Sec Form 4 Filing - Cannon Reuben @ Gaucho Group Holdings, Inc. - 2022-06-07

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 Cannon Reuben 2. Issuer Name and Ticker or Trading Symbol Gaucho Group Holdings, Inc. [ VINO] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) X __ Director _____ 10% Owner _____ Officer (give title below) _____ Other (specify below) (Last) (First) (Middle) 280 S. BEVERLY DRIVE #208 3. Date of Earliest Transaction (MM/DD/YY) 06/07/2022 (Street) BEVERLY HILLS,, CA90212 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( 1 ) 06/07/2022 A 61,958 A $ 0.807 70,374 D Common Stock( 1 ) 06/07/2022 A 46,469 A $ 0.807 116,843 D Common Stock 1,960 I Seefootnote( 2 )

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 Warrants( 3 ) $ 6 02/19/2021 08/19/2022 Common Stock 3,333 3,333 D Stock Option $ 8.09 ( 4 ) 09/20/2023 Common Stock 1,000 1,000 D Stock Option $ 9.08 ( 5 ) 09/28/2025 Common Stock 6,667 6,667 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Cannon Reuben 280 S. BEVERLY DRIVE #208 BEVERLY HILLS,, CA90212 X Signatures /s/ Reuben Cannon 06/09/2022 Signature of Reporting Person Date

Explanation of Responses:

( 1 )Acquisition of restricted common stock of the Company as approved by the Compensation Committee and Board of Directors pursuant to the 2018 Equity Incentive Plan for services provided to the Company as a director for 2021 and half of 2022. ( 2 )Held by Reuben Cannon Productions, controlled by Mr. Cannon. ( 3 )Purchased pursuant to a public offering of Units at a price of $6.00 per Unit, with each Unit consisting of one share of common stock and one common stock purchase warrant; each warrant has an exercise price equal to 100% of the offering price. ( 4 )Options granted pursuant to 2018 Equity Incentive Plan; options to acquire 250 shares vest on 9/20/19; options to acquire 63 shares vest on 12/20/19; thereafter options to acquire 62 shares vest every three months. ( 5 )Options granted pursuant to AWLD's 2018 Equity Incentive Plan; options to acquire 1,667 shares vest on 9/28/21; thereafter options to acquire 417 shares vest every three months.

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).

** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).

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