Sec Form 3 Filing - Madryn Asset Management, LP @ Greenbrook TMS Inc. - 2024-01-01

FORM 3 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 Madryn Asset Management, LP 2. Issuer Name and Ticker or Trading Symbol Greenbrook TMS Inc. [ GBNH] 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) 330 MADISON AVENUE - FLOOR 33 3. Date of Earliest Transaction (MM/DD/YY) 01/01/2024 (Street) NEW YORK, NY10017 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 6,363,636 I See footnotes ( 1 ) ( 2 ) ( 3 )

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 Common Share Conversion Instruments ( 4 ) $ 1.9 07/14/2022 09/30/2027 Common Stock 3,910,604 I See footnotes ( 1 ) ( 2 ) ( 5 ) Subordinated Convertible Notes ( 6 ) $ 0.2168 ( 7 ) ( 8 ) 08/15/2023 03/31/2028 Common Stock 13,837,637 I See footnotes ( 1 ) ( 2 ) ( 9 ) Subordinated Convertible Notes ( 6 ) $ 0.2315 ( 7 ) ( 10 ) 10/12/2023 03/31/2028 Common Stock 6,479,481 I See footnotes ( 1 ) ( 2 ) ( 11 )

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Madryn Asset Management, LP 330 MADISON AVENUE - FLOOR 33 NEW YORK, NY10017 X Madryn Health Partners, LP 330 MADISON AVENUE - FLOOR 33 NEW YORK, NY10017 X MADRYN HEALTH PARTNERS II (CAYMAN MASTER), LP 330 MADISON AVENUE - FLOOR 33 NEW YORK, NY10017 X Madryn Select Opportunities, LP 330 MADISON AVENUE - FLOOR 33 NEW YORK, NY10017 X MADRYN HEALTH ADVISORS II, LP 330 MADISON AVENUE - FLOOR 33 NEW YORK, NY10017 X MADRYN HEALTH ADVISORS GP II, LLC 330 MADISON AVENUE - FLOOR 33 NEW YORK, NY10017 X MADRYN SELECT ADVISORS, LP 330 MADISON AVENUE - FLOOR 33 NEW YORK, NY10017 X MADRYN SELECT ADVISORS GP, LLC 330 MADISON AVENUE - FLOOR 33 NEW YORK, NY10017 X Signatures Madryn Asset Management, LP, By: /s/ Matthew Girandola, Name: Matthew Girandola, Title: Authorized Signatory 01/11/2024 Signature of Reporting Person Date Madryn Health Partners II, LP, By: /s/ Matthew Girandola, Name: Matthew Girandola, Title: Authorized Signatory 01/11/2024 Signature of Reporting Person Date Madryn Health Partners II (Cayman Master), LP, By: /s/ Matthew Girandola, Name: Matthew Girandola, Title: Authorized Signatory 01/11/2024 Signature of Reporting Person Date Madryn Select Opportunities, LP, By: /s/ Matthew Girandola, Name: Matthew Girandola, Title: Authorized Signatory 01/11/2024 Signature of Reporting Person Date Madryn Health Advisors II, LP, By: /s/ Matthew Girandola, Name: Matthew Girandola, Title: Authorized Signatory 01/11/2024 Signature of Reporting Person Date Madryn Health Advisors GP II, LLC, By: /s/ Matthew Girandola, Name: Matthew Girandola, Title: Authorized Signatory 01/11/2024 Signature of Reporting Person Date Madryn Select Advisors, LP, By: /s/ Matthew Girandola, Name: Matthew Girandola, Title: Authorized Signatory 01/11/2024 Signature of Reporting Person Date Madryn Select Advisors GP, LLC, By: /s/ Matthew Girandola, Name: Matthew Girandola, Title: Authorized Signatory 01/11/2024 Signature of Reporting Person Date

Explanation of Responses:

( 1 )Represents securities held directly by Madryn Health Partners II, LP ("Health Partners"), Madryn Health Partners II (Cayman Master), LP ("Cayman Master") and, in the case of the Common Share Conversion Instruments described in Table II, Madryn Select Opportunities, LP ("Select Opportunities" and together with Health Partners and Cayman Master, the "Funds"). Madryn Asset Management, LP ("Madryn"), as investment advisor for each of the Funds, and each of Madryn Health Advisors II, LP, Madryn Health Advisors GP II, LLC, Madryn Select Advisors, LP, and Madryn Select Advisors GP, LLC, as general partners for each of the Funds, may be deemed to be beneficial owners of the shares held directly by the Funds. ( 2 )Each of the Reporting Persons disclaims beneficial ownership of the securities reported herein, except to the extent of such Reporting Person's pecuniary interest therein. ( 3 )Health Partners and Cayman Master directly hold 393,459 and 5,970,177 shares of the Company's common stock ("Common Shares"), respectively. ( 4 )Each of the Funds entered into a common share conversion instrument on July 14, 2022 (collectively, as amended and/or restated from time to time, the "Conversion Instruments") in connection with loans provided under the Company's senior secured credit facility with Madryn and its affiliates. ( 5 )Health Partners, Cayman Master, and Select Opportunities may receive (a) 202,423, (b) 3,071,480 and (c) 636,701 Common Shares, respectively, upon the exercise of the Conversion Instruments. ( 6 )On each of August 15, 2023, September 1, 2023, and October 12, 2023, Health Partners and Cayman Master acquired from the Company subordinated convertible promissory notes (the "Subordinated Convertible Notes"). ( 7 )The Subordinated Convertible Notes are convertible at a price equal to the lesser of (a) 85% of the closing price per Common Shares on Nasdaq or any other market as of the closing date for such Subordinated Convertible Notes and (b)(i) 85% of the 30-day volume weighted average trading price of the Common Shares prior to conversion, or (ii) if the Common Share s are not listed on any of Nasdaq or another trading market at the time of conversion, a per share price based equal to 85% of the fair market value per Common Share as of such date; provided, that, in any event, the Subordinated Convertible Note conversion price shall not be lower than $0.078. The conversion price of the Subordinated Convertible Notes is also subject to customary anti-dilution adjustments ( 8 )The conversion price of the Subordinated Convertible Notes issued on each of August 15, 2023 and September 1, 2023 is $0.2168. ( 9 )With respect to the Subordinated Convertible Notes issued on August 15, 2023 and September 1, 2023, Health Partners and Cayman Master may convert such Subordinated Convertible Notes into an aggregate of 855,571 and 12,982,066 Common Shares, respectively. ( 10 )The conversion price of the Subordinated Convertible Notes issued on October 12, 2023 is $0.2315. ( 11 )With respect to the Subordinated Convertible Notes issued on October 12, 2023, Health Partners and Cayman Master may convert such Subordinated Convertible Notes into an aggregate of 400,622 and 6,078,859 Common Shares, respectively.

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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