SUNE / SUNation Energy Inc. - SEC Filings, Annual Report, Proxy Statement

SUNation Energy Inc.
US ˙ NasdaqCM ˙ US86732Y1091

Basic Stats
LEI 549300QI9W6WNCHUTR82
CIK 22701
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to SUNation Energy Inc.
SEC Filings (Chronological Order)
This page provides a complete, chronological list of SEC Filings, excluding ownership filings which we provide elsewhere.
August 18, 2025 EX-99.1

sunation ENERGY ANNOUNCES 2025 SECOND QUARTER RESULTS AND REITERATES full year FINANCIAL GUIDANCE FY 2025 Total Sales Expected to Rise 14% - 23% from FY 2024 with Positive Adjusted EBITDA

Exhibit 99.1 sunation ENERGY ANNOUNCES 2025 SECOND QUARTER RESULTS AND REITERATES full year FINANCIAL GUIDANCE FY 2025 Total Sales Expected to Rise 14% - 23% from FY 2024 with Positive Adjusted EBITDA Q2 2025 Select Highlights ● Gross Margin Expanded to 37% ● Total Debt Declined by $11.7 Million, a 61% Improvement from December 31, 2024 ● Residential Backlog at June 30, 2025 Increased to $27.1 Mil

August 18, 2025 424B5

$30,000,000 of Common Stock

Filed pursuant to Rule 424(b)(5) Registration No. 333-286663 PROSPECTUS SUPPLEMENT (To Prospectus dated April 29, 2025) $30,000,000 of Common Stock We have entered into a Sales Agreement (the “Sales Agreement”), dated August 18, 2025, with Needham & Company, LLC (the “Sales Agent”), relating to the shares of our Common Stock, par value $0.05 per share (the “Common Stock”), offered by this prospect

August 18, 2025 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): August 11, 2025 SUNation Energy,

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): August 11, 2025 SUNation Energy, Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission F

August 18, 2025 EX-10.1

SUNation Energy, Inc. Shares of Common Stock SALES AGREEMENT

Exhibit 10.1 SUNation Energy, Inc. Shares of Common Stock SALES AGREEMENT August 18, 2025 Needham & Company, LLC 250 Park Avenue New York, New York 10177 Ladies and Gentlemen: SUNation Energy, Inc., a Delaware corporation (the “Company”), confirms as follows its agreements with Needham & Company, LLC (the “Sales Agent”). 1. Issuance and Sale of Shares. (a) On the basis of the representations, warr

August 15, 2025 10-Q

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

‎ UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-31588 SUNATION EN

August 14, 2025 NT 10-Q

SEC FILE NUMBER

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SEC FILE NUMBER 001-31588 CUSIP NUMBER 72303P503 FORM 12b-25 NOTIFICATION OF LATE FILING (Check One): ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☒ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended: June 30, 2025 ☐ Transition Report on Form 10-K ☐ Transition Report on Form 20-F ☐ Transition Report on Form 11-K ☐ Transit

July 24, 2025 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): July 18, 2025 SUNation Energy, In

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): July 18, 2025 SUNation Energy, Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission Fil

July 24, 2025 EX-16.1

Letter of UHYLLP, dated July 24, 2025

EX-16.1 2 ea025008501ex16-1sunation.htm LETTER OF UHYLLP, DATED JULY 24, 2025 Exhibit 16.1 UHY LLP 201 Old Country Road Suite 205 Melville, NY 11747 (631) 712-6860 uhy-us.com July 24, 2025 Securities and Exchange Commission 100 F. Street, N.E. Washington, DC 20549-7561 Re: SUNation Energy, Inc. Commission File Number: 001-31588 Commissioners: We have read the statements made by SUNation Energy, In

June 26, 2025 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): June 26, 2025 SUNation Energy, In

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): June 26, 2025 SUNation Energy, Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission Fil

June 16, 2025 EX-99.1

SUNation Energy RETAINS NASDAQ LISTING

Exhibit 99.1 SUNation Energy RETAINS NASDAQ LISTING RONKONKOMA, N.Y., June 16 , 2025 - SUNation Energy, Inc. (Nasdaq: SUNE) (“the Company”), a leading provider of sustainable solar energy and backup power solutions for households, businesses, and municipalities, today announced that, by a decision dated June 10, 2025, the Nasdaq Hearings Panel (the “Panel”) made a finding that the Company Is not i

June 16, 2025 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): June 10, 2025 SUNation Energy, In

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): June 10, 2025 SUNation Energy, Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission Fil

May 16, 2025 EX-99.1

sunation ENERGY ANNOUNCES 2025 FIRST QUARTER RESULTS AND INTRODUCES FINANCIAL GUIDANCE for 2025 Substantial Progress in Reducing Debt, Lowering Costs, Enhancing Cash Flow Strong Commercial Project Backlog

Exhibit 99.1 sunation ENERGY ANNOUNCES 2025 FIRST QUARTER RESULTS AND INTRODUCES FINANCIAL GUIDANCE for 2025 Substantial Progress in Reducing Debt, Lowering Costs, Enhancing Cash Flow Strong Commercial Project Backlog RONKONKOMA, NY – May 15, 2025 – SUNation Energy, Inc. (Nasdaq: SUNE) (the “Company”), a leading provider of sustainable solar energy and backup power to households, businesses, munic

May 16, 2025 8-K

Results of Operations and Financial Condition, Financial Statements and Exhibits

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): May 15, 2025 SUNation Energy, Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission File

May 15, 2025 EX-19

Insider Trading Policy

POLICY STATEMENT ON CONFIDENTIAL INFORMATION AND SECURITIES TRADING BY SUNATION ENERGY, INC.

May 15, 2025 10-Q

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

‎ UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-31588 SUNATION E

April 30, 2025 10-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 ☐ TRAN

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-315

April 28, 2025 CORRESP

SUNation Energy, Inc. 171 Remington Boulevard Ronkonkoma, NY 11779

SUNation Energy, Inc. 171 Remington Boulevard Ronkonkoma, NY 11779 April 28, 2025 via EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, DC 20549 Attention: Ms. Sarah Sidwell Re: SUNation Energy, Inc. Registration Statement on Form S-3 Filed April 22, 2025 Securities Act File No. 333-286663 Request for Acceleration of Effectiveness Dear Ms. Sidw

April 22, 2025 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables FORM S-3 (Form Type) SUNATION ENERGY, INC.

April 22, 2025 S-3

As filed with the Securities and Exchange Commission on April 22, 2025

As filed with the Securities and Exchange Commission on April 22, 2025 Registration No.

April 17, 2025 EX-10.2

Security Agreement, dated April 14, 2025

Exhibit 10.2 SECURITY AGREEMENT This Security Agreement (this “Agreement”) is made on April 14, 2025 (“Effective Date”) by SUNation Energy, Inc., a Delaware corporation having an office located at 171 Remington Boulevard, Ronkonkoma, New York 11779 (“Debtor”) in favor of MBB Energy, LLC, a New York limited liability company having an office located at 40 Grassmere Avenue, Oakdale, New York 11769 (

April 17, 2025 EX-99.1

SUNation Energy ANNOUNCES REVERSE STOCK SPLIT

Exhibit 99.1 SUNation Energy ANNOUNCES REVERSE STOCK SPLIT RONKONKOMA, N.Y., April 16, 2025 - SUNation Energy, Inc. (Nasdaq: SUNE) (“SUNation” or “the Company”), a leading provider of sustainable solar energy and backup power solutions for households, businesses, and municipalities, today announced that its Board of Directors approved a 200 - for 1 reverse stock split of the Company’s outstanding

April 17, 2025 EX-3.1

Certificate of Amendment to Certificate of Incorporation, filed with the Delaware Secretary of State on April 16, 2025

Exhibit 3.1 CERTIFICATE OF AMENDMENT OF CERTIFICATE OF INCORPORATION OF SUNATION ENERGY, INC., a Delaware Corporation SUNation Energy, Inc. (the “Corporation”), a corporation organized and existing under the General Corporation Law of the State of Delaware, hereby certifies as follows: 1. This Certificate of Amendment (the “Certificate of Amendment”) amends the provisions of the Corporation's Cert

April 17, 2025 8-K

Regulation FD Disclosure, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Material Modification to Rights of Security Holders, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): April 11, 2025 SUNation Energy, Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission Fi

April 17, 2025 EX-10.1

Secured Revolving Line of Credit Agreement, dated April 14, 2025

Exhibit 10.1 SECURED REVOLVING LINE OF CREDIT AGREEMENT This Secured Revolving Line of Credit Agreement (this “Agreement”) is made on April 14, 2025 (“Effective Date”) between SUNation Energy, Inc., a Delaware corporation having an office located at 171 Remington Boulevard, Ronkonkoma, New York 11779 (“Borrower”) and MBB Energy, LLC, a New York limited liability company having an office located at

April 15, 2025 EX-10.53

Amended and Restated Long-Term Senior Secured Promissory Note, dated April 10, 2025, between SUNation Energy, Inc. and both Scott Maskin and James Brennan

Exhibit 10.53 EXECUTION COPY  AMENDED AND RESTATED LONG-TERM SENIOR SECURED PROMISSORY NOTE $5,605,435.52April 10, 2025, Effective as of April 1, 2025 Ronkonkoma, New York  FOR VALUE RECEIVED, SUNation Energy, Inc. (f/k/a Pineapple Energy Inc.), a Delaware corporation (“Maker”), hereby promises to pay to the order of Scott Maskin, a resident of the State of New York (“Maskin”), and James Brennan

April 15, 2025 10-K

TABLE OF CONTENTS RISK FACTOR SUMMARY PART I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-31588 SUNATION ENERGY,

April 15, 2025 EX-10.54

Pledge and Security Agreement, dated April 10, 2025, by and between SUNation Energy, Inc. and Scott Maskin and James Brennan

Exhibit 10.54 EXECUTION COPY   PLEDGE AND SECURITY AGREEMENT THIS PLEDGE AND SECURITY AGREEMENT dated as of April 10, 2025 (the “Pledge Agreement”) is made by SUNATION ENERGY, INC. (f/k/a Pineapple Energy Inc.), a Delaware corporation (“Pledgor”), in favor of Scott Maskin, a resident of the State of New York (“Maskin”), and James Brennan, a resident of the State of Florida (“Brennan” and, togeth

April 15, 2025 EX-10.55

Senior Secured Contingent Note, dated April 10, 2025, between SUNation Energy, Inc. and both Scott Maskin and James Brennan

EXECUTION COPY  SENIOR SECURED CONTINGENT NOTE INSTRUMENT Relevant Note Amount (Up to $2,500,000.

