EX-4.27



 Exhibit 4.27 

NEITHER THIS SECURITY NOR THE SECURITIES INTO WHICH THIS SECURITY IS CONVERTIBLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE
SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE
REGISTRATION STATEMENT UNDER THE SECURITIES ACT OR PURSUANT TO AN AVAILABLE EXEMPTION FROM, OR IN A TRANSACTION NOT SUBJECT TO, THE REGISTRATION REQUIREMENTS OF THE SECURITIES ACT AND IN ACCORDANCE WITH APPLICABLE STATE SECURITIES LAWS AS EVIDENCED
BY A LEGAL OPINION OF COUNSEL TO THE TRANSFEROR TO SUCH EFFECT, THE SUBSTANCE OF WHICH SHALL BE REASONABLY ACCEPTABLE TO THE COMPANY. 
 Original Issue
Date: June     , 2015 
 Original Conversion Price (subject to adjustment herein): $0.25 

Principal Amount: $             

AUTHENTIDATE HOLDING CORP. 

9% SENIOR SECURED CONVERTIBLE DEBENTURE 

THIS 9% SENIOR SECURED CONVERTIBLE DEBENTURE is one of a series of duly authorized and validly issued 9% Senior Secured Convertible Debentures
of Authentidate Holding Corp., a Delaware corporation, (the “Company”), having its principal place of business at 300 Connell Drive, 5th Floor, Berkeley Heights, NJ 07922, designated as its 9% Senior Secured Convertible Debenture
due June     , 2016 (this debenture, the “Debenture” and, collectively with the other debentures of such series, the “Debentures”). This Debenture is being issued pursuant to the Purchase
Agreement (as defined below) among the Company and the original holders of the Debentures. By its acceptance of this Debenture, each Holder agrees to be bound by the terms of the Purchase Agreement. The Debentures are secured obligations of the
Company, to the extent provided for in the Security Agreement dated as of the date of the Purchase Agreement (the “Security Agreement”) entered into among the Company and the holders of the Debenture, and shall be senior in right of
payment to all other Indebtedness of the Company and its Subsidiaries subject to the terms herein. This Debenture is a direct obligation of the Company and ranks pari passu in right of payment with all other Debentures now or hereafter issued
in accordance with the Purchase Agreement under the terms set forth herein. 
 FOR VALUE RECEIVED, the Company promises to pay to
                    or its registered assigns (the “Holder”), or shall have paid pursuant to the terms hereunder, the principal sum
of $                    on June     , 2016 (the “Maturity Date”) or such earlier date as this Debenture is
required or permitted to be repaid as provided hereunder, and to pay Interest to the Holder on the aggregate unconverted and then outstanding principal amount of this Debenture in accordance with the provisions hereof. This Debenture is subject to
the following additional provisions: 
 Section 1. Definitions. For the purposes hereof, in addition to the terms defined
elsewhere in this Debenture, (a) capitalized terms not otherwise defined herein shall have the meanings set forth in the Purchase Agreement and (b) the following terms shall have the following meanings: 

“Alternate Consideration” shall have the meaning set forth in Section 5(d). 

“Bankruptcy Event” means any of the following events: (a) the Company commences a case or other proceeding under any
bankruptcy, reorganization, arrangement, adjustment of debt, relief of debtors, dissolution, insolvency or liquidation or similar law of any jurisdiction relating to the Company, 

  
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(b) there is commenced against the Company any such case or proceeding that is not dismissed within 60 days after commencement, (c) the Company is adjudicated insolvent or bankrupt or
any order of relief or other order approving any such case or proceeding is entered, (d) the Company suffers any appointment of any custodian or the like for it or any substantial part of its property that is not discharged or stayed within 60
calendar days after such appointment, (e) the Company makes a general assignment for the benefit of creditors, (f) the Company calls a meeting of its creditors with a view to arranging a composition, adjustment or restructuring of its
debts or (g) the Company, by any act or failure to act, expressly indicates its consent to, approval of or acquiescence in any of the foregoing. 

“Base Conversion Price” shall have the meaning set forth in Section 5(c). 

“Beneficial Ownership Limitation” shall have the meaning set forth in Section 4(d). 

“Business Day” means any day except any Saturday, any Sunday, any day which is a federal legal holiday in the United States
or any day on which banking institutions in the State of New York are authorized or required by law or other governmental action to close. 

