Document:

EX-4.1

 Exhibit 4.1 

FIFTH SUPPLEMENTAL INDENTURE 

between 
 APOLLO INVESTMENT
CORPORATION 
 and 
 U.S. BANK
NATIONAL ASSOCIATION, 
 as Trustee 

Dated as of July 16, 2021 

FIFTH SUPPLEMENTAL INDENTURE 

THIS FIFTH SUPPLEMENTAL INDENTURE (this “Fifth Supplemental Indenture”), dated as of July 16, 2021, is between Apollo
Investment Corporation, a Maryland corporation (the “Company”), and U.S. Bank National Association, as trustee (the “Trustee”). All capitalized terms used herein shall have the meaning set forth in the Base Indenture (as defined
below) unless otherwise defined herein. 
 RECITALS OF THE COMPANY 

The Company and the Trustee executed and delivered an Indenture, dated as of October 9, 2012 (the “Base Indenture,” and, as
amended and supplemented by one or more supplemental indentures, including this Fifth Supplemental Indenture, the “Indenture”), to provide for the issuance by the Company from time to time of the Company’s unsecured debentures, notes
or other evidences of indebtedness (the “Securities”), to be issued in one or more series as provided in the Indenture. 
 The
Company desires to issue and sell $125,000,000 aggregate principal amount of the Company’s 4.500% Notes due 2026 (the “Notes”). 

The Company previously entered into the Fourth Supplemental Indenture, dated as of March 3, 2015 (the “Fourth Supplemental
Indenture”), which amended and supplemented the Base Indenture. The Fourth Supplemental Indenture is not applicable to the Notes. 

Sections 9.01(2), 9.01(3), 9.01(5) and 9.01(7) of the Base Indenture provide that without the consent of Holders of the Securities of any
series issued under the Base Indenture, the Company, when authorized by or pursuant to a Board Resolution, and the Trustee, at any time and from time to time, may enter into one or more indentures supplemental to the Base Indenture to (i) add
to the covenants of the Company for the benefit of the Holders of all or any series of Securities (and if such covenants are to be for the benefit of less than all series of Securities, stating that such covenants are expressly being included solely
for the benefit of such series); (ii) add any additional Events of Default for the benefit of the Holders of all or any series of Securities (and if such Events of Default are to be for the benefit of less than all series of Securities, stating that
such Events of Default are expressly being included solely for the benefit of such series); (iii) change or eliminate any of the provisions of the Base Indenture when there is no Security Outstanding of any series created prior to the execution of a
supplemental indenture that is entitled to the benefit of such provision; and (iv) establish the form or terms of Securities of any series as permitted by Section 2.01 and Section 3.01 of the Base Indenture. 

The Company desires to establish the form and terms of the Notes, modify, alter, supplement and change certain provisions of the Base
Indenture for the benefit of the Holders of the Notes and eliminate certain provisions of the Base Indenture (except as may be provided in a future supplemental indenture to the Indenture (“Future Supplemental Indenture”)). 

 The Company has duly authorized the execution and delivery of this Fifth Supplemental
Indenture to provide for the issuance of the Notes and all acts and things necessary to make this Fifth Supplemental Indenture a valid, binding, and legal obligation of the Company and to constitute a valid agreement of the Company, in accordance
with its terms, have been done and performed. 
 NOW, THEREFORE, THIS INDENTURE WITNESSETH: 

For and in consideration of the premises and the purchase of the Notes by the Holders thereof, it is mutually agreed, for the equal and
proportionate benefit of all Holders of the Notes, as follows: 
 ARTICLE I 

TERMS OF THE NOTES 

Section 1.01. Terms of the Notes. The following terms relating to the Notes are hereby established: 

(a) The Notes shall constitute a series of Securities having the title “4.500% Notes due 2026” and shall be designated as Senior
Securities under the Indenture. The Notes shall bear a CUSIP number of 03761U AH9 and an ISIN number of US03761UAH95. 
 (b) The aggregate
principal amount of the Notes that may be initially authenticated and delivered under the Indenture (except for Notes authenticated and delivered upon registration of, transfer of, or in exchange for, or in lieu of, other Notes pursuant to Sections
3.04, 3.05, 3.06, 9.06 or 11.07 of the Base Indenture) shall be $125,000,000. Under a Board Resolution, Officers’ Certificate pursuant to Board Resolutions or an indenture supplement, the Company may from time to time, without the consent of
the Holders of Notes, issue additional Notes (in any such case “Additional Notes”) having the same ranking and the same interest rate, maturity and other terms as the Notes; provided that, if such Additional Notes are not fungible
with the Notes (or any other tranche of Additional Notes) for U.S. federal income tax purposes, then such Additional Notes will have different CUSIP and ISIN numbers from the Notes (and any such other tranche of Additional Notes). Any Additional
Notes and the existing Notes will constitute a single series under the Indenture and all references to the relevant Notes herein shall include the Additional Notes unless the context otherwise requires. 

(c) The entire Outstanding principal amount of the Notes shall be payable on July 16, 2026, unless earlier redeemed or repurchased in
accordance with the provisions of this Fifth Supplemental Indenture. 
 (d) The rate at which the Notes shall bear interest shall be 4.500%
per annum. The date from which interest shall accrue on the Notes shall be July 16, 2021, or the most recent Interest Payment Date to which interest has been paid or provided for; the Interest Payment Dates for the Notes shall be
January 16 and July 16 of each year, commencing January 16, 2022 (if an Interest Payment Date falls on a day that is not a Business Day, then the applicable interest payment will be made on the next succeeding Business Day and no
additional interest will accrue as a result of such delayed payment); the initial interest period will be the period from and including July 16, 2021 (or the most recent Interest Payment Date to which interest has been paid or provided for),
to, but excluding, the initial Interest Payment Date, and the subsequent interest periods will be the periods from and including an Interest Payment Date to, but excluding, the next Interest Payment Date or the Stated Maturity, as the case may be;
the interest so payable, and punctually paid or duly provided for, on any Interest Payment Date, will be paid to the Person in whose name the Note (or one or more predecessor Notes) is registered at the close of business on the Regular Record Date
for such interest, which shall be January 1 and July 1 (whether or not a Business Day), as the case may be, next preceding such Interest Payment Date. Payment of principal of (and premium, if any) and any such interest on the Notes will be
made at the Corporate Trust Office of the Trustee in New York, New York in such coin or currency of the United States of America as at the time of payment is legal tender for payment of public and private debts; provided, however, that
at the option of the Company payment of interest may be made by check mailed to the address of the Person entitled thereto as such address shall appear in the Security Register. Interest on the Notes will be computed on the basis of a 360-day year of twelve 30-day months. 
 (e) The Notes shall be
initially issuable in global form (each such Note, a “Global Note”). The Global Notes and the Trustee’s certificate of authentication thereon shall be substantially in the form of Exhibit A to this Fifth
Supplemental Indenture. Each Global Note shall represent the aggregate amount of the 

  
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Outstanding Notes as shall be specified therein and each shall provide that it shall represent the aggregate amount of Outstanding Notes from time to time endorsed thereon and that the aggregate
amount of Outstanding Notes represented thereby may from time to time be reduced or increased, as appropriate, to reflect exchanges, redemptions and repurchases. Any endorsement of a Global Note to reflect the amount of any increase or decrease in
the amount of Outstanding Notes represented thereby shall be made by the Trustee or the Security Registrar, in accordance with Sections 2.03 and 3.05 of the Base Indenture. 

(f) The depositary for such Global Notes shall be the Depository. The Security Registrar with respect to the Global Notes shall be the
Trustee. 
 (g) The Notes shall be defeasible pursuant to Section 14.02 or Section 14.03 of the Base Indenture. Covenant
defeasance contained in Section 14.03 of the Base Indenture shall apply to the covenants contained in Sections 10.08 and 10.09 of the Indenture. 

(h) The Notes shall be redeemable pursuant to Section 11.01 of the Base Indenture and as follows: 

(i) The Notes will be redeemable in whole or in part at any time or from time to time, at the option of the Company, at a Redemption Price
calculated by the Company equal to the greater of the following amounts, plus, in each case, accrued and unpaid interest to, but excluding, the Redemption Date: 
  

	 	(A)	 100% of the principal amount of the Notes to be redeemed; or 

 

	 	(B)	 the sum of the present values of the remaining scheduled payments of principal and interest (exclusive of
accrued and unpaid interest to the Redemption Date) on the Notes to be redeemed, discounted to the Redemption Date on a semi-annual basis (assuming a 360-day year consisting of twelve 30-day months) using the applicable Treasury Rate plus 50 basis points; 

 provided,
however, that if the Company redeems any Notes on or after June 16, 2026, the Redemption Price for the Notes will be equal to 100% of the principal amount of the Notes to be redeemed, plus accrued and unpaid interest, if any, to, but excluding,
the Redemption Date. 
 For purposes of calculating the Redemption Price in connection with the redemption of the Notes, on any Redemption
Date, the following terms have the meanings set forth below: 
 “Treasury Rate” means, with respect to any Redemption Date,
the rate per annum equal to the semi-annual equivalent yield-to-maturity of the Comparable Treasury Issue (computed as of the third Business Day immediately preceding
the Redemption Date), assuming a price for the Comparable Treasury Issue (expressed as a percentage of its principal amount) equal to the Comparable Treasury Price for such Redemption Date. The Redemption Price and the Treasury Rate will be
determined by the Company. 
 “Comparable Treasury Issue” means the United States Treasury security selected by the
Reference Treasury Dealer as having a maturity comparable to the remaining term of the Notes to be redeemed that would be utilized, at the time of selection and in accordance with customary financing practice, in pricing new issues of corporate debt
securities of comparable maturity to the remaining term of the Notes being redeemed. 
 “Comparable Treasury Price” means
(1) the average of the Reference Treasury Dealer Quotations for the Redemption Date, after excluding the highest and lowest Reference Treasury Dealer Quotations, or (2) if the Quotation Agent obtains fewer than four such Reference Treasury
Dealer Quotations, the average of all such quotations. 
 “Quotation Agent” means a Reference Treasury Dealer selected by
the Company. 

  
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 “Reference Treasury Dealer” means (1) BofA Securities, Inc. and its
affiliates which are primary U.S. government securities dealers (a “Primary Treasury Dealer”) and their respective successors; provided, however, that if any of the foregoing shall cease to be a Primary Treasury Dealer, we
shall select another Primary Treasury Dealer; and (2) at least four other nationally recognized investment banking firms that are Primary Treasury Dealers selected from time to time by us. 

