1(b), (c) and (d) and Amendments Thereto Filed Pursuant to ? 240.13d-2 UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1)* Lemonade, Inc. (Name of Issuer) Common Stock, par value $0.00001 (Title of Class of Securities) 525

February 14, 2022 SC 13G/A

LMND / Lemonade Inc / Aleph, L.P. - SC 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1 (b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2 (b) (Amendment No. 1)* Lemonade, Inc. (Name of Issuer) Common Stock, par value $0.00001 (Title of Class of Securities) 52567D107 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Fi

February 14, 2022 SC 13G

LMND / Lemonade Inc / Lemonade, Inc. - SC 13G Passive Investment

United States Securities and Exchange Commission Washington, D.C. 20549 Schedule 13G (Rule 13d-102) Information to be Included in Statements Filed Pursuant to ? 240.13d-1(b), (c) and (d) and Amendments Thereto Filed Pursuant to ? 240.13d-2 UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1)* Lemonade, Inc. (Name of Issuer) Common Stock, par value $0.00001 (Title of Class of Securities) 525

February 11, 2022 SC 13G/A

LMND / Lemonade Inc / SEQUOIA CAPITAL ISRAEL VENTURE V HOLDINGS, L.P. - SC 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G (Rule 13d-102) Information to be Included in Statements Filed Pursuant to ? 240.13d-1(b), (c) and (d) and Amendments Thereto Filed Pursuant to ? 240.13d-2 Under the Securities Exchange Act of 1934 (Amendment No. 1)* Lemonade, Inc. (Name of Issuer) Common Stock, par value $0.00001 per share (Title of Class of Securities) 52567D1

February 10, 2022 SC 13G

LMND / Lemonade Inc / VANGUARD GROUP INC - SCHEDULE 13G Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 Name of issuer: Lemonade Inc. Title of Class of Securities: Common Stock CUSIP Number: 52567D107 Date of Event Which Requires Filing of this Statement: December 31, 2021 Check the appropriate box to designate the rule pursuant to which this Schedule is filed: ☒ Rule 13d-1(b) ☐ Rule 13d-

December 29, 2021 424B3

MERGER PROPOSAL — YOUR VOTE IS VERY IMPORTANT

TABLE OF CONTENTS ? Filed Pursuant to Rule 424(b)(3)? ?Registration No. 333-261629? MERGER PROPOSAL???YOUR VOTE IS VERY IMPORTANT Dear Metromile Stockholder: You are cordially invited to attend a special meeting (the ?Metromile special meeting?) of the stockholders of Metromile, Inc., a Delaware corporation (the ?Company,? ?Metromile?, ?we? or ?us?), to be held on February 1, 2022, at 9:00 a.m., P

December 28, 2021 S-4/A

As filed with the U.S. Securities and Exchange Commission on December 27, 2021

TABLE OF CONTENTS As filed with the U.S. Securities and Exchange Commission on December 27, 2021 Registration No. 333-261629? ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? Amendment No. 1 to FORM S-4 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 ? Lemonade, Inc. (Exact Name of Registrant as Specified in Its Charter) ? ? Delaware (State of Incorporation) ?

December 27, 2021 CORRESP

Lemonade, Inc. 5 Crosby Street, 3rd Floor New York, NY 10013

Lemonade, Inc. 5 Crosby Street, 3rd Floor New York, NY 10013 December 27, 2021 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549-6010 Re: Lemonade, Inc. Registration Statement on Form S-4 File No. 333-261629 Request for Acceleration of Effectiveness Ladies and Gentlemen: In accordance with Rule 461 promulgated under

December 14, 2021 EX-99.2

Form of Proxy Card for Special Meeting of Metromile, Inc.

Exhibit 99.2 ? VIEW MATERIALS & VOTE w SCAN TO METROMILE, INC. 425 MARKET STREET #700 SAN FRANCISCO, CALIFORNIA 94105 (888) 242-5204 VOTE BY INTERNET Before The Meeting - Go to www.proxyvote.com or scan the QR Barcode above Use the Internet to transmit your voting instructions and for electronic delivery of information up until 11:59 p.m. Eastern Time the day before the cut-off date or meeting dat

December 14, 2021 EX-10.13

At-Will Employment, Confidential Information, Invention Assignment and Arbitration Agreement, dated February 7, 2013, by and between MetroMile, Inc. and Dan Preston (included as Exhibit 10.25 to Legacy Metromile’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 13, 2021).

Exhibit 10.13 ? METROMILE, INC. AT-WILL EMPLOYMENT, CONFIDENTIAL INFORMATION, INVENTION ASSIGNMENT, AND ARBITRATION AGREEMENT ? As a condition of my employment with MetroMile, Inc., its subsidiaries, affiliates, successors or assigns (together, the ?Company?), and in consideration of my employment with the Company and my receipt of the compensation now and hereafter paid to me by Company, I agree

December 14, 2021 EX-10.6

Metromile, Inc. Amended and Restated 2011 Equity Incentive Plan, as amended (included as Exhibit 10.17 to Legacy Metromile’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on December 31, 2021).

Exhibit 10.6 METROMILE, INC. 2011 EQUITY INCENTIVE PLAN 1. Purposes of the Plan. The purposes of this Plan are: ? to attract and retain the best available personnel for positions of substantial responsibility, ? to provide additional incentive to Employees, Directors and Consultants, and ? to promote the success of the Company?s business. The Plan permits the grant of Incentive Stock Options, Nons

December 14, 2021 EX-10.10

Offer Letter, dated September 21, 2017, by and between MetroMile, Inc. and Lindsay Alexovich (included as Exhibit 10.21 to Legacy Metromile’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 13, 2021).

? Exhibit 10.10 ? ? September 21, 2017 ? Lindsay Alexovich, ? I am pleased to offer you a full-time position with Metromile, Inc. (the ?Company?) in San Francisco (Headquarters), as a Vice President, Controller, commencing on or before October 30, 2017. ? Duties and Responsibilities. You will initially report to Carrie Dolan, CFO. You shall have such job duties and responsibilities commensurate wi

December 14, 2021 EX-10.12

Form of MetroMile, Inc. Confidential Information and Invention Assignment Agreement (included as Exhibit 10.24 to Legacy Metromile’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 13, 2021).

