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 OF SECURITIES
                                                                                  
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Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934 or Section 30(h) of the Investment Company Act of 1940
                      

1. Name and Address of Reporting Person *

SAMPSON RANDALL D		 2. Issuer Name and Ticker or Trading Symbol

Pineapple Energy 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)

10900 RED CIRCLE DRIVE		 3. Date of Earliest Transaction (MM/DD/YYYY)

6/14/2023
(Street)

MINNETONKA, MN 55343		 4. If Amendment, Date Original Filed (MM/DD/YYYY)

 
 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)
Rule 10b5-1(c) Transaction Indication
☐ Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1.Title of Security
(Instr. 3) 		2. Trans. Date 2A. Deemed Execution Date, if any 3. Trans. 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 6/14/2023  G  V 23773 A$0 58101 D 
 
Common Stock         170333 I See footnotes (1)(2)

Table II - Derivative Securities Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivate Security
(Instr. 3)		2. Conversion or Exercise Price of Derivative Security3. Trans. Date3A. Deemed Execution Date, if any4. Trans. Code
(Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date7. Title and Amount of Securities Underlying Derivative Security
(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)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Explanation of Responses:
(1) Held as of June 14, 2023 by the Sampson Family Real Estate Holdings, LLC (SFREH), of which Mr. Sampson is the sole manager. Members of SFREH include the Marian Arlis Sampson 2012 Family Revocable Trust, the Curtis A. Sampson Family Trust, and the Randall D. Sampson GST Trust, of which Mr. Sampson is the grantor and his grandchildren are beneficiaries. Mr. Sampson and his children are among the beneficiaries of the Marian Arlis Sampson 2012 Family Irrevocable Trust and the Curtis A. Sampson Family Trust. Mr. Sampson disclaims beneficial ownership in membership interests of SFREH in which he has no pecuniary interest.
(2) Following the death of Curtis A. Sampson on July 16, 2020, Randall D. Sampson became the executor of the estate of Curtis A. Sampson, became the trustee of certain trusts of Curtis A. Sampson that held Company stock and was granted other fiduciary powers relating to Company stock. Transactions by Mr. Sampson in Company stock in his fiduciary capacity subsequent to July 16, 2020 are exempt from reporting under Rule 16a-2(d)(1).

Reporting Owners
Reporting Owner Name / Address
Relationships
Director10% OwnerOfficerOther
SAMPSON RANDALL D
10900 RED CIRCLE DRIVE
MINNETONKA, MN 55343		X
Signatures
/s/ Christine G. Long, Attorney-in-fact for Randall D. Sampson6/16/2023
**Signature of Reporting PersonDate
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
*If the form is filed by more than one reporting person, see Instruction 4(b)(v).
**Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note:File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB control number.
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