“Reference Treasury Dealer Quotations” means, with respect to each Reference Treasury Dealer and any Redemption Date, the
average, as determined by the Quotation Agent, of the bid and asked prices for the Comparable Treasury Issue (expressed in each case as a percentage of its principal amount) quoted in writing to the Quotation Agent by such Reference Treasury Dealer
at 3:30 p.m. New York City time on the third Business Day preceding such Redemption Date. 
 All determinations made by any Reference
Treasury Dealer, including the Quotation Agent, with respect to determining the Redemption Price will be final and binding absent manifest error. 

(ii) Notice of redemption shall be given in writing and mailed, first-class postage prepaid or by overnight courier guaranteeing next-day delivery, or sent electronically in accordance with applicable procedures of the Trustee and, so long as the Notes are registered to the Depositary or its nominee, the Depositary, to each Holder of the
Notes to be redeemed, not less than thirty (30) nor more than sixty (60) days prior to the Redemption Date, at the Holder’s address appearing in the Security Register. All notices of redemption shall contain the information set forth
in Section 11.04 of the Base Indenture and the delivery of such shall be subject to the terms of the Indenture. 
 (iii) Any exercise
of the Company’s option to redeem the Notes will be done in compliance with the Indenture and the Investment Company Act, to the extent applicable. 

(iv) If the Company elects to redeem only a portion of the Notes, the particular Notes to be redeemed will be selected in accordance with the
applicable procedures of the Trustee and, so long as the Notes are registered to the Depositary or its nominee, the Depositary; provided, however, that no such partial redemption shall reduce the portion of the principal amount of a
Note not redeemed to less than $2,000. 
 (v) Unless the Company defaults in payment of the Redemption Price, on and after the Redemption
Date, interest will cease to accrue on the Notes called for redemption hereunder. 
 (i) The Notes shall not be subject to any sinking fund
pursuant to Section 12.01 of the Base Indenture. 
 (j) The Notes shall be issuable in minimum denominations of $2,000 and integral
multiples of $1,000 in excess thereof. 
 (k) Holders of the Notes will not have the option to have the Notes repaid prior to the Stated
Maturity other than in accordance with Article XIII of the Indenture. 
 ARTICLE II 

DEFINITIONS AND OTHER PROVISIONS OF GENERAL APPLICATION 

Section 2.01. Except as may be provided in a Future Supplemental Indenture, for the benefit of the Holders of the Notes but no other
series of Securities under the Indenture, whether now or hereafter issued and Outstanding, Article I of the Base Indenture shall be amended by adding the following defined terms to Section 1.01 in appropriate alphabetical sequence, as
follows: 
 “Below Investment Grade Rating Event” means the Notes are downgraded below Investment Grade by the Rating
Agency on any date from the date of the public notice of an arrangement that results in a Change of Control until the end of the 60-day period following public notice of the occurrence of a Change of Control
(which period shall be extended so long as the rating of the Notes is under publicly announced consideration for possible downgrade by the Rating Agency); provided that a Below Investment Grade Rating Event otherwise arising by virtue of a
particular reduction in rating shall not be deemed to have occurred in respect of a particular Change of 

  
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Control (and thus shall not be deemed a Below Investment Grade Rating Event for purposes of the definition of Change of Control Repurchase Event hereunder) if the Rating Agency does not announce
or publicly confirm or inform the Trustee in writing that the reduction was the result, in whole or in part, of any event or circumstance comprised of or arising as a result of, or in respect of, the applicable Change of Control (whether or not the
applicable Change of Control shall have occurred at the time of the Below Investment Grade Rating Event). 
 “Change of
Control” means the occurrence of any of the following: 
 (1) the direct or indirect sale, lease, transfer, conveyance or other
disposition (other than by way of merger or consolidation) in one or a series of related transactions, of all or substantially all of the assets of the Company and its Controlled Subsidiaries taken as a whole to any “person” or
“group” (as those terms are used in Section 13(d)(3) of the Exchange Act), other than to any Permitted Holders; provided that, for the avoidance of doubt, a pledge of assets pursuant to any secured debt instrument of the
Company or its Controlled Subsidiaries shall not be deemed to be any such sale, lease, transfer, conveyance or disposition; 
 (2) the
consummation of any transaction (including, without limitation, any merger or consolidation) the result of which is that any “person” or “group” (as those terms are used in Section 13(d)(3) of the Exchange Act) (other than
any Permitted Holders) becomes the “beneficial owner” (as defined in Rules 13d-3 and 13d-5 under the Exchange Act), directly or indirectly, of more than 50% of
the outstanding Voting Stock of the Company, measured by voting power rather than number of shares; or 
 (3) the approval by the
Company’s stockholders of any plan or proposal relating to the liquidation or dissolution of the Company. 
 “Change of Control
Repurchase Event” means the occurrence of a Change of Control and a Below Investment Grade Rating Event. 
 “Controlled
Subsidiary” means any Subsidiary of the Company, 50% or more of the outstanding equity interests of which are owned by the Company and its direct or indirect Subsidiaries and of which the Company possesses, directly or indirectly, the power
to direct or cause the direction of the management or policies, whether through the ownership of voting equity interests, by agreement or otherwise. 

“Depositary” means, with respect to each Note in global form, The Depository Trust Company, until a successor shall have been
appointed and becomes such person, and thereafter, Depositary shall mean or include such successor. 
 “GAAP” means
generally accepted accounting principles in the United States set forth in the opinions and pronouncements of the Accounting Principles Board of the American Institute of Certified Public Accountants, the opinions and pronouncements of the Public
Company Accounting Oversight Board and the statements and pronouncements of the Financial Accounting Standards Board or in such other statements by such other entity as have been approved by a significant segment of the accounting profession in the
United States, which are in effect from time to time. 
 “Kroll” means Kroll Bond Rating Agency, Inc., or any successor
thereto. 
 “Investment Company Act” means the Investment Company Act of 1940, as amended, and the rules, regulations and
interpretations promulgated thereunder, to the extent applicable, and any statute successor thereto. 
 “Investment Grade”
means a rating of BBB- or better by Kroll (or its equivalent under any successor rating categories of Kroll) (or if such Rating Agency ceases to rate the Notes for reasons outside of the Company’s
control, the equivalent investment grade credit rating from any Rating Agency selected by the Company as a replacement Rating Agency). 

  
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 “Permitted Holders” means (i) the Company, (ii) one or more of
the Company’s Controlled Subsidiaries and (iii) Apollo Investment Management, L.P. or any affiliate of Apollo Investment Management, L.P. that is organized under the laws of a jurisdiction located in the United States of America and in the
business of managing or advising clients. 
 “Rating Agency” means (1) Kroll; and (2) if Kroll ceases to rate the
Notes or fails to make a rating of the Notes publicly available for reasons outside of our control, a “nationally recognized statistical rating organization” as defined in Section 3(a)(62) of the Exchange Act selected by the Company
as a replacement agency for Kroll.. 
 “Significant Subsidiary” means any Subsidiary that would be a “significant
subsidiary” as defined in Article 1, Rule 1-02 of Regulation S-X under the Exchange Act, as such regulation is in effect on the date of this Indenture (but
excluding any Subsidiary which is (a) a non-recourse or limited recourse Subsidiary, (b) a bankruptcy remote special purpose vehicle or (c) is not consolidated with the Company for purposes of
GAAP). 
 “Voting Stock” as applied to stock of any Person, means shares, interests, participations or other equivalents in
the equity interest (however designated) in such Person having ordinary voting power for the election of a majority of the directors (or the equivalent) of such Person, other than shares, interests, participations or other equivalents having such
power only by reason of the occurrence of a contingency. 
 Section 2.02 Except as may be provided in a Future Supplemental Indenture,
for the benefit of the Holders of the Notes but no other series of Securities under the Indenture, whether now or hereafter issued and Outstanding, Article I of the Base Indenture shall be amended by amending the definition of “Subsidiary”
in Section 1.01 to add the following sentence at the end of such definition: 
 “In addition, for purposes of this definition,
“Subsidiary” shall exclude any investments held by the Company in the ordinary course of business which are not, under GAAP, consolidated on the financial statements of the Company and its Subsidiaries.” 

ARTICLE III 
 SECURITIES FORMS 

Section 3.01. Except as may be provided in a Future Supplemental Indenture, for the benefit of the Holders of the Notes but no other
series of Securities under the Indenture, whether now or hereafter issued and Outstanding, Article II of the Base Indenture shall be amended by adding the following new Section 2.04 thereto, as set forth below: 

“Section 2.04. Certificated Notes.  

Notwithstanding anything to the contrary in the Indenture, Notes in physical, certificated form will be issued and delivered
to each person that the Depositary identifies as a beneficial owner of the related Notes only if: 
 (a) the Depositary
notifies the Company at any time that it is unwilling or unable to continue as depositary for the Notes in global form or the Company becomes aware that the Depositary has ceased to be registered as a clearing agency under the Exchange Act and, in
any such case the Company fails to appoint a successor depositary within 60 calendar days; 
 (b) the Company, in its sole
discretion, determines that the Notes shall be exchangeable for Notes in certificated form; or 
 (c) an Event of Default
with respect to the Notes has occurred and is continuing.” 