? Exhibit 10.12 ? METROMILE, INC. CONFIDENTIAL INFORMATION AND INVENTION ASSIGNMENT AGREEMENT ? As a condition of my business relationship with MetroMile, Inc., its subsidiaries, affiliates, successors or assigns (together, the ?Company?), and in consideration of my business relationship with the Company and my receipt of the compensation now and hereafter paid to me on behalf of Company, I agree

December 14, 2021 EX-10.15

Office Lease, dated May 16, 2019, by and between 425 MKT REIT, LLC and Metromile, Inc. (included as Exhibit 10.15 to Legacy Metromile’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on December 31, 2020).

Exhibit 10.15 ? OFFICE LEASE ? 425 MKT REIT, LLC (LANDLORD) ? AND ? METROMILE, INC. (TENANT) ? 425 MARKET STREET San Francisco, California ? ? ? ? TABLE OF CONTENTS ? Page ARTICLE ONE BASIC LEASE PROVISIONS 1 1.01 BASIC LEASE PROVISIONS 1 1.02 ENUMERATION OF EXHIBITS & RIDER(S) 3 1.03 DEFINITIONS 3 ARTICLE TWO PREMISES, TERM AND FAILURE TO GIVE POSSESSION 9 2.01 LEASE OF PREMISES 9 2.02 TERM 9 2.0

December 14, 2021 EX-10.9

Offer Letter, dated January 18, 2019, by and between MetroMile, Inc. and Paw Andersen (included as Exhibit 10.20 to Legacy Metromile’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 13, 2021).

? Exhibit 10.9 ? ? January 18, 2019 ? Paw Andersen, ? I am pleased to offer you a full-time position with Metromile, Inc. (the ?Company?) in San Francisco, as a Chief Technology Officer, commencing on or before March 12, 2019. ? Duties and Responsibilities. You will initially report to Dan Preston, CEO. You shall have such job duties and responsibilities commensurate with your position, which duti

December 14, 2021 S-4

As filed with the U.S. Securities and Exchange Commission on December 14, 2021

Table of Contents As filed with the U.S. Securities and Exchange Commission on December 14, 2021 Registration No. 333- ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-4 ? REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Lemonade, Inc. (Exact Name of Registrant as Specified in Its Charter) ? ? ? ? Delaware (State of Incorporation) 4899 (Primary Standard Ind

December 14, 2021 EX-10.2

Form of Indemnification Agreement by and between Legacy Metromile and its directors and officers (included as Exhibit 10.1 to Legacy Metromile’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on February 11, 2021).

Exhibit 10.2 ? METROMILE, INC. ? INDEMNIFICATION AGREEMENT ? This INDEMNIFICATION AGREEMENT (this ?Agreement?) is dated as of , 20 and is between Metromile, Inc., a Delaware corporation (the ?Company?), and (?Indemnitee?). ? RECITALS ? A. Indemnitee?s service to the Company substantially benefits the Company. ? B. Individuals are reluctant to serve as directors or officers of corporations or in ce

December 14, 2021 EX-10.3

Metromile, Inc. 2021 Equity Incentive Plan (included as Annex B to Legacy Metromile’s Proxy Statement/Prospectus included in the Registration Statement on Form S-4, filed with the Securities and Exchange Commission on January 15, 2021).

Table of Contents Exhibit 10.3 METROMILE, INC. 2021 EQUITY INCENTIVE PLAN ADOPTED BY THE BOARD OF DIRECTORS: [DATE] APPROVED BY THE STOCKHOLDERS: [DATE] ? ? ? Table of Contents TABLE OF CONTENTS Annex B Page 1. GENERAL. B-1 2. SHARES SUBJECT TO THE PLAN. B-1 3. ELIGIBILITY AND LIMITATIONS. B-2 4. OPTIONS AND STOCK APPRECIATION RIGHTS. B-3 5. AWARDS OTHER THAN OPTIONS AND STOCK APPRECIATION RIGHTS.

December 14, 2021 EX-10.7

Forms of Option Agreement, Stock Option Grant Notice and Notice of Exercise under the Metromile, Inc. Amended and Restated 2011 Equity Incentive Plan (included as Exhibit 10.18 to Legacy Metromile’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on December 31, 2020).

Exhibit 10.7 METROMILE, INC. 2011 EQUITY INCENTIVE PLAN STOCK OPTION AGREEMENT ? EARLY EXERCISE Unless otherwise defined herein, the terms defined in the 2011 Equity Incentive Plan (the ?Plan?) shall have the same defined meanings in this Stock Option Agreement ? Early Exercise (the ?Option Agreement?). I. NOTICE OF STOCK OPTION GRANT Name: Address: The undersigned Participant has been granted an

December 14, 2021 EX-99.1

Consent of Allen & Company LLC

Exhibit 99.1 ? Consent of Allen & Company LLC ? The Board of Directors Metromile, Inc. 425 Market Street, #700 San Francisco, California 94105 Irving, Texas 75039 The Board of Directors: ? We hereby consent to the inclusion of our opinion letter, dated November 8, 2021, to the Board of Directors of Metromile, Inc. (?Metromile?) as Annex B to, and reference to such opinion letter under the headings

December 14, 2021 EX-10.16

Offer Letter, dated April 16, 2021, by and between Metromile, Inc. and Regi Vengalil (included as Exhibit 10.1 to Metromile's Quarterly Report on Form 10-Q, filed with the Securities and Exchange Commission on August 10, 2021).