“Change of Control Transaction” means the occurrence after the date hereof of any of (a) an acquisition after the date
hereof by an individual or legal entity or “group” (as described in Rule 13d-5(b)(1) promulgated under the Exchange Act) of effective control (whether through legal or beneficial ownership of capital stock of the Company, by contract or
otherwise) of in excess of 50% of the voting securities of the Company (other than by means of conversion or exercise of the Debentures and the Securities issued together with the Debentures), (b) the Company merges into or consolidates with
any other Person, or any Person merges into or consolidates with the Company and, after giving effect to such transaction, the stockholders of the Company immediately prior to such transaction own less than 50% of the aggregate voting power of the
Company or the successor entity of such transaction, (c) the Company sells or transfers all or substantially all of its assets to another Person and the stockholders of the Company immediately prior to such transaction own less than 50% of the
aggregate voting power of the acquiring entity immediately after the transaction, (d) a replacement at one time or within a three year period of more than one-half of the members of the Board of Directors which is not approved by a majority of
those individuals who are members of the Board of Directors on the Original Issue Date (or by those individuals who are serving as members of the Board of Directors on any date whose nomination to the Board of Directors was approved by a majority of
the members of the Board of Directors who are members on the date hereof), or (e) the execution by the Company of an agreement to which the Company is a party or by which it is bound, providing for any of the events set forth in clauses
(a) through (d) above. 
 “Closing Bid Price” and “Closing Sale Price” means, for any security
as of any date, the last closing bid price and last closing trade price, respectively, for such security on the Trading Market, as reported by the Nasdaq Stock Market, or, if the Trading Market begins to operate on an extended hours basis and does
not designate the closing bid price or the closing trade price (as the case may be) then the last bid price or last trade price, respectively, of such security prior to 4:00:00 p.m., New York time, as reported by the Nasdaq Stock Market, or, if the
Trading Market is not the principal securities exchange or trading market for such security, the last closing bid price or last trade price, respectively, of such security on the principal securities exchange or trading market where such security is
listed or traded as reported by the Nasdaq Stock Market, or if the foregoing do not apply, the last closing bid price or last trade price, respectively, of such security in the over-the-counter market on the electronic bulletin board for such
security as reported by the Nasdaq Stock Market, or, if no closing bid price or last trade price, respectively, is reported for such security by the Nasdaq Stock Market, the average of the bid prices, or the ask prices, respectively, of any market
makers for such security as reported in the “pink sheets” by OTC Markets Group Inc. (formerly Pink Sheets LLC). If the Closing Bid Price or the Closing Sale Price 

  
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cannot be calculated for a security on a particular date on any of the foregoing bases, the Closing Bid Price or the Closing Sale Price (as the case may be) of such security on such date shall be
the fair market value as mutually determined by the Company and the Holder. If the Company and the Holder are unable to agree upon the fair market value of such security, then such dispute shall be resolved in accordance with the procedures in
Section 9(j). All such determinations shall be appropriately adjusted for any stock dividend, stock split, stock combination or other similar transaction during such period. 

“Conversion Date” shall have the meaning set forth in Section 4(a). 

“Conversion Price” shall have the meaning set forth in Section 4(b). 

“Conversion Schedule” means the Conversion Schedule in the form of Schedule 1 attached hereto. 

“Conversion Shares” means, collectively, the shares of Common Stock issuable upon conversion of this Debenture in accordance
with the terms hereof. 
 “Effectiveness Period” shall have the meaning set forth in the Registration Rights Agreement.

 “Event of Default” shall have the meaning set forth in Section 8(a). 

“Exempt Issuance” means the issuance of (a) shares of Common Stock, restricted stock units, options or other Common
Stock Equivalents to employees, officers or directors of the Company or other eligible persons pursuant to any equity compensation plan presently existing or duly adopted for such purpose by a majority of the non-employee members of the Board of
Directors or a majority of the members of a committee of non-employee directors of the Company (for purposes of clarity, the issuance of shares of Common Stock upon exercise of options, vesting of restricted stock units or otherwise in accordance
with the terms of an award granted pursuant to such a Company plan subsequent to the date hereof shall also be an Exempt Issuance), (b) securities upon the exercise or exchange of or conversion of any Securities issued hereunder and/or other
securities exercisable or exchangeable for or convertible into shares of securities of the Company issued and outstanding on the date of this Agreement (including shares of common stock that the Company may issue pursuant to the presently
outstanding shares of Series D Preferred Stock in lieu of cash dividends thereon) provided that such securities have not been amended since the date of this Agreement to increase the number of such securities or to decrease the exercise price,
exchange price or conversion price of such securities (except that amendments or modifications to existing common stock purchase warrants to reduce the exercise price thereof and/or alter the number or type of securities issuable upon exercise
thereof shall be included within the definition of an Exempt Issuance), (c) securities in connection with a rights offering to the Company’s stockholders, including any securities which may be issued upon exercise of the rights distributed
to the Company’s stockholders, (d) securities issued pursuant to mergers, acquisitions or strategic transactions approved by a majority of the disinterested directors of the Company, provided that any such issuance shall only be to a
Person (or to the equityholders of a Person) which is, itself or through its subsidiaries, an operating company or an owner of an asset in a business synergistic with the business of the Company and shall provide to the Company additional benefits
in addition to the investment of funds, but shall not include a transaction in which the Company is issuing securities primarily for the purpose of raising capital or to an entity whose primary business is investing in securities, (e) shares of
Common Stock (or securities convertible into or exercisable or exchangeable for shares of Common Stock) which may be issued to consultants, vendors, lessors, distributors or similar persons, to the Company as consideration for services or assets
provided to the Company (and the shares of Common Stock which may be issued upon exercise or conversion of convertible securities issued to the class persons specified in this clause) up to a maximum of 2,000,000 shares of Common Stock,
(f) shares of Common Stock or other securities issued 