April 15, 2025 EX-10.56

Subordination and Intercreditor Agreement among SUNation Energy, Inc., Scott Maskin and James Brennan

EXECUTION COPY SUBORDINATION AND INTERCREDITOR AGREEMENT THIS SUBORDINATION AND INTERCREDITOR AGREEMENT, dated as of April 10, 2025 (as from time to time amended, restated, supplemented or otherwise modified from time to time in accordance with the terms hereof, this “Agreement”), is made and entered into by and among (i) Scott Maskin, a resident of the State of New York (“Maskin”), (ii) James Brennan, a resident of the State of Florida (“Brennan” and, together with Maskin, the “Senior Creditors”), and (iii) MBB Energy, LLC, a New York limited liability company (the “Subordinated Creditor”), and is acknowledged and agreed to by SUNation Energy, Inc.

April 15, 2025 EX-4.1

Description of Registrant’s Securities Registered Pursuant to Section 12 of the Securities Exchange Act of 1934

Exhibit 4.1  DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 (as updated, April 11, 2025)  SUNation Energy, Inc. (“SUNE,” “we,” “our,” “us,” or the “Company”) has one class of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended: our common stock.  DESCRIPTION OF COMMON STOCK  The following

April 15, 2025 EX-21

Subsidiaries of the Registrant

Exhibit 21 SUBSIDIARIES OF SUNATION ENERGY, INC.   Subsidiaries Jurisdiction of Incorporation Austin Taylor Communications, Ltd. United Kingdom JDL Technologies, Inc. Minnesota Ecessa Corporation Minnesota Pineapple Energy LLC Delaware Hawaii Energy Connection, LLC Hawaii SUNation Solar Systems, Inc. New York SUNation Commercial, Inc. New York SUNation Service, LLC New York   All these subsidi

April 7, 2025 EX-99.1

SUNation Energy Announces closing of second and fINAL Tranche OF REGISTERED DIRect Offering generating gross proceeds of $5 Million

Exhibit 99.1 SUNation Energy Announces closing of second and fINAL Tranche OF REGISTERED DIRect Offering generating gross proceeds of $5 Million RONKONKOMA, N.Y., April 7, 2025 - SUNation Energy, Inc. (“SUNation” or the “Company”) (Nasdaq: SUNE), a leading provider of sustainable solar energy and backup power solutions for households, businesses, and municipalities, today announced the second and

April 7, 2025 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-3 (Form Type) SUNation Energy, Inc.

April 7, 2025 S-3MEF

As filed with the Securities and Exchange Commission on April 7, 2025

As filed with the Securities and Exchange Commission on April 7, 2025 No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-3 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 SUNation Energy, Inc. (Exact name of registrant as specified in its charter) Delaware 41-0957999 (State or other jurisdiction of (I.R.S. Employer incorporation or organization) Identif

April 7, 2025 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): April 7, 2025 SUNation Energy, In

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): April 7, 2025 SUNation Energy, Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission Fil

April 7, 2025 424B5

Up to 4,347,826 Shares of Common Stock Series A Warrants to Purchase up to 17,391,306 Shares of Common Stock Series B Warrants to Purchase up to 17,391,306 Shares of Common Stock

Filed pursuant to Rule 424(b)(5) Registration No. 333-267066 PROSPECTUS SUPPLEMENT dated April 7, 2025 (To Prospectus dated September 2, 2022) Up to 4,347,826 Shares of Common Stock Series A Warrants to Purchase up to 17,391,306 Shares of Common Stock Series B Warrants to Purchase up to 17,391,306 Shares of Common Stock We are offering up to (i) 4,347,826 shares of common stock at a public offerin

April 4, 2025 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): April 3, 2025 SUNation Energy Inc

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): April 3, 2025 SUNation Energy Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission File

April 4, 2025 EX-3.1

Amended Certificate of Incorporation of SUNation Energy, Inc.

Exhibit 3.1 CERTIFICATE OF AMENDMENT OF CERTIFICATE OF INCORPORATION OF SUNATION ENERGY, INC., a Delaware Corporation SUNation Energy, Inc. (the “Corporation”), a corporation organized and existing under the General Corporation Law of the State of Delaware, hereby certifies as follows: 1. This Certificate of Amendment (the “Certificate of Amendment”) amends the provisions of the Corporation’s Cert

March 31, 2025 NT 10-K

SEC FILE NUMBER

OMB Number: 3235-0058 Expires: April 30, 2025 Estimated average burden hours per response .

March 17, 2025 EX-99.1

Investor Presentation March 2025 Nasdaq: SUNE Powering the Energy Transition Since 2003 2 / Powering the Energy Transition Forward Looking Statements This presentation includes certain forward - looking statements within the meaning of the Private Se

Exhibit 99.1 Investor Presentation March 2025 Nasdaq: SUNE Powering the Energy Transition Since 2003 2 / Powering the Energy Transition Forward Looking Statements This presentation includes certain forward - looking statements within the meaning of the Private Securities Litigation Reform Act of 1995 , including statements regarding future financial performance, future growth, and future acquisiti

March 17, 2025 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): March 17, 2025 SUNation Energy Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission Fil

March 14, 2025 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): March 3, 2025 SUNation Energy Inc

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): March 3, 2025 SUNation Energy Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission File

March 10, 2025 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934                     ☑     Filed by the Registrant      ☐     Filed by a Party other than the Registrant                     Check the appropriate box:  ☐ Preliminary Proxy Statement  ☐ Confidential, For Use of the Co

March 7, 2025 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): March 3, 2025 SUNation Energy Inc

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): March 3, 2025 SUNation Energy Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission File

February 28, 2025 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): February 27, 2025 SUNation Energy

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): February 27, 2025 SUNation Energy, Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

February 28, 2025 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934                     ☑     Filed by the Registrant      ☐     Filed by a Party other than the Registrant                     Check the appropriate box: ☑ Preliminary Proxy Statement  ☐ Confidential, For Use of the Com

February 28, 2025 EX-99.1

SUNation Energy Announces initial clOSING OF REGISTRED DIRect Offering generating gross proceeds of $15 Million

Exhibit 99.1 SUNation Energy Announces initial clOSING OF REGISTRED DIRect Offering generating gross proceeds of $15 Million RONKONKOMA, N.Y., February 28, 2025 - SUNation Energy, Inc. (Nasdaq: SUNE), a leading provider of sustainable solar energy and backup power solutions for households, businesses, and municipalities, today announced the initial closing of its previously announced securities pu

February 27, 2025 EX-4.1

Form of Series A Warrant

Exhibit 4.1 SERIES A COMMON STOCK PURCHASE WARRANT sunation energy, inc. Warrant Shares: Initial Exercise Date: , 2025 Issue Date: , 2025 THIS SERIES A COMMON STOCK PURCHASE WARRANT (the “Warrant”) certifies that, for value received, or its assigns (the “Holder”) is entitled, upon the terms and subject to the limitations on exercise and the conditions hereinafter set forth, at any time on or after

February 27, 2025 EX-4.2

Form of Series B Warrant

Exhibit 4.2 SERIES B COMMON STOCK PURCHASE WARRANT sunation energy, inc. Warrant Shares: Initial Exercise Date: , 2025 Issue Date: , 2025 THIS SERIES B COMMON STOCK PURCHASE WARRANT (the “Warrant”) certifies that, for value received, or its assigns (the “Holder”) is entitled, upon the terms and subject to the limitations on exercise and the conditions hereinafter set forth, at any time on or after

February 27, 2025 EX-4.3

Form of Pre-Funded Warrant

Exhibit 4.3 COMMON STOCK PURCHASE WARRANT sunation energy, inc. Warrant Shares: Initial Exercise Date: , 2025 THIS COMMON STOCK PURCHASE WARRANT (the “Warrant”) certifies that, for value received, or its assigns (the “Holder”) is entitled, upon the terms and subject to the limitations on exercise and the conditions hereinafter set forth, at any time on or after the date hereof (the “Initial Exerci

February 27, 2025 424B5

Up to 1,965,000 Shares of Common Stock Pre-Funded Warrants to Purchase up to 11,078,480 Shares of Common Stock

Filed pursuant to Rule 424(b)(5) Registration No. 333-267066 PROSPECTUS SUPPLEMENT dated February 27, 2025 (To Prospectus dated September 2, 2022) Up to 1,965,000 Shares of Common Stock Pre-Funded Warrants to Purchase up to 11,078,480 Shares of Common Stock We are offering up to 13,043,480 shares of common stock (or pre-funded warrant to purchase common stock (the “Pre-Funded Warrants”)) in lieu t

February 27, 2025 EX-3.1

Certificate of Designation of Series D Preferred Stock

Exhibit 3.1 SUNATION ENERGY, INC. CERTIFICATE OF DESIGNATION OF PREFERENCES, RIGHTS AND LIMITATIONS OF SERIES D CONVERTIBLE PREFERRED STOCK PURSUANT TO SECTION 151 OF THE GENERAL CORPORATION LAW OF THE STATE OF DELAWARE The undersigned, Scott Maskin, does hereby certify that: 1. I am the Chief Executive Officer of SUNation Energy, Inc., a Delaware corporation (the “Corporation”). 2. The Corporatio

February 27, 2025 EX-1.1

Form of Placement Agency Agreement, dated February 27, 2025, between the Company and Roth Capital Partners, LLC

Exhibit 1.1 PLACEMENT AGENCY AGREEMENT February 27, 2025 Roth Capital Partners, LLC 888 San Clemente Drive, Suite 400 Newport Beach, CA 92660 Ladies and Gentlemen: Introduction. Subject to the terms and conditions herein (this “Agreement”), SUNation Energy, Inc., a Delaware corporation (the “Company”), hereby agrees to sell up to an aggregate of $ of registered securities of the Company, including

February 27, 2025 EX-10.1

Form of Securities Purchase Agreement, dated February 27, 2025, between the Company and purchasers identified therein

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This Securities Purchase Agreement (this “Agreement”) is dated as of February 27, 2025, between SUNation Energy, Inc., a Delaware corporation (the “Company”), and each purchaser identified on the signature pages hereto (each, including its successors and assigns, a “Purchaser” and collectively the “Purchasers”). WHEREAS, subject to the terms and condition

February 27, 2025 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Other Events

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): February 27, 2025 SUNation Energy, Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

February 27, 2025 8-K

Regulation FD Disclosure, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): February 24, 2025 SUNation Energy, Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

February 27, 2025 EX-99.1

SUNation Energy Announces $20 Million Registered Direct Offering Priced At the Market Under Nasdaq Rules

Exhibit 99.1 SUNation Energy Announces $20 Million Registered Direct Offering Priced At the Market Under Nasdaq Rules RONKONKOMA, N.Y., February 27, 2025 - SUNation Energy, Inc. (Nasdaq: SUNE), a leading provider of sustainable solar energy and backup power solutions for households, businesses, and municipalities, today announced that it has entered into a securities purchase agreement with certai

