<SEC-DOCUMENT>0000897101-24-000539.txt : 20241018
<SEC-HEADER>0000897101-24-000539.hdr.sgml : 20241018
<ACCEPTANCE-DATETIME>20241018171157
ACCESSION NUMBER:		0000897101-24-000539
CONFORMED SUBMISSION TYPE:	DEFA14A
PUBLIC DOCUMENT COUNT:		1
FILED AS OF DATE:		20241018
DATE AS OF CHANGE:		20241018

FILER:

	COMPANY DATA:	
		COMPANY CONFORMED NAME:			Pineapple Energy Inc.
		CENTRAL INDEX KEY:			0000022701
		STANDARD INDUSTRIAL CLASSIFICATION:	TELEPHONE & TELEGRAPH APPARATUS [3661]
		ORGANIZATION NAME:           	04 Manufacturing
		IRS NUMBER:				410957999
		STATE OF INCORPORATION:			MN
		FISCAL YEAR END:			1231

	FILING VALUES:
		FORM TYPE:		DEFA14A
		SEC ACT:		1934 Act
		SEC FILE NUMBER:	001-31588
		FILM NUMBER:		241381419

	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:	Pineapple Holdings, Inc.
		DATE OF NAME CHANGE:	20220328

	FORMER COMPANY:	
		FORMER CONFORMED NAME:	COMMUNICATIONS SYSTEMS INC
		DATE OF NAME CHANGE:	19950401
</SEC-HEADER>
<DOCUMENT>
<TYPE>DEFA14A
<SEQUENCE>1
<FILENAME>pegy241095_defa14a.htm
<DESCRIPTION>DEFA14A
<TEXT>
<HTML>
<HEAD>
     <TITLE></TITLE>
</HEAD>
<BODY STYLE="font: 10pt Arial, Helvetica, Sans-Serif">
<p style="font: bold 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt; text-align: center">&#160;</p>

<!-- Field: Rule-Page --><div style="text-align: left"><div style="border-top: Black 4pt solid; border-bottom: Black 1pt solid; font-size: 1pt; width: 100%">&#160;</div></div><!-- Field: /Rule-Page -->

<p style="font: bold 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt; text-align: center">&#160;</p>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 14pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>UNITED STATES</B></P>

<P STYLE="font: 14pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>SECURITIES AND EXCHANGE COMMISSION</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Washington, D.C. 20549 </B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 14pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>SCHEDULE 14A</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Proxy Statement Pursuant to Section&nbsp;14(a)
of the Securities Exchange Act of 1934</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>(Amendment No. &nbsp;)</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 10pt">Filed by the Registrant&nbsp;&nbsp;<FONT STYLE="font-family: Times New Roman, Times, Serif">&#9746;</FONT></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 10pt">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 10pt">Filed by a Party other than the Registrant&nbsp;&nbsp;<FONT STYLE="font-family: Times New Roman, Times, Serif">&#9744;</FONT></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 10pt">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 10pt">Check the appropriate box:</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 10pt">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="font: 10pt Times New Roman, Times, Serif; width: 100%">
<TR>
    <TD STYLE="width: 5%; padding-bottom: 6pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif">&#9744;</FONT></TD>
    <TD STYLE="width: 95%; padding-bottom: 6pt">Preliminary Proxy Statement</TD></TR>
<TR>
    <TD STYLE="padding-bottom: 6pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif">&#9744;</FONT></TD>
    <TD STYLE="padding-bottom: 6pt">Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))</TD></TR>
<TR>
    <TD STYLE="padding-bottom: 6pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif">&#9744;</FONT></TD>
    <TD STYLE="padding-bottom: 6pt">Definitive Proxy Statement</TD></TR>
<TR>
    <TD STYLE="padding-bottom: 6pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif">&#9746;</FONT></TD>
    <TD STYLE="padding-bottom: 6pt">Definitive Additional Materials</TD></TR>
<TR>
    <TD STYLE="text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif">&#9744;</FONT></TD>
    <TD>Soliciting Material under &sect;240.14a-12</TD></TR>
</TABLE>
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 18pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>Pineapple Energy Inc.</B></P>



