Sec Form 4 Filing - Jackson Investment Group, LLC @ Staffing 360 Solutions, Inc. - 2020-01-21

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 Jackson Investment Group, LLC 2. Issuer Name and Ticker or Trading Symbol Staffing 360 Solutions, Inc. [ STAF] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) _____ Director X __ 10% Owner _____ Officer (give title below) _____ Other (specify below) (Last) (First) (Middle) 2655 NORTHWINDS PARKWAY 3. Date of Earliest Transaction (MM/DD/YY) 01/21/2020 (Street) ALPHARETTA, GA30009 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) _____ Form filed by One Reporting Person __ X __ 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 ) 01/21/2020( 1 ) J( 1 ) 100,000 ( 1 ) A $ 0 ( 1 ) 1,668,696 ( 2 ) ( 3 ) D ( 2 ) Common Stock ( 1 ) 02/07/2020( 1 ) J( 1 ) 100,000 ( 1 ) A $ 0 ( 1 ) 1,768,696 ( 2 ) ( 3 ) D ( 2 ) Common Stock ( 1 ) 03/02/2020( 1 ) J( 1 ) 100,000 ( 1 ) A $ 0 ( 1 ) 1,868,696 ( 2 ) ( 3 ) D ( 2 ) Common Stock ( 1 ) 04/01/2020( 1 ) J( 1 ) 100,000 ( 1 ) A $ 0 ( 1 ) 1,968,696 ( 2 ) ( 3 ) D ( 2 ) Common Stock ( 1 ) 05/01/2020( 1 ) J( 1 ) 100,000 ( 1 ) A $ 0 ( 1 ) 2,068,696 ( 2 ) ( 3 ) D ( 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 Warrant to purchase Common Stock $ 1.66 ( 4 ) 10/26/2020 J( 4 ) 905,508 ( 4 ) 01/26/2024 Common Stock 905,508 $ 0 0 D ( 2 ) Warrant to purchase Common Stock $ 1 ( 4 ) 10/26/2020 J( 4 ) 905,508 ( 4 ) 01/26/2026( 4 ) Common Stock 905,508 $ 0 905,508 D ( 2 ) Series E Convertible Preferred Stock $ 1.78 ( 5 ) 10/26/2020 J( 5 ) 13,000 10/31/2020( 5 ) ( 5 ) Common Stock 7,293,000 $ 1,000 0 D ( 2 ) Series E Convertible Preferred Stock $ 1 ( 5 ) 10/26/2020 J( 5 ) 13,000 10/31/2022( 5 ) ( 5 ) Common Stock 13,000,000 ( 5 ) $ 1,000 0 ( 5 ) D ( 2 ) Series E-1 Convertible Preferred Stock $ 1.66 ( 6 ) 10/26/2020 J( 6 ) 1,267 11/15/2020( 6 ) ( 6 ) Common Stock 763,253 $ 1,000 0 D ( 2 ) Series E-1 Convertible Preferred Stock $ 1 ( 6 ) 10/26/2020 J( 6 ) 1,267 10/31/2020( 6 ) ( 6 ) Common Stock 1,267,139 ( 6 ) $ 1,000 1,267,139 ( 6 ) D ( 2 )

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Jackson Investment Group, LLC 2655 NORTHWINDS PARKWAY ALPHARETTA, GA30009 X Jackson Richard Lee 2655 NORTHWINDS PARKWAY ALPHARETTA, GA30009 X Signatures /s/ Richard L. Jackson Signature of Jackson Investment Group, LLC By: Richard L. Jackson, Manager and CEO 11/10/2020 Signature of Reporting Person Date /s/ Richard L. Jackson 11/10/2020 Signature of Reporting Person Date

Explanation of Responses:

( 1 )On each of January 21, 2020, February 7, 2020, March 2, 2020, April 1, 2020 and May 1, 2020, Jackson Investment Group, LLC ("JIG LLC") received 100,000 shares of Common Stock of the Issuer as a result of certain defaults under the loan agreement between JIG LLC and the Issuer. ( 2 )Richard L. Jackson, the sole manager and controlling owner of JIG LLC, may be deemed the indirect beneficial owner, but he disclaims beneficial ownership of the reported securities except to the extent of his pecuniary interest therein. ( 3 )Total does not include 144 shares of common stock personally owned by Richard L. Jackson, the chief executive officer of JIG LLC. These shares are directly and beneficially owned by Richard L. Jackson, one of the Reporting Persons; however, they are not owned by JIG LLC, the designated Reporting Person. ( 4 )JIG LLC and the Issuer amended that certain Amended and Restated Warrant, dated April 25, 2018, as amended on August 27, 2018 and November 15, 2018, by entering into that certain Amendment No. 3 to the Amended and Restated Warrant Agreement, dated October 26, 2020 between the Issuer and JIG LLC. The transaction involved an amendment to an outstanding warrant, resulting in a reduced exercise price of $1.00 and extended expiration date of January 26, 2026. These shares are included as being beneficially owned in Table II. ( 5 )When originally issued, the Series E Convertible Preferred Stock ("Series E Stock") was convertible at the holder's option at any time after October 31, 2020 or upon the occurrence of an event of default specified in the Certificate of Designation of Series E Convertible Preferred Stock (the "Certificate") at a conversion price of $1.78. Pursuant to the Second Certificate of Amendment to the Certificate dated October 23, 2020 (the "Second Amendment"), each share of Series E Stock is now convertible at the holder's option at any time after October 31, 2022 or upon an event of default specified therein at a conversion price of $1.00. The resulting change in the terms of the Series E Stock is being reported in Table II as a disposition and acquisition of the Series E Stock, but such shares are not included as being beneficially owned in Table II because they are not convertible within 60 days. ( 6 )When originally issued, the Series E-1 Convertible Preferred Stock ("Series E-1 Stock") was convertible at the holder's option at any time after November 15, 2020 or upon the occurrence of an event of default specified in the Certificate at a conversion price of $1.66. Pursuant to the Second Amendment, each share of Series E-1 Stock is now convertible at the holder's option at any time after October 31, 2020 or upon an event of default specified therein at a conversion price of $1.00. The resulting change in the terms of the Series E-1 Stock is being reported in Table II as a disposition and acquisition of the Series E-1 Stock and such shares are included as being beneficially owned in Table II.

Remarks: This form is filed by both JIG LLC and Richard L. Jackson, the sole manager and controlling owner of JIG LLC.

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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