Exhibit 10.16 April 16, 2021 Regi Vengalil I am pleased to offer you a full-time position with Metromile, Inc. (the ?Company? as its Chief Financial Officer commencing on or before May 24, 2021. Duties and Responsibilities. You will report to the CEO of the Company. You shall have such job duties and responsibilities commensurate with and customary for your position, which duties may change from t

December 14, 2021 EX-10.11

Offer Letter, dated January 3, 2020, by and between MetroMile, Inc. and Jesse McKendry (included as Exhibit 10.23 to Legacy Metromile’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 13, 2021).

? Exhibit 10.11 ? ? 1/3/2020 ? Jesse McKendry, ? I am pleased to offer you a full-time position with Metromile, Inc. (the ?Company?) in Cleveland, as an Insurance Product Manager, commencing on or before January 13, 2020. ? Duties and Responsibilities. You will initially report to Jeff Briglia, COO. You shall have such job duties and responsibilities commensurate with your position, which duties m

December 14, 2021 EX-10.4

Metromile, Inc. 2021 Employee Stock Purchase Plan (included as Annex C to Legacy Metromile’s Proxy Statement/Prospectus included in the Registration Statement on Form S-4, filed with the Securities and Exchange Commission on January 15, 2021).

? Exhibit 10.4 METROMILE, INC. 2021 EMPLOYEE STOCK PURCHASE PLAN ADOPTED BY THE BOARD OF DIRECTORS: [DATE] APPROVED BY THE STOCKHOLDERS: [DATE] 1. GENERAL; PURPOSE. (a) The Plan provides a means by which Eligible Employees of the Company and certain designated Related Corporations may be given an opportunity to purchase shares of Common Stock. The Plan permits the Company to grant a series of Purc

December 14, 2021 EX-10.1

Amended and Restated Registration Rights Agreement, dated February 9, 2021, by and among Legacy Metromile and certain security holders of Legacy Metromile (included as Exhibit 4.1 to Legacy Metromile’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on February 11, 2021).

Exhibit 10.1 ? AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT ? THIS AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT (this ?Agreement?), dated as of February 9, 2021, is made and entered into by and among each of INSU Acquisition Corp. II, a Delaware corporation (the ?Company?), Insurance Acquisition Sponsor II, LLC, a Delaware limited liability company, Dioptra Advisors II, LLC, a Delaware

December 14, 2021 EX-10.14

At-Will Employment, Confidential Information, Invention Assignment and Arbitration Agreement, dated November 4, 2017, by and between MetroMile, Inc. and Lindsay Alexovich (included as Exhibit 10.26 to Legacy Metromile’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 13, 2021).

Exhibit 10.14 ? METROMlLE, INC. AT-WILL EMPLOYMENT, CONFIDENTIAL INFORMATION, INVENTION ASSIGNMENT, AND ARBITRATION AGREEMENT ? As a condition of my employment with MetroMile, Inc., its subsidiaries, affiliates, successors or assigns (together, the ?Company?), and in consideration of my employment with the Company and my receipt of the compensation now and hereafter paid to me by Company, I agree

December 14, 2021 EX-10.8

Offer Letter, dated February 11, 2021, by and between Metromile, Inc. and Dan Preston (included as Exhibit 10.24 to Legacy Metromile’s Annual Report on Form 10-K, filed with the Securities and Exchange Commission on March 31, 2021.)

Exhibit 10.8 ? METROMILE, INC. ? February 11, 2021 ? Dan Preston via email: [email protected] ? Re: Employment Terms ? Dear Dan: ? On behalf of Metromile, Inc. (the ?Company?), I am pleased to offer you continued employment at the Company on the terms set forth in this offer letter agreement (the ?Agreement?). This Agreement shall become effective on the date that it is signed by you (the ?Effecti

December 14, 2021 EX-10.5

Omnibus Amendment No. 2 to Note Purchase and Security Agreement, dated February 9, 2021, by and among Metromile, Inc., HSCM Bermuda Fund Ltd., and the Schedule of Holders listed on Exhibit B (included as Exhibit 10.5 to Legacy Metromile’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on February 11, 2021).

Exhibit 10.5 ? METROMILE, INC. ? OMNIBUS AMENDMENT NO. 2 TO THE NOTE PURCHASE AND SECURITY AGREEMENT ? February 9, 2021 ? This OMNIBUS AMENDMENT NO. 2 (this ?Amendment?) to the Note Purchase and Security Agreement, dated as of April 14, 2020, by and among Metromile, Inc. (the ?Company?), INSU Acquisition Corp. II, a Delaware corporation (the ?Parent?), the other undersigned Guarantors, the Holders

November 9, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

November 9, 2021 EX-99.3

Lemonade Acquisition of Metromile November 8, 2021 2 Forward Looking Statement Safe Harbor This presentation contains forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. All statements contained in t

Lemonade Acquisition of Metromile November 8, 2021 2 Forward Looking Statement Safe Harbor This presentation contains forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995.

November 9, 2021 EX-10.2

Form of Voting and Support Agreement

EX-10.2 4 lmnd-20210930xxex102xformo.htm EX-10.2 VOTING AND SUPPORT AGREEMENT THIS VOTING AND SUPPORT AGREEMENT (this “Agreement”) is made and entered into as of November 8, 2021, by and among Lemonade, Inc., a Delaware corporation (“Parent”); and [ ], a [ ] (“Stockholder”). WHEREAS, contemporaneously with the execution of this Agreement, Parent, Citrus Merger Sub A, Inc., a Delaware corporation a

November 9, 2021 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 8, 2021 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Nu

November 9, 2021 EX-99.1

Shareholder Letter Q3 2021 2 Dear Shareholders, Let's begin with the most exciting news - Lemonade Car was launched last week, and today, as part of our continued investment in our car business, we announce the acquisition of Metromile. While we have

Shareholder Letter Q3 2021 2 Dear Shareholders, Let's begin with the most exciting news - Lemonade Car was launched last week, and today, as part of our continued investment in our car business, we announce the acquisition of Metromile.