<!-- Field: Rule-Page --><DIV ALIGN="LEFT" STYLE="margin-top: 1pt; margin-bottom: 1pt"><DIV STYLE="font-size: 1pt; border-top: black 1pt solid; width: 100%">&nbsp;</DIV></DIV><!-- Field: /Rule-Page -->

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>(Name of Registrant as Specified In Its
Charter) </B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<!-- Field: Rule-Page --><DIV ALIGN="LEFT" STYLE="margin-top: 1pt; margin-bottom: 1pt"><DIV STYLE="font-size: 1pt; border-top: black 1pt solid; width: 100%">&nbsp;</DIV></DIV><!-- Field: /Rule-Page -->

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>(Name of Person(s) Filing Proxy Statement,
if other than the Registrant) </B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 10pt">Payment of Filing Fee (Check all boxes that apply):</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0 0pt 10pt">&nbsp;</P>

<TABLE CELLSPACING="0" CELLPADDING="0" STYLE="font: 10pt Times New Roman, Times, Serif; width: 100%">
<TR STYLE="vertical-align: top">
    <TD STYLE="width: 5%; padding-bottom: 6pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif">&#9746;</FONT></TD>
    <TD STYLE="width: 95%; padding-bottom: 6pt">No fee required</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="padding-bottom: 6pt; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif">&#9744;</FONT></TD>
    <TD STYLE="padding-bottom: 6pt">Fee paid previously with preliminary materials</TD></TR>
<TR STYLE="vertical-align: top">
    <TD STYLE="text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif">&#9744;</FONT></TD>
    <TD>Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11</TD></TR>
</TABLE>




<p style="font: bold 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt; text-align: center">&#160;</p>

<!-- Field: Rule-Page --><div style="text-align: left"><div style="border-top: Black 4pt solid; border-bottom: Black 1pt solid; font-size: 1pt; width: 100%">&#160;</div></div><!-- Field: /Rule-Page -->

<p style="font: bold 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt; text-align: center">&#160;</p>





<!-- Field: Page; Sequence: 1 -->
    <DIV STYLE="border-bottom: Gray 3pt solid; margin-top: 12pt; margin-bottom: 6pt"><P STYLE="font: 9pt Times New Roman, Times, Serif; margin-top: 0pt; text-align: center; margin-bottom: 0pt"></P></DIV>
    <DIV STYLE="page-break-before: always; margin-top: 6pt; margin-bottom: 6pt"><P STYLE="margin: 0pt">&#160;</P></DIV>
    <!-- Field: /Page -->