  
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in connection with any stock split, stock dividend or recapitalization of the Company, (g) a firm commitment underwritten public offering of equity securities of the Company for at least
$5,000,000 of gross proceeds, and (h) securities issued in the Alternative Transaction (as defined in the Purchase Agreement). 

“Fair Market Value” means, on any given day: (A) if the shares of Common Stock of the Company are exchange-traded, the
average of the closing sales prices per share of Common Stock for the ten (10) consecutive Trading Days ending on the day that is two (2) Trading Days prior to the applicable date of determination of Fair Market Value; or (B) if the
shares of Common Stock of the Company are not listed or admitted to trading on any securities exchange but are regularly traded in any over-the-counter market, then the average of the bid and ask prices per share of Common Stock for the ten
(10) consecutive Trading Days ending on the day that is two (2) Trading Days prior to the applicable date of determination of Fair Market Value; or (C) if the shares of Common Stock of the Company are not traded as described in
clauses (A) or (B), then the per share fair market value of the Common Stock as determined in good faith by the Company’s Board of Directors. 

“Fundamental Transaction” shall have the meaning set forth in Section 5(d). 

“Indebtedness” shall have the meaning ascribed to such term in the Purchase Agreement. 

“Interest Payment Date” shall have the meaning set forth in Section 2(a). 

“Issuable Maximum” shall have the meaning set forth in Section 4(e). 

“Majority in Interest” means, at any time of determination, fifty-one percent (51%) in interest (based on
then-outstanding principal amounts of Debentures at the time of such determination) of the holders of Debentures. 
 “Mandatory
Redemption” shall have meaning set forth in Section 6(b). 
 “Mandatory Redemption Amount” means the dollar
amount equal to 80% of the revenue recognizable under GAAP generated through the Company’s “Inscrybe Referral and Order Management” and “Inscrybe Hospital Discharge” solutions for the calendar month preceding the relevant
Collateral Sweep Date (as defined in Section 6(b)). 
 “Notice of Conversion” shall have the meaning set forth in
Section 4(a). 
 “Optional Redemption” shall have the meaning set forth in Section 6(a). 

“Optional Redemption Amount” means the sum of (a) 110% of the then outstanding principal amount of the Debenture and
(b) accrued but unpaid interest through the Option Redemption Date. 
 “Original Issue Date” means the date of the
first issuance of the Debentures, regardless of any transfers of any Debenture and regardless of the number of instruments which may be issued to evidence such Debentures. 

“Purchase Agreement” means the Securities Purchase Agreement, dated as of May 29, 2015 by and among the Company and the
original Holders, as amended, modified or supplemented from time to time in accordance with its terms. 

  
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 “Registration Rights Agreement” means the Registration Rights Agreement, dated
as of the date of the Purchase Agreement, among the Company and the original Holders, in the form attached to the Purchase Agreement. 

“Registration Statement” means a registration statement meeting the requirements set forth in the Registration Rights
Agreement and covering the resale of the Registrable Securities (as such term is defined in the Registration Rights Agreement) by each Holder as provided for in the Registration Rights Agreement. 

“Securities Act” means the Securities Act of 1933, as amended, and the rules and regulations promulgated thereunder. 

“Share Delivery Date” shall have the meaning set forth in Section 4(c)(ii). 

“Successor Entity” shall have the meaning set forth in Section 5(d). 

“Trading Day” means a day on which the principal Trading Market is open for trading. 

“Trading Market” means any of the following markets or exchanges on which the Common Stock is listed or quoted for trading on
the date in question: the NYSE MKT, the Nasdaq Capital Market, the Nasdaq Global Market, the Nasdaq Global Select Market, the New York Stock Exchange, the OTC Bulletin Board or the OTC Markets Inc. (or any successors to any of the foregoing). 

Section 2. Interest. 