January 8, 2025 EX-99.1

sunation ENERGY ANNOUNCES BITCOIN TREASURY STRATEGY

Exhibit 99.1 sunation ENERGY ANNOUNCES BITCOIN TREASURY STRATEGY RONKONKOMA, N.Y., Jan. 7, 2025 (GLOBE NEWSWIRE) – SUNation Energy, Inc. (Nasdaq: SUNE), a leading provider of sustainable solar energy and backup power solutions for households, businesses, and municipalities, today announced that its Board of Directors has approved the inclusion of bitcoin (BTC) as an asset in the Company’s treasury

January 8, 2025 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): January 7, 2025 SUNation Energy,

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): January 7, 2025 SUNation Energy, Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission F

January 7, 2025 424B5

$10,000,000 of Common Stock

Filed pursuant to Rule 424(b)(5) Registration No. 333-267066 AMENDMENT NO. 1, dated January 6, 2025, to PROSPECTUS SUPPLEMENT dated October 21, 2024 (To Prospectus dated September 2, 2022) $10,000,000 of Common Stock This Amendment No. 1 to Prospectus Supplement (this “Amendment”) amends and updates our prospectus supplement dated October 21, 2024 (the “Prospectus Supplement”). This Amendment shou

January 7, 2025 8-K

Regulation FD Disclosure, Financial Statements and Exhibits

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): December 30, 2024 SUNation Energy, Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

January 7, 2025 EX-10.1

Second Amendment to Contingent Value Rights Agreement dated March 25, 2022 by and among the Company, Equiniti Trust Company, as Rights Agent, and Richard A. Primuth in his capacity as the initial CVR Holders’ Representative, dated December 30, 2024

Exhibit 10.1 SECOND AMENDMENT TO CONTINGENT VALUE RIGHTS AGREEMENT THIS SECOND AMENDMENT TO CONTINGENT VALUE RIGHTS AGREEMENT, dated as of December 30, 2024 (“Second Amendment to CVR Agreement”), is by and among SUNation Energy, Inc., a Delaware corporation (formerly named Pineapple Energy, Inc. and hereafter “Parent”), Equiniti Trust Company, as Rights Agent (the “Rights Agent”), and Richard A. P

December 13, 2024 EX-99.1

2

Exhibit 99.1 SUNation Energy Names Scott Maskin Chief Executive Officer Scott Maskin, CEO of SUNation Energy, Inc. Pictured: Scott Maskin, the CEO of SUNation Energy, Inc. (NASDAQ: SUNE) RONKONKOMA, N.Y., Dec. 10, 2024 (GLOBE NEWSWIRE) - SUNation Energy Inc. (Nasdaq: SUNE) (“SUNation” or the “Company”), a leading provider of sustainable solar energy and backup power to households, businesses, muni

December 13, 2024 EX-10.1

Employment Agreement, dated December 9, 2024, between SUNation Energy Inc. and Scott Maskin

Exhibit 10.1 EMPLOYMENT AGREEMENT This Employment Agreement (“Agreement”) is effective as December 9, 2024 (“Effective Date”), by and between SUNation Energy, Inc., a Delaware corporation (the “Company”) (formally known as Pineapple Energy, Inc.) and Scott Maskin (the “Employee”) as its Chief Executive Officer. The Company desires to hire Employee as detailed below. During his employment, Employee

December 13, 2024 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): December 9, 2024 SUNation Energy Inc. (Exact name of Registrant as Specified in its Charter) Delaware (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission F

December 13, 2024 EX-10.2

Employment Agreement, dated December 9, 2024, between SUNation Energy, Inc. and Jim Brennan

Exhibit 10.2 EMPLOYMENT AGREEMENT This Employment Agreement (“Agreement”) is effective as December 9, 2024 (“Effective Date”), by and between SUNation Energy, Inc., a Delaware corporation (the “Company”) (formally known as Pineapple Energy, Inc.) and James Brennan (the “Employee”) as its Chief Operations Officer. The Company desires to hire Employee as detailed below. During his employment, Employ

November 19, 2024 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Material Modification to Rights of Security Holders, Financial Statements and Exhibits

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): November 14, 2024 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commissio

November 19, 2024 EX-3.1

Certificate of Incorporation of SUNation Energy, Inc.

Exhibit 3.1 CERTIFICATE of INCORPORATION of SUNATION ENERGY, INC. The undersigned, being of legal age, do hereby certify pursuant to the provisions of the General Corporation Law of the State of Delaware (“GCL”), as follows: Article I. Name: The name of this corporation is SUNation Energy, Inc. (“Corporation”). Article II. Registered and Principal Office: The address of the Corporation’s registere

November 19, 2024 EX-3.2

Bylaws SUNation Energy, Inc.

Exhibit 3.2 BYLAWS of SUNATION ENERGY, INC. These Bylaws of SUNation Energy, Inc. (the “Corporation”), a Delaware corporation, are effective November 14, 2024. Article I. Meetings of Stockholders Section 1.01 Annual Meetings. The annual meeting of the stockholders (an “annual meeting”) for the election of directors and the transaction of such other business as may properly come before it shall be

November 14, 2024 EX-10.16

Consent and Amendment No. 4 to Loan and Security Agreement, dated September 20, 2024, by and among Pineapple Energy LLC, Pineapple Energy Inc. and each other person that has delivered a Joinder Agreement

Exhibit 10.16 EXECUTION VERSION   CONSENT AND AMENDMENT NO. 4 TO LOAN AND SECURITY AGREEMENT THIS CONSENT AND AMENDMENT NO. 4 TO LOAN AND SECURITY AGREEMENT (this “Amendment”) is made and dated as of September 20, 2024 (the “Third Amendment Date”) and is entered into by and among PINEAPPLE ENERGY LLC (“PE LLC”), a Delaware limited liability company, for itself and on behalf of any Subsidiary, PI

November 14, 2024 EX-10.19

Amendment to Secured Credit Note, dated November 1, 2024, between Pineapple Energy Inc. and MBB Energy, LLC

Exhibit 10.19 AMENDMENT TO SECURED CREDIT NOTE  This Amendment is made on November 1, 2024, and is retroactive to July 22, 2024 (the “Effective Date”), between Pineapple Energy, Inc. (“Borrower”) and MBB Energy, LLC (“Lender”). This Amendment amends the Secured Credit Note, dated July 22, 2024 between Borrower and Lender (the “Credit Note”) as provided herein, and to the defined term of the Secur

November 14, 2024 EX-10.15

Second Amendment to Revenue Loan and Security Agreement, dated September 12, 2024, by and among Pineapple Energy Inc., the Guarantors party thereto, and Decathlon Specialty Finance LLC

Exhibit 10.15 SECOND AMENDMENT TO REVENUE LOAN AND SECURITY AGREEMENT This second amendment (this “Amendment”) to that certain Revenue Loan and Security Agreement dated June 1, 2023, as amended by the First Amendment executed on or about July 18, 2024 (as amended, the “Agreement”), by and among Pineapple Energy Inc. (the “Company”), the parties listed under the heading “Guarantors” on the signatur

November 14, 2024 10-Q

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

‎ UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-31588 PINEAP

November 14, 2024 EX-10.20

Amendment to Second Amended and Restated Convertible Secured Credit Note; and to the Credit Agreement, dated November 1, 2024, between Pineapple Energy Inc. and Conduit Capital U.S. Holdings LLC

Exhibit 10.20 AMENDMENT TO SECOND AMENDED AND RESTATED CONVERTIBLE SECURED CREDIT NOTE; and TO THE CREDIT AGREEMENT  This Amendment is made on November 1, 2024, and is retroactive to July 22, 2024 (“Effective Date”), between Pineapple Energy, Inc. (“Borrower”) and Conduit Capital U.S. Holdings LLC (“Lender”). This Amendment amends the Second Amended and Restated Convertible Secured Credit Note, d

November 8, 2024 SC 13G/A

PEGY / Pineapple Energy Inc. / Hudson Bay Capital Management LP - PEGY 13G/A Passive Investment

SC 13G/A 1 pegy13ga.htm PEGY 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 3)* Pineapple Energy Inc. (Name of Issuer) Common Stock, par value $0.05 per share (Title of Class of Securities) 72303P305 (CUSIP Number) September 30, 2024 (Date of Event Which Requires Filing of this Statement) Check the appropriate

November 7, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): November 4, 2024 Pineapple Energy

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): November 4, 2024 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

November 7, 2024 SC 13G

US203CVR0142 / CONTRA COMMUNICATIONS / Cavalry Fund I LP Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Pineapple Energy Inc. (Name of Issuer) Common stock, par value $0.05 per share (Title of Class of Securities) 72303P404 (CUSIP Number) September 9, 2024 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to

October 21, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): October 21, 2024 Pineapple Energy

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): October 21, 2024 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

October 21, 2024 424B5

$10,000,000 of Common Stock

Filed pursuant to Rule 424(b)(5) Registration No. 333-267066 PROSPECTUS SUPPLEMENT (To Prospectus dated September 2, 2022) $10,000,000 of Common Stock We have entered into a Sales Agreement (the “Sales Agreement”), dated October 21, 2024, with Roth Capital Partners, LLC (the “Sales Agent”), relating to the shares of our Common Stock, par value $0.05 per share (the “Common Stock”), offered by this

October 21, 2024 EX-10.1

At The Market Offering Agreement dated as of October 21, 2024, between Pineapple Energy Inc. and Roth Capital Partners, LLC

Exhibit 10.1 AT THE MARKET OFFERING AGREEMENT October 21, 2024 Roth Capital Partners, LLC 888 San Clemente Drive, Suite 400 Newport Beach, CA 92660 Ladies and Gentlemen: Pineapple Energy Inc., a corporation organized under the laws of Minnesota (the “Company”), confirms its agreement (this “Agreement”) with Roth Capital Partners, LLC (the “Manager”) as follows: 1. Definitions. The terms that follo

October 18, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

October 17, 2024 8-K

Regulation FD Disclosure, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Material Modification to Rights of Security Holders, Financial Statements and Exhibits

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): October 15, 2024 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

October 17, 2024 EX-99.1

Pineapple Energy Announces Previously Approved Reverse Stock Split, Effective October 17, 2024

Exhibit 99.1 Pineapple Energy Announces Previously Approved Reverse Stock Split, Effective October 17, 2024 RONKONKOMA, NY, October 15, 2024 - Pineapple Energy Inc. (the “Company”) (NASDAQ: PEGY) announced today that effective at 12:01 a.m. Central Time on October 17, 2024, the Company will implement a 1-for-50 reverse stock split of its outstanding common stock, which is within the range approved

October 17, 2024 EX-3.1

Articles of Amendment to Articles of Incorporation, dated October 17, 2024 (incorporated by reference in Exhibit 3.1 to the Company’s Current Report on Form 8-K filed on October 17, 2024)

Exhibit 3.1 ARTICLES OF AMENDMENT OF THE FOURTH AMENDED AND RESTATED ARTICLES OF INCORPORATION OF PINEAPPLE ENERGY INC. The undersigned, Interim Chief Executive Officer of Pineapple Energy Inc., a Minnesota corporation (the “Corporation”), hereby certifies that the following Articles of Amendment have been duly adopted by the Corporation’s Board of Directors and shareholders pursuant to the provis