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center"><FONT STYLE="text-transform: uppercase"><B>PINEAPPLE
ENERGY INC.</B></FONT></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center"><FONT STYLE="text-transform: uppercase">&nbsp;</FONT></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>Supplement to Proxy Statement for the</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>2024 Annual Meeting of Shareholders</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center"><B>To be Held on July 1, 2024</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: center">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">The following information supplements the Definitive Proxy Statement on
Schedule 14A (the &ldquo;Proxy Statement&rdquo;) that was filed by Pineapple Energy Inc. (the &ldquo;Company,&rdquo; &ldquo;we,&rdquo;
&ldquo;us&rdquo; and &ldquo;our&rdquo;) with the Securities and Exchange Commission (the &ldquo;SEC&rdquo;) on October 10, 2024 and provided
to the Company&rsquo;s shareholders in connection with the solicitation of proxies by the Company&rsquo;s Board of Directors for the Company&rsquo;s
Special Meeting of Shareholders (the &ldquo;November 2024 Special Meeting&rdquo;) to be held on November 4, 2024. This supplement to the
Proxy Statement (this &ldquo;Supplement&rdquo;) is being filed with the SEC on October 17, 2024. All capitalized terms not otherwise defined
herein shall have the respective meanings as set forth in the Proxy Statement.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">The information in this Supplement is in addition to the information provided
by the Proxy Statement, and except for the changes herein, this Supplement does not modify any other information set forth in the Proxy
Statement. The Proxy Statement contains important additional information and this Supplement should be read in conjunction with the Proxy
Statement.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">The Company is providing this Supplement to provide supplemental disclosure
regarding the receipt from The Nasdaq Stock Market of a minimum bid price deficiency notice, and implementation of the Company&rsquo;s
1-for-50 reverse stock split, which took effect on October 17, 2024.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0"><U>Nasdaq Listing Compliance</U></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">As previously disclosed, on October 1, 2024, the Company received a Minimum
Bid Price Deficiency Letter from the Listing Qualifications Department (the &ldquo;Staff&rdquo;) of The Nasdaq Stock Market (&ldquo;Nasdaq&rdquo;)
notifying the Company that, for the 30 consecutive business day period from August 16 through September 30, 2024, the Company&rsquo;s
common stock had not maintained a minimum closing bid price of $1.00 per share (the &ldquo;Minimum Bid Price Requirement&rdquo;) required
for continued listing on The Nasdaq Capital Market pursuant to Nasdaq Listing Rule 5550(a)(2). The Nasdaq letter does not result in the
immediate delisting of the Company&rsquo;s common stock from The Nasdaq Capital Market.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">Normally, a company would be afforded a 180-calendar day period (&ldquo;Cure
Period&rdquo;) to demonstrate compliance with the Minimum Bid Price Requirement. However, pursuant to the previously disclosed Nasdaq
hearing panel decision, dated July 18, 2024, the Company was subject to a mandatory panel monitor (&ldquo;Panel&rdquo;) under Nasdaq&rsquo;s
listing Rule 5815(d)(4)(B) for a period of one year. Accordingly, due to the most recent Minimum Bid Price Requirement deficiency, as
is customary in similar situations, the Staff notified the Company that it will not be afforded a Cure Period. Instead, the Company was
offered an opportunity to appeal any deficiency related to a delisting determination to Nasdaq by or before October 8, 2024. The Company
timely filed with the Staff an appeal hearing request. The hearing request automatically stayed any suspension or delisting action pending
the hearing and the expiration of any additional extension period if granted by the Panel following the hearing.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">In the event that the Company regains compliance with the Minimum Bid Price
Requirement prior to any scheduled hearing date, including based on the below-described reverse stock split, then a hearing may not be
necessary, as the Company may be mooted out of the hearings process.</P>