November 9, 2021 EX-99.2

Lemonade To Acquire Metromile New York (November 8, 2021)—Lemonade (NYSE: LMND) the insurance company powered by AI and social good, and Metromile (NASDAQ: MILE, MILEW), the data science company focused on auto insurance, have entered into a definiti

Lemonade To Acquire Metromile New York (November 8, 2021)?Lemonade (NYSE: LMND) the insurance company powered by AI and social good, and Metromile (NASDAQ: MILE, MILEW), the data science company focused on auto insurance, have entered into a definitive agreement pursuant to which Lemonade will acquire Metromile in an all-stock transaction that implies a fully diluted equity value of approximately $500 million, or just over $200 million net of cash.

November 9, 2021 EX-2.1

Agreement and Plan of Merger, dated as of November 8, 2021, by and among Lemonade, Inc., Citrus Merger Sub A, Inc., Citrus Merger Sub B, LLC and Metromile, Inc. (incorporated by reference to Exhibit 2.1 to the Company’s Quarterly Report on Form 10-Q, filed with the SEC on November 9, 2021).*

EX-2.1 2 lmnd-20210930xxex21xmerger.htm EX-2.1 EXECUTION VERSION AGREEMENT AND PLAN OF MERGER by and among LEMONADE, INC., a Delaware corporation; CITRUS MERGER SUB A, INC., a Delaware corporation; CITRUS MERGER SUB B, LLC, a Delaware limited liability company; and METROMILE, INC., a Delaware corporation Dated as of November 8, 2021 |US-DOCS\127176889.14|| TABLE OF CONTENTS Page Section 1. THE MER

November 9, 2021 EX-10.1

Severance Agreement

EX-10.1 3 lmnd-20210930xxex101xsever.htm EX-10.1 Severance Agreement THIS SEVERANCE AGREEMENT (the “Severance Agreement”) is entered into as of the Effective Date (as defined below) between Lemonade, Inc. (together with any Affiliate that may employ you from time to time, the “Company”) and Adina Eckstein (“Executive” or “you”). 1.Definitions. The following capitalized terms used herein shall have

August 11, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

August 11, 2021 EX-10.5

Amendment to the Whole Account Quota Share Reinsurance Contract issued to Lemonade Insurance Company and Lemonade Insurance N.V. by the Subscribing Reinsurer MAPFRE Re (Spain), dated May 12, 2020.

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10).

August 11, 2021 EX-10.4

Amendment to the Whole Account Quota Share Reinsurance Contract issued to Lemonade Insurance Company and Lemonade Insurance N.V. by the Subscribing Reinsurer Tokio Marine & Nichido Fire Insurance Co. Ltd., dated May 12, 2020.

EX-10.4 5 lmnd-20210630xxex104xadden.htm EX-10.4 [***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10). Such excluded information is both not material and is the type that the registrant treats as private or confidential. ADDENDUM NO. 2 to the WHOLE ACCOUNT QUOTA SHARE REINSURANCE CONTRACT Effective: July 1, 2020 (the “Contract”) issued to LEMON

August 11, 2021 EX-10.3

Amendment to the Whole Account Quota Share Reinsurance Contract issued to Lemonade Insurance Company and Lemonade Insurance N.V. by the Subscribing Reinsurer Hannover Ruck SE, dated April 4, 2020

EX-10.3 4 lmnd-20210630xxex103xadden.htm EX-10.3 [***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10). Such excluded information is both not material and is the type that the registrant treats as private or confidential. ADDENDUM NO. 2 to the WHOLE ACCOUNT QUOTA SHARE REINSURANCE CONTRACT Effective: July 1, 2020 (the “Contract”) issued to LEMON

August 11, 2021 EX-10.1

Severance Agreement by and between Adina Eckstein and Lemonade, Inc. dated August 5, 2021

EX-10.1 2 lmnd-20210630xxex101xsever.htm EX-10.1 Severance Agreement THIS SEVERANCE AGREEMENT (the “Severance Agreement”) is entered into as of the Effective Date (as defined below) between Lemonade, Inc. (together with any Affiliate that may employ you from time to time, the “Company”) and Adina Eckstein (“Executive” or “you”). 1.Definitions. The following capitalized terms used herein shall have

August 11, 2021 EX-10.2

Form of Restricted Stock Unit Agreement under the 2020 Incentive Award Plan (Israel)

EX-10.2 3 lmnd-20210630xxex102xformo.htm EX-10.2 LEMONADE, INC. 2020 INCENTIVE AWARD PLAN RESTRICTED STOCK UNIT AWARD GRANT NOTICE AND RESTRICTED STOCK UNIT AGREEMENT Lemonade, Inc., a Delaware corporation (the “Company”), pursuant to its 2020 Incentive Award Plan, as amended from time to time (the “Plan”), hereby grants to the holder listed below (“Participant”) the number of Restricted Stock Uni

August 4, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 4, 2021 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numb

August 4, 2021 EX-99.1

Shareholder Letter Q2 2021 2 Dear Shareholders, We're happy to report that Q2 saw positive trends and metrics across the board. With healthy unit economics and robust customer demand, the overarching theme of Q1 21 was leaning in to growth investment

Shareholder Letter Q2 2021 2 Dear Shareholders, We're happy to report that Q2 saw positive trends and metrics across the board.

July 26, 2021 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 21, 2021 LEMONADE, INC. (Exa

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 21, 2021 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numbe

June 14, 2021 8-K

Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): June 9, 2021 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Number

May 12, 2021 EX-10.1

Form of Option Agreement under the 2020 Incentive Award Plan (Israel)

EX-10.1 2 lmnd-20210331xex101xformof.htm EX-10.1 Exhibit 10.1 LEMONADE, INC. 2020 INCENTIVE AWARD PLAN STOCK OPTION GRANT NOTICE AND STOCK OPTION AGREEMENT Lemonade, Inc., a Delaware corporation (the “Company”), pursuant to its 2020 Incentive Award Plan, as amended from time to time (the “Plan”) and the Israeli Appendix for Israeli Taxpayers, as amended from time to time (the “IL Appendix”), hereb

May 12, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2021 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

May 11, 2021 EX-99.1

Shareholder Letter Q1 2021 2 Dear Shareholders, During our Q4 2020 earnings call, we hinted at a yet-to-be-announced product that is occupying a larger proportion of the Lemonade team than any of our existing products. We’ve since revealed that - you

Shareholder Letter Q1 2021 2 Dear Shareholders, During our Q4 2020 earnings call, we hinted at a yet-to-be-announced product that is occupying a larger proportion of the Lemonade team than any of our existing products.