October 16, 2024 SC 13D

PEGY / Pineapple Energy Inc. / Conroy Jeffrey J. Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. )* Pineapple Energy Inc. (Name of Issuer) Common Stock, par value, $0.05 per share (Title of Class of Securities) 72303P305 (CUSIP Number) 7 Mayflower Drive Basking Ridge, NJ 07920 Attn: Jeffrey J. Conroy (Name, Address and Telephone Number of Person Authori

October 10, 2024 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.  )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.  ) Filed by the Registrant ☒ Filed by a Party other than the Registrant  ☐ Check the appropriate box:  ☐ Preliminary Proxy Statement  ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ D

October 4, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): October 1, 2024 Pineapple Energy

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): October 1, 2024 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

September 30, 2024 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.  )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.  ) Filed by the Registrant ☒ Filed by a Party other than the Registrant  ☐ Check the appropriate box: ☒ Preliminary Proxy Statement  ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))  ☐ D

September 26, 2024 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): September 23, 2024 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commissi

September 26, 2024 EX-3.1

Certificate of Correction to Certificate of Designation

Exhibit 3.1 CERTIFICATE OF CORRECTION REGARDING PINEAPPLE energy inc. Pursuant to Minnesota Statute Section 5.16, the undersigned the interim Chief Executive Officer of Pineapple Energy Inc. hereby files this Certificate of Correction with respect to the Pineapple Energy Inc. Certificate of Designation of Preferences, Rights and Limitations of Series C Convertible Preferred Stock (the “Certificate

September 26, 2024 EX-10.2

Second Amended and Restated Convertible Secured Credit Note, dated September 23, 2024, between Pineapple Energy Inc. and Conduit Capital U.S. Holdings, LLC

EX-10.2 3 pegy240998ex10-2.htm CONVERTIBLE SECURED CREDIT NOTE, DATED SEPTEMBER 23, 2024, Exhibit 10.2 THIS NOTE HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “1933 ACT”), OR ANY STATE SECURITIES LAWS AND MAY NOT BE OFFERED, SOLD, PLEDGED, ASSIGNED, OR OTHERWISE TRANSFERRED UNLESS A REGISTRATION STATEMENT WITH RESPECT THERETO IS EFFECTIVE UNDER THE SECURITIES ACT AND AN

September 9, 2024 EX-10.2

Amended and Restated Convertible Secured Credit Note, dated September 9, 2024, between Pineapple Energy Inc. and Conduit Capital U.S. Holdings, LLC

Exhibit 10.2 THIS NOTE HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “1933 ACT”), OR ANY STATE SECURITIES LAWS AND MAY NOT BE OFFERED, SOLD, PLEDGED, ASSIGNED, OR OTHERWISE TRANSFERRED UNLESS A REGISTRATION STATEMENT WITH RESPECT THERETO IS EFFECTIVE UNDER THE SECURITIES ACT AND ANY APPLICABLE STATE SECURITIES LAWS OR BORROWER (AS DEFINED BELOW) RECEIVES AN OPINION OF C

September 9, 2024 EX-99.1

PINEAPPLE ENERGY ANNOUNCES RESTRUCTURING OF EXISTING SERIES A CONVERTIBLE PREFERRED STOCK AND RELATED WARRANTS

Exhibit 99.1 PINEAPPLE ENERGY ANNOUNCES RESTRUCTURING OF EXISTING SERIES A CONVERTIBLE PREFERRED STOCK AND RELATED WARRANTS MINNETONKA, MN – SEPTEMBER 9, 2024 – Pineapple Energy Inc. (Nasdaq: PEGY) (“Pineapple” or the “Company”), a leading provider of sustainable solar energy and back-up power to households and small businesses, announced today that they have entered into Securities Exchange Agree

September 9, 2024 EX-3.1

Certificate of Designation of Preferences, Rights and Limitations of Series C Convertible Preferred Stock

Exhibit 3.1 PINEAPPLE ENERGY INC. CERTIFICATE OF DESIGNATION OF PREFERENCES, RIGHTS AND LIMITATIONS OF SERIES C CONVERTIBLE PREFERRED STOCK PURSUANT TO SECTION 302A.401 and 302A.133 OF THE minnesota Business CORPORATION LAW The undersigned, Scott Maskin, does hereby certify that: 1. I am the Interim Chief Executive Officer of Pineapple Energy Inc., a Minnesota corporation (the “Corporation”). 2. T

September 9, 2024 EX-10.3

Form of Securities Exchange Agreement between Pineapple Energy, Inc. and the holder signatory hereto

Exhibit 10.3 PINEAPPLE ENERGY, INC. SECURITIES EXCHANGE AGREEMENT This Securities Exchange Agreement (this “Agreement”) is made as of September 9, 2024 (“Effective Date”), by and between Pineapple Energy, Inc., a Minnesota corporation (the “Company”), and the holder signatory hereto. (collectively, the “Holder”). RECITALS WHEREAS, the Holder currently holds a number of shares of Series A Convertib

September 9, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): September 9, 2024 Pineapple Energ

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): September 9, 2024 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commissio

September 4, 2024 EX-10.1

Offer Letter dated August 28, 2024, between Pineapple Energy Inc. and Andrew Childs

8-28-2024 Dear Andrew (“Andy”) Childs, It is our pleasure to offer you the position of Interim CFO (Chief Financial Officer) and Corporate Secretary with Pineapple Energy, Inc.

September 4, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): August 28, 2024 Pineapple Energy

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): August 28, 2024 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

August 23, 2024 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): August 19, 2024 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

August 19, 2024 10-Q

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

‎ UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-31588 PINEAPPLE E

August 19, 2024 EX-3.7

Statement of Cancellation of the Certificate of Designation of Series B Preferred Stock, effective as of August 14, 2024

Exhibit 3.7 STATEMENT OF CANCELLATION OF THE CERTIFICATE OF DESIGNATION OF THE SERIES B PREFERRED STOCK OF pineapple energy inc.   The undersigned officer of Pineapple Energy Inc. (the “Company”) hereby certifies that:  1.The name of the Company is Pineapple Energy Inc.  2.The Company’s Board of Directors has directed that the statement fixing the rights and preferences of the Company’s Series

August 14, 2024 NT 10-Q

PART IV — OTHER INFORMATION

UNITED STATES SEC FILE NUMBER SECURITIES AND EXCHANGE COMMISSION 001-31588 WASHINGTON D.

July 26, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): July 22, 2024 Pineapple Energy In

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): July 22, 2024 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission Fi

July 26, 2024 EX-10.9

Consent and Amendment No. 3 to Loan and Security Agreement, dated July 22, 2024 by and among Pineapple Energy LLC, Pineapple Energy Inc. and each other person that has delivered a Joinder Agreement

Exhibit 10.9 CONSENT AND AMENDMENT NO. 3 TO LOAN AND SECURITY AGREEMENT THIS CONSENT AND AMENDMENT NO. 3 TO LOAN AND SECURITY AGREEMENT (this “Amendment”) is made and dated as of July 22, 2024 (the “Third Amendment Date”) and is entered into by and among PINEAPPLE ENERGY LLC (“PE LLC”), a Delaware limited liability company, for itself and on behalf of any Subsidiary, PINEAPPLE ENERGY INC. (PE Inc.

July 26, 2024 EX-10.8

Amendment and Joinder to Subordination Agreement, dated July 22, 2024 among Pineapple Energy Inc., Decathlon Growth Credit, LLC, Hercules Capital, Inc., and MBB Energy, LLC and Conduit Capital U.S. Holdings, LLC

Exhibit 10.8 AMENDMENT AND JOINDER TO SUBORDINATION AGREEMENT THIS AMENDMENT AND JOINDER TO SUBORDINATION AGREEMENT (this “Amendment”) is made as of July [22], 2024, among Pineapple Energy Inc. (f/k/a Pineapple Holdings, Inc.), a Minnesota corporation (“Debtor”), Decathlon Growth Credit, LLC, a Delaware limited liability company (the “Senior Creditor”), Hercules Capital, Inc. (the “Subordinating C

July 26, 2024 EX-10.5

Secured Credit Note, dated July 22, 2024, between Pineapple Energy Inc. and MBB Energy, LLC. Security

Exhibit 10.5 THIS NOTE HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “1933 ACT”), OR ANY STATE SECURITIES LAWS AND MAY NOT BE OFFERED, SOLD, PLEDGED, ASSIGNED, OR OTHERWISE TRANSFERRED UNLESS A REGISTRATION STATEMENT WITH RESPECT THERETO IS EFFECTIVE UNDER THE SECURITIES ACT AND ANY APPLICABLE STATE SECURITIES LAWS OR BORROWER (AS DEFINED BELOW) RECEIVES AN OPINION OF C

July 26, 2024 EX-10.3

Security Agreement, dated July 22, 2024, between Pineapple Energy Inc. and Conduit Capital U.S. Holdings, LLC

Exhibit 10.3 SECURITY AGREEMENT This Security Agreement (this “Agreement”) is made on July 22, 2024 (“Effective Date”) by PINEAPPLE ENERGY, INC., a Minnesota corporation having an office located at 10900 Red Circle Drive, Minnetonka, Minnesota 55343 (“Debtor”) in favor of CONDUIT CONDUIT CAPITAL U.S. HOLDINGS LLC, a Delaware limited liability company having an office located at 1451 Fort Cassin Ro

July 26, 2024 EX-10.7

First Amendment to Revenue Loan and Security Agreement, dated July 22, 2024, by and among Pineapple Energy Inc., the Guarantors party thereto, and Decathlon Specialty Finance LLC

Exhibit 10.7 FIRST AMENDMENT TO REVENUE LOAN AND SECURITY AGREEMENT This first amendment (this “Amendment”) to that certain Revenue Loan and Security Agreement dated June 1, 2023 (the “Agreement”), by and among Pineapple Energy Inc. (the “Company”), the parties listed under the heading “Guarantors” on the signature pages attached hereto (each, a “Guarantor,” collectively, the “Guarantors;” each of

July 26, 2024 EX-10.4

Secured Credit Agreement, dated July 22, 2024, between Pineapple Energy Inc. and MBB Energy, LLC

Exhibit 10.4 SECURED CREDIT AGREEMENT This Secured Credit Agreement (this “Agreement”) is made on July 22, 2024 (“Effective Date”) between Pineapple Energy, Inc., a Minnesota corporation having an office located at 10900 Red Circle Drive, Minnetonka, Minnesota 55343 (“Borrower”) and MBB Energy, LLC, a New York limited liability company having an office located at 171 Remington Boulevard, Ronkonkom

July 26, 2024 EX-10.6

Security Agreement, dated July 22, 2024, between Pineapple Energy Inc. and MBB Energy, LLC