(a) Payment of Interest. The Company shall pay interest to the Holder on the aggregate unconverted and then outstanding principal
amount of this Debenture at the rate of 9% per annum, payable in arrears on (i) each Optional Redemption Date or Mandatory Redemption Date (as to that principal amount then being redeemed), (ii) each date on which any principal amount
of this Debenture is being converted (as to that principal amount being converted), and (iii) on the Maturity Date (each such date, an “Interest Payment Date”) (if any Interest Payment Date is not a Business Day, then the
applicable payment shall be due on the next succeeding Business Day), in cash. 
 (b) Interest Calculations. Interest shall be
calculated on the basis of a 360-day year, consisting of twelve 30 calendar day periods, and shall accrue daily commencing on the Original Issue Date until payment in full of the outstanding principal, has been made. 

(c) Reserved. 
 (d)
Prepayment. Except as otherwise set forth in this Debenture, the Company may not prepay any portion of the principal amount of this Debenture without the prior written consent of the Holder. 

Section 3. Registration of Transfers and Exchanges. 

(a) Different Denominations. This Debenture is exchangeable for an equal aggregate principal amount of Debentures of different
authorized denominations, as requested by the Holder surrendering the same. No service charge or other cost will be payable by the Holder for such registration of transfer or exchange. 

  
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 (b) Investment Representations. This Debenture has been issued subject to certain
investment representations of the original Holder set forth in the Purchase Agreement and may be transferred or exchanged only in compliance with the Purchase Agreement and applicable federal and state securities laws and regulations. 

(c) Reliance on Debenture Register. Prior to due presentment for transfer to the Company of this Debenture, the Company and any agent
of the Company may treat the Person in whose name this Debenture is duly registered on the Debenture Register as the owner hereof for the purpose of receiving payment as herein provided and for all other purposes, whether or not this Debenture is
overdue, and neither the Company nor any such agent shall be affected by notice to the contrary. 
 Section 4.
Conversion. 
 (a) Voluntary Conversion. At any time after the Original Issue Date until this Debenture is no longer
outstanding, this Debenture shall be convertible, in whole or in part, into shares of Common Stock at the option of the Holder, at any time and from time to time (subject to the conversion limitations set forth in Section 4(d) and
Section 4(e) hereof). The Holder shall effect conversions by delivering to the Company a Notice of Conversion, the form of which is attached hereto as Annex A (each, a “Notice of Conversion”), specifying therein the
principal amount of this Debenture to be converted and the date on which such conversion shall be effected (such date, the “Conversion Date”). If no Conversion Date is specified in a Notice of Conversion, the Conversion Date shall
be the date that such Notice of Conversion is deemed delivered hereunder. No ink-original Notice of Conversion shall be required, nor shall any medallion guarantee (or other type of guarantee or notarization) of any Notice of Conversion form be
required. To effect conversions hereunder, the Holder shall not be required to physically surrender this Debenture to the Company unless the entire principal amount of this Debenture has been so converted. Conversions hereunder shall have the effect
of lowering the outstanding principal amount of this Debenture in an amount equal to the applicable conversion. The Holder and the Company shall maintain records showing the principal amount(s) converted and the date of such conversion(s). The
Company may deliver an objection to any Notice of Conversion within two (2) Business Days of delivery of such Notice of Conversion. In the event of any dispute or discrepancy, the records of the Company shall be controlling and determinative in
the absence of manifest error. The Holder, and any assignee by acceptance of this Debenture, acknowledge and agree that, by reason of the provisions of this paragraph, following conversion of a portion of this Debenture, the unpaid and
unconverted principal amount of this Debenture may be less than the amount stated on the face hereof.  
 (b) Conversion Price.
The conversion price in effect on any Conversion Date shall be equal to $0.25, subject to adjustment herein (the “Conversion Price”). 

(c) Mechanics of Conversion. 

(i) Conversion Shares Issuable Upon Conversion of Principal Amount. The number of Conversion Shares issuable upon a conversion of the
principal amount of this Debenture shall be equal to the quotient obtained by dividing (x) the outstanding principal amount of this Debenture to be converted by (y) the Conversion Price. 

(ii) Delivery of Certificate Upon Conversion. Not later than three (3) Trading Days after each Conversion Date (the
“Share Delivery Date”), the Company shall deliver, or cause to be delivered, to the Holder (A) a certificate or certificates representing the number of Conversion Shares being acquired upon the conversion of this Debenture and
(B) a bank check in the amount of accrued and unpaid interest. On or after the earlier of (i) the six month anniversary of the Original Issue Date or (ii) the Effective Date (as defined in the Purchase Agreement), the Company shall
use its reasonable best 