May 11, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 11, 2021 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Number

April 30, 2021 DEF 14A

proxy statement on Schedule 14A for Lemonade’s 2020 annual meeting of stockholders, filed with the SEC on April 30, 2021;

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

April 30, 2021 DEFA14A

- DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.

April 26, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 21, 2021 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numb

March 9, 2021 S-8

- S-8

As filed with the Securities and Exchange Commission on March 8, 2021 Registration No.

March 8, 2021 10-K

Annual Report - 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 for the transition period from to Commission file number: 001-39367 Lemonad

March 8, 2021 EX-4.3

Description of Securities

Exhibit 4.3 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934, AS AMENDED Lemonade, Inc. has one class of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”): our common stock, par value $0.00001 per share. References herein to, “we,” “us,” “our”, and “our company” refer to

March 2, 2021 EX-99.1

Shareholder Letter Q4 2020 $50M 92% YOY GROSS EARNED PREMIUM Q4 18 Q4 19 Q4 20 Q4 18 Q4 19 Q4 20 113% 79% 71% 71% 10% YOY ANNUAL GROSS LOSS RATIO FY 18 FY 19 FY 20 $213 20% YOY PREMIUM PER CUSTOMER 1,000,802 56% YOY CUSTOMERS $213M 87% YOY IN FORCE P

q42020lmndshareholderlet Shareholder Letter Q4 2020 $50M 92% YOY GROSS EARNED PREMIUM Q4 18 Q4 19 Q4 20 Q4 18 Q4 19 Q4 20 113% 79% 71% 71% 10% YOY ANNUAL GROSS LOSS RATIO FY 18 FY 19 FY 20 $213 20% YOY PREMIUM PER CUSTOMER 1,000,802 56% YOY CUSTOMERS $213M 87% YOY IN FORCE PREMIUM (IFP) 2 Dear Shareholders, In recent quarters we attempted to walk and chew gum at the same time, and we’re happy to report that we seem to have mastered this feat without too much drama.

March 2, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 1, 2021 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation) (Commission File Numbe

February 16, 2021 SC 13G

United States Securities and Exchange Commission Washington, D.C. 20549 Schedule 13G (Rule 13d-102) Information to be Included in Statements Filed Pursuant to § 240.13d-1(b), (c) and (d) and Amendments Thereto Filed Pursuant to § 240.13d-2 UNDER THE

United States Securities and Exchange Commission Washington, D.C. 20549 Schedule 13G (Rule 13d-102) Information to be Included in Statements Filed Pursuant to § 240.13d-1(b), (c) and (d) and Amendments Thereto Filed Pursuant to § 240.13d-2 UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )* Lemonade, Inc. (Name of Issuer) Common Stock, par value $0.00001 (Title of Class of Securities) 5256

February 16, 2021 SC 13G

United States Securities and Exchange Commission Washington, D.C. 20549 Schedule 13G (Rule 13d-102) Information to be Included in Statements Filed Pursuant to § 240.13d-1(b), (c) and (d) and Amendments Thereto Filed Pursuant to § 240.13d-2 UNDER THE

United States Securities and Exchange Commission Washington, D.C. 20549 Schedule 13G (Rule 13d-102) Information to be Included in Statements Filed Pursuant to § 240.13d-1(b), (c) and (d) and Amendments Thereto Filed Pursuant to § 240.13d-2 UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )* Lemonade, Inc. (Name of Issuer) Common Stock, par value $0.00001 (Title of Class of Securities) 5256

February 16, 2021 SC 13G

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1 (b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2 (b) (Amendment No. _____)*

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1 (b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2 (b) (Amendment No. )* Lemonade, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 52567D107 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of this Statemen

February 12, 2021 SC 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G* Under the Securities Exchange Act of 1934 Lemonade, Inc. (Name of Issuer) Common Stock, $0.00001 par value per share (Title of Class of Securities) 52567D 107 (CUSI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G* Under the Securities Exchange Act of 1934 Lemonade, Inc. (Name of Issuer) Common Stock, $0.00001 par value per share (Title of Class of Securities) 52567D 107 (CUSIP Number) December 31, 2020 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which

February 12, 2021 SC 13G

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G (Rule 13d-102) Information to be Included in Statements Filed Pursuant to § 240.13d-1(b), (c) and (d) and Amendments Thereto Filed Pursuant to § 240.13d-2 Under the Securities Exc

SC 13G SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G (Rule 13d-102) Information to be Included in Statements Filed Pursuant to § 240.13d-1(b), (c) and (d) and Amendments Thereto Filed Pursuant to § 240.13d-2 Under the Securities Exchange Act of 1934 (Amendment No. )* Lemonade, Inc. (Name of Issuer) Common Stock, par value $0.00001 per share (Title of Class of Securities) 5

February 12, 2021 SC 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G* Under the Securities Exchange Act of 1934 Lemonade, Inc. (Name of Issuer) Common Stock, $0.00001 par value per share (Title of Class of Securities) 52567D 107 (CUSI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G* Under the Securities Exchange Act of 1934 Lemonade, Inc. (Name of Issuer) Common Stock, $0.00001 par value per share (Title of Class of Securities) 52567D 107 (CUSIP Number) December 31, 2020 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which

January 14, 2021 424B4

4,824,314 Shares Lemonade, Inc. Common Stock

TABLE OF CONTENTS  Filed Pursuant to Rule 424(b)(4)  Registration No. 333-252017 PRELIMINARY PROSPECTUS 4,824,314 Shares Lemonade, Inc. Common Stock We are offering 3,300,000 shares of our common stock and the selling stockholders in this prospectus are offering 1,524,314 shares of our common stock. We will not receive any of the proceeds from the sale of shares by the selling stockholders in this

January 13, 2021 S-1MEF

- S-1MEF

As filed with the Securities and Exchange Commission on January 13, 2021 Registration No.