Exhibit 10.6 SECURITY AGREEMENT This Security Agreement (this “Agreement”) is made on July 22, 2024 (“Effective Date”) by Pineapple Energy, Inc., a Minnesota corporation having an office located at 10900 Red Circle Drive, Minnetonka, Minnesota 55343 (“Debtor”) in favor of MBB Energy, LLC, a New York limited liability company having an office located at 171 Remington Boulevard, Ronkonkoma, New York

July 26, 2024 EX-10.2

Secured Credit Note, dated July 22, 2024, between Pineapple Energy Inc. and Conduit Capital U.S. Holdings, LLC

Exhibit 10.2 THIS NOTE HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “1933 ACT”), OR ANY STATE SECURITIES LAWS AND MAY NOT BE OFFERED, SOLD, PLEDGED, ASSIGNED, OR OTHERWISE TRANSFERRED UNLESS A REGISTRATION STATEMENT WITH RESPECT THERETO IS EFFECTIVE UNDER THE SECURITIES ACT AND ANY APPLICABLE STATE SECURITIES LAWS OR BORROWER (AS DEFINED BELOW) RECEIVES AN OPINION OF C

July 26, 2024 EX-10.1

Secured Credit Agreement, dated July 22, 2024, between Pineapple Energy Inc. and Conduit Capital U.S. Holdings LLC

Exhibit 10.1 SECURED CREDIT AGREEMENT This Secured Credit Agreement (this “Agreement”) is made on July 22, 2024 (“Effective Date”) between PINEAPPLE ENERGY, INC., a Minnesota corporation having an office located at 10900 Red Circle Drive, Minnetonka, Minnesota 55343 (“Borrower”) and CONDUIT CAPITAL U.S. HOLDINGS LLC, a Delaware limited liability company having an office located at 1451 Fort Cassin

July 25, 2024 EX-10.1

Pineapple Energy Inc. 2022 Equity Incentive Plan, as amended through July 19, 2024

Exhibit 10.1 PINEAPPLE ENERGY INC. 2022 EQUITY INCENTIVE PLAN (As proposed to be amended July 1, 2024) 1. Purpose. The purpose of the Plan is to assist the Company in attracting, retaining, motivating and rewarding certain key employees, officers, directors, and consultants of the Company and its Affiliates, promoting the creation of long-term value for shareholders of the Company by closely align

July 25, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): July 19, 2024 Pineapple Energy In

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): July 19, 2024 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission Fi

July 25, 2024 EX-3.1

Articles of Amendment to the Articles of Incorporation, dated July 24, 2024 (incorporated by reference to Exhibit 3.1 to the Company’s Current Report on Form 8-K filed on July 25, 2024)

Exhibit 3.1 ARTICLES OF AMENDMENT OF THE FOURTH AMENDED AND RESTATED ARTICLES OF INCORPORATION OF PINEAPPLE ENERGY INC. The undersigned, Interim Chief Executive Officer of Pineapple Energy Inc., a Minnesota corporation (the “Corporation”), hereby certifies that: 1. The name of the Corporation is: Pineapple Energy Inc. 2. The first sentence of Article V (Capital Stock) of the Corporation’s Fourth A

July 9, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

July 8, 2024 EX-99.1

PINEAPPLE ENERGY FORMALIZES AGREEMENT WITH CONDUIT CAPITAL FOR SERVICES AND TO PURSUE WORKING CAPITAL INVESTMENT

Exhibit 99.1 PINEAPPLE ENERGY FORMALIZES AGREEMENT WITH CONDUIT CAPITAL FOR SERVICES AND TO PURSUE WORKING CAPITAL INVESTMENT MINNETONKA, MN – JULY 8, 2024 – Pineapple Energy Inc. (Nasdaq: PEGY) (“Pineapple” or the “Company”), a leading provider of sustainable solar energy and back-up power to households and small businesses, has engaged Conduit Capital to provide structural internal support, staf

July 8, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 1, 2024 Pineapple Energy Inc

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 1, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commission Fil

July 8, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

July 1, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 1, 2024 Pineapple Energy Inc

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 1, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commission Fil

June 25, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

June 24, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

June 17, 2024 EX-3.1

Articles of Amendment of Fourth Amended and Restated Articles of Incorporation, effective as of June 12, 2024 (incorporated by reference to Exhibit 3.1 to the Company’s Current Report on Form 8-K filed on June 17, 2024)

Exhibit 3.1 ARTICLES OF AMENDMENT OF THE FOURTH AMENDED AND RESTATED ARTICLES OF INCORPORATION OF PINEAPPLE ENERGY INC. The undersigned, Interim Chief Executive Officer of Pineapple Energy Inc., a Minnesota corporation (the “Corporation”), hereby certifies that: 1. The name of the Corporation is: Pineapple Energy Inc. 2. The first sentence of Article V (Capital Stock) of the Corporation’s Fourth A

June 17, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 12, 2024 Pineapple Energy In

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 12, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commission Fi

June 13, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

June 13, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

June 12, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

June 3, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 28, 2024 Pineapple Energy Inc

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 28, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commission Fil

June 3, 2024 EX-10.1

Employment Agreement, dated November 9, 2022, between Pineapple Energy Inc. and James R. Brennan

Exhibit 10.1 November 9, 2022 To: Jim Brennan Re: Offer of Employment Dear Jim: I am pleased to offer you the full-time position of Senior Vice President, Corporate Development of Pineapple Energy Inc., (the “Company”), reporting to Kyle Udseth, Chief Executive Officer, beginning Thursday November 10, 2022. Your salary will be annualized at $235,000. Your bonus opportunity will be 35% of your base

May 29, 2024 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defin

May 23, 2024 EX-10.2

Separation Agreement between Kyle Udseth and Pineapple Energy Inc. dated May 19, 2024

Exhibit 10.2 SEPARATION AGREEMENT This Separation Agreement (“Agreement”) is effective as of the 19th day of May, 2024 (“Effective Date”), by and between Pineapple Energy Inc., a Minnesota corporation (“Company”) and Kyle Udseth (“Employee”). Employee has been employed by the Company and desires to separate from employment. In consideration of the foregoing, and other good and valuable considerati

May 23, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 17, 2024 Pineapple Energy Inc

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 17, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commission Fil

May 23, 2024 EX-99.1

Pineapple Energy Announces Chief Executive Officer Transition

Exhibit 99.1 Pineapple Energy Announces Chief Executive Officer Transition May 17, 2024, at 4:15 p.m. EST MINNETONKA, MN, May 17, 2024 /Globe Newswire/ - Pineapple Energy Inc. (“Pineapple”), a leading provider of sustainable solar energy and backup power to households and small business, today announced that Chief Executive Officer Kyle Udseth has decided to resign his position, effective immediat

May 22, 2024 EX-10.1

Form of Limited Waiver and Amendment

May 17, 2024 Holder of Warrant to Purchase Common Stock Re: Limited Waiver and Amendment Dear Holder: Reference is made to the Certificate of Designation of Preferences, Rights and Limitations of Series A Convertible Preferred Stock of Pineapple Energy Inc.

May 22, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 22, 2024 Pineapple Energy Inc

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 22, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commission Fil

May 22, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 17, 2024 Pineapple Energy Inc

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 17, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commission Fil

May 17, 2024 EX-10.1

Subscription and Investment Representation Agreement, dated April 23, 2024, by and between Pineapple Energy Inc. and Lake Street Solar, LLC

EXHIBIT 10.1 Execution Version It is the responsibility of any investor purchasing these securities to satisfy itself as to full observance of the laws of any relevant territory outside the United States in connection with any such purchase, including obtaining any required governmental or other consents or observing any other applicable requirements. We are not making an offer to sell these secur

May 17, 2024 EX-3.1

Certificate of Designation of Series B Preferred Stock, dated May 14, 2024

EXHIBIT 3.1 Execution Version PINEAPPLE ENERGY INC. CERTIFICATE OF DESIGNATION OF SERIES B PREFERRED STOCK Pursuant to Sections 302A.133 and 302A.401 of the Minnesota Business Corporation Act THE UNDERSIGNED DOES HEREBY CERTIFY, on behalf of Pineapple Energy Inc., a Minnesota corporation (the “Corporation”), that the following resolution was duly adopted by the board of directors of the Corporatio

May 17, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 13, 2024 Pineapple Energy Inc

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 13, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commission Fil

May 16, 2024 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

May 10, 2024 10-Q

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

‎ UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-31588 PINEAPPLE

May 9, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 9, 2024 Pineapple Energy Inc.

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 9, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commission File

May 9, 2024 EX-99.1

Pineapple Energy Reports First Quarter 2024 Financial Results

Exhibit 99.1 Pineapple Energy Reports First Quarter 2024 Financial Results May 9, 2024, at 4:00 p.m. EST First Quarter 2024: ● Revenue down 40% from Q1 2023 ● Gross profit down 40% from Q1 2023 ● Operating Expenses down 31% from Q1 2023 ● Operating Loss increased 2% from Q1 2023 ● Net Income of $1.2M, Net Loss attributable to common shareholders of $10.1M ● Adjusted EBITDA loss of $1.5M MINNETONKA

April 29, 2024 10-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-315

April 22, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 19, 2024 Pineapple Energy I

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 19, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commission F

April 15, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 12, 2024 Pineapple Energy I

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 12, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commission F

April 8, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

April 1, 2024 EX-4.1

Description of Registrant’s Securities Registered Pursuant to Section 12 of the Securities Exchange Act of 1934

Exhibit 4.1 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 (as updated, MARCH 15, 2024)  Pineapple Energy Inc. (“PEGY,” “we,” “our,” “us,” or the “Company”) has one class of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended: our common stock.  DESCRIPTION OF COMMON STOCK  The following s

April 1, 2024 EX-97

Pineapple Energy Inc. Compensation Recovery Policy

Exhibit 97 PINEAPPLE ENERGY INC. COMPENSATION RECOVERY POLICY  Effective October 2, 2023  Policy The Board of Directors (the “Board”) of Pineapple Energy Inc. (the “Company”) has adopted this Compensation Recovery Policy (this “Policy”) pursuant to Rule 10D-1 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), the Securities and Exchange Commission (“SEC”) regulations promul

April 1, 2024 EX-10.46

First Amendment to Contingent Value Rights Agreement, dated March 27, 2024, by and among the Company, Equiniti Trust Company, as Rights Agent, and Richard A. Primuth in his capacity as the initial CVR Holders’ Representative.

