FOXO TECHNOLOGIES INC.

ITEM 2. UNREGISTERED SALES OF EQUITY SECURITIES AND USE OF PROCEEDS

Promissory Notes Extension Shares

On April 27, 2026, the Company entered into Amendment No. 1 to Promissory Note (the “ClearThink Note Amendment”), which extended the maturity date of the note to May 15, 2026. As compensation for the extension of the maturity date: 50,000 shares of the Company’s Class A Common Stock were issued by the Company to the holder.

Shares Issued Pursuant to Series A Conversions

On April 13, 2026, a holder of our Series A Preferred Stock was issued 93,333 shares of Class A Common Stock pursuant to the conversion of 28.0 shares of Series A Preferred Stock.

On May 7, 2026, a holder of our Series A Preferred Stock was issued 33,000 shares of Class A Common Stock pursuant to the conversion of 9.9 shares of Series A Preferred Stock.

Series D Preferred Stock Issued to J.H. Darbie & Co., Inc.

On May 15, 2026, in connection with a Settlement Agreement and Release with J.H. Darbie & Co., Inc., the Company issued 400 shares of its Series D Preferred Stock in satisfaction of $348,454 of finder’s fees owed to J.H. Darbie under a prior finder’s fee agreement, as more fully discussed in Note 12 to the accompanying condensed consolidated financial statements.

Senior Notes Issued in Exchange for Series A Preferred Stock

On May 12, 2026, the Company issued senior unsecured, non-convertible promissory notes in the aggregate principal amount of approximately $7.8 million to two institutional investors in exchange for, and in cancellation of, an aggregate of 7,775 shares of the Company’s Series A Preferred Stock, as more fully discussed in Note 9 to the accompanying condensed consolidated financial statements.

The shares of Class A Common Stock issued upon conversion of the Series A Preferred Stock and the Senior Notes issued in exchange for the Series A Preferred Stock, in each case described above, were issued in reliance upon the exemption from registration afforded by Section 3(a)(9) of the Securities Act, as securities exchanged by the Company with its existing security holders where no commission or other remuneration was paid or given directly or indirectly for soliciting such exchange.

The 400 shares of Series D Preferred Stock issued to J.H. Darbie & Co., Inc., and the shares of Class A Common Stock issued as inducement and extension consideration in connection with promissory notes, in each case described above, were issued in reliance upon the exemption from registration afforded by Section 4(a)(2) of the Securities Act and Rule 506(b) of Regulation D thereunder, based in part on the representations of the recipients, each of whom the Company believes was an accredited investor that acquired the securities for investment and not with a view to distribution.