January 11, 2021 CORRESP

-

Goldman Sachs & Co. LLC 200 West Street New York, NY 10282 Morgan Stanley & Co. LLC 1585 Broadway New York, New York 10036 January 11, 2021 VIA EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Re: Lemonade, Inc. Registration Statement on Form S-1 (File No. 333-252017) Ladies and Gentlemen: Pursuant to Rule 461 under the Securit

January 11, 2021 EX-1.1

Form of Underwriting Agreement.

Exhibit 1.1 Lemonade, Inc. Common Stock, par value $0.00001 per share Underwriting Agreement [•], 2021 Goldman Sachs & Co. LLC Morgan Stanley & Co. LLC As representatives (the “Representatives”) of the several Underwriters named in Schedule I hereto c/o Goldman Sachs & Co. LLC 200 West Street New York, New York 10282-2198 c/o Morgan Stanley & Co. LLC 1585 Broadway, 29th Floor New York, New York 10

January 11, 2021 CORRESP

-

Lemonade, Inc. 5 Crosby Street, 3rd Floor New York, New York 10013 January 11, 2021 VIA EDGAR TRANSMISSION Division of Corporate Finance United States Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549-6010 Attention: Jessica Livingston Re: Lemonade, Inc. Registration Statement on Form S-1 (Registration No. 333-252017) Request for Acceleration of Effective Date Ladies and

January 11, 2021 EX-10.6

Form of Option Agreement under the Amended and Restated 2015 Incentive Share Option Plan (Israel).

Exhibit 10.6 LEMONADE, INC. 102 OPTION AGREEMENT Made as of the day of BETWEEN: Lemonade, Inc. A company incorporated under the laws of the State of Delaware (hereinafter the “Company”) on the one part; AND: I.D. No: Address: (hereinafter the “Optionee”) on the other part; WHEREAS, the Company duly adopted and the Board approved the A&R 2015 Incentive Share Option Plan, as might be further amended

January 11, 2021 EX-10.7

Form of Option Agreement under the Amended and Restated 2015 Incentive Share Option Plan (U.S.).

EX-10.7 5 lmnd-20210111xex10d7.htm EXHIBIT-10.7 Exhibit 10.7 LEMONADE, INC. US OPTION AGREEMENT Made as of the [] day of [] BETWEEN: Lemonade, Inc. A company incorporated under the laws of the State of Delaware (hereinafter the “Company”) on the one part; AND: [] Address: [] (hereinafter the “Optionee”) on the other part; WHEREAS the Company duly adopted and the Board approved the A&R 2015 Incenti

January 11, 2021 S-1

Registration Statement - FORM S-1

Table of Contents As filed with the Securities and Exchange Commission on January 11, 2021 Registration No.

January 11, 2021 EX-10.9

Form of Option Agreement under the 2020 Incentive Award Plan.

EX-10.9 6 lmnd-20210111xex10d9.htm EXHIBIT-10.9 Exhibit 10.9 LEMONADE, INC. 2020 INCENTIVE AWARD PLAN STOCK OPTION GRANT NOTICE AND STOCK OPTION AGREEMENT Lemonade, Inc., a Delaware corporation (the “Company”), pursuant to its 2020 Incentive Award Plan, as amended from time to time (the “Plan”), hereby grants to the holder listed below (“Participant”) an option to purchase the number of Shares set

December 31, 2020 DRS

-

TABLE OF CONTENTS ?CONFIDENTIAL TREATMENT REQUESTED PURSUANT TO 17 C.F.R. SECTION 200.83 As confidentially submitted to the Securities and Exchange Commission on December 31, 2020 Registration No. 333-????? ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Lemonade, Inc. (Exact name of registrant as specifie

December 31, 2020 EX-10.9

LEMONADE, INC. 2020 INCENTIVE AWARD PLAN STOCK OPTION GRANT NOTICE AND STOCK OPTION AGREEMENT

Exhibit 10.9 LEMONADE, INC. 2020 INCENTIVE AWARD PLAN STOCK OPTION GRANT NOTICE AND STOCK OPTION AGREEMENT Lemonade, Inc., a Delaware corporation (the ?Company?), pursuant to its 2020 Incentive Award Plan, as amended from time to time (the ?Plan?), hereby grants to the holder listed below (?Participant?) an option to purchase the number of Shares set forth below (the ?Option?). The Option is subje

December 31, 2020 DRSLTR

-

53rd at Third 885 Third Avenue New York, New York 10022-4834 Tel: +1.212.906.1200 Fax: +1.212.751.4864 www.lw.com FIRM / AFFILIATE OFFICES December 31, 2020 Beijing Moscow Boston Munich Brussels New York Century City Orange County Chicago Paris Dubai Riyadh D?sseldorf San Diego Frankfurt San Francisco Hamburg Seoul Hong Kong Shanghai Houston Silicon Valley London Singapore Los Angeles Tokyo Madrid

December 31, 2020 EX-10.6

LEMONADE, INC. 102 OPTION AGREEMENT Made as of the day of

EX-10.6 2 filename2.htm Exhibit 10.6 LEMONADE, INC. 102 OPTION AGREEMENT Made as of the day of BETWEEN: Lemonade, Inc. A company incorporated under the laws of the State of Delaware (hereinafter the “Company”) on the one part; AND: I.D. No: Address: (hereinafter the “Optionee”) on the other part; WHEREAS, the Company duly adopted and the Board approved the A&R 2015 Incentive Share Option Plan, as

December 31, 2020 EX-10.7

LEMONADE, INC. US OPTION AGREEMENT Made as of the [_______] day of [______]

Exhibit 10.7 LEMONADE, INC. US OPTION AGREEMENT Made as of the [] day of [] BETWEEN: Lemonade, Inc. A company incorporated under the laws of the State of Delaware (hereinafter the ?Company?) on the one part; AND: [] Address: [] (hereinafter the ?Optionee?) on the other part; WHEREAS the Company duly adopted and the Board approved the A&R 2015 Incentive Share Option Plan, as might be further amende

November 12, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 10, 2020 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation or organization) (C

November 12, 2020 EX-99.1

Shareholder Letter Q3 2020 2 Dear Shareholders, The third quarter saw continued good news for Lemonade. Despite concern that the pandemic might disrupt migratory patterns, and with them our seasonably strongest quarter, Q3 saw stronger growth than we

q32020shareholderletter- Shareholder Letter Q3 2020 2 Dear Shareholders, The third quarter saw continued good news for Lemonade.