Exhibit 10.46 FIRST AMENDMENT TO CONTINGENT VALUE RIGHTS AGREEMENT  THIS FIRST AMENDMENT TO CONTINGENT VALUE RIGHTS AGREEMENT, dated as of March 27, 2024 (“First Amendment to CVR Agreement”), is by and among PINEAPPLE ENERGY INC., a Minnesota corporation (the “Parent”), Equiniti Trust Company, as Rights Agent (the “Rights Agent”), and Richard A. Primuth, in his capacity as the initial CVR Holders

April 1, 2024 EX-21

Subsidiaries of the Registrant

Exhibit 21 SUBSIDIARIES OF PINEAPPLE ENERGY INC.   Subsidiaries Jurisdiction of Incorporation Austin Taylor Communications, Ltd. United Kingdom JDL Technologies, Inc. Minnesota Ecessa Corporation Minnesota Pineapple Energy LLC Delaware Hawaii Energy Connection, LLC Hawaii SUNation Solar Systems, Inc. New York SUNation Commercial, Inc. New York SUNation Service, LLC New York   All these subsidi

April 1, 2024 10-K

TABLE OF CONTENTS RISK FACTOR SUMMARY PART I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-31588 PINEAPPLE ENERGY

March 29, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

March 28, 2024 EX-99.1

Pineapple Energy Reports Fourth Quarter and Full Year 2023 Financial Results

Exhibit 99.1 Pineapple Energy Reports Fourth Quarter and Full Year 2023 Financial Results March 28, 2024, at 4:00 p.m. EST Fourth Quarter 2023: ● Revenue up 13% from Q4 2022 ● Gross profit up 10% from Q4 2022 ● Operating Expenses down 8% from Q4 2022 ● Operating Loss decreased 34% from Q4 2022 ● Net Loss from continuing operations decreased 91% from Q4 2022 ● Pro forma adjusted EBITDA up 222% from

March 28, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 28, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commission F

March 20, 2024 SC 13D

PEGY / Pineapple Energy Inc. / GAMCO INVESTORS, INC. ET AL - EXHIBIT A Activist Investment

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March 20, 2024 SC 13D

PEGY / Pineapple Energy Inc. / GAMCO INVESTORS, INC. ET AL Activist Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 Pineapple Holdings, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 72303P107 (CUSIP Number) David Goldman GAMCO Investors, Inc. One Corporate Center Rye, New York 10580-1435 (914) 921-5000 (Name, Address and Telephone Number of Person Authorized to Receive Notices and

March 6, 2024 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defin

March 4, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 27, 2024 Pineapple Energ

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 27, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commissio

February 26, 2024 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

February 13, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 13, 2024 Pineapple Energ

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 13, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commissio

February 12, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 12, 2024 Pineapple Energ

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 12, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commissio

February 7, 2024 424B5

2,702,703 Shares of Common Stock

Filed pursuant to Rule 424(b)(5) Registration No. 333-267066 PROSPECTUS SUPPLEMENT (To Prospectus dated September 2, 2022) 2,702,703 Shares of Common Stock We are offering 2,702,703 shares of our common stock, par value $0.05 per share, or Common Stock, pursuant to this prospectus supplement and the accompanying prospectus. Our Common Stock is listed on The Nasdaq Capital Market under the symbol “

February 6, 2024 SC 13G/A

PEGY / Pineapple Energy Inc. / Hudson Bay Capital Management LP - PEGY 13GA Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 2)* Pineapple Energy Inc. (f/k/a Communications Systems, Inc.) (Name of Issuer) Common Stock, par value $0.05 per share (Title of Class of Securities) 72303P107 (CUSIP Number) December 31, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriat

February 5, 2024 EX-10.1

Form of Securities Purchase Agreement between Pineapple Energy, Inc. and each purchaser identified therein

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This Securities Purchase Agreement (this “Agreement”) is dated as of February , 2024, between Pineapple Energy, Inc., a Minnesota corporation (the “Company”), and each purchaser identified on the signature pages hereto (each, including its successors and assigns, a “Purchaser” and collectively the “Purchasers”). WHEREAS, subject to the terms and condition

February 5, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 5, 2024 Pineapple Energy

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 5, 2024 Pineapple Energy Inc. (Exact name of registrant as specified in its charter) Minnesota 001-31588 41-0957999 (State or other jurisdiction of incorporation) (Commission

February 5, 2024 EX-10.2

Form of Waiver and Amendment

Exhibit 10.2 February , 2024 Holder of Series A Convertible Preferred Stock Re: Limited Waiver and Amendment Dear Holder: Reference is made to the Certificate of Designation of Preferences, Rights and Limitations of Series A Convertible Preferred Stock of Pineapple Energy Inc. (the “Company”) that was filed with the State of Minnesota on March 25, 2022 (the “Certificate of Designation”) and the Se

February 5, 2024 EX-3.1

Fourth Amended and Restated Articles of Incorporation, dated January 30, 2024 (incorporated by reference to Exhibit 3.2 to the Company’s Current Report on Form 8-K filed on February 5, 2024)

Exhibit 3.1 ARTICLES OF AMENDMENT OF ARTICLES OF INCORPORATION OF PINEAPPLE ENERGY INC. The undersigned, Eric Ingvaldson, in his capacity as Chief Financial Officer and Secretary of Pineapple Energy Inc., a Minnesota corporation (the “Corporation”), hereby certifies that: 1.            The name of the Corporation is Pineapple Energy Inc. 2.            The first paragraph of Article V of the Corpor

February 5, 2024 EX-3.2

Certificate of Designation of Preferences, Rights and Limitations of Series A Convertible Preferred Stock of Communications Systems, Inc. (n/k/a Pineapple Energy Inc.) filed on March 25, 2022

Exhibit 3.2 FOURTH AMENDED AND RESTATED ARTICLES OF INCORPORATION OF PINEAPPLE ENERGY INC. I, the undersigned, Kyle Udseth, the Chief Executive Officer of Pineapple Energy Inc., a Minnesota corporation (the “Company”), subject to the provisions of Chapter 302A, Minnesota Statutes, do hereby certify that: 1. The Fourth Amended and Restated Articles of Incorporation of the Company attached hereto as

February 5, 2024 EX-99.1

Pineapple Energy Prices $1.0 Million Registered Direct Offering of Common Stock

Exhibit 99.1 Pineapple Energy Prices $1.0 Million Registered Direct Offering of Common Stock MINNETONKA, Minn., February 5, 2024 (GLOBE NEWSWIRE) - Pineapple Energy Inc. (NASDAQ: PEGY) (“Pineapple” or the “Company”), a leading provider of sustainable solar energy and back-up power to households and small businesses, today announced it has entered into a definitive agreement with investors for the

February 5, 2024 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): January 30, 2024 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

January 4, 2024 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): December 29, 2023 Pineapple Energ

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): December 29, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commissio

December 21, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

December 21, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

December 20, 2023 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): December 14, 2023 Pineapple Energ

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): December 14, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commissio

December 1, 2023 SC 13D/A

PEGY / Pineapple Energy Inc / NORTHERN PACIFIC GROWTH INVESTMENT ADVISORS, LLC - SC 13D/A Activist Investment

SC 13D/A 1 pine231225sch13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 3)* Pineapple Energy Inc. (Name of Issuer) Common Stock, $0.05 par value per share (Title of Class of Securities) 72303P107 (CUSIP Number) Scott Honour Lake Street Solar, LLC 3109 W 50th St #207 Minneapolis, MN 554

November 13, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): November 9, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

November 13, 2023 EX-99.1

Pineapple Energy Reports Third Quarter 2023 Financial Results

Exhibit 99.1 Pineapple Energy Reports Third Quarter 2023 Financial Results November 9, 2023, at 4:15 p.m. EST ● Revenue up 211% from Q3 2022 ● Gross profit up 401% from Q3 2022 ● Operating Expenses up 125% from Q3 2022 ● Net Loss from continuing operations decreased 8% from Q3 2022 ● Pro forma adjusted EBITDA up 156% from Q3 2022 ● Positive cash flow from operations of $869,851 MINNETONKA, MN, Nov

November 13, 2023 EX-99.1

Pineapple Energy Inc. (NASDAQ:

Exhibit 99.1 Pineapple Energy Inc. (NASDAQ:PEGY) Q3 2023 Earnings Call Transcript November 10, 2023 Operator: Good morning. And welcome to the Pineapple Energy Third Quarter 2023 Conference Call. As a reminder, today’s call is being recorded. All participants are in a listen-only mode. For opening remarks and introductions, I would like to turn the call over to Eric Ingvaldson, CFO of Pineapple En

November 13, 2023 10-Q

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

‎ UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-31588 PINEAP

November 13, 2023 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): November 9, 2023 Pineapple Energy

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): November 9, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

November 3, 2023 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defin

November 3, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

November 1, 2023 8-K

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): October 27, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

October 23, 2023 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

October 2, 2023 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): October 2, 2023 Pineapple Energy

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): October 2, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

August 16, 2023 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): August 10, 2023 Pineapple Energy

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): August 10, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

August 16, 2023 EX-16.1

Letter from Baker Tilly US, LLP, dated August 14, 2023

Baker Tilly US, LLP 225 S Sixth St, Ste 2300 Minneapolis, MN 55402-4661 T: +1 (612) 876 4500 August 14, 2023 F: +1 (612) 238 8900 bakertilly.

August 14, 2023 10-Q

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

‎ UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-31588 PINEAPPLE E

August 11, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): August 10, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

August 11, 2023 EX-99.1

Pineapple Energy Reports Second Quarter 2023 Financial Results

Exhibit 99.1 Pineapple Energy Reports Second Quarter 2023 Financial Results August 10, 2023, at 4:15 p.m. EST ● Revenue up 370% from Q2 2022 ● Gross profit up 691% from Q2 2022 ● Operating Expenses up 122% from Q2 2022 ● Positive adjusted EBITDA MINNETONKA, MN, August 10, 2023 /Globe Newswire/ - Pineapple Energy Inc. (NASDAQ: PEGY), a leading provider of sustainable solar energy and back-up power

August 7, 2023 SC 13D

PEGY / Pineapple Energy Inc / Maskin Scott - SC 13D Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. )* Pineapple Energy, Inc. (Name of Issuer) Common Stock, $0.05 par value per share (Title of Class of Securities) 72303P107 (CUSIP Number) Scott Maskin 10900 Red Circle Drive Minnetonka, MN 55343 Telephone: (952) 996-1674 (Name, Address and Telephone Number

July 7, 2023 EX-99.1

Pineapple Energy Reports Sale of Substantially All of the Assets of Legacy Subsidiaries JDL Technologies, Incorporated and Ecessa Corporation

Exhibit 99.1 Pineapple Energy Reports Sale of Substantially All of the Assets of Legacy Subsidiaries JDL Technologies, Incorporated and Ecessa Corporation July 7, 2023, at 7:00 a.m. EST MINNETONKA, MN, July 7, 2023 /Globe Newswire/ - Pineapple Energy Inc. (NASDAQ: PEGY), a leading provider of sustainable solar energy and back-up power to households and small businesses, today announced the sale of

July 7, 2023 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): June 30, 2023 Pineapple Energy In

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): June 30, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission Fi