  
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 ARTICLE IV 

REMEDIES 
 Section 4.01.
Except as may be provided in a Future Supplemental Indenture, for the benefit of the Holders of the Notes but no other series of Securities under the Indenture, whether now or hereafter issued and Outstanding, Section 5.01 of the Base Indenture
shall be amended by replacing clause (2) thereof with the following: 
 “(2) default in the payment of the
principal of (or premium, if any, on) any Note when it becomes due and payable at its Maturity including upon any Redemption Date or required repurchase date; or” 

Section 4.02. Except as may be provided in a Future Supplemental Indenture, for the benefit of the Holders of the Notes but no other
series of Securities under the Indenture, whether now or hereafter issued and Outstanding, Section 5.01 of the Base Indenture shall be amended by replacing clause (4) thereof with the following: 

“(4) default in the performance, or breach, of any covenant or agreement of the Company in this Indenture or the Notes
(other than a covenant or agreement a default in whose performance or whose breach is elsewhere in this Section specifically dealt with or which has expressly been included in this Indenture solely for the benefit of a series of securities other
than the Notes), and continuance of such default or breach for a period of 60 consecutive days after there has been given, by registered or certified mail, to the Company by the Trustee or to the Company and the Trustee by the Holders of at least
25% in principal amount of the Outstanding Notes a written notice specifying such default or breach and requiring it to be remedied and stating that such notice is a “Notice of Default” hereunder; or” 

Section 4.03. Except as may be provided in a Future Supplemental Indenture, for the benefit of Holders of the Notes but no other series
of Securities under the Indenture, whether now or hereafter issued and Outstanding, Section 5.01 of the Base Indenture shall be amended by amending clause (6) of Section 5.01 thereof as follows: the words “90 consecutive
days” in the final clause thereof shall be replaced with the words “60 consecutive days”. 
 Section 4.04. Except as may
be provided in a Future Supplemental Indenture, for the benefit of the Holders of the Notes but no other series of Securities under the Indenture, whether now or hereafter issued and Outstanding, Section 5.01 of the Base Indenture shall be
amended by adding as clause (8) of Section 5.01 thereof the following: 
 “(8) default by the Company or any
of its Significant Subsidiaries, with respect to any mortgage, agreement or other instrument under which there may be outstanding, or by which there may be secured or evidenced, any indebtedness for money borrowed in excess of $50 million in
the aggregate of the Company and/or any such Significant Subsidiary, whether such indebtedness now exists or shall hereafter be created (i) resulting in such indebtedness becoming or being declared due and payable or (ii) constituting a
failure to pay the principal or interest of any such debt when due and payable at its stated maturity, upon required repurchase, upon declaration of acceleration or otherwise, unless, in either case, such indebtedness is discharged, or such
acceleration is rescinded, stayed or annulled, within a period of 30 calendar days after written notice of such failure is given to the Company by the Trustee or to the Company and the Trustee by the Holders of at least 25% in aggregate principal
amount of the Notes then Outstanding; or” 
 Section 4.05. Except as may be provided in a Future Supplemental Indenture, for the
benefit of the Holders of the Notes but no other series of Securities under the Indenture, whether now or hereafter issued and Outstanding, Section 5.01 of the Base Indenture shall be amended by adding as clause (9) of Section 5.01
thereof the following: 
 “(9) if, pursuant to Section 18(a)(1)(c)(ii) and Section 61 of the Investment
Company Act, on the last business day of each of 24 consecutive calendar months, any class of securities shall have an asset coverage (as such term is used in the Investment Company Act) of less than 100%.” 

  
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 Section 4.06. Except as may be provided in a Future Supplemental Indenture, for the
benefit of the Holders of the Notes but no other series of Securities under the Indenture, whether now or hereafter issued and Outstanding, Article V of the Base Indenture shall be amended by replacing Section 5.02 with the following: 

“Section 5.02. Acceleration of Maturity; Rescission and Annulment. 

If an Event of Default with respect to the Notes occurs and is continuing, then and in every such case (other than an Event of
Default specified in Section 5.01(5) or Section 5.01(6)) the Trustee or the Holders of not less than 25% in principal amount of the Outstanding Notes may declare the principal of all the Outstanding Notes to be due and payable immediately,
by a notice in writing to the Company (and to the Trustee if given by the Holders), and upon any such declaration such principal or specified portion thereof shall become immediately due and payable; provided that 100% of the principal of,
and accrued and unpaid interest on, the Notes will automatically become due and payable in the case of an Event of Default specified in Section 5.01(5) or Section 5.01(6) hereof. 

At any time after such a declaration of acceleration with respect to the Notes has been made and before a judgment or decree
for payment of the money due has been obtained by the Trustee as hereinafter provided in this Article, the Holders of a majority in principal amount of the Outstanding Notes, by written notice to the Company and the Trustee, may rescind and annul
such declaration and its consequences if: 
 (1) the Company has paid or deposited with the Trustee a sum sufficient to pay
in the Currency in which the Notes are payable (except as otherwise specified pursuant to Section 3.01 for the Notes and except, if applicable, as provided in Sections 3.12(b), 3.12(d) and 3.12(e)): 

(A) all overdue installments of interest, if any, on all Outstanding Notes, 

(B) the principal of (and premium, if any, on) all Outstanding Notes which have become due otherwise than by such declaration
of acceleration and interest thereon at the rate or rates borne by or provided for in such Notes, 
 (C) to the extent that
payment of such interest is lawful, interest upon overdue installments of interest at the rate or rates borne by or provided for in such Notes, and 

(D) all sums paid or advanced by the Trustee hereunder and the reasonably agreed upon compensation, expenses, disbursements
and advances of the Trustee, its agents and counsel; and 
 (2) all Events of Default with respect to the Notes, other than
the nonpayment of the principal of (or premium, if any) or interest on the Notes which have become due solely by such declaration of acceleration, have been cured or waived as provided in Section 5.13. 

No such rescission shall affect any subsequent default or impair any right consequent thereon.” 

Section 4.07. Except as may be provided in a Future Supplemental Indenture, for the benefit of the Holders of the Notes but no other
series of Securities under the Indenture, whether now or hereafter issued and Outstanding, Section 5.07 of the Base Indenture shall be amended by replacing clause (3) thereof with the following: 

“(3) such Holder or Holders have offered to the Trustee reasonable indemnity against the costs, expenses and liabilities to be incurred in
compliance with such request;” 

  
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 Section 4.08. Except as may be provided in a Future Supplemental Indenture, for the
benefit of the Holders of the Notes but no other series of Securities under the Indenture, whether now or hereafter issued and Outstanding, Section 5.12 of the Base Indenture shall be amended by replacing clause (3) thereof with the
following: 
 “(3) the Trustee need not take any action that it determines in good faith may involve it in personal liability or be
unjustly prejudicial to the Holders of Securities of such series not consenting.” 
 ARTICLE V 

THE TRUSTEE 
 Section 5.01.
Except as may be provided in a Future Supplemental Indenture, for the benefit of the Holders of the Notes but no other series of Securities under the Indenture, whether now or hereafter issued and Outstanding, Section 6.01 of the Base Indenture
shall be amended by replacing Section 6.01 with the following: 
 “Within 90 days after the occurrence of any
Default hereunder with respect to the Securities of any series, the Trustee shall transmit in the manner and to the extent provided in TIA Section 313(c), notice of such Default hereunder known to the Trustee, unless such Default shall have
been cured or waived; provided, however, that, except in the case of a Default in the payment of the principal of (or premium, if any) or interest, if any, on any Security of such series, or in the payment of any sinking or purchase
fund installment with respect to the Securities of such series, the Trustee shall be protected in withholding such notice if and so long as the board of directors, the executive committee or a trust committee of directors of the Trustee in good
faith determines that the withholding of such notice is in the interest of the Holders of the Securities and coupons of such series; and provided further that in the case of any Default or breach of the character specified in Section 5.01(4)
with respect to the Securities and coupons of such series, no such notice to Holders shall be given until at least 60 days after the occurrence thereof. For the purposes of this Section, the term “default” means any event which is or after
notice or lapse of time would become an Event of Default with respect to Securities of such series.” 
 Section 5.02. Except as
may be provided in a Future Supplemental Indenture, for the benefit of the Holders of the Notes but no other series of Securities under the Indenture, whether now or hereafter issued and Outstanding, Section 6.02 of the Base Indenture shall be
amended by replacing clause (e)(5) thereof with the following: 
 “(5) The Trustee shall be under no obligation to exercise any of
the rights or powers vested in it by this Indenture at the request or direction of any of the Holders of Securities of any series or any related coupons pursuant to this Indenture, unless such Holders shall have offered to the Trustee reasonable
security or indemnity against the costs, expenses and liabilities which might be incurred by it in compliance with such request or direction.” 

ARTICLE VI 
 COVENANTS 

Section 6.01. Except as may be provided in a Future Supplemental Indenture, for the benefit of the Holders of the Notes but no other
series of Securities under the Indenture, whether now or hereafter issued and Outstanding, Article X of the Base Indenture shall be amended by eliminating Section 10.06 thereof. 

Section 6.02. Except as may be provided in a Future Supplemental Indenture, for the benefit of the Holders of the Notes but no other
series of Securities under the Indenture, whether now or hereafter issued and Outstanding, Article X of the Base Indenture shall be amended by adding the following new Sections 10.08 and 10.09, each as set forth below: 

“Section 10.08. Section 18(a)(1)(A) of the
Investment Company Act. 

  
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 The Company hereby agrees that for the period of time during which Notes are
Outstanding, the Company will not violate, whether or not it is subject to, Section 18(a)(1)(A) as modified by Section 61(a) of the Investment Company Act or any successor provisions thereto of the Investment Company Act, but
giving effect, in either case, to any exemptive relief granted to the Company by the Commission.” 

“Section 10.09. Commission Reports and Reports to Holders. 

If, at any time, the Company is not subject to the reporting requirements of Sections 13 or 15(d) of the Exchange Act to
file any periodic reports with the Commission, the Company agrees to furnish to the Holders of Notes and the Trustee for the period of time during which the Notes are Outstanding: (i) within 90 days after the end of each fiscal year of the
Company, audited annual consolidated financial statements of the Company and (ii) within 45 days after the end of each fiscal quarter of the Company (other than the Company’s fourth fiscal quarter), unaudited interim consolidated financial
statements of the Company. All such financial statements shall be prepared, in all material respects, in accordance with GAAP, as applicable.” 

ARTICLE VII 
 OFFER TO
REPURCHASE UPON A CHANGE OF CONTROL REPURCHASE EVENT 
 Except as may be provided in a Future Supplemental Indenture, for the benefit of the
Holders of the Notes but no other series of Securities under the Indenture, whether now or hereafter issued and Outstanding, Article XIII of the Base Indenture shall be amended by replacing Sections 13.01 to 13.05 with the following: 

“Section 13.01. Change of Control. 

If a Change of Control Repurchase Event occurs, unless the Company shall have exercised its right to redeem the Notes in full, the Company
shall make an offer to each Holder of the Notes to repurchase all or any part (in minimum denominations of $2,000 and integral multiples of $1,000 principal amount in excess thereof) of that Holder’s Notes at a repurchase price in cash equal to
100% of the aggregate principal amount of Notes repurchased plus any accrued and unpaid interest on the Notes repurchased to, but not including, the date of purchase. Within 30 days following any Change of Control Repurchase Event or, at the
Company’s option, prior to any Change of Control, but after the public announcement of the Change of Control, the Company shall mail a notice to each Holder describing the transaction or transactions that constitute or may constitute the Change
of Control Repurchase Event and offering to repurchase Notes on the payment date specified in the notice, which date will be no earlier than 30 days and no later than 60 days from the date such notice is mailed. The notice shall, if mailed prior to
the date of consummation of the Change of Control, state that the offer to purchase is conditioned on the Change of Control Repurchase Event occurring on or prior to the payment date specified in the notice. The Company shall comply with the
requirements of Rule 14e-1 under the Exchange Act and any other securities laws and regulations thereunder to the extent those laws and regulations are applicable in connection with the repurchase of the Notes
as a result of a Change of Control Repurchase Event. 
 To the extent that the provisions of any securities laws or regulations conflict
with this Section 13.01, the Company shall comply with the applicable securities laws and regulations and shall not be deemed to have breached its obligations under this Section 13.01 by virtue of such conflict. 