November 12, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2020 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

August 12, 2020 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): August 11, 2020 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation or organization) (Com

August 12, 2020 EX-10.11

Severance Agreement by and between Tim Bixby and Lemonade, Inc., dated July 7, 2020.

Severance Agreement THIS SEVERANCE AGREEMENT (the “Severance Agreement”) is entered into as of the Effective Date (as defined below) between Lemonade, Inc.

August 12, 2020 EX-10.12

Amended and Restated Employment Agreement, by and between Daniel Schreiber and Lemonade Ltd., dated July 7, 2020.

AMENDED AND RESTATED PERSONAL EMPLOYMENT AGREEMENT This Amended and Restated Personal Employment Agreement (“Agreement”) is entered into as of the Effective Date (as defined below), by and between Lemonade Ltd.

August 12, 2020 EX-10.10

Severance Agreement by and between Jorge Espinel and Lemonade, Inc., dated July 7, 2020.

Severance Agreement THIS SEVERANCE AGREEMENT (the “Severance Agreement”) is entered into as of the Effective Date (as defined below) between Lemonade, Inc.

August 12, 2020 EX-10.14

Amended and Restated Employment Agreement by and between John Peters and Lemonade, Inc., dated July 7, 2020

LEMONADE, INC. AMENDED AND RESTATED EMPLOYMENT AGREEMENT THIS AMENDED AND RESTATED EMPLOYMENT AGREEMENT (“Agreement”) is made as of the Effective Date (as defined below), between Lemonade, Inc., a Delaware corporation (the “Company”) and John Peters.(the “Employee”) (collectively referred to herein as the “Parties”). RECITALS WHEREAS, the Employee is currently employed by the Company as its Chief

August 12, 2020 EX-10.13

Amended and Restated Employment Agreement by and between Shai Wininger and Lemonade Ltd., dated July 7, 2020.

Execution Version AMENDED AND RESTATED PERSONAL EMPLOYMENT AGREEMENT This Amended and Restated Personal Employment Agreement (“Agreement”) is entered into as of the Effective Date (as defined below), by and between Lemonade Ltd.

August 12, 2020 10-Q

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2020 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39367 Lemonade, Inc.

August 12, 2020 EX-99.1

Shareholder Letter Inaugural edition, Q2 2020  2 Dear Shareholders, With millions of people fired or furloughed and billions in lockdown, Lemonade entered Q2 on a defensive footing. At the start of the quarter we significantly slowed our marketing s

shareholderletterq220208 Shareholder Letter Inaugural edition, Q2 2020  2 Dear Shareholders, With millions of people fired or furloughed and billions in lockdown, Lemonade entered Q2 on a defensive footing.

July 10, 2020 EX-3.2

Amended and Restated By-laws of Lemonade, Inc.

Exhibit 3.2 Amended and Restated Bylaws of Lemonade, Inc. (a Delaware Public Benefit Corporation) Table of Contents Page Article I - Corporate Offices 1 1.1 Registered Office 1 1.2 Other Offices 1 Article II - Meetings of Stockholders 1 2.1 Place of Meetings 1 2.2 Annual Meeting 1 2.3 Special Meeting 1 2.4 Advance Notice Procedures for Business Brought before a Meeting 2 2.5 Advance Notice Procedu

July 10, 2020 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 7, 2020 LEMONADE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39367 32-0469673 (State or other jurisdiction of incorporation or organization) (Commis

July 10, 2020 EX-3.1

Amended and Restated Certificate of Incorporation of Lemonade, Inc.

EX-3.1 2 tm2024563d1ex3-1.htm EXHIBIT 3.1 Exhibit 3.1 AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF LEMONADE, INC. A PUBLIC BENEFIT CORPORATION (Pursuant to Sections 242 and 245 of the General Corporation Law of the State of Delaware) LEMONADE, INC., a corporation organized and existing under and by virtue of the provisions of the General Corporation Law of the State of Delaware (the “DGCL”

July 2, 2020 S-8

- S-8

As filed with the Securities and Exchange Commission on July 2, 2020 Registration No.

July 2, 2020 8-A12B

Form 8-A dated July 2, 2020 (File No. 001-39367)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR (g) OF THE SECURITIES EXCHANGE ACT OF 1934 Lemonade, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 32-0469673 (I.R.S. Employer Identification No.) 5 Crosb

July 2, 2020 424B4

TABLE OF CONTENTS

Filed pursuant to Rule 424(b)(4) Registration No. 333-239007 TABLE OF CONTENTS Page PROSPECTUS SUMMARY 1 RISK FACTORS 21 CAUTIONARY NOTE REGARDING FORWARD-LOOKING STATEMENTS 73 MARKET AND INDUSTRY DATA 75 USE OF PROCEEDS 77 DIVIDEND POLICY 78 CAPITALIZATION 79 DILUTION 81 SELECTED HISTORICAL CONSOLIDATED FINANCIAL DATA 83 MANAGEMENT'S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF O

July 1, 2020 S-1/A

- S-1/A

As filed with the Securities and Exchange Commission on June 30, 2020 Registration No.

