<SEC-DOCUMENT>0001615594-22-000023.txt : 20220329
<SEC-HEADER>0001615594-22-000023.hdr.sgml : 20220329
<ACCEPTANCE-DATETIME>20220329105026
ACCESSION NUMBER:		0001615594-22-000023
CONFORMED SUBMISSION TYPE:	4
PUBLIC DOCUMENT COUNT:		1
CONFORMED PERIOD OF REPORT:	20220328
FILED AS OF DATE:		20220329
DATE AS OF CHANGE:		20220329

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			PRIMUTH RICHARD A
		CENTRAL INDEX KEY:			0001013832

	FILING VALUES:
		FORM TYPE:		4
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-31588
		FILM NUMBER:		22778529

ISSUER:		

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			Pineapple Holdings, Inc.
		CENTRAL INDEX KEY:			0000022701
		STANDARD INDUSTRIAL CLASSIFICATION:	TELEPHONE & TELEGRAPH APPARATUS [3661]
		IRS NUMBER:				410957999
		STATE OF INCORPORATION:			MN
		FISCAL YEAR END:			1231

	BUSINESS ADDRESS:	
		STREET 1:		10900 RED CIRCLE DRIVE
		CITY:			MINNETONKA
		STATE:			MN
		ZIP:			55343
		BUSINESS PHONE:		9529961674

	MAIL ADDRESS:	
		STREET 1:		10900 RED CIRCLE DRIVE
		CITY:			MINNETONKA
		STATE:			MN
		ZIP:			55343

	FORMER COMPANY:	
		FORMER CONFORMED NAME:	COMMUNICATIONS SYSTEMS INC
		DATE OF NAME CHANGE:	19950401
</SEC-HEADER>
<DOCUMENT>
<TYPE>4
<SEQUENCE>1
<FILENAME>primary_doc.xml
<DESCRIPTION>PRIMARY DOCUMENT
<TEXT>
<XML>
<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0306</schemaVersion>

    <documentType>4</documentType>

    <periodOfReport>2022-03-28</periodOfReport>

    <notSubjectToSection16>1</notSubjectToSection16>

    <issuer>
        <issuerCik>0000022701</issuerCik>
        <issuerName>Pineapple Holdings, Inc.</issuerName>
        <issuerTradingSymbol>PEGY</issuerTradingSymbol>
    </issuer>

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001013832</rptOwnerCik>
            <rptOwnerName>PRIMUTH RICHARD A</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>10900 RED CIRCLE DRIVE</rptOwnerStreet1>
            <rptOwnerStreet2></rptOwnerStreet2>
            <rptOwnerCity>MINNETONKA</rptOwnerCity>
            <rptOwnerState>MN</rptOwnerState>
            <rptOwnerZipCode>55343</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>1</isDirector>
            <isOfficer>0</isOfficer>
            <isTenPercentOwner>0</isTenPercentOwner>
            <isOther>0</isOther>
        </reportingOwnerRelationship>
    </reportingOwner>

    <nonDerivativeTable>
        <nonDerivativeHolding>
            <securityTitle>
                <value>Common Stock</value>
            </securityTitle>
            <postTransactionAmounts>
                <sharesOwnedFollowingTransaction>
                    <value>12567</value>
                    <footnoteId id="F1"/>
                </sharesOwnedFollowingTransaction>
            </postTransactionAmounts>
            <ownershipNature>
                <directOrIndirectOwnership>
                    <value>D</value>
                </directOrIndirectOwnership>
            </ownershipNature>
        </nonDerivativeHolding>
    </nonDerivativeTable>

    <footnotes>
        <footnote id="F1">The reporting person is no longer serving as a director of Pineapple Holdings, Inc.  As a result, the reporting person is no longer subject to Section 16 in connection with his transactions in the equity securities of Pineapple Holdings, Inc. and therefore will no longer report any such transaction on Form 4 or Form 5.</footnote>
    </footnotes>

    <ownerSignature>
        <signatureName>Suzette McNally, Attorney-in-Fact for Richard A. Primuth</signatureName>
        <signatureDate>2022-03-29</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