On the Change of Control Repurchase Event payment date, subject to extension if necessary to comply with the provisions of the Investment
Company Act, the Company shall, to the extent lawful: 
 (1) accept for payment all Notes or portions of Notes properly tendered pursuant to
its offer; 
 (2) deposit with the Paying Agent an amount equal to the aggregate purchase price in respect of all Notes or portions of Notes
properly tendered; and 

  
 10 

 (3) deliver or cause to be delivered to the Trustee the Notes properly accepted, together
with an Officers’ Certificate stating the aggregate principal amount of Notes being purchased by the Company. 
 The Paying Agent will
promptly remit to each Holder of Notes properly tendered the purchase price for the Notes, and the Trustee will promptly authenticate and mail (or cause to be transferred by book-entry) to each Holder a new Note equal in principal amount to any
unpurchased portion of any Notes surrendered; provided that each new Note will be in a minimum principal amount of $2,000 or an integral multiple of $1,000 in excess thereof. 

If any Repayment Date upon a Change of Control Repurchase Event falls on a day that is not a Business Day, then the required payment will be
made on the next succeeding Business Day and no additional interest will accrue as a result of such delayed payment. 
 The Company will not
be required to make an offer to repurchase the Notes upon a Change of Control Repurchase Event if a third party makes an offer in respect of the Notes in the manner, at the time and otherwise in compliance with the requirements for an offer made by
the Company and such third party purchases all Notes properly tendered and not withdrawn under its offer.” 
 ARTICLE VIII 

MISCELLANEOUS 
 Section 8.01.
This Fifth Supplemental Indenture and the Notes shall be governed by and construed in accordance with the laws of the State of New York without regard to principles of conflicts of laws that would cause the application of laws of another
jurisdiction. This Fifth Supplemental Indenture is subject to the provisions of the Trust Indenture Act that are required to be part of the Indenture and shall, to the extent applicable, be governed by such provisions. If any provision of the
Indenture limits, qualifies or conflicts with the duties imposed by Section 318(c) of the Trust Indenture Act, the imposed duties will control. 

Section 8.02. In case any provision in this Fifth Supplemental Indenture or in the Notes shall be invalid, illegal or unenforceable, the
validity, legality and enforceability of the remaining provisions shall not in any way be affected or impaired thereby. 

Section 8.03. This Fifth Supplemental Indenture may be executed in any number of counterparts, each of which will be an original, but
such counterparts will together constitute but one and the same Fifth Supplemental Indenture. The exchange of copies of this Fifth Supplemental Indenture and of signature pages by facsimile, .pdf transmission, email or other electronic means
shall constitute effective execution and delivery of this Fifth Supplemental Indenture for all purposes. Signatures of the parties hereto transmitted by facsimile, .pdf transmission, email or other electronic means shall be deemed to be their
original signatures for all purposes. 
 Section 8.04. The Base Indenture, as supplemented and amended by this Fifth Supplemental
Indenture, is in all respects ratified and confirmed, and the Base Indenture and this Fifth Supplemental Indenture shall be read, taken and construed as one and the same instrument with respect to the Notes. All provisions included in this Fifth
Supplemental Indenture supersede any conflicting provisions included in the Base Indenture with respect to the Notes, unless not permitted by law. The Trustee accepts the trusts created by the Base Indenture, as supplemented by this Fifth
Supplemental Indenture, and agrees to perform the same upon the terms and conditions of the Base Indenture, as supplemented by this Fifth Supplemental Indenture. 

Section 8.05. The provisions of this Fifth Supplemental Indenture shall become effective as of the date hereof. 

Section 8.06. Notwithstanding anything else to the contrary herein, the terms and provisions of this Fifth Supplemental Indenture shall
apply only to the Notes and shall not apply to any other series of Securities under the Indenture and this Fifth Supplemental Indenture shall not and does not otherwise affect, modify, alter, supplement or change the terms and provisions of any
other series of Securities under the Indenture, whether now or hereafter issued and Outstanding. 

  
 11 

 Section 8.07. The recitals contained herein and in the Notes shall be taken as the
statements of the Company, and the Trustee assumes no responsibility for their correctness. The Trustee makes no representations as to the validity or sufficiency of this Fifth Supplemental Indenture, the Notes or any Additional Notes, except that
the Trustee represents that it is duly authorized to execute and deliver this Fifth Supplemental Indenture, authenticate the Notes and any Additional Notes and perform its obligations hereunder. The Trustee shall not be accountable for the use or
application by the Company of the Notes or any Additional Notes or the proceeds thereof. 

  
 12 

 IN WITNESS WHEREOF, the parties hereto have caused this Fifth Supplemental Indenture to be
duly executed as of the date first above written. 
  

			
	APOLLO INVESTMENT CORPORATION
		
	By:	 	/s/ Gregory W. Hunt
	Name:	 	Gregory W. Hunt
	Title:	 	Chief Financial Officer and Treasurer

 
			
	
	U.S. BANK NATIONAL ASSOCIATION, as Trustee
		
	By:	 	/s/ Beverly A. Freeney
	Name:	 	Beverly A. Freeney
	Title:	 	Vice President

 [Signature Page to Supplemental Indenture] 

  
 13 

 EXHIBIT A 

FORM OF GLOBAL NOTE 
 THIS SECURITY IS A
GLOBAL NOTE WITHIN THE MEANING OF THE INDENTURE HEREINAFTER REFERRED TO AND IS REGISTERED IN THE NAME OF THE DEPOSITORY TRUST COMPANY OR A NOMINEE THEREOF. THIS SECURITY MAY NOT BE EXCHANGED IN WHOLE OR IN PART FOR A SECURITY REGISTERED, AND NO
TRANSFER OF THIS SECURITY IN WHOLE OR IN PART MAY BE REGISTERED, IN THE NAME OF ANY PERSON OTHER THAN THE DEPOSITORY TRUST COMPANY OR A NOMINEE THEREOF, EXCEPT IN THE LIMITED CIRCUMSTANCES DESCRIBED IN THE INDENTURE. 

UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY TO THE ISSUER OR ITS AGENT FOR REGISTRATION OF TRANSFER,
EXCHANGE OR PAYMENT AND SUCH CERTIFICATE ISSUED IN EXCHANGE FOR THIS CERTIFICATE IS REGISTERED IN THE NAME OF CEDE & CO., OR SUCH OTHER NAME AS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, ANY TRANSFER, PLEDGE
OR OTHER USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL, AS THE REGISTERED OWNER HEREOF, CEDE & CO., HAS AN INTEREST HEREIN. 

Apollo Investment Corporation 
  

			
	 No. 1
	  	                                      
                      $
		  	                                      
                      CUSIP No. 03761U AH9
		  	                                      
                      ISIN No. US03761UAH95

 4.500% Notes due 2026 

Apollo Investment Corporation, a corporation duly organized and existing under the laws of Maryland (herein called the “Company”,
which term includes any successor Person under the Indenture hereinafter referred to), for value received, hereby promises to pay to Cede & Co., or registered assigns, the principal sum of one hundred twenty five million dollar (U.S.
$125,000,000) on July 16, 2026, and to pay interest thereon from July 16, 2021 or from the most recent Interest Payment Date to which interest has been paid or duly provided for, semi-annually on January 16 and July 16 in each
year, commencing January 16, 2022, at the rate of 4.500% per annum, until the principal hereof is paid or made available for payment. The interest so payable, and punctually paid or duly provided for, on any Interest Payment Date will, as
provided in such Indenture, be paid to the Person in whose name this Security is registered at the close of business on the Regular Record Date for such interest, which shall be January 1 and July 1 (whether or not a Business Day), as the
case may be, next preceding such Interest Payment Date. Any such interest not so punctually paid or duly provided for will forthwith cease to be payable to the Holder on such Regular Record Date and may either be paid to the Person in whose name
this Security is registered at the close of business on a Special Record Date for the payment of such Defaulted Interest to be fixed by the Trustee, notice whereof shall be given to Holders of Securities of this series not less than 10 days
prior to such Special Record Date, or be paid at any time in any other lawful manner not inconsistent with the requirements of any securities exchange on which the Securities of this series may be listed, and upon such notice as may be required by
such exchange, all as more fully provided in said Indenture. This Security may be issued as part of a series. 
 Payment of the principal of
(and premium, if any) and any such interest on this Security will be made at the Corporate Trust Office of the Trustee in New York, New York in such coin or currency of the United States of America as at the time of payment is legal tender for
payment of public and private debts; provided, however, that at the option of the Company payment of interest may be made by check mailed to the address of the Person entitled thereto as such address shall appear in the
Security Register. 
 Reference is hereby made to the further provisions of this Security set forth on the reverse hereof, which further
provisions shall for all purposes have the same effect as if set forth at this place. 

  
 A-1 

 Unless the certificate of authentication hereon has been executed by the Trustee referred to
on the reverse hereof by manual signature, this Security shall not be entitled to any benefit under the Indenture or be valid or obligatory for any purpose. 

  
 A-2 

 IN WITNESS WHEREOF, the Company has caused this instrument to be duly executed by the
undersigned officer. 
  

			
	 APOLLO INVESTMENT CORPORATION

		
	 By:
	 	 
		 	 Name: Gregory W. Hunt

		 	 Title: Chief Financial Officer and Treasurer

  

			
	 Attest

		
	 By:
	 	 
		 	 Name: Joseph D. Glatt

		 	 Title: Vice President and Secretary

 Dated: July 16, 2021 

  
 A-3 

 This is one of the Securities of the series designated therein referred to in the
within-mentioned Indenture. 
  