<P STYLE="font: 10pt Arial, Helvetica, Sans-Serif; margin: 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0"><U>October 2024 Reverse Stock Split</U></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">As previously disclosed, on July 19, 2024, the Company held its 2024 Annual
Meeting of Shareholders, at which the Company&rsquo;s shareholders approved a reverse stock split of the outstanding shares of the Company&rsquo;s
common stock, at a ratio within a range of 1-for-2 to 1-for-200, as determined by the Board (the &ldquo;July Reverse Stock Split Approval&rdquo;).</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">As a result of the receipt of the October 1, 2024 Nasdaq Minimum Bid Price
Deficiency letter, in an effort to address and satisfy the Minimum Bid Price Requirement of Nasdaq for continued listing, on October 4,
2024 the Board approved the implementation of a reverse stock split pursuant to the July Reverse Stock Split Approval at the ratio of
1-for-50, which took effect on October 17, 2024 (the &ldquo;October 2024 Reverse Stock Split&rdquo;).&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">Upon the effectiveness of the October 2024 Reverse Stock Split, every 50
shares of issued and outstanding Company common stock as of 12:01 a.m. Central Time, on October 17, 2024 (the &ldquo;Effective Time&rdquo;)
were automatically combined into one issued and outstanding share of common stock, with no change in par value per share. Proportionate
adjustments were made to the conversion number and exercise prices of the Company&rsquo;s outstanding stock purchase warrants, stock options,
convertible preferred stock, convertible notes, and to the number of shares issued and issuable under the Company&rsquo;s equity incentive
plans. Immediately prior to the Effective Time, there were 67,260,696 shares of common stock issued and outstanding, which were reverse
split to reflect approximately 1,345,214 shares of common stock issued and outstanding immediately thereafter.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">The October 2024 Reverse Stock Split also proportionally reduced the number
of shares of the Company&rsquo;s authorized common stock from 133,333,333 to 2,666,267. No fractional shares were issued as a result of
the October 2024 Reverse Stock Split. Any fractional shares that resulted from the October 2024 Reverse Stock Split will be settled in
cash. &nbsp;The October 2024 Reverse Stock Split affected all common shareholders uniformly and did not alter any shareholder&rsquo;s
percentage interest in the Company&rsquo;s common stock, except to the extent that the October 2024 Reverse Stock Split resulted in some
shareholders experiencing an adjustment of a fractional share as described above.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>
<!-- Field: Page; Sequence: 1 -->
    <DIV STYLE="border-bottom: Gray 3pt solid; margin-top: 12pt; margin-bottom: 6pt"><P STYLE="font: 9pt Times New Roman, Times, Serif; margin-top: 0pt; text-align: center; margin-bottom: 0pt"></P></DIV>
    <DIV STYLE="page-break-before: always; margin-top: 6pt; margin-bottom: 6pt"><P STYLE="margin: 0pt">&#160;</P></DIV>
    <!-- Field: /Page -->
<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0"><U>Forward Looking Statements</U></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0">The Proxy Statement and this Supplement include certain forward-looking
statements within the meaning of the Private Securities Litigation Reform Act of 1995. These statements are based on the Company&rsquo;s
current expectations or beliefs and are subject to uncertainty and changes in circumstances, including any ability to regain compliance
with Nasdaq&rsquo;s continued listing standards. While the Company believes its plans, intentions, and expectations reflected in those
forward-looking statements are reasonable, these plans, intentions, or expectations may not be achieved. For information about the factors
that could cause such differences, please refer to the Company&rsquo;s filings with the Securities and Exchange Commission, including,
without limitation, the statements made under the heading &ldquo;Risk Factors&rdquo; in the Company's Annual Report on Form 10-K for the
year ended December 31, 2023 and in subsequent filings. The Company does not undertake any obligation to update or revise these forward-looking
statements for any reason, except as required by law.</P>


<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0; color: #262626">&nbsp;</P>




<P STYLE="font: 10pt Arial, Helvetica, Sans-Serif; margin: 0">&nbsp;</P>
<!-- Field: Page; Sequence: 6 -->
    <DIV STYLE="border-bottom: Gray 3pt solid; margin-top: 12pt; margin-bottom: 6pt"><P STYLE="font: 9pt Times New Roman, Times, Serif; margin-top: 0pt; text-align: center; margin-bottom: 0pt"></P></DIV>

    <!-- Field: /Page -->


</BODY>
</HTML>
<!-- Field: Set; Name: xdx; ID: xdx_08B_extensions -->
<!-- eJxFjV0KwjAQhE/QOyx5ltoGK9I3LVrEKlJEfI12lWCbLZv4dyRvaWwRl4VlmflmhBiInBa6RobDrCxgh01bK4dQ4hkZzQm9I1uuUvC3xIu2jpVx3fsDM/IMeiYJ4/HRC531ri1WKcRyGE2GUkI0SpMEpmsRfPWMzFlXaJxWNShTwZapZY1O8atP2KknGWpeXdUe2WoyPi6MevkNMoolbOiuHsRXC0WRiWDQTSByplv7rblZRw3Ma2x8l+3R/wYfFGJJQg== -->
</TEXT>
</DOCUMENT>
</SEC-DOCUMENT>