June 6, 2023 EX-10.2

Consent and Amendment No. 2 to Loan and Security Agreement dated as of May 31, 2023 by and between Pineapple Energy LLC as Borrower and Hercules Capital, Inc. as Lender and Agent

Exhibit 10.2 CONSENT AND AMENDMENT NO. 2 TO LOAN AND SECURITY AGREEMENT THIS CONSENT AND AMENDMENT NO. 2 TO LOAN AND SECURITY AGREEMENT (this “Amendment”) is made and dated as of May 31, 2023 and is entered into by and among PINEAPPLE ENERGY LLC (“PE LLC”), a Delaware limited liability company, for itself and on behalf of any Subsidiary, and each other Person that has delivered a Joinder Agreement

June 6, 2023 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): May 31, 2023 Pineapple Energy Inc

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): May 31, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission Fil

June 6, 2023 EX-10.1

Revenue Loan and Security Agreement dated as of June 1, 2023 by and among Pineapple Energy Inc., the Guarantors party thereto, and Decathlon Specialty Finance, LLC

Exhibit 10.1 CERTAIN CONFIDENTIAL PORTIONS OF THIS EXHIBIT HAVE BEEN OMITTED AND REPLACED WITH “[***]”. SUCH INFORMATION HAS BEEN REDACTED FROM THIS EXHIBIT BECAUSE IT IS (I) NOT MATERIAL AND (II) THE REGISTRANT CUSTOMARILY AND ACTUALLY TREATS THAT INFORMATION AS PRIVATE OR CONFIDENTIAL. Execution Copy REVENUE LOAN AND SECURITY AGREEMENT THIS REVENUE LOAN AND SECURITY AGREEMENT (as amended from ti

May 17, 2023 EX-16.1

Letter from Baker Tilly US, LLP, dated May 17, 2023

Baker Tilly US, LLP 225 S Sixth St, Ste 2300 Minneapolis, MN 55402-4661 May 17, 2023 T: +1 (612) 876 4500 F: +1 (612) 238 8900 bakertilly.

May 17, 2023 8-K/A

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A (AMENDMENT NO.1) CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): April 28, 2023

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A (AMENDMENT NO.1) CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): April 28, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-09

May 12, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): May 11, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission Fil

May 12, 2023 10-Q

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

‎ UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-31588 PINEAPPLE

May 12, 2023 EX-99.1

Pineapple Energy Reports First Quarter 2023 Financial Results

Exhibit 99.1 Pineapple Energy Reports First Quarter 2023 Financial Results May 11, 2023, at 4:15 p.m. EST ● Revenue up 28% from Q4 2022 ● Gross profit up 60% from Q4 2022 ● Positive adjusted EBITDA and cash flow from continuing operations ● $7.6 million of cash, restricted cash and investments MINNETONKA, MN, May 11, 2023 /Globe Newswire/ - Pineapple Energy Inc. (NASDAQ: PEGY), a leading provider

May 3, 2023 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): April 28, 2023 Pineapple Energy I

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): April 28, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission F

May 3, 2023 EX-16.1

Letter from Baker Tilly US, LLP, dated May 2, 2023

Baker Tilly US, LLP 225 S Sixth St, Ste 2300 Minneapolis, MN 55402-4661 May 2, 2023 T: +1 (612) 876 4500 F: +1 (612) 238 8900 bakertilly.

May 1, 2023 10-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-315

April 14, 2023 EX-4.1

Description of Registrant’s Securities Registered Pursuant to Section 12 of the Securities Exchange Act of 1934

Exhibit 4.1 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 (as updated, MARCH 31, 2023)  Pineapple Energy Inc. (“PEGY,” “we,” “our,” “us,” or the “Company”) has one class of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended: our common stock.  DESCRIPTION OF COMMON STOCK  The following s

April 14, 2023 EX-21

Subsidiaries of the Registrant

Exhibit 21 SUBSIDIARIES OF PINEAPPLE ENERGY INC.   Subsidiaries Jurisdiction of Incorporation Austin Taylor Communications, Ltd. United Kingdom JDL Technologies, Inc. Minnesota Ecessa Corporation Minnesota Pineapple Energy LLC Delaware SUNation Solar Systems, Inc. New York SUNation Commercial, Inc. New York SUNation Service, LLC New York   All these subsidiaries are 100%-owned directly by Pine

April 14, 2023 10-K

TABLE OF CONTENTS PART I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-31588 PINEAPPLE ENERGY

March 31, 2023 EX-99.1

Pineapple Energy Reports Fourth Quarter 2022 Financial Results

Pineapple Energy Reports Fourth Quarter 2022 Financial Results March 30, 2023, at 4:15 p.

March 31, 2023 NT 10-K

SEC FILE NUMBER

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SEC FILE NUMBER 001-31588 CUSIP NUMBER 72303P107 FORM 12b-25 NOTIFICATION OF LATE FILING (Check One): x Form 10-K ¨ Form 20-F ¨ Form 11-K ¨ Form 10-Q ¨ Form 10-D ¨ Form N-CEN ¨ Form N-CSR For Period Ended: December 31, 2022 ¨ Transition Report on Form 10-K ¨ Transition Report on Form 20-F ¨ Transition Report on Form 11-K ¨ Tra

March 31, 2023 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): March 30, 2023 Pineapple Energy I

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): March 30, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission F

March 29, 2023 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): March 29, 2023 Pineapple Energy I

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): March 29, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission F

March 21, 2023 8-K

Other Events

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): March 21, 2023 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission F

February 10, 2023 SC 13G/A

PEGY / Pineapple Holdings Inc / Hudson Bay Capital Management LP - PEGY 13GA Passive Investment

SC 13G/A 1 pegy13ga.htm PEGY 13GA SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 1)* Pineapple Energy Inc. (f/k/a Communications Systems, Inc.) (Name of Issuer) Common Stock, par value $0.05 per share (Title of Class of Securities) 72303P107 (CUSIP Number) December 31, 2022 (Date of Event Which Requires Filing of th

January 23, 2023 8-K/A

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT NO. 3 TO FORM 8-K ON FORM 8-K/A CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported):

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT NO. 3 TO FORM 8-K ON FORM 8-K/A CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): November 9, 2022 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation)

January 23, 2023 EX-99.1

UnAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION

Exhibit 99.1 UnAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION The following unaudited pro forma condensed combined financial information is based on the historical financial statements of Pineapple Energy Inc. (the “Company”, “Pineapple”, or “PEGY”), after giving pro forma effect to: (i) the acquisition of SUNation Solar Systems, Inc. and five of its affiliated entities: SUNation Comme

December 16, 2022 SC 13D/A

PEGY / Pineapple Holdings Inc / NORTHERN PACIFIC GROWTH INVESTMENT ADVISORS, LLC - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 2)* Pineapple Energy Inc. (Name of Issuer) Common Stock, $0.05 par value per share (Title of Class of Securities) 72303P107 (CUSIP Number) Scott Honour 315 East Lake Street Suite 301 Wayzata, MN 55391 Telephone: (952) 456-5300 (Name, Address and Telephone Nu

December 14, 2022 EX-99.2

SOLAR BUSINESS UNIT OF SUNATION SOLAR SYSTEMS, INC. AND AFFILIATES CARVE-OUT FINANCIAL STATEMENTS NINE MONTHS ENDED SEPTEMBER 30, 2022 AND 2021 Solar Business Unit of SUNation Solar Systems, Inc. and Affiliates Table of Contents Nine Months Ended Sep

Exhibit 99.2 SOLAR BUSINESS UNIT OF SUNATION SOLAR SYSTEMS, INC. AND AFFILIATES CARVE-OUT FINANCIAL STATEMENTS NINE MONTHS ENDED SEPTEMBER 30, 2022 AND 2021 Solar Business Unit of SUNation Solar Systems, Inc. and Affiliates Table of Contents Nine Months Ended September 30, 2022 and 2021 Page Independent Accountant’s Review Report 1 Carve-Out Financial Statements: Balance Sheets 2 Statements of Inc

December 14, 2022 8-K/A

Financial Statements and Exhibits

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No.2 TO FORM 8-K ON FORM 8-K/A CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): November 9, 2022 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation)

December 14, 2022 EX-99.1

SOLAR BUSINESS UNIT OF SUNATION SOLAR SYSTEMS, INC. AND AFFILIATES CARVE-OUT FINANCIAL STATEMENTS YEARS ENDED DECEMBER 31, 2021 AND 2020 Solar Business Unit of SUNation Solar Systems, Inc. and Affiliates Table of Contents Years Ended December 31, 202

Exhibit 99.1 SOLAR BUSINESS UNIT OF SUNATION SOLAR SYSTEMS, INC. AND AFFILIATES CARVE-OUT FINANCIAL STATEMENTS YEARS ENDED DECEMBER 31, 2021 AND 2020 Solar Business Unit of SUNation Solar Systems, Inc. and Affiliates Table of Contents Years Ended December 31, 2021 and 2020 Page Independent Auditor’s Report 1 Carve-Out Financial Statements: Balance Sheets 3 Statements of Income 4 Statements of Memb

December 13, 2022 S-8 POS

As filed with the Securities and Exchange Commission on December 13, 2022

As filed with the Securities and Exchange Commission on December 13, 2022 Registration No.

December 13, 2022 S-8 POS

As filed with the Securities and Exchange Commission on December 13, 2022

As filed with the Securities and Exchange Commission on December 13, 2022 Registration No.

December 13, 2022 S-8 POS

As filed with the Securities and Exchange Commission on December 13, 2022

As filed with the Securities and Exchange Commission on December 13, 2022 Registration No.

December 13, 2022 S-8

As filed with the Securities and Exchange Commission on December 13, 2022

S-8 1 pegy221414s8.htm S-8 As filed with the Securities and Exchange Commission on December 13, 2022 Registration No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 PINEAPPLE ENERGY INC. (Exact name of registrant as specified in its charter) Minnesota 41-0957999 (State or other jurisdiction of (I.R.S. Em

December 13, 2022 S-8

As filed with the Securities and Exchange Commission on December 13, 2022

As filed with the Securities and Exchange Commission on December 13, 2022 Registration No.

December 13, 2022 S-8 POS

As filed with the Securities and Exchange Commission on December 13, 2022

As filed with the Securities and Exchange Commission on December 13, 2022 Registration No.

December 13, 2022 S-8 POS

As filed with the Securities and Exchange Commission on December 13, 2022

As filed with the Securities and Exchange Commission on December 13, 2022 Registration No.