			
	 U.S. BANK NATIONAL ASSOCIATION, as Trustee

		
	 By:
	 	 
		 	 Authorized Signatory

 Dated: July 16, 2021 

  
 A-4 

 Apollo Investment Corporation 

4.500% Notes due 2026 
 This
Security is one of a duly authorized issue of securities of the Company (herein called the “Securities”), issued and to be issued in one or more series under an Indenture, dated as of October 9, 2012 (herein called the “Base
Indenture”), between the Company and U.S. Bank National Association, as Trustee (herein called the “Trustee”, which term includes any successor trustee under the Base Indenture), and reference is hereby made to the Base Indenture for
a statement of the respective rights, limitations of rights, duties and immunities thereunder of the Company, the Trustee, and the Holders of the Securities and of the terms upon which the Securities are, and are to be, authenticated and
delivered, as amended and supplemented by the Fifth Supplemental Indenture, dated as of July 16, 2021 (the “Fifth Supplemental Indenture” and, together with the Base Indenture collectively referred to herein as the
“Indenture”). In the event of any conflict between the Base Indenture and the Fifth Supplemental Indenture, the Fifth Supplemental Indenture shall govern and control. 

This Security is one of the series designated on the face hereof, initially limited in aggregate principal amount to $125,000,000. Under
a Board Resolution, an Officers’ Certificate pursuant to Board Resolutions or an indenture supplement, the Company may from time to time, without the consent of the Holders of Securities, issue additional Securities of this series (in any such
case “Additional Securities”) having the same ranking and the same interest rate, maturity, CUSIP number and other terms as the Securities; provided that, if such Additional Securities are not fungible with the Securities (or any
other tranche of Additional Securities) for U.S. federal income tax purposes, then such Additional Securities will have different CUSIP and ISIN numbers from the Securities represented hereby (and any such other tranche of Additional Securities).
Any Additional Securities and the existing Securities will constitute a single series under the Indenture and all references to the relevant Securities herein shall include the Additional Securities unless the context otherwise requires. The
aggregate amount of outstanding Securities represented hereby may from time to time be reduced or increased, as appropriate, to reflect exchanges, redemptions and repurchases. 

The Securities of this series are subject to redemption in whole or in part at any time or from time to time, at the option of the Company, at
a Redemption Price calculated by the Company per security equal to the greater of the following amounts, plus, in each case, accrued and unpaid interest to, but excluding, the Redemption Date: 

 

	 	(A)	 100% of the principal amount of the Notes to be redeemed, or 

 

	 	(B)	 the sum of the present values of the remaining scheduled payments of principal and interest (exclusive of
accrued and unpaid interest to the Redemption Date) on the Notes to be redeemed, discounted to the Redemption Date on a semi-annual basis (assuming a 360-day year consisting of twelve 30-day months) using the applicable Treasury Rate plus 50 basis points; 

 provided,
however, that if the Company redeems any Notes on or after June 16, 2026, the Redemption Price for the Notes will be equal to 100% of the principal amount of the Notes to be redeemed, plus accrued and unpaid interest, if any, to, but excluding,
the Redemption Date. 
 For purposes of calculating the Redemption Price in connection with the redemption of the Securities, on any
Redemption Date, the following terms have the meanings set forth below: 
 “Treasury Rate” means, with respect to any Redemption
Date, the rate per annum equal to the semi-annual equivalent yield-to-maturity of the Comparable Treasury Issue (computed as of the third Business Day immediately
preceding the Redemption Date), assuming a price for the Comparable Treasury Issue (expressed as a percentage of its principal amount) equal to the Comparable Treasury Price for such Redemption Date. The Redemption Price and the Treasury Rate will
be determined by the Company. 
 “Comparable Treasury Issue” means the United States Treasury security selected by the Reference
Treasury Dealer as having a maturity comparable to the remaining term of the Securities to be redeemed that would be utilized, at the time of selection and in accordance with customary financing practice, in pricing new issues of corporate debt
securities of comparable maturity to the remaining term of the Securities being redeemed. 

 “Comparable Treasury Price” means (1) the average of the Reference Treasury
Dealer Quotations for the Redemption Date, after excluding the highest and lowest Reference Treasury Dealer Quotations, or (2) if the Quotation Agent obtains fewer than four such Reference Treasury Dealer Quotations, the average of all such
quotations. 
 “Quotation Agent” means a Reference Treasury Dealer selected by the Company. 

“Reference Treasury Dealer” means (1) BofA Securities, Inc. and its affiliates which are primary U.S. government securities
dealers (a “Primary Treasury Dealer”) and their respective successors; provided, however, that if any of the foregoing shall cease to be a Primary Treasury Dealer, we shall select another Primary Treasury Dealer; and (2) at least four
other nationally recognized investment banking firms that are Primary Treasury Dealers selected from time to time by us. 
 “Reference
Treasury Dealer Quotations” means, with respect to each Reference Treasury Dealer and any Redemption Date, the average, as determined by the Quotation Agent, of the bid and asked prices for the Comparable Treasury Issue (expressed in each case
as a percentage of its principal amount) quoted in writing to the Quotation Agent by such Reference Treasury Dealer at 3:30 p.m. New York City time on the third Business Day preceding such Redemption Date. 

All determinations made by any Reference Treasury Dealer, including the Quotation Agent, with respect to determining the Redemption Price will
be final and binding absent manifest error. 
 Notice of redemption shall be given in writing and mailed, first-class postage prepaid or by
overnight courier guaranteeing next-day delivery, to each Holder of the Securities to be redeemed, not less than thirty (30) nor more than sixty (60) days prior to the Redemption Date, at the
Holder’s address appearing in the Security Register. All notices of redemption shall contain the information set forth in Section 11.04 of the Base Indenture. 

Any exercise of the Company’s option to redeem the Securities will be done in compliance with the Indenture and the Investment Company
Act, to the extent applicable. 
 If the Company elects to redeem only a portion of the Securities, the particular Securities to be redeemed
will be selected in accordance with the applicable procedures of the Trustee and, so long as the Securities are registered to the Depositary or its nominee, the Depositary. In the event of redemption of this Security in part only, a new Security or
Securities of this series and of like tenor for the unredeemed portion hereof will be issued in the name of the Holder hereof upon the cancellation hereof; provided, however, that no such partial redemption shall reduce the portion of
the principal amount of a Security not redeemed to less than $2,000. 
 Unless the Company defaults in payment of the Redemption Price, on
and after the Redemption Date, interest will cease to accrue on the Securities called for redemption. 
 Holders will have the right to
require the Company to repurchase their Securities upon the occurrence of a Change of Control Repurchase Event as set forth in the Indenture. 

The Indenture contains provisions for defeasance at any time of the entire indebtedness of this Security or certain restrictive covenants and
Events of Default with respect to this Security, in each case upon compliance with certain conditions set forth in the Indenture. 
 If an
Event of Default with respect to Securities of this series shall occur and be continuing (other than Events of Default related to certain events of bankruptcy, insolvency or reorganization as set forth in the Indenture), the principal of the
Securities of this series may be declared due and payable in the manner and with the effect provided in the Indenture. In the case of certain events of bankruptcy, insolvency or reorganization described in the Indenture, 100% of the principal of and
accrued and unpaid interest on the Securities will automatically become due and payable. 

  
 6 

 The Indenture permits, with certain exceptions as therein provided, the amendment thereof
and the modification of the rights and obligations of the Company and the rights of the Holders of the Securities of each series to be affected under the Indenture at any time by the Company and the Trustee with the consent of the Holders of not
less than a majority in principal amount of the Securities at the time Outstanding of each series to be affected. The Indenture also contains provisions permitting the Holders of specified percentages in principal amount of the Securities of each
series at the time Outstanding, on behalf of the Holders of all Securities of such series, to waive compliance by the Company with certain provisions of the Indenture and certain past defaults under the Indenture and their consequences. Any such
consent or waiver by the Holder of this Security shall be conclusive and binding upon such Holder and upon all future Holders of this Security and of any Security issued upon the registration of transfer hereof or in exchange herefor or in lieu
hereof, whether or not notation of such consent or waiver is made upon this Security. 
 As provided in and subject to the provisions of the
Indenture, the Holder of this Security shall not have the right to institute any proceeding with respect to the Indenture or for the appointment of a receiver or trustee or for any other remedy thereunder, unless (1) such Holder shall have
previously given the Trustee written notice of a continuing Event of Default with respect to the Securities of this series, (2) the Holders of not less than 25% in principal amount of the Securities of this series at the time Outstanding shall
have made written request to the Trustee to institute proceedings in respect of such Event of Default as Trustee, (3) such Holder offered to the Trustee reasonable indemnity against the costs, expenses and liabilities to be incurred in
compliance with such request, (4) for sixty (60) days after receipt of such notice, request and offer of indemnity, the Trustee shall have failed to institute any such proceeding, and (5) the Trustee shall not have received from the
Holders of a majority in principal amount of Securities of this series at the time Outstanding a direction inconsistent with such request. The foregoing shall not apply to any suit instituted by the Holder of this Security for the enforcement of any
payment of principal hereof or any premium or interest hereon on or after the respective due dates expressed herein. 
 No reference herein
to the Indenture and no provision of this Security or of the Indenture shall alter or impair the obligation of the Company, which is absolute and unconditional, to pay the principal of and any premium and interest on this Security at the times,
place and rate, and in the coin or currency, herein prescribed. 
 As provided in the Indenture and subject to certain limitations therein
set forth, the transfer of this Security is registrable in the Security Register, upon surrender of this Security for registration of transfer at the office or agency of the Company in any place where the principal of and any premium and interest on
this Security are payable, duly endorsed by, or accompanied by a written instrument of transfer in form satisfactory to the Company and the Security Registrar duly executed by, the Holder hereof or his attorney duly authorized in writing, and
thereupon one or more new Securities of this series and of like tenor, of authorized denominations and for the same aggregate principal amount, will be issued to the designated transferee or transferees. 

The Securities of this series are issuable only in registered form without coupons in minimum denominations of $2,000 and any integral
multiples of $1,000 in excess thereof. As provided in the Indenture and subject to certain limitations therein set forth, Securities of this series are exchangeable for a like aggregate principal amount of Securities of this series and of like tenor
of a different authorized denomination, as requested by the Holder surrendering the same. 
 No service charge shall be made for any such
registration of transfer or exchange of Securities, but the Company or Trustee may require payment of a sum sufficient to cover any tax or other governmental charge payable in connection therewith. 

Prior to due presentment of this Security for registration of transfer, the Company, the Trustee and any agent of the Company or the Trustee
may treat the Person in whose name this Security is registered as the owner hereof for all purposes, whether or not this Security be overdue, and neither the Company, the Trustee nor any such agent shall be affected by notice to the contrary. 

  
 7 

 All terms used in this Security which are defined in the Indenture shall have the meanings
assigned to them in the Indenture. 
 The Indenture and this Security shall be governed by and construed in accordance with the laws of the
State of New York without regard to principles of conflicts of laws that would cause the application of laws of another jurisdiction. 
  

