<SEC-DOCUMENT>0001415889-22-003402.txt : 20220328
<SEC-HEADER>0001415889-22-003402.hdr.sgml : 20220328
<ACCEPTANCE-DATETIME>20220328211506
ACCESSION NUMBER:		0001415889-22-003402
CONFORMED SUBMISSION TYPE:	3
PUBLIC DOCUMENT COUNT:		2
CONFORMED PERIOD OF REPORT:	20220328
FILED AS OF DATE:		20220328
DATE AS OF CHANGE:		20220328

REPORTING-OWNER:	

	OWNER DATA:	
		COMPANY CONFORMED NAME:			Adler Marilyn S.
		CENTRAL INDEX KEY:			0001918713

	FILING VALUES:
		FORM TYPE:		3
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-31588
		FILM NUMBER:		22777179

	MAIL ADDRESS:	
		STREET 1:		315 LAKE STREET EAST
		STREET 2:		SUITE 301
		CITY:			WAYZATA
		STATE:			MN
		ZIP:			55391

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>
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<TYPE>3
<SEQUENCE>1
<FILENAME>form3-03282022_060357.xml
<TEXT>
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<?xml version="1.0"?>
<ownershipDocument>

    <schemaVersion>X0206</schemaVersion>

    <documentType>3</documentType>

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

    <noSecuritiesOwned>1</noSecuritiesOwned>

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

    <reportingOwner>
        <reportingOwnerId>
            <rptOwnerCik>0001918713</rptOwnerCik>
            <rptOwnerName>Adler Marilyn S.</rptOwnerName>
        </reportingOwnerId>
        <reportingOwnerAddress>
            <rptOwnerStreet1>315 EAST LAKE  STREET</rptOwnerStreet1>
            <rptOwnerStreet2>SUITE 301</rptOwnerStreet2>
            <rptOwnerCity>WAYZATA</rptOwnerCity>
            <rptOwnerState>MN</rptOwnerState>
            <rptOwnerZipCode>55391</rptOwnerZipCode>
            <rptOwnerStateDescription></rptOwnerStateDescription>
        </reportingOwnerAddress>
        <reportingOwnerRelationship>
            <isDirector>true</isDirector>
            <isOfficer>false</isOfficer>
            <isTenPercentOwner>false</isTenPercentOwner>
            <isOther>false</isOther>
            <officerTitle></officerTitle>
            <otherText></otherText>
        </reportingOwnerRelationship>
    </reportingOwner>