June 30, 2020 EX-10.17

Whole Account Quota Share Reinsurance Contract issued to Lemonade Insurance Company and Lemonade Insurance N.V. by the Subscribing Reinsurers Arch Re (Bermuda), Lloyd's Underwriter Syndicate No. 1084 CSL and Swiss Re America (US), dated May 13, 2020.

EX-10.17 6 a2241997zex-1017.htm EX-10.17 Exhibit 10.17 [***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10). Such excluded information is not material and would likely cause competitive harm to the registrant if publicly disclosed. WHOLE ACCOUNT QUOTA SHARE REINSURANCE CONTRACT issued to LEMONADE INSURANCE COMPANY New York, New York and LEMONAD

June 30, 2020 EX-10.15

Property Per Risk Excess of Loss Reinsurance Contract issued to Lemonade Insurance Company and Lemonade Insurance N.V. by the Subscribing Reinsurers Aspen Insurance UK Limited, AXIS Reinsurance Company, Hannover Ruck SE, Lloyd's Underwriter Syndicate No. 1084 CSL, Lloyd's Underwriter Syndicate No. 2001 AML, Lloyd's Underwriter Syndicate No. 2791 MAP, Lloyd's Underwriter Syndicate No. 4000 HAM and Swiss Re, dated June 12, 2020.

EX-10.15 4 a2241997zex-1015.htm EX-10.15 Exhibit 10.15 [***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10). Such excluded information is not material and would likely cause competitive harm to the registrant if publicly disclosed. PROPERTY PER RISK EXCESS OF LOSS REINSURANCE CONTRACT issued to LEMONADE INSURANCE COMPANY New York, New York and

June 30, 2020 EX-10.1

Whole Account Quota Share Reinsurance Contract issued to Lemonade Insurance Company and Lemonade Insurance N.V. by the Subscribing Reinsurers Tokio Marine & Nichido Fire Insurance Co. Ltd. and Mapfre Re (Spain), dated May 12, 2020.

Exhibit 10.1 [***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10). Such excluded information is not material and would likely cause competitive harm to the registrant if publicly disclosed. WHOLE ACCOUNT QUOTA SHARE REINSURANCE CONTRACT issued to LEMONADE INSURANCE COMPANY New York, New York and LEMONADE INSURANCE N.V. Amsterdam, Netherlands in

June 30, 2020 CORRESP

-

June 30, 2020 VIA EDGAR AND OVERNIGHT DELIVERY 53rd at Third 885 Third Avenue New York, New York 10022-4834 Tel: +1.

June 30, 2020 EX-10.16

Automatic Facultative Property Per Risk Excess of Loss Reinsurance Contract issued to Lemonade Insurance Company by the Subscribing Reinsurer Arch Reinsurance Company, dated June 12, 2020.

Exhibit 10.16 [***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10). Such excluded information is not material and would likely cause competitive harm to the registrant if publicly disclosed. AUTOMATIC FACULTATIVE PROPERTY PER RISK EXCESS OF LOSS REINSURANCE CONTRACT issued to LEMONADE INSURANCE COMPANY New York, New York including any and/or al

June 30, 2020 CORRESP

-

Goldman Sachs & Co. LLC 200 West Street New York, NY 10282 Morgan Stanley & Co. LLC 1585 Broadway New York, New York 10036 June 30, 2020 VIA EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Re: Lemonade, Inc. Registration Statement on Form S-1 (File No. 333-239007) Ladies and Gentlemen: Pursuant to Rule 461 under the Securities

June 30, 2020 S-1/A

- S-1/A

As filed with the Securities and Exchange Commission on June 30, 2020 Registration No.

June 30, 2020 EX-10.14

Whole Account Quota Share Reinsurance Contract issued to Lemonade Insurance Company and Lemonade Insurance N.V. by the Subscribing Reinsurer Hannover Ruck SE, dated April 4, 2020.

EX-10.14 3 a2241997zex-1014.htm EX-10.14 Exhibit 10.14 [***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10). Such excluded information is not material and would likely cause competitive harm to the registrant if publicly disclosed. WHOLE ACCOUNT QUOTA SHARE REINSURANCE CONTRACT issued to LEMONADE INSURANCE COMPANY New York, New York and LEMONAD

June 30, 2020 EX-10.18

Whole Account Quota Share Reinsurance Contract issued to Lemonade Insurance Company and Lemonade Insurance N.V. by the Subscribing Reinsurer AXA XL (Catlin Re Switzerland), dated February 28, 2020.

Exhibit 10.18 [***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10). Such excluded information is not material and would likely cause competitive harm to the registrant if publicly disclosed. WHOLE ACCOUNT QUOTA SHARE REINSURANCE CONTRACT issued to LEMONADE INSURANCE COMPANY New York, New York and LEMONADE INSURANCE N.V. Amsterdam, Netherlands i

June 30, 2020 CORRESP

-

CORRESP 1 filename1.htm Lemonade, Inc. 5 Crosby Street, 3rd Floor New York, New York 10013 June 30, 2020 VIA EDGAR TRANSMISSION Division of Corporate Finance United States Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549-6010 Attention: John Sickel Susan Block Bonnie Baynes Mark Brunhofer Re: Lemonade, Inc. Registration Statement on Form S-1 (Registration No. 333-239007

June 25, 2020 S-1/A

- S-1/A

As filed with the Securities and Exchange Commission on June 25, 2020 Registration No.

June 23, 2020 EX-3.4

Form of Restated Bylaws of Lemonade, Inc., to be effective immediately prior to the completion of this offering.

Exhibit 3.4 Amended and Restated Bylaws of Lemonade, Inc. (a Delaware Public Benefit Corporation) Table of Contents Page Article I - Corporate Offices 3 1.1 Registered Office 3 1.2 Other Offices 3 Article II - Meetings of Stockholders 3 2.1 Place of Meetings 3 2.2 Annual Meeting 3 2.3 Special Meeting 4 2.4 Advance Notice Procedures for Business Brought before a Meeting 4 2.5 Advance Notice Procedu

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