DWIN Delwinds Insurance Acquisition Corp

Item 1.01 Entry into a Material Definitive Agreement.

FOXO Technologies Inc. (the “Company”) entered into two separate general release agreements with each of Baboon Partners, LLC (“Baboon Partners”) and Inpixon (collectively, with Baboon Partners, the “Investors”), dated as of June 16, 2023 and June 20, 2023, respectively (collectively, the “General Release Agreements”). The Investors are former registered holders of 10% Original Issue Discount Convertible Debentures issued pursuant to securities purchase agreement (the “Purchase Agreements”) in 2022 by FOXO Technologies Operating Company (“Legacy FOXO”) in a private placement (the “2022 Debentures”), which 2022 Debentures were automatically converted into Class A common stock of Legacy FOXO and exchanged by the Company for the Company’s Class A common stock, par value $0.0001 per share (“Class A Common Stock”), in connection with the business combination of the Company’s predecessor, Delwinds Insurance Acquisition Corp., and Legacy FOXO consummated on September 15, 2022.

Pursuant to their respective General Release Agreement, each Investor released, waived and discharged the Company from any and all claims that such Investor had, have or may have against the Company from the beginning of time through the effective date of their respective General Release Agreement (the “Release”). As consideration for the Release and each Investor’s other obligations, covenants, agreements, representations and warranties set forth in their respective General Release Agreement, the Company issued to each Investor 0.67 shares of Class A Common Stock for every $1.00 of Subscription Amount (as defined in the Purchase Agreements) of 2022 Debentures purchased by such Investor (the “Shares”). Pursuant to the General Release Agreements, the Company issued an aggregate of 7,035,000 Shares consisting of: (a) 3,350,000 Shares to Baboon Partners and (b) 3,685,000 Shares to Inpixon.

The Shares are “restricted securities” within the meaning of Rule 144(a)(3) under the Securities Act of 1933, as amended (the “Securities Act”), and may be sold by the Investors only pursuant to registration under the Securities Act or an available exemption from registration. The General Release Agreements require the Company to file a resale registration statement with the U.S. Securities and Exchange Commission (the “SEC”) covering all of the Shares (the “Registration Statement”) within thirty (30) days of the issuance of the Shares; and to use commercially reasonable efforts to keep the Registration Statement “evergreen” for twelve (12) months from the date it is declared effective by the SEC or until Rule 144 is available to the holders of Shares who are not and have not been affiliates of the Company with respect to all of their Shares, whichever is earlier. The Company will pay all expenses in connection with preparation and filing of the Registration Statement. Each Investor will be responsible for its own sales commissions, if any, transfer taxes and the expenses of any attorney or other advisor that such Investor decides to employ.

The foregoing description of the General Release Agreements does not purport to be complete and is qualified in its entirety by reference to the full text of the form of General Release Agreement that is filed as Exhibit 10.1 to this Current Report on Form 8-K and is incorporated herein by reference.