December 13, 2022 EX-FILING FEES

Filing Fee Table

Exhibit 107.1 Calculation of Filing Fee Tables Form S-8 (Form Type) Pineapple Energy Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered(1)(2) Proposed Maximum Offering Price Per Unit(3) Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Common Stock, par

December 13, 2022 EX-FILING FEES

Filing Fee Table

Exhibit 107.1 Calculation of Filing Fee Tables Form S-8 (Form Type) Pineapple Energy Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered(1)(2) Proposed Maximum Offering Price Per Unit(3) Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Common Stock, par

December 9, 2022 EX-10.1

Pineapple Energy Inc. 2022 Employee Stock Purchase Plan

Exhibit 10.1 PINEAPPLE ENERGY INC. 2022 EMPLOYEE STOCK PURCHASE PLAN 1. Purpose of Plan. The purpose of this Pineapple Energy Inc. (hereinafter referred to as the “Company”) 2022 Employee Stock Purchase Plan (the “Plan”) is to encourage stock ownership by all eligible Employees of the Company and by eligible Employees of any Subsidiaries authorized by the Board of Directors to participate hereunde

December 9, 2022 EX-3.1

Articles of Amendment to the Articles of Incorporation, dated December 9, 2022

Exhibit 3.1 ARTICLES OF AMENDMENT OF ARTICLES OF INCORPORATION OF PINEAPPLE ENERGY INC. The undersigned, Eric Ingvaldson, in his capacity as Chief Financial Officer and Secretary of Pineapple Energy Inc., a Minnesota corporation (the “Corporation”), hereby certifies that: 1.            The name of the Corporation is Pineapple Energy Inc. 2.            The first paragraph of Article V of the Corpor

December 9, 2022 EX-10.2

Pineapple Energy Inc. 2022 Equity Incentive Plan, as amended through December 7, 2022.

Exhibit 10.2 PINEAPPLE ENERGY INC. 2022 EQUITY INCENTIVE PLAN (As amended December 7, 2022) 1. Purpose. The purpose of the Plan is to assist the Company in attracting, retaining, motivating and rewarding certain key employees, officers, directors, and consultants of the Company and its Affiliates, promoting the creation of long-term value for shareholders of the Company by closely aligning the int

December 9, 2022 8-K

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): December 5, 2022 Pineapple Energy

United States SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): December 5, 2022 Pineapple Energy Inc. (Exact name of Registrant as Specified in its Charter) Minnesota (State Or Other Jurisdiction Of Incorporation) 001-31588 41-0957999 (Commission

December 9, 2022 EX-10.5

Employment Agreement, dated as of December 5, 2022, between Pineapple Energy Inc. and Eric Ingvaldson

Exhibit 10.5 EMPLOYMENT AGREEMENT This Employment Agreement (“Agreement”) is effective as of the 5th day of December, 2022 (“Effective Date”), by and between Pineapple Energy Inc., a Minnesota corporation (the “Company”) and Eric Ingvaldson (the “Employee”). A. Employee has been employed by the Company. B. The Company desires to continue to employ Employee as detailed below. Employee has thoroughl

December 9, 2022 EX-10.6

Change in Control Agreement, dated as of December 5, 2022, between Pineapple Energy Inc. and Eric Ingvaldson

Exhibit 10.6 PINEAPPLE ENERGY INC. CHANGE IN CONTROL AGREEMENT This CHANGE IN CONTROL Agreement is entered into effective as of the 5th day of December, 2022 (the “Effective Date”) by and between PINEAPPLE ENERGY INC., a Minnesota corporation (the “Company”), and Eric Ingvaldson (the “Executive”). The Board of Directors of the Company (the “Board”) has determined that it is in the best interests o

December 9, 2022 EX-10.4

Change in Control Agreement, dated as of December 5, 2022, between Pineapple Energy Inc. and Kyle Udseth

Exhibit 10.4 PINEAPPLE ENERGY INC. CHANGE IN CONTROL AGREEMENT This CHANGE IN CONTROL Agreement is entered into effective as of the 5th day of December, 2022 (the “Effective Date”) by and between PINEAPPLE ENERGY INC., a Minnesota corporation (the “Company”), and Kyle Udseth (the “Executive”). The Board of Directors of the Company (the “Board”) has determined that it is in the best interests of th

December 9, 2022 EX-3.2

Certificate of Designation of Preferences, Rights and Limitations of Series A Convertible Preferred Stock of Communications Systems, Inc. (n/k/a Pineapple Energy Inc.) filed on March 25, 2022 (included in Exhibit 3.1)

EX-3.2 3 pegy221408ex3-2.htm THIRD AMENDED AND RESTATED ARTICLES OF INCORPORATION, AS AMENDED THROUGH DECEMBER 9, 2022 Exhibit 3.2 THIRD AMENDED AND RESTATED ARTICLES OF INCORPORATION OF PINEAPPLE ENERGY INC. I, the undersigned, Kyle Udseth, the Chief Executive Officer of Pineapple Energy Inc., a Minnesota corporation (the “Company”), subject to the provisions of Chapter 302A, Minnesota Statutes,

December 9, 2022 EX-10.3

Employment Agreement, dated as of December 5, 2022, between Pineapple Energy Inc. and Kyle Udseth

Exhibit 10.3 EMPLOYMENT AGREEMENT This Employment Agreement (“Agreement”) is effective as of the 5th day of December, 2022 (“Effective Date”), by and between Pineapple Energy Inc., a Minnesota corporation (the “Company”) and Kyle Udseth (the “Employee”). A. Employee has been employed by the Company. B. The Company desires to continue to employ Employee as detailed below. Employee has thoroughly re

November 15, 2022 EX-10.1

Restricted Stock Unit Award Agreement (Inducement Grant) between Scott Maskin and Pineapple Energy Inc., dated as of November 15, 2022.

Exhibit 10.1 PINEAPPLE ENERGY INC. Restricted Stock Unit Award Agreement (Inducement Grant) Pineapple Energy Inc. (the “Company”) hereby grants an award of Restricted Stock Units (this “Award”) to you, the Participant named below. The terms and conditions of this Award are set forth in this Restricted Stock Unit Award Agreement (Inducement Grant) (this “Agreement”), consisting of this cover page a

November 15, 2022 EX-FILING FEES

Filing Fee Table

Exhibit 107.1 Calculation of Filing Fee Tables Form S-8 (Form Type) Pineapple Energy Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered(1)(2) Proposed Maximum Offering Price Per Unit(3) Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Common Stock, par

November 15, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

November 15, 2022 EX-10.2

Restricted Stock Unit Award Agreement (Inducement Grant) between James Brennan and Pineapple Energy Inc., dated as of November 15, 2022.

Exhibit 10.2 PINEAPPLE ENERGY INC. Restricted Stock Unit Award Agreement (Inducement Grant) Pineapple Energy Inc. (the “Company”) hereby grants an award of Restricted Stock Units (this “Award”) to you, the Participant named below. The terms and conditions of this Award are set forth in this Restricted Stock Unit Award Agreement (Inducement Grant) (this “Agreement”), consisting of this cover page a

November 15, 2022 S-8

As filed with the Securities and Exchange Commission on November 15, 2022

S-8 1 pegy221323s8.htm S-8 As filed with the Securities and Exchange Commission on November 15, 2022 Registration No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 PINEAPPLE ENERGY INC. (Exact name of registrant as specified in its charter) Minnesota 41-0957999 (State or other jurisdiction of (I.R.S. Em

November 14, 2022 EX-10.4

Form of Non-Qualified Stock Option Award Agreement under the 2022 Equity Incentive Plan

Exhibit 10.4 PINEAPPLE ENERGY INC. ? Non-Qualified Stock Option Agreement Under the 2022 Equity Incentive Plan ? Pineapple Energy Inc. (the ?Company?), pursuant to its 2022 Equity Incentive Plan (the ?Plan?), hereby grants an Option to purchase shares of the Company?s common stock to you, the Participant named below. The terms and conditions of the Option Award are set forth in this Agreement, con

November 14, 2022 EX-10.1

Form of Restricted Stock Unit Award Agreement under the 2022 Equity Incentive Plan

Exhibit 10.1 PINEAPPLE ENERGY INC. 2022 EQUITY INCENTIVE PLAN ? Restricted Stock Unit Award Agreement ? Pineapple Energy Inc. (the ?Company?), pursuant to its 2022 Equity Incentive Plan (the ?Plan?), hereby grants an award of Restricted Stock Units to you, the Participant named below. The terms and conditions of this Award are set forth in this Restricted Stock Unit Award Agreement (the ?Agreement

November 14, 2022 EX-10.2

Form of Performance Stock Unit Award Agreement under the 2022 Equity Incentive Plan

Exhibit 10.2 PINEAPPLE ENERGY INC. 2022 EQUITY INCENTIVE PLAN ? Performance Stock Unit Agreement ? Pineapple Energy Inc. (the ?Company?), pursuant to its 2022 Equity Incentive Plan (the ?Plan?), hereby grants an award of Performance Stock Units to you, the Participant named below. The terms and conditions of this Award are set forth in this Performance Stock Unit Agreement (the ?Agreement?), consi

November 14, 2022 10-Q

NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2022 ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-31588 PINEAP

November 14, 2022 EX-10.3

Form of Incentive Stock Option Award Agreement under the 2022 Equity Incentive Plan

Exhibit 10.3 PINEAPPLE ENERGY INC. ? Incentive Stock Option Agreement Under the 2022 Equity Incentive Plan ? Pineapple Energy Inc. (the ?Company?), pursuant to its 2022 Equity Incentive Plan (the ?Plan?), hereby grants an Option to purchase shares of the Company?s common stock to you, the Participant named below. The terms and conditions of the Option Award are set forth in this Agreement, consist

November 14, 2022 EX-99.1

Press Release dated November 14, 2022 Announcing Third Quarter Results

Exhibit 99.1 ? Pineapple Energy Reports Third Quarter 2022 Financial Results November 14, 2022 at 4:15 p.m. EST ? ? Increased revenue +31% from Q2 2022 ? Increased gross profit +58% from Q2 2022 ? Increased kW sold +105% YoY ? Increased pending installations +40% from Q2 2022 ? $10.2 million of cash, restricted cash, and investments ? Step-function growth going forward from SUNation acquisition ?

November 10, 2022 EX-2.1

Transaction Agreement, dated November 9, 2022, by and among Pineapple Energy Inc., Solar Merger Sub, LLC, Scott Maskin, James Brennan, Scott Sousa, Brian Karp and Scott Maskin as representative of each seller, including the forms of the Plan of Merger, the Pledge and Security Agreement, the Short-Term Limited Recourse Secured Promissory Note and the Long-Term Promissory Note

Exhibit 2.1 Execution Version TRANSACTION AGREEMENT by and among PINEAPPLE ENERGY INC., the Sellers listed herein, and SCOTT MASKIN, as Seller Representative FOR THE ACQUISITION OF SUNATION SOLAR SYSTEMS, INC. SUNATION SERVICE, INC., SUNATION COMMERCIAL, INC., SUNATION ELECTRIC, INC., SUNATION ENERGY, LLC, and SUNATION ROOFING, LLC Dated November 9, 2022 Table of Contents Page Article 1 Terms of t

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