    <nonDerivativeTable></nonDerivativeTable>

    <derivativeTable></derivativeTable>

    <footnotes></footnotes>

    <ownerSignature>
        <signatureName>/s/ Tyler J. Vivian, Attorney-in-Fact</signatureName>
        <signatureDate>2022-03-28</signatureDate>
    </ownerSignature>
</ownershipDocument>
</XML>
</TEXT>
</DOCUMENT>
<DOCUMENT>
<TYPE>EX-24
<SEQUENCE>2
<FILENAME>ex24-03282022_060357.htm
<TEXT>
<!DOCTYPE html PUBLIC "-//IETF//DTD HTML//EN">
<html><head><title>ex24-03282022_060357.htm</title></head><body style="margin-top:0;font-family:Times New Roman; font-size:10pt; color:#000000">
<p style="margin:0px"><br></p>
<p style="margin:0px; font-size:11pt" align="center">POWER OF ATTORNEY</p>
<p style="margin:0px; text-indent:48px; font-size:11pt" align="justify">I, Marilyn S. Adler, hereby authorize and designate each of Steven C. Kennedy, Steven J. Conley, Jonathan R. Zimmerman, Tyler J. Vivian, Kareem S. Tawfic, Ellie Houser, and Amra Hoso, signing singly, as my true and lawful attorneyinfact to:</p>
<p style="margin-top:0px; margin-bottom:-2px; text-indent:96px; width:144px; font-size:11pt; float:left">(1)</p>
<p style="margin:0px; text-indent:-2px; font-size:11pt" align="justify">prepare and execute for and on my behalf, in my capacity as an officer and/or director of Pineapple Holdings, Inc., a Minnesota Corporation (the <font style="font-family:Arial Unicode MS,Times New Roman">&ldquo;</font>Company<font style="font-family:Arial Unicode MS,Times New Roman">&rdquo;</font>), a Form ID and Forms 3, 4 and 5 in accordance with Section&nbsp;16(a) of the Securities Exchange Act of 1934 (the <font style="font-family:Arial Unicode MS,Times New Roman">&ldquo;</font>Exchange Act<font style="font-family:Arial Unicode MS,Times New Roman">&rdquo;</font>) and the rules and regulations promulgated thereunder and other forms or reports on my behalf as may be required to be filed in connection with my ownership, acquisition, or disposition of securities of the Company, including Form 144;</p>
<p style="margin-top:0px; margin-bottom:-2px; text-indent:96px; width:144px; font-size:11pt; clear:left; float:left">(2)</p>
<p style="margin:0px; text-indent:-2px; font-size:11pt" align="justify">do and perform any and all acts for and on my behalf that may be necessary or desirable to complete and execute any such Form ID, Form 3, 4 or 5 or Form 144, and any amendments to any of the foregoing, and timely file any such form with the Securities and Exchange Commission and any stock exchange or similar authority; and</p>
<p style="margin-top:0px; margin-bottom:-2px; text-indent:96px; width:144px; font-size:11pt; clear:left; float:left">(3)</p>
<p style="margin:0px; text-indent:-2px; font-size:11pt" align="justify">take any other action of any type whatsoever in connection with the foregoing which, in the opinion of such attorneyinfact, may be to my benefit, in my best interest, or legally required of me, it being understood that the statements executed by such attorneyinfact on my behalf pursuant to this Power of Attorney shall be in such form and shall contain such terms and conditions as such attorneyinfact may approve in such attorneyinfact<font style="font-family:Arial Unicode MS,Times New Roman">&rsquo;</font>s discretion.</p>
<p style="margin:0px; text-indent:48px; font-size:11pt; clear:left" align="justify">I hereby further grant to each such attorneyinfact full power and authority to do and perform any and every act and thing whatsoever requisite, necessary, or proper to be done in the exercise of any of the rights and powers herein granted, as fully to all intents and purposes as I might or could do if personally present, with full power of substitution or revocation, hereby ratifying and confirming all that such attorneyinfact, or such attorneyinfact<font style="font-family:Arial Unicode MS,Times New Roman">&rsquo;</font>s substitute or substitutes, shall lawfully do or cause to be done by virtue of this Power of Attorney and the rights and powers herein granted. &nbsp;I hereby acknowledge that the foregoing attorneysinfact, in serving in such capacity at my request, are not assuming, nor is the Company assuming, any of my responsibilities to comply with Section 16 of the Exchange Act or Rule 144 under the Securities Act of 1933, as amended (the <font style="font-family:Arial Unicode MS,Times New Roman">&ldquo;</font>Securities Act<font style="font-family:Arial Unicode MS,Times New Roman">&rdquo;</font>).</p>
<p style="margin:0px; text-indent:48px; font-size:11pt" align="justify">This Power of Attorney shall remain in full force and effect until I am no longer required to file Form ID or Forms 3, 4 and 5 or Form 144 with respect to my holdings of and transactions in securities issued by the Company, unless earlier revoked by me in a signed writing delivered to the foregoing attorneysinfact. &nbsp;Notwithstanding the foregoing, if any such attorney-in-fact hereafter ceases to be at least one of the following: (i) an employee of the Company, (ii) a partner of Faegre Drinker Biddle &amp; Reath LLP or (iii) an employee of Faegre Drinker Biddle &amp; Reath LLP, then this Power of Attorney shall be automatically revoked solely as to such individual, immediately upon such cessation, without any further action on my part.</p>
<p style="margin:0px; text-indent:48px; font-size:11pt" align="justify">I hereby revoke all previous Powers of Attorney that have been granted by me in connection with my reporting obligations, if any, under Section 16 of the Exchange Act and Rule 144 under the Securities Act with respect to my holdings of and transactions in securities issued by the Company. </p>
<p style="margin:0px; text-indent:48px; font-size:11pt" align="justify">IN WITNESS WHEREOF, I have caused this Power of Attorney to be duly executed as of this 28<sup>th</sup> day of March, 2022.</p>
<p style="margin:0px; padding-left:312px; font-size:11pt" align="justify">/s/ Marilyn S. Adler</p>
<p style="margin:0px" align="justify"><br><br></p>
<p style="margin:0px; font-size:8pt">fb.us.7494444.01</p>
<p style="margin:0px; font-size:8pt"><b><i><u>dms.us.53093708.01</u></i></b></p>
<div style="width:268.8px">
<p style="margin:0px; width:268.8px; font-family:Arial; font-size:8pt">US.137503999.01</p>
<p style="margin:0px"><br></p>
</div>
<p style="margin:0px"><br></p>
</body></html>
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
