Sec Form 4 Filing - Holland Tom @ Pineapple Holdings, Inc. - 2022-03-28

FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person Holland Tom 2. Issuer Name and Ticker or Trading Symbol Pineapple Holdings, Inc. [ PEGY] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) X __ Director _____ 10% Owner _____ Officer (give title below) _____ Other (specify below) (Last) (First) (Middle) 315 EAST LAKE STREET, SUITE 301 3. Date of Earliest Transaction (MM/DD/YY) 03/28/2022 (Street) WAYZATA, MN55391 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price Common Stock 03/28/2022 A 22,620 A 22,620 I By Trust

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Holland Tom 315 EAST LAKE STREET SUITE 301 WAYZATA, MN55391 X Signatures /s/ Tyler J. Vivian, Attorney-in-Fact 03/28/2022 Signature of Reporting Person Date

Explanation of Responses:

( 1 )The reporting person acquired 7,945 shares of issuer common stock, par value $0.05 per share (the "Common Stock"), in exchange for 81,301 Class A Units of Pineapple Energy, LLC ("Pineapple") pursuant to Pineapple's merger into the issuer (the "Merger") on March 28, 2022 (the "Closing Date"). Additionally, on the Closing Date, the reporting person became entitled to receive 4,554 shares of Common Stock pursuant to an "earn-out" provision (the "Earn-Out Consideration") in the Merger agreement, which entitled certain Pineapple shareholders to receive additional shares of Common Stock if a funding-related condition to the closing of the Merger was satisfied by Pineapple or waived by the issuer. Of the 4,554 shares of Common Stock of Earn-Out Consideration, 1,518 shares of Common Stock are being held in escrow by a third-party escrow agent, (CONTINUED IN FOOTNOTE 2) ( 2 )(CONTINUING FROM FOOTNOTE 1) and will be distributed according to the terms of an escrow agreement that was entered into on the Closing Date by and among the issuer and certain Pineapple shareholders (the "Escrow Agreement"), which states that if the volume weighted average trading price of the Common Stock for the 30 consecutive trading days beginning on April 4, 2022 ("VWAP") is $8.00 per share of Common Stock or higher, the reporting person shall receive all of the 1,518 escrowed shares of Common Stock; however, to the extent the VWAP is below $8.00, the number of shares of Common Stock to be issued shall be reduced in accordance with the formula outlined in Section 6(c)(ii) of the Escrow Agreement. The remaining 3,036 shares of Earn-Out Consideration were issued to the reporting person in connection with the closing of the Merger. The closing price of the issuer's common stock on the Closing Date was $8.18.

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