Sec Form 4 Filing - Fernandez Charles M. @ Progressive Care Inc. - 2023-05-09

FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person Fernandez Charles M. 2. Issuer Name and Ticker or Trading Symbol Progressive Care Inc. [ RXMD] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) X __ Director _____ 10% Owner X __ Officer (give title below) _____ Other (specify below) Chairman and CEO (Last) (First) (Middle) C/O NEXTPLAT CORP, 3250 MARY ST.,, SUITE 410 3. Date of Earliest Transaction (MM/DD/YY) 05/09/2023 (Street) COCONUT GROVE, FL33133 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price Common Stock 05/09/2023 C 228,240 ( 1 ) A $ 2.2 303,517 ( 8 ) I By eAperion Partners LLC ( 7 ) Common Stock 05/09/2023 P 455,000 ( 4 ) A $ 2.2 758,517 ( 8 ) I By NextPlat Corp ( 6 ) Common Stock 05/09/2023 C 570,599 ( 1 ) A $ 2.2 1,329,116 ( 8 ) I By NextPlat Corp ( 6 )

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares Convertible Note $ 2.2 05/09/2023 C 09/08/2022 08/31/2027 Common Stock 228,240 $ 0 0 I By eAperion Partners LLC ( 7 ) Common Stock Warrant $ 2.2 05/09/2023 P 228,240 05/09/2023 05/09/2028 Common Stock 228,240 ( 2 ) $ 0 ( 2 ) 228,240 I By eAperion Partners LLC ( 7 ) Common Stock Warrant $ 2.2 05/09/2023 P 190,000 05/09/2023 05/09/2026 Common Stock 190,000 ( 3 ) $ 0 ( 3 ) 190,000 I By eAperion Partners LLC ( 7 ) Common Stock Warrant $ 2.2 05/09/2023 P 455,000 ( 4 ) 05/09/2026 Common Stock 455,000 $ 1,000,000 645,000 I By NextPlat Corp ( 6 ) Convertible Note $ 2.2 05/09/2023 C 09/08/2022 08/31/2027 Common Stock 570,599 ( 1 ) $ 0 0 I By NextPlat Corp ( 6 ) Common Stock Warrant $ 2.2 05/09/2023 P 570,599 05/09/2023 05/09/2028 Common Stock 570,599 ( 2 ) $ 0 ( 2 ) 798,839 I By NextPlat Corp ( 6 ) Convertible Note $ 0.03 11/16/2022 C 11/16/2022 11/16/2025 Common Stock $ 10,000,000 ( 5 ) ( 5 ) 0 I By NextPlat Corp ( 6 ) Convertible Note $ 2.2 11/16/2022 C 11/16/2022 11/16/2025 Common Stock $ 10,000,000 ( 5 ) ( 5 ) 0 I By NextPlat Corp ( 6 )

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Fernandez Charles M. C/O NEXTPLAT CORP, 3250 MARY ST., SUITE 410 COCONUT GROVE, FL33133 X Chairman and CEO Signatures /s/ Charles M. Fernandez 06/30/2023 Signature of Reporting Person Date

Explanation of Responses:

( 1 )On May 9, 2023, the Reporting Person and NextPlat Corp entered into a Debt Conversion Agreement whereby Issuer issued 228,240 shares of the Issuer's common stock to eAperion Partners LLC, an entity wholly owned by the Reporting Person, and 570,599 shares of the Issuer's common stock to NextPlat Corp upon conversion of the Reporting Person's share of outstanding principal and accrued and unpaid interest of a Secured Promissory Note dated September 2, 2022, at a conversion price of $2.20 per share. ( 2 )Pursuant to the Debt Conversion Agreement dated May 9, 2023, Issuer agreed to issue one warrant for a number of shares equal to the number of conversion shares issued to the Reporting Person. The warrants have a five-year term, are immediately exercisable, and have an exercise price of $2.20. ( 3 )On May 9, 2023, the Reporting Person was issued warrants to purchase 190,000 shares of common stock of the Issuer as an inducement to approve the transaction contemplated by the Securities Purchase Agreement dated May 5, 2023. The warrants have a three-year term, are immediately exercisable, and have an exercise price of $2.20. ( 4 )On May 5, 2023, the Issuer entered into a Securities Purchase Agreement with NextPlat Corp, whereby NextPlat Corp. agreed to purchase 455,000 units of securities, consisting of one share of common stock and one warrant. Each warrant is exercisable at $2.20 per share. The warrants are immediately exercisable and have a term of three years. ( 5 )On May 9, 2023, NextPlat Corp entered into a First Amendment to the Securities Purchase Agreement dated November 16, 2022 (the "Debenture Purchase Agreement"), resulting in the cancellation of the "old" convertible note and the purchase of a replacement convertible note. Pursuant to the Amendment, NextPlat Corp agreed to amend the Debenture Purchase Agreement and the Form of Debenture to increase the conversion price to $2.20 per share. The debentures are convertible at any time, upon NextPlat Corp.'s election, to shares of the Issuer's common stock. No debentures have been purchased to date. ( 6 )The Reporting Person disclaims beneficial ownership of these securities except to the extent of his pecuniary interest therein, and the inclusion of these shares in this report shall not be deemed an admission that the reporting person is the beneficial owner of such securities for purposes of Section 16 or for any other purpose. ( 7 )The Reporting Person is the sole member and managing member of eAperion Partners LLC. ( 8 )Includes 18,261 shares of common stock directly held by the Reporting Person; 45,652 shares of common stock held indirectly by NextPlat Corp., of which the Reporting Person is the Chief Executive Officer; and 11,364 shares of common stock held indirectly by eAperion Partners LLC, of which the Reporting person is the sole member and managing member.

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).

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