  
 8EX-10.16

 Exhibit 10.16 

STANDARD FORM 
 2013
Stock Incentive Plan 
 1. Purpose. 

The purpose of this plan (the “Plan”) is to secure for Pear Therapeutics, Inc., a Delaware corporation (the
“Company”) and its shareholders the benefits arising from capital stock ownership by employees, officers and directors of, and consultants or advisors to, the Company and its parent and subsidiary corporations who are
expected to contribute to the Company’s future growth and success. Under the Plan recipients may be awarded both (i) Options (as defined in Section 2.1) to purchase the Company’s common stock, par value $.0001 (“Common
Stock”) and (ii) shares of Common Stock (“Restricted Stock Awards”). Except where the context otherwise requires, the term “Company” shall include any parent and all present and
future subsidiaries of the Company as defined in Sections 424(e) and 424(f) of the Internal Revenue Code of 1986, as amended or replaced from time to time (the “Code”). Those provisions of the Plan which make express
reference to Section 422 of the Code shall apply only to Incentive Stock Options (as that term is defined below). Appendix A to this Plan shall apply only to participants in the Plan who are residents of the State of California. 

2. Types of Awards and Administration. 

2.1 Options. Options granted pursuant to the Plan (“Options”) shall be authorized by action of the
Board of Directors of the Company (the “Board” or “Board of Directors”) and may be either incentive stock options (“Incentive Stock Options”) meeting the requirements of
Section 422 of the Code or non-statutory Options which are not intended to meet the requirements of Section 422. All Options when granted are intended to be
non-statutory Options, unless the applicable Option Agreement (as defined in Section 5.1) explicitly states that the Option is intended to be an Incentive Stock Option. The vesting of Options may be
conditioned upon the completion of a specified period of employment with the Company and/or such other conditions or events as the Board may determine. The Board may also provide that Options are immediately exercisable subject to certain repurchase
rights in the Company dependent upon the continued employment of the optionee and/or such other conditions or events as the Board may determine. 

2.1.1 Incentive Stock Options. Incentive Stock Options may only be granted to employees of the Company. For so long as
the Code shall so provide, Options granted to any employee under the Plan (and any other incentive stock option plans of the Company) which are intended to constitute Incentive Stock Options shall not constitute Incentive Stock Options to the extent
that such Options, in the aggregate, become exercisable for the first time in any one calendar year for shares of Common Stock with an aggregate fair market value (determined as of the respective date or dates of grant) of more than $100,000. If an
Option is intended to be an Incentive Stock Option, and if for any reason such Option (or any portion thereof) shall not qualify as an Incentive Stock Option, then, to the extent of such nonqualification, such Option (or portion thereof) shall be
regarded as a non-statutory Option appropriately granted under the Plan provided that such Option (or portion thereof) otherwise meets the Plan’s requirements relating to
non-statutory Options. 

  
 - 1 - 

 2.2 Restricted Stock Awards. The Board in its discretion may grant
Restricted Stock Awards, entitling the recipient to acquire, for a purchase price determined by the Board, shares of Common Stock subject to such restrictions and conditions as the Board may determine at the time of grant (“Restricted
Stock”), including continued employment and/or achievement of pre-established performance goals and objectives. 

2.3 Administration. The Plan shall be administered by the Board, whose construction and interpretation of the terms and
provisions of the Plan shall be final and conclusive. The Board may in its sole discretion authorize issuance of Restricted Stock, the grant of Options and the issuance of shares upon exercise of such Options as provided in the Plan. The Board shall
have authority, subject to the express provisions of the Plan, to construe Restricted Stock Agreements, Option Agreements and the Plan, to prescribe, amend and rescind rules and regulations relating to the Plan, to determine the terms and provisions
of Restricted Stock Agreements and Option Agreements, and to make all other determinations in the judgment of the Board necessary or desirable for the administration of the Plan. The Board may correct any defect or supply any omission or reconcile
any inconsistency in the Plan or in any Restricted Stock Agreement or Option Agreement in the manner and to the extent it shall deem expedient to carry the Plan into effect and it shall be the sole and final judge of such expediency. No director or
person acting pursuant to authority delegated by the Board shall be liable for any action or determination under the Plan made in good faith. The Board may, to the full extent permitted by or consistent with applicable laws or regulations, delegate
any or all of its powers under the Plan to a committee (the “Committee”) appointed by the Board, and if the Committee is so appointed, to the extent of such delegation, all references to the Board in the Plan shall mean and
relate to such Committee, other than references to the Board in this sentence and in Section 18 (as to amendment or termination of the Plan) and Section 22. 

3. Eligibility. 

Options may be granted, and Restricted Stock may be issued, to persons who are, at the time of such grant or issuance, employees, officers or
directors of, or consultants or advisors to, the Company; provided that the class of persons to whom Incentive Stock Options may be granted shall be limited to employees of the Company. 

3.1 10% Shareholder. If any employee to whom an Incentive Stock Option is to be granted is, at the time of the grant of
such Option, the owner of stock possessing more than 10% of the total combined voting power of all classes of stock of the Company (after taking into account the attribution of stock ownership rules of Section 424(d) of the Code) (a
“Greater Than 10% Shareholder”), any Incentive Stock Option granted to such individual must: (i) have an exercise price per share of not less than 110% of the fair market value of one share of Common Stock at the time of
grant; and (ii) expire by its terms not more than five years from the date of grant. 

  
 - 2 - 

 4. Stock Subject to Plan. 

Subject to adjustment as provided in Section 14.2 below, the maximum number of shares of Common Stock which may be issued under the Plan
is 16,727,451 shares, all of which may be issued with respect to Incentive Stock Options. If an Option shall expire or terminate for any reason without having been exercised in full, the unpurchased shares subject to such Option shall again be
available for subsequent Option grants or Restricted Stock Awards under the Plan. If shares of Restricted Stock shall be forfeited to, or otherwise repurchased by, the Company pursuant to a Restricted Stock Agreement, such repurchased shares shall
again be available for subsequent Option grants or Restricted Stock Awards under the Plan. If shares issued upon exercise of an Option are tendered to the Company in payment of the exercise price of an Option, such tendered shares shall again be
available for subsequent Option grants or Restricted Stock Awards under the Plan. 
 5. Forms of Restricted Stock Agreements and
Option Agreements. 
 5.1 Option Agreement. Each recipient of an Option shall execute an option agreement
(“Option Agreement”) in such form not inconsistent with the Plan as may be approved by the Board of Directors. Such Option Agreements may differ among recipients. 

5.2 Restricted Stock Agreement. Each recipient of a grant of Restricted Stock shall execute an agreement (“Restricted Stock
Agreement”) in such form not inconsistent with the Plan as may be approved by the Board of Directors. Such Restricted Stock Agreements may differ among recipients. 

5.3 “Lock-Up” Agreement. Unless the Board specifies otherwise, each
Restricted Stock Agreement and Option Agreement shall provide that upon the request of the Company or the managing underwriter(s) of any offering of securities of the Company that is the subject of a registration statement filed under the United
States Securities Act of 1933, as amended from time to time (the “Act”), the holder of any Option or the purchaser of any Restricted Stock shall, in connection therewith, agree in writing (in such form as the Company or such
managing underwriter(s) shall request) to the general effect that for a period of time (not to exceed 180 days, plus such additional number of days (not to exceed 35) as may reasonably be requested to enable the underwriter(s) of such offering to
comply with Rule 2711(f) of the Financial Industry Regulatory Authority or any amendment or successor thereto) from the effective date of the registration statement under the Act for such offering, the holder or purchaser will not sell, make any
short sale of, loan, grant any option for the purchase of, or otherwise dispose of any shares of the common stock of the Company owned or controlled by him or her. 

6. Purchase Price. 

6.1 General. The purchase price per share of Restricted Stock and per share of stock deliverable upon the exercise of an
Option shall be determined by the Board, provided, however, that in the case of any Option, the exercise price shall not be less than 100% of the fair market value of such stock, as determined by the Board, at the time of grant of such Option, or
less than 110% of such fair market value in the case of any Incentive Stock Option granted to a Greater Than 10% Shareholder. 
 6.2
Payment of Purchase Price. Option Agreements may provide for the payment of the exercise price by delivery of cash or a check to the order of the Company in an amount equal to the exercise price of such Options, or, to the
extent provided in the applicable Option Agreement, by one of the following methods: 

  
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 (i) with the consent of the Board, by delivery to the Company of shares of Common
Stock; such surrendered shares shall have a fair market value equal in amount to the exercise price of the Options being exercised, 

(ii) with the consent of the Board, a personal recourse note issued by the optionee to the Company in a principal amount equal
to such aggregate exercise price and with such other terms, including interest rate and maturity, as the Company may determine in its discretion; provided, however, that the interest rate borne by such note shall not be less than the lowest
applicable federal rate, as defined in Section 1274(d) of the Code, 
 (iii) with the consent of the Board, if the class
of Common Stock is registered under the Securities Exchange Act of 1934 at such time, subject to rules as may be established by the Board, by delivery to the Company of a properly executed exercise notice along with irrevocable instructions to a
broker to promptly deliver to the Company cash or a check payable and acceptable to the Company for the purchase price, 

(iv) with the consent of the Board, by reducing the number of Option shares otherwise issuable to the optionee upon exercise of
the Option by a number of shares of Common Stock having a fair market value equal to such aggregate exercise price, 
 (v)
with the consent of the Board, by any combination of such methods of payment. 
 The fair market value of any shares of Common Stock
or other non-cash consideration which may be delivered upon exercise of an Option shall be determined by the Board of Directors. Restricted Stock Agreements may provide for the payment of any purchase price in
any manner approved by the Board of Directors at the time of authorizing the issuance thereof. 
 7. Option Period.

 Notwithstanding any other provision of the Plan or any Option Agreement, each Option and all rights thereunder shall expire on the
date specified in the applicable Option Agreement, provided that such date shall not be later than ten years after the date on which the Option is granted (or five years in the case of an Incentive Stock Option granted to a Greater Than 10%
Shareholder), and in either case, shall be subject to earlier termination as provided in the Plan or Option Agreement. 
 8.
Exercise of Options. 
 8.1 General. Each Option shall be exercisable either in full or in
installments at such time or times and during such period as shall be set forth in the Option Agreement evidencing such Option, subject to the provisions of the Plan. To the extent not exercised, installments shall accumulate and be exercisable, in
whole or in part, at any time after becoming exercisable, but not later than the date the Option expires. 