  
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efforts to deliver any certificate or certificates required to be delivered by the Company under this Section 4(c) electronically through The Depository Trust Company or another established
clearing corporation performing similar functions. 
 (iii) Company’s Failure to Timely Convert. If the Company shall fail, for
any reason or for no reason, to issue to the Holder within three (3) Trading Days after the Company’s receipt of a Conversion Notice (whether via facsimile or otherwise), a certificate for the number of shares of Common Stock to which the
Holder is entitled and register such shares of Common Stock on the Company’s share register or to credit the Holder’s or its designee’s balance account with DTC for such number of shares of Common Stock to which the Holder is entitled
upon the Holder’s conversion of any Conversion Amount (as the case may be) (a “Conversion Failure”), then, in addition to all other remedies available to the Holder, (1) the Company shall pay in cash to the Holder on each
day after such third (3rd) Trading Day that the issuance of such shares of Common Stock is not timely effected an amount equal to 0.5% of the product of (A) the sum of the number of shares of Common Stock not issued to the Holder on a
timely basis and to which the Holder is entitled multiplied by (B) the Closing Sale Price of the Common Stock on the Trading Day immediately preceding the last possible date which the Company could have issued such shares of Common Stock to the
Holder without violating Section 3(c)(i) and (2) the Holder, upon written notice to the Company, may void its Conversion Notice with respect to, and retain or have returned (as the case may be) any portion of this Debenture that has not
been converted pursuant to such Conversion Notice, provided that the voiding of a Conversion Notice shall not affect the Company’s obligations to make any payments which have accrued prior to the date of such notice pursuant to this
Section 4(c)(iii) or otherwise. The Holder agrees, however, that the maximum aggregate damages payable to a Holder hereunder for a Conversion Failure shall be 2% of the amount determined pursuant to the formula set forth in the immediately
preceding sentence. In addition to the foregoing, if within three (3) Trading Days after the Company’s receipt of a Conversion Notice (whether via facsimile or otherwise), the Company shall fail to issue and deliver a certificate to the
Holder and register such shares of Common Stock on the Company’s share register or credit the Holder’s or its designee’s balance account with DTC for the number of shares of Common Stock to which the Holder is entitled upon the
Holder’s conversion hereunder (as the case may be), and if on or after such third (3rd) Trading Day the Holder purchases (in an open market transaction or otherwise) shares of Common Stock to deliver in satisfaction of a sale by the Holder
of shares of Common Stock issuable upon such conversion that the Holder anticipated receiving from the Company, then, in addition to all other remedies available to the Holder, the Company shall, within three (3) Business Days after the
Holder’s request and in the Holder’s discretion, either (i) pay cash to the Holder in an amount equal to the Holder’s total purchase price (including brokerage commissions and other out-of-pocket expenses, if any) for the shares
of Common Stock so purchased (the “Buy-In Price”), at which point the Company’s obligation to deliver such certificate (and to issue such shares of Common Stock) shall terminate, or (ii) promptly honor its obligation to
deliver to the Holder a certificate or certificates representing such shares of Common Stock or credit the Holder’s balance account with DTC for the number of shares of Common Stock to which the Holder is entitled upon the Holder’s
conversion hereunder (as the case may be) and pay cash to the Holder in an amount equal to the excess (if any) of the Buy-In Price over the product of (A) such number of shares of Common Stock multiplied by (B) the Closing Sale Price of
the Common Stock on the Trading Day immediately preceding the Conversion Date. 
 (iv) Obligation Absolute. The Company’s
obligations to issue and deliver the Conversion Shares upon conversion of this Debenture in accordance with the terms hereof are absolute and unconditional, irrespective of any action or inaction by the Holder to enforce the same, any waiver or
consent with respect to any provision hereof, the recovery of any judgment against any Person or any action to enforce the same, or any setoff, counterclaim, recoupment, limitation or termination, or any breach or alleged breach by the Holder or any
other Person of any obligation to the Company or any violation or alleged violation of law by the Holder or any other Person, and irrespective of any other 

  
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circumstance which might otherwise limit such obligation of the Company to the Holder in connection with the issuance of such Conversion Shares; provided, however, that such
delivery shall not operate as a waiver by the Company of any such action the Company may have against the Holder. Nothing herein shall limit a Holder’s right to pursue actual damages or declare an Event of Default pursuant to Section 8
hereof for the Company’s failure to deliver Conversion Shares within the period specified herein and the Holder shall have the right to pursue all remedies available to it hereunder, at law or in equity including, without limitation, a decree
of specific performance and/or injunctive relief. The exercise of any such rights shall not prohibit the Holder from seeking to enforce damages pursuant to any other Section hereof or under applicable law. 

(v) Reservation of Shares Issuable Upon Conversion. The Company covenants that it will at all times reserve and keep available out of
its authorized and unissued shares of Common Stock for the sole purpose of issuance upon conversion of this Debenture, free from preemptive rights or any other actual contingent purchase rights of Persons other than the Holder (and the other holders
of the Debentures), not less than 125% of such aggregate number of shares of the Common Stock as shall (subject to the terms and conditions set forth in the Purchase Agreement) be issuable (taking into account the adjustments and restrictions of
Section 5) upon the conversion of the then outstanding principal amount of this Debenture. The Company covenants that all shares of Common Stock that shall be so issuable shall, upon issue, be duly authorized, validly issued, fully paid and
non-assessable and, if the Registration Statement is then effective under the Securities Act, shall be registered for public resale in accordance with such Registration Statement (subject to such Holder’s compliance with its obligations under
the Registration Rights Agreement). 
 (vi) Fractional Shares. No fractional shares or scrip representing fractional shares shall be
issued upon the conversion of this Debenture. As to any fraction of a share which the Holder would otherwise be entitled to purchase upon such conversion, the Company shall round up such fractional share to the next whole share. 

