0001213900-22-010375 Sample Contracts

REGISTRATION RIGHTS AGREEMENT
Registration Rights Agreement • March 2nd, 2022 • Delwinds Insurance Acquisition Corp. • Blank checks • New York

This REGISTRATION RIGHTS AGREEMENT (this “Agreement”), dated as of February 24, 2022, is by and between CF Principal Investments LLC, a Delaware limited liability company (the “Investor”), and Delwinds Insurance Acquisition Corp., a Delaware corporation (the “Company”). For purposes of this Agreement, references to the “Company” shall also include any successor entity to the Company by the transactions contemplated by that certain Agreement and Plan of Merger (the “Business Combination Agreement”), dated as of February 24, 2022, by and among the Company, DWIN Merger Sub Inc. and FOXO Technologies Inc (“FOXO”), such transactions being referred to herein as the “Merger.”

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COMMON STOCK PURCHASE AGREEMENT
Common Stock Purchase Agreement • March 2nd, 2022 • Delwinds Insurance Acquisition Corp. • Blank checks • New York

This COMMON STOCK PURCHASE AGREEMENT is made and entered into as of February 24, 2022 (this “Agreement”), by and between CF Principal Investments LLC, a Delaware limited liability company (the “Investor”), and Delwinds Insurance Acquisition Corp., a Delaware corporation (the “Company”). For purposes of this Agreement, references to the “Company” shall also include any successor entity to the Company by any Fundamental Transaction (as defined below), but only from and after the closing of such Fundamental Transaction, including but not limited to, the resulting publicly listed company pursuant to the transactions contemplated by that certain Agreement and Plan of Merger (the “Business Combination Agreement”), dated as of February 24, 2022, by and among the Company, DWIN Merger Sub Inc. and FOXO Technologies Inc. (“FOXO”), such transactions being referred to herein as the “Merger.”

AGREEMENT AND PLAN OF MERGER by and among DELWINDS INSURANCE ACQUISITION CORP., as the Purchaser, DWIN MERGER SUB INC., as Merger Sub, DIAC SPONSOR LLC, in the capacity as the Purchaser Representative, and FOXO TECHNOLOGIES INC., as the Company, Dated...
Merger Agreement • March 2nd, 2022 • Delwinds Insurance Acquisition Corp. • Blank checks • New York

This Agreement and Plan of Merger (this “Agreement”) is made and entered into as of February 24, 2022, by and among (i) Delwinds Insurance Acquisition Corp., a Delaware corporation (together with its successors, the “Purchaser”), (ii) DWIN Merger Sub Inc., a Delaware corporation and a wholly-owned subsidiary of the Purchaser (“Merger Sub”), (iii) DIAC Sponsor LLC, a Delaware limited liability company, in the capacity as the representative from and after the Effective Time (as defined herein) for the stockholders of the Purchaser (other than the Company Security Holders (as defined below) as of immediately prior to the Effective Time and their successors and assignees) in accordance with the terms and conditions of this Agreement (the “Purchaser Representative”), and (iv) FOXO Technologies Inc., a Delaware corporation (the “Company”). The Purchaser, Merger Sub, the Purchaser Representative and the Company are sometimes referred to herein individually as a “Party” and, collectively, as t

FORM OF NON-COMPETITION AND NON-SOLICITATION AGREEMENT
Non-Competition and Non-Solicitation Agreement • March 2nd, 2022 • Delwinds Insurance Acquisition Corp. • Blank checks • New York

THIS NON-COMPETITION AND NON-SOLICITATION AGREEMENT (this “Agreement”) is being executed and delivered as of February 24, 2022, by ________________(the “Subject Party”) in favor of and for the benefit of Delwinds Insurance Acquisition Corp., a Delaware corporation, (including any successor entity thereto, the “Purchaser”), FOXO Technologies Inc., a Delaware corporation (the “Company”), and each of the Purchaser’s and/or the Company’s respective present and future Affiliates, successors and direct and indirect subsidiaries (collectively with the Purchaser and the Company, the “Covered Parties”). Any capitalized term used but not defined in this Agreement will have the meaning ascribed to such term in the Merger Agreement.

FORM OF VOTING AND SUPPORT AGREEMENT
Voting and Support Agreement • March 2nd, 2022 • Delwinds Insurance Acquisition Corp. • Blank checks • New York

This Voting and Support Agreement (this “Agreement”) is made as of February 24, 2022, by and among (i) Delwinds Insurance Acquisition Corp., a Delaware corporation (together with its successors, the “Purchaser”), (ii) FOXO Technologies Inc., a Delaware corporation (the “Company”), and (iii) the undersigned holder (“Holder”) of capital stock and/or securities convertible into capital stock of the Company. Any capitalized term used but not defined in this Agreement will have the meaning ascribed to such term in the Merger Agreement.

BACKSTOP SUBSCRIPTION AGREEMENT February __, 2022
Backstop Subscription Agreement • March 2nd, 2022 • Delwinds Insurance Acquisition Corp. • Blank checks • New York

In connection with the contemplated business combination (the “Transaction”) between Delwinds Insurance Acquisition Corp., a Delaware corporation (together with any successor, the “Company”), and FOXO Technologies Inc., a Delaware corporation (“Target”), pursuant to that certain Agreement and Plan of Merger, dated as of the date hereof (as it may be amended, the “Transaction Agreement”), by and among, the Company, Target and certain other parties named therein, the Company is seeking commitments to purchase shares of the Company’s common stock, par value $0.0001 per share (the “Common Stock”), for a purchase price of $10.00 per share (the “Purchase Price”). The Company is offering shares of Common Stock in a private placement (the “Offering”) in which the Company expects to sell and issue a number of shares of Common Stock pursuant to backstop commitments through subscription agreements on substantially the same terms hereof for an aggregate commitment amount, when combined with the co

FORM OF LOCK-UP AGREEMENT
Lock-Up Agreement • March 2nd, 2022 • Delwinds Insurance Acquisition Corp. • Blank checks • New York

THIS LOCK-UP AGREEMENT (this “Agreement”) is made and entered into as of February 24, 2022 by and among (i) Delwinds Insurance Acquisition Corp. a Delaware corporation, (including any successor entity thereto, the “Purchaser”), (ii) DIAC Sponsor LLC, in the capacity under the Merger Agreement (as defined below) as the Purchaser Representative (including any successor Purchaser Representative appointed in accordance therewith, the “Purchaser Representative”), and (iii) the undersigned (“Holder”). Any capitalized term used but not defined in this Agreement will have the meaning ascribed to such term in the Merger Agreement (defined below).

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