  
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 8.2 Notice of Exercise. An Option may be exercised by the optionee by
delivering to the Company on any business day a written notice specifying the number of shares of Common Stock the optionee then desires to purchase and specifying the address to which the certificates for such shares are to be mailed (the
“Notice”), accompanied by payment for such shares. In addition, the Company may require any individual to whom an Option is granted, as a condition of exercising such Option, to give written assurances (the
“Investment Letter”) in a substance and form satisfactory to the Company to the effect that such individual is acquiring the Common Stock subject to the Option for his or her own account for investment and not with a view to
the resale or distribution thereof, and to such other effects as the Company deems necessary or advisable in order to comply with any securities law(s). 

8.3 Delivery. As promptly as practicable after receipt of the Notice, the Investment Letter (if required) and payment, the
Company shall deliver or cause to be delivered to the optionee certificates for the number of shares with respect to which such Option has been so exercised, issued in the optionee’s name; provided, however, that such delivery shall be deemed
effected for all purposes when the Company or a stock transfer agent shall have deposited such certificates in the United States mail, addressed to the optionee, at the address specified in the Notice. 

9. Transferability of Options. 

No Incentive Stock Option shall be assignable or transferable by the person to whom it is granted, either voluntarily or by operation of law,
except by will or the laws of descent and distribution, and during the life of an optionee, an Incentive Stock Option shall be exercisable only by the optionee. The Board may, in its discretion, determine the extent to which a non-statutory Option shall be transferable 
 9. Termination of Employment; Disability;
Death. Except as may be otherwise expressly provided in the terms and conditions of the Option Agreement, Options shall terminate on the earliest to occur of: 
  

	 	(i)	 the date of expiration thereof; 

 

	 	(ii)	 [0-30] days after termination of the optionee’s employment with,
or provision of services to, the Company by the Company for Cause (as hereinafter defined); 

  

	 	(iii)	 [0-30] days after the date of voluntary termination of
the optionee’s employment with, or provision of services to, the Company by the optionee (other than for death or permanent disability as defined below); or 

 

	 	(iv)	 [0-30] days after the date of termination of the optionee’s
employment with, or provision of services to, the Company by the Company without Cause (other than for death or permanent disability as defined below). 

Until the date on which the Option so expires, the optionee may exercise that portion of his or her Option which is exercisable at the time of termination of
the employment or service relationship. 

  
 - 5 - 

 An employment or service relationship between the Company and the optionee shall be deemed to
exist during any period during which the optionee is employed by or providing services to the Company. Whether an authorized leave of absence or an absence due to military or government service shall constitute termination of the employment
relationship between the Company and the optionee shall be determined by the Board at the time thereof. 
 For purposes of this
Section 10, the term “Cause” shall mean (a) any material breach by the optionee of any agreement to which the optionee and the Company are both parties, (b) any act (other than retirement) or omission to act by
the optionee which may have a material and adverse effect on the Company’s business or on the optionee’s ability to perform services for the Company, including, without limitation, the commission of any crime (other than minor traffic
violations), or (c) any material misconduct or material neglect of duties by the optionee in connection with the business or affairs of the Company. An optionee’s employment shall be deemed to have been terminated for Cause if the Company
determines within thirty (30) days of the termination of employment (whether such termination was voluntary or involuntary) that termination for Cause was warranted. 

In the event of the permanent and total disability or death of an optionee while in an employment or other relationship with the Company, any
Option held by such optionee shall terminate on the earlier of the date of expiration of the Option or 180 days after disability or death, the optionee (or in the case of death, his or her executor, administrator or any person or persons to whom
this option may be transferred by will or by laws of descent and distribution) shall have the right, at any time prior to such termination of an Option , to exercise the Option to the extent the optionee was entitled to exercise such Option as of
the date of his or her disability or death. An optionee is permanently and totally disabled if he or she is unable to engage in any substantial gainful activity by reason of any medically determinable physical or mental impairment which can be
expected to last for a continuous period of not less than 12 months; permanent and total disability shall be determined in accordance with Section 22(e)(3) of the Code and the regulations issued thereunder. 

10. Rights as a Shareholder. The holder of an Option shall have no rights as a shareholder with respect to any
shares covered by the Option (including, without limitation, any rights to receive dividends or non-cash distributions with respect to such shares) until the date of issue of a stock certificate to him or her
for such shares. No adjustment shall be made for dividends or other rights for which the record date is prior to the date such stock certificate is issued. 

11. Additional Provisions. The Board of Directors may, in its sole discretion, include additional provisions in
Restricted Stock Agreements and Option Agreements, including, without limitation, restrictions on transfer, rights of the Company to repurchase shares of Restricted Stock or shares of Common Stock acquired upon exercise of Options, commitments to
pay cash bonuses, to make, arrange for or guaranty loans or to transfer other property to optionees upon exercise of Options, or such other provisions as shall be determined by the Board of Directors; provided that such additional provisions
shall not be inconsistent with any other term or condition of the Plan and such additional provisions shall not be such as to cause any Incentive Stock Option to fail to qualify as an Incentive Stock Option within the meaning of Section 422 of
the Code. 

  
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 12. Acceleration, Extension, Etc. The Board of Directors may, in its sole
discretion, (i) accelerate the date or dates on which all or any particular Option or Options may be exercised or (ii) extend the period or periods of time during which all, or any particular, Option or Options may be exercised. 

13. Adjustment Upon Changes in Capitalization 

13.1 No Effect of Options upon Certain Corporate Transactions. The existence of outstanding Options shall not affect in any way
the right or power of the Company to make or authorize any or all adjustments, recapitalizations, reorganizations or other changes in the Company’s capital structure or its business, or any merger or consolidation, or any issue of Common Stock,
or any issue of bonds, debentures, preferred or prior preference stock ahead of or affecting the Common Stock or the rights thereof, or the dissolution or liquidation of the Company, or any sale or transfer of all or any part of its assets or
business, or any other corporate act or proceeding, whether of a similar character or otherwise. 
 13.2 Adjustment
Provisions. If, through or as a result of any merger, consolidation, sale of all or substantially all of the assets of the Company, reorganization, recapitalization, reclassification, stock dividend, stock split, reverse stock split
or other similar transaction, (i) the outstanding shares of Common Stock are increased, decreased or exchanged for a different number or kind of shares or other securities of the Company, or (ii) additional shares or new or different
shares or other securities of the Company or other non-cash assets are distributed with respect to such shares of Common Stock or other securities, an appropriate and proportionate adjustment shall be made in
(x) the maximum number and kind of shares reserved for issuance under the Plan, (y) the number and kind of shares or other securities subject to any then outstanding Options, and (z) the price for each share or other security subject
to any then outstanding Options, so that upon exercise of such Options, in lieu of the shares of Common Stock for which such Options were then exercisable, the relevant optionee shall be entitled to receive, for the same aggregate consideration, the
same total number and kind of shares or other securities, cash or property that the owner of an equal number of outstanding shares of Common Stock immediately prior to the event requiring adjustment would own as a result of the event. If any such
event shall occur, appropriate adjustment shall also be made in the application of the provisions of this Section 14 and Section 15 with respect to Options and the rights of optionees after the event so that the provisions of such Sections
shall be applicable after the event and be as nearly equivalent as practicable in operation after the event as they were before the event. 

13.3 No Adjustment in Certain Cases. Except as hereinbefore expressly provided, the issue by the Company of shares of
stock of any class, or securities convertible into shares of stock of any class, for cash or property or for labor or services, either upon direct sale or upon the exercise of rights or warrants to subscribe therefor, or upon conversion of shares or
obligations of the Company convertible into such shares or other securities, shall not affect, and no adjustment by reason thereof shall be made with respect to, the number or price of shares of Common Stock then subject to outstanding options. 

  
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 13.4 Board Authority to Make Adjustments. Any adjustments under this
Section 14 will be made by the Board of Directors, whose determination as to what adjustments, if any, will be made and the extent thereof will be final, binding and conclusive. No fractional shares will be issued under the Plan on account of
any such adjustments. 
 14. Effect of Certain Transactions 

14.1 General. Except as provided in any Option Agreement or Restricted Stock Agreement to the contrary, if the Company is
merged with or into or consolidated with another corporation under circumstances where the stockholders of the Company immediately prior to such merger or consolidation do not own after such merger or consolidation shares representing at least fifty
percent (50%) of the voting power of the Company or the surviving or resulting corporation, as the case may be, or if shares representing fifty percent (50%) or more of the voting power of the Company are transferred to an Unrelated Third Party, as
hereinafter defined, or if the Company is liquidated, or sells or otherwise disposes of all or substantially all its assets (each such transaction is referred to herein as a “Change in Control Transaction”), the Board, or the board of
directors of any corporation assuming the obligations of the Company, may, in its discretion, take any one or more of the following actions, as to some or all outstanding Options or Restricted Stock Awards (and need not take the same action as to
each such Option or Restricted Stock Award): (i) provide that such Options shall be assumed, or equivalent Options shall be substituted, by the acquiring or succeeding corporation (or an affiliate thereof), provided that any such Options
substituted for Incentive Stock Options shall meet the requirements of Section 424(a) of the Code, (ii) upon written notice to the optionees, provide that all unexercised Options will terminate immediately prior to the consummation of the
Change in Control Transaction unless exercised by the optionee to the extent otherwise then exercisable within a specified period following the date of such notice, (iii) upon written notice to the grantees, provide that all unvested
shares of Restricted Stock shall be repurchased at cost, (iv) make or provide for a cash payment to the optionees equal to the difference between (A) the fair market value of the per share consideration (whether cash, securities or other
property or any combination of the above) the holder of a share of Common Stock will receive upon consummation of the Change in Control Transaction (the “Per Share Transaction Price”) times the number of shares of Common
Stock subject to outstanding vested Options (to the extent then exercisable at prices not equal to or in excess of the Per Share Transaction Price) and (B) the aggregate exercise price of such outstanding vested Options, in exchange for the
termination of such Options, or (v) provide that all or any outstanding Options shall become exercisable and all or any outstanding Restricted Stock Awards shall vest in part or in full immediately prior to such event. To the extent that any
Options are exercisable at a price equal to or in excess of the Per Share Transaction Price, the Board may provide that such Options shall terminate immediately upon the consummation of the Change in Control Transaction without any payment being
made to the holders of such Options. “Unrelated Third Party” shall mean any person who is not, on the date of adoption of this Plan by the Board, a holder of stock of any class or preference or any stock option of the
Company. 