(vii) Transfer Taxes and Expenses. The issuance of certificates for shares of the Common Stock on conversion of this Debenture shall
be made without charge to the Holder hereof for any documentary stamp or similar taxes that may be payable in respect of the issue or delivery of such certificates, provided that, the Company shall not be required to pay any tax that may be payable
in respect of any transfer involved in the issuance and delivery of any such certificate upon conversion in a name other than that of the Holder of this Debenture so converted and the Company shall not be required to issue or deliver such
certificates unless or until the Person or Persons requesting the issuance thereof shall have paid to the Company the amount of such tax or shall have established to the satisfaction of the Company that such tax has been paid. The Company shall pay
all Transfer Agent fees required for same-day processing of any Notice of Conversion. 
 (d) Holder’s Conversion Limitations.
The Company shall not effect any conversion of this Debenture, and a Holder shall not have the right to convert any portion of this Debenture, to the extent that after giving effect to the conversion set forth on the applicable Notice of Conversion,
the Holder (together with the Holder’s Affiliates, and any Persons acting as a group together with the Holder or any of the Holder’s Affiliates) would beneficially own in excess of the Beneficial Ownership Limitation (as defined
below). For purposes of the foregoing sentence, the number of shares of Common Stock beneficially owned by the Holder and its Affiliates shall include the number of shares of Common Stock issuable upon conversion of this Debenture with respect
to which such determination is being made, but shall exclude the number of shares of Common Stock which are issuable upon (i) conversion of the remaining, unconverted principal amount of this Debenture beneficially owned by the Holder or any of
its Affiliates and (ii) exercise or conversion of the unexercised or unconverted portion of any other securities of the Company, in both cases which are subject to a limitation on conversion or exercise


  
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analogous to the limitation contained herein (including, without limitation, any other Debentures or the Warrants) beneficially owned by the Holder or any of its Affiliates. Except as set
forth in the preceding sentence, for purposes of this Section 4(d), beneficial ownership shall be calculated in accordance with Section 13(d) of the Exchange Act and the rules and regulations promulgated thereunder. To the extent that the
limitation contained in this Section 4(d) applies, the determination of whether this Debenture is convertible (in relation to other securities owned by the Holder together with any Affiliates) and of which principal amount of this Debenture is
convertible shall be in the sole discretion of the Holder, and the submission of a Notice of Conversion shall be deemed to be the Holder’s determination of whether this Debenture may be converted (in relation to other securities owned by the
Holder together with any Affiliates) and which principal amount of this Debenture is convertible, in each case subject to the Beneficial Ownership Limitation. To ensure compliance with this restriction, the Holder will be deemed to represent to the
Company each time it delivers a Notice of Conversion that such Notice of Conversion has not violated the restrictions set forth in this paragraph and the Company shall have no obligation to verify or confirm the accuracy of such determination. In
addition, a determination as to any group status as contemplated above shall be determined in accordance with Section 13(d) of the Exchange Act and the rules and regulations promulgated thereunder. For purposes of this Section 4(d), in
determining the number of outstanding shares of Common Stock, the Holder may rely on the number of outstanding shares of Common Stock as stated in the most recent of the following: (i) the Company’s most recent periodic or annual report
filed with the Commission, as the case may be, (ii) a more recent public announcement by the Company, or (iii) a more recent written notice by the Company or the Company’s transfer agent setting forth the number of shares of Common
Stock outstanding. Upon the written or oral request of a Holder, the Company shall within two Trading Days confirm orally and in writing to the Holder the number of shares of Common Stock then outstanding. In any case, the number of
outstanding shares of Common Stock shall be determined after giving effect to the conversion or exercise of securities of the Company, including this Debenture, by the Holder or its Affiliates since the date as of which such number of outstanding
shares of Common Stock was reported. The “Beneficial Ownership Limitation” shall be 4.99% of the number of shares of the Common Stock outstanding immediately after giving effect to the issuance of shares of Common Stock issuable
upon conversion of this Debenture held by the Holder. The Holder, upon not less than 61 days’ prior notice to the Company, may increase or decrease the Beneficial Ownership Limitation provisions of this Section 4(d), provided that the
Beneficial Ownership Limitation in no event exceeds 9.99% of the number of shares of the Common Stock outstanding immediately after giving effect to the issuance of shares of Common Stock upon conversion of this Debenture held by the Holder and the
Beneficial Ownership Limitation provisions of this Section 4(d) shall continue to apply. Any such increase or decrease will not be effective until the 61st day after such notice is delivered
to the Company. The Beneficial Ownership Limitation provisions of this paragraph shall be construed and implemented in a manner otherwise than in strict conformity with the terms of this Section 4(d) to correct this paragraph (or any portion
hereof) which may be defective or inconsistent with the intended Beneficial Ownership Limitation contained herein or to make changes or supplements necessary or desirable to properly give effect to such limitation. The limitations contained in this
paragraph shall apply to a successor holder of this Debenture. 
 (e) Issuance Limitations. Notwithstanding anything herein to the
contrary, if the Company has not obtained Shareholder Approval, then the Company may not issue, upon conversion of either the principal amount of, or Interest thereon, this Debenture, a number of shares of Common Stock which, when aggregated with
any shares of Common Stock issued on or after the Original Issue Date and prior to such Conversion Date (i) in connection with the conversion of any Debentures issued pursuant to the Purchase Agreement, and (ii) in connection with the
exercise of any Warrants issued pursuant to the Purchase Agreement, would exceed 19.99% of the number of shares of Common Stock outstanding on the Trading Day immediately preceding the Original Issue Date (subject to adjustment for forward and
reverse stock splits, recapitalizations and the like) (such number of shares, the “Issuable Maximum”). Each Holder shall be entitled to a portion of the Issuable Maximum equal to the quotient obtained by


