As filed with the Securities and Exchange Commission on September 15, 2023 Registration No. 333-268636 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 5 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 PINEAPPLE FINANCIAL INC. (Exact Name of Registrant as Specified in its Charter) (State or Other Jurisdiction of Incorporation or Organization) (Primary Standard Industrial Classification Code Number) Canada 6199 Not applicable (I.R.S. Employer Identificati ...

As filed with the Securities and Exchange Commission on July 5, 2023 Registration No. 333-268636 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 (Primary Standard Industrial Classification Code Number) Ontario, Canada 6199 Not applicable (I.R.S. Employer Identification Number) Unit 200, 111 Gordon Baker Road North York, Ontario M2H 3R1 Tel: (416) 669-2046 (Address, including zip code, and telephone number, including area code, of Registrant's principal executive offices) Amendment No ...

As filed with the Securities and Exchange Commission on June 21, 2023 Registration No. 333-268636 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 3 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 PINEAPPLE FINANCIAL INC. (Exact Name of Registrant as Specified in its Charter) (State or Other Jurisdiction of Incorporation or Organization) (Primary Standard Industrial Classification Code Number) Ontario, Canada 6199 Not applicable (I.R.S. Employer Identifi ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 2 FORM S-1 As filed with the Securities and Exchange Commission on May 16, 2023 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Registration No. 333-268636 PINEAPPLE FINANCIAL INC. (Exact Name of Registrant as Specified in its Charter) (State or Other Jurisdiction of Incorporation or Organization) (Primary Standard Industrial Classification Code Number) Ontario, Canada 6199 Not applicable (I.R.S. Employer Identific ...