  
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 14.2 Substitute Options. The Company may grant Options in substitution for
options held by employees, officers or directors of, or consultants or advisors to, another corporation who become employees, officers or directors of, or consultants or advisors to, the Company, as the result of a merger or consolidation of
the employing corporation with the Company or as a result of the acquisition by the Company of property or stock of the employing corporation. The Company may direct that substitute Options be granted on such terms and conditions as the Board
considers appropriate in the circumstances. 
 14.3 Restricted Stock. In the event of a business combination or other
transaction of the type detailed in Section 15.1, any securities, cash or other property received in exchange for shares of Restricted Stock shall continue to be governed by the provisions of any Restricted Stock Agreement pursuant to which
they were issued, including any provision regarding vesting, and such securities, cash, or other property may be held in escrow on such terms as the Board of Directors may direct, to insure compliance with the terms of any such Restricted Stock
Agreement. 
 15. No Special Employment Rights. Nothing contained in the Plan or in any Option Agreement or
Restricted Stock Agreement shall confer upon any optionee or holder of Restricted Stock any right with respect to the continuation of his or her employment by the Company or interfere in any way with the right of the Company at any time to terminate
such employment or to increase or decrease his or her compensation. 
 16. Other Employee Benefits. The amount of
any compensation deemed to be received by an employee as a result of the issuance of shares of Restricted Stock or the grant or exercise of an Option or the sale of shares received upon issuance of a Restricted Stock Award or exercise of an Option
will not constitute compensation with respect to which any other employee benefits of such employee are determined, including, without limitation, benefits under any bonus, pension, profit-sharing, life insurance or salary continuation plan, except
as otherwise specifically determined by the Board of Directors. 
 17. Amendment of the Plan. 

17.1 The Board may at any time, and from time to time, modify or amend in any respect or terminate the Plan. If shareholder approval is not
obtained within twelve months after any amendment increasing the number of shares authorized under the Plan or changing the class of persons eligible to receive Options under the Plan, no Options granted pursuant to such amendments shall be deemed
to be Incentive Stock Options and no Incentive Stock Options shall be issued pursuant to such amendments thereafter. 
 17.2 The termination
or any modification or amendment of the Plan shall not, without the consent of an optionee or the holder of Restricted Stock, adversely affect his or her rights under an Option or Restricted Stock Award previously granted to him or her. With the
consent of the recipient of Restricted Stock or optionee affected, the Board may amend outstanding Restricted Stock Agreements or Option Agreements in a manner not inconsistent with the Plan. 

  
 - 9 - 

 18. Withholding. The Company shall have the right to deduct from
payments of any kind otherwise due to the optionee or recipient of Restricted Stock, any federal, state or local taxes of any kind required by law to be withheld with respect to issuance of any shares of Restricted Stock or shares issued upon
exercise of Options. Prior to delivery of any Common Stock pursuant to the terms of this Plan, the Board has the right to require that the optionee or recipient of Restricted Stock remit to the Company an amount sufficient to satisfy any minimum tax
withholding obligation. Subject to the prior approval of the Company, which may be withheld by the Company in its sole discretion, the obligor may elect to satisfy any minimum withholding obligations, in whole or in part, (i) by causing the
Company to withhold shares of Common Stock otherwise issuable, or (ii) by delivering to the Company a sufficient number of shares of Common Stock. The shares so withheld shall have a fair market value equal to such minimum withholding
obligation. The fair market value of the shares used to satisfy such minimum withholding obligation shall be determined by the Company as of the date that the amount of tax to be withheld is to be determined. A person who has made an election
pursuant to this Section 19 may only satisfy his or her withholding obligation with shares of Common Stock which are not subject to any repurchase, forfeiture, unfulfilled vesting or other similar restrictions. 

19. Effective Date and Duration of the Plan. 

19.1 Effective Date. The Plan shall become effective when adopted by the Board of Directors. If shareholder approval is
not obtained within twelve months after the date of the Board’s adoption of the Plan, no Options previously granted under the Plan shall be deemed to be Incentive Stock Options and no Incentive Stock Options shall be granted thereafter.
Amendments to the Plan not requiring shareholder approval shall become effective when adopted by the Board. Amendments requiring shareholder approval shall become effective when adopted by the Board, but if shareholder approval is not obtained
within twelve months of the Board’s adoption of such amendment, any Incentive Stock Options granted pursuant to such amendment shall be deemed to be non-statutory Options provided that such Options are
authorized by the Plan. Subject to this limitation, Options may be granted under the Plan at any time after the effective date and before the date fixed for termination of the Plan. 

19.2 Termination. Unless sooner terminated by action of the Board of Directors, the Plan shall terminate upon the close of
business on the day next preceding the tenth anniversary of the date of its adoption by the Board of Directors. 
 20. Provision
for Foreign Participants. The Board of Directors may, without amending the Plan, modify the terms of Option Agreements or Restricted Stock Agreements to differ from those specified in the Plan with respect to participants who are
foreign nationals or employed outside the United States to recognize differences in laws, rules, regulations or customs of such foreign jurisdictions with respect to tax, securities, currency, employee benefit or other matters. 

  
 - 10 - 

 21. Requirements of Law. The Company shall not be required to sell or
issue any shares under any Option or Restricted Stock Award if the issuance of such shares shall constitute a violation by the optionee, the Restricted Stock Award recipient, or by the Company of any provision of any law or regulation of any
governmental authority. In addition, in connection with the Act, the Company shall not be required to issue any shares upon exercise of any Option unless the Company has received evidence satisfactory to it to the effect that the holder of such
Option will not transfer such shares except pursuant to a registration statement in effect under the Act or unless an opinion of counsel satisfactory to the Company has been received by the Company to the effect that such registration is not
required in connection with any such transfer. Any determination in this connection by the Board shall be final, binding and conclusive. In the event the shares issuable on exercise of an Option are not registered under the Act or under the
securities laws of each relevant state or other jurisdiction, the Company may imprint on the certificate(s) appropriate legends that counsel for the Company considers necessary or advisable to comply with the Act or any such state or other
securities law. The Company may register, but in no event shall be obligated to register, any securities covered by the Plan pursuant to the Act; and in the event any shares are so registered the Company may remove any legend on certificates
representing such shares. The Company shall not be obligated to take any affirmative action in order to cause the exercise of an Option, the grant of any Restricted Stock Award or the issuance of shares pursuant thereto to comply with any law or
regulation of any governmental authority. 
 22. Conversion of Incentive Stock Options into
Non-Qualified Options; Termination. The Board of Directors, with the consent of any optionee, may in its discretion take such actions as may be necessary to convert such optionee’s
Incentive Stock Options (or any installments or portions of installments thereof) that have not been exercised on the date of conversion into non-statutory Options at any time prior to the expiration of such
Incentive Stock Options, regardless of whether the optionee is an employee of the Company or a parent or subsidiary of the Company at the time of such conversion. At the time of such conversion, the Board of Directors (with the consent of the
optionee) may impose such conditions on the exercise of the resulting non-statutory Options as the Board of Directors in its discretion may determine, provided that such conditions shall not be inconsistent
with this Plan. Nothing in this Plan shall be deemed to give any optionee the right to have such optionee’s Incentive Stock Options converted into non-statutory Options, and no such conversion shall occur
until and unless the Board of Directors takes appropriate action. The Board of Directors, with the consent of the optionee, may also terminate any portion of any Incentive Stock Option that has not been exercised at the time of such termination.

 23. Non-Exclusivity of this Plan; Non-Uniform
Determinations. Neither the adoption of this Plan by the Board of Directors nor the approval of this Plan by the stockholders of the Company shall be construed as creating any limitations on the power of the Board of Directors to
adopt such other incentive arrangements as it may deem desirable, including, without limitation, the granting of stock options otherwise than under this Plan, and such arrangements may be either applicable generally or only in specific cases. 

  
 - 11 - 

 The determinations of the Board of Directors under this Plan need not be uniform and may be made
by it selectively among persons who receive or are eligible to receive Options or Restricted Stock Awards under this Plan (whether or not such persons are similarly situated). Without limiting the generality of the foregoing, the Board of Directors
shall be entitled, among other things, to make non-uniform and selective determinations, and to enter into non-uniform and selective Option Agreements and Restricted
Stock Agreements, as to (a) the persons to receive Options or Restricted Stock Awards under this Plan, (b) the terms and provisions of Options or Restricted Stock Awards, (c) the exercise by the Board of Directors of its discretion in
respect of the exercise of Options pursuant to the terms of this Plan, and (d) the treatment of leaves of absence pursuant to Section 10 hereof. 

24. Governing Law. This Plan and each Option or Restricted Stock Award shall be governed by the laws of The Commonwealth of
Massachusetts, without regard to its principles of conflicts of law. 

  
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 APPENDIX A 

TO PEAR THERAPEUTICS, INC. 2013 STOCK INCENTIVE PLAN 

FOR CALIFORNIA RESIDENTS ONLY 

This Appendix to the Pear Therapeutics, Inc. 2013 Stock Incentive Plan (the “Plan”) shall have application only to
participants in the Plan who are residents of the State of California. Capitalized terms contained herein shall have the same meanings given to them in the Plan, unless otherwise provided in this Appendix. Notwithstanding any provision contained
in the Plan to the contrary and to the extent required by applicable law, the following terms and conditions shall apply to all Options and Restricted Stock Awards (collectively “Awards”) granted to residents of the State of California,
until such time as the Common Stock becomes subject to registration under the Securities Act of 1933: 
 1. Awards shall be
nontransferable other than by will or the laws of descent and distribution. Notwithstanding the foregoing, and to the extent permitted by Section 422 of the Code, the Board, in its discretion, may permit distribution of an Award to an inter
vivos or testamentary trust in which the Award is to be passed to beneficiaries upon the death of the trustor (settlor), or by gift to “immediate family” as that term is defined in Rule 16a-1(e) of
the United States Exchange Act of 1934. 
 2. Unless employment is terminated for Cause, the right to exercise an Option in the event of
termination of employment, to the extent that the optionee is otherwise entitled to exercise an Option on the date employment terminates, shall be 

(a) at least six months from the date of termination of employment if termination was caused by death or permanent disability; and 

(b) at least 30 days from the date of termination if termination of employment was caused by other than death or permanent disability; 

(c) but in no event later than the remaining term of the Option. 

3. Any Award exercised before shareholder approval is obtained shall be rescinded if shareholder approval is not obtained within 12 months of
the Board’s adoption of the Plan.

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