  
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dividing (x) the original principal amount of the Holder’s Debenture by (y) the aggregate original principal amount of all Debentures issued on the Original Issue Date to all
Holders. In addition, each Holder may allocate its pro-rata portion of the Issuable Maximum among Debentures and Warrants held by it in its sole discretion. Such portion shall be adjusted upward ratably in the event a Holder no longer holds any
Debentures or Warrants and the amount of shares issued to the Holder pursuant to the Holder’s Debentures and Warrants was less than the Holder’s pro-rata share of the Issuable Maximum. The Company and the Holder understand and agree that
shares of Common Stock issued to and then held by the Holder as a result of conversions of Debentures shall not be entitled to cast votes on any resolution to obtain Shareholder Approval pursuant hereto. 

Section 5. Certain Adjustments. 

(a) Stock Dividends and Stock Splits. If the Company, at any time while this Debenture is outstanding: (i) pays a stock dividend
or otherwise makes a distribution or distributions payable in shares of Common Stock on shares of Common Stock or any Common Stock Equivalents (which, for avoidance of doubt, shall not include any shares of Common Stock issued by the Company upon
conversion of the Debentures or upon the exercise of any options or warrants), (ii) subdivides outstanding shares of Common Stock into a larger number of shares, (iii) combines (including by way of a reverse stock split) outstanding shares
of Common Stock into a smaller number of shares or (iv) issues, in the event of a reclassification of shares of the Common Stock, any shares of capital stock of the Company, then the Conversion Price shall be multiplied by a fraction of which
the numerator shall be the number of shares of Common Stock (excluding any treasury shares of the Company) outstanding immediately before such event, and of which the denominator shall be the number of shares of Common Stock outstanding immediately
after such event. Any adjustment made pursuant to this Section shall become effective immediately after the record date for the determination of stockholders entitled to receive such dividend or distribution and shall become effective immediately
after the effective date in the case of a subdivision, combination or re-classification. 
 (b) Pro Rata Distributions. During such
time as this Debenture is outstanding, if the Company shall declare or make any dividend or other distribution of its assets (or rights to acquire its assets) to holders of shares of Common Stock, by way of return of capital or otherwise (including,
without limitation, any distribution of cash, stock or other securities, property or options by way of a dividend, spin off, reclassification, corporate rearrangement, scheme of arrangement or other similar transaction) (a
“Distribution”), at any time after the issuance of this Debenture, then, in each such case, the Holder shall be entitled to participate in such Distribution to the same extent that the Holder would have participated therein if the
Holder had held the number of shares of Common Stock acquirable upon complete exercise of this Debenture (without regard to any limitations on exercise hereof, including without limitation, the Beneficial Ownership Limitation) immediately before the
date of which a record is taken for such Distribution, or, if no such record is taken, the date as of which the record holders of shares of Common Stock are to be determined for the participation in such Distribution (provided,
however, to the extent that the Holder’s right to participate in any such Distribution would result in the Holder exceeding the Beneficial Ownership Limitation, then the Holder shall not be entitled to participate in such Distribution to
such extent (or in the beneficial ownership of any shares of Common Stock as a result of such Distribution to such extent) and the portion of such Distribution shall be held in abeyance for the benefit of the Holder until such time, if ever, as its
right thereto would not result in the Holder exceeding the Beneficial Ownership Limitation). Notwithstanding the foregoing, no adjustment will be made under this Section 5(b) in respect of an Exempt Issuance. 

(c) Subsequent Equity Sales. If, at any time while this Debenture is outstanding, the Company sells or grants any option to purchase or
reduces the conversion or exercise price of any outstanding securities, grants any right to reduce, or otherwise disposes of or issues, any Common Stock 

  
 10 








 
or Common Stock Equivalents entitling any Person to acquire shares of Common Stock at a price per share that is lower than the then Conversion Price, other than in connection with any Common
Stock Equivalents outstanding on the Original Issue Date (such lower price, the “Base Conversion Price” and such issuances, collectively, a “Dilutive Issuance”) then the Conversion Price shall be reduced to equal
the product of (i) 0.85 and (ii) the Base Conversion Price; provided, however, that such adjustment to the Conversion Price shall be made only to the extent that after taking into account such adjustment to the Conversion Price the number
of authorized but unissued shares of Common Stock available for issuance under the Company’s Certificate of Incorporation is sufficient for the issuance of the maximum number of Conversion Shares issuable upon conversion of the Debenture
at such adjusted Conversion Price. In the event that the Company at such time does not have a sufficient number of authorized but unissued shares of Common Stock available for issuance at an adjusted Conversion Price, the Company shall
immediately use all commercially reasonable efforts to convene a meeting of its stockholders for the purpose of further amending its Certificate of Incorporation for the purpose of increasing the authorized number of shares of Common Stock in such
an amount as is necessary to permit conversion of the Debentures into the additional Conversion Shares issuable on account of such adjustment. Such adjustment shall be made whenever such Common Stock or Common Stock Equivalents are issued. For
purposes of clarity, if the holder of Common Stock or Common Stock Equivalents so issued shall at any time, whether by operation of purchase price adjustments, reset provisions, floating conversion, exercise or exchange prices or otherwise, or due
to warrants, options or rights per share which are issued in connection with such issuance, be entitled to receive shares of Common Stock at a price per share that is lower than the Conversion Price, such issuance shall be deemed to be a Dilutive
Issuance. The Company shall notify the Holder in writing, no later than the Trading Day following the issuance of any Common Stock or Common Stock Equivalents subject to this Section 5(c), indicating therein the applicable issuance price, or
applicable reset price, exchange price, conversion price and other pricing terms (such notice, the “Dilutive Issuance Notice”). For purposes of clarification, whether or not the Company provides a Dilutive Issuance Notice pursuant
to this Section 5(c), upon the occurrence of any Dilutive Issuance, the Holder is entitled to receive a number of Conversion Shares based upon the Base Conversion Price on or after the date of such Dilutive Issuance, regardless of whether the
Holder accurately refers to the Base Conversion Price in the Notice of Conversion. Notwithstanding the foregoing, no adjustment will be made under this Section 5(c) in respect of an Exempt Issuance. 

(d) Fundamental Transaction. If, at any time while this Debenture is outstanding, (i) the Company, directly or indirectly, in one
or more related transactions effects any merger or consolidation of the Company with or into another Person, (ii) the Company, directly or indirectly, effects any sale, lease, license, assignment, transfer, conveyance or other disposition of
all or substantially all of its assets in one or a series of related transactions, (iii) any, direct or indirect, purchase offer, tender offer or exchange offer (whether by the Company or another Person) is completed pursuant to which holders
of Common Stock are permitted to sell, tender or exchange their shares for other securities, cash or property and has been accepted by the holders of more than 50% of the outstanding Common Stock, (iv) the Company, directly or indirectly, in
one or more related transactions effects any reclassification, reorganization or recapitalization of the Common Stock or any compulsory share exchange pursuant to which the shares of Common Stock of the Company are effectively converted into or
exchanged for other securities, cash or property, or (v) the Company, directly or indirectly, in one or more related transactions consummates a business combination (including, without limitation, a reorganization, recapitalization, spin-off or
scheme of arrangement) with another Person or group of Persons whereby such other Person or group acquires more than 50% of the outstanding shares of Common Stock (not including any shares of Common Stock held by the other Person or other Persons
making or party to, or associated or affiliated with the other Persons making or party to, such stock or share purchase agreement or other business combination) (each a “Fundamental Transaction”), then, upon any subsequent
conversion of this Debenture, the Holder shall have the right to receive, for each Conversion Share that would have been issuable upon such conversion immediately prior to the occurrence of such Fundamental Transaction (without regard to any
limitation in 

  
 11 








 
Section 4(d) and Section 4(e) on the conversion of this Debenture), the number of shares of Common Stock of the successor or acquiring corporation or of the Company, if it is the
surviving corporation, and any additional consideration (the “Alternate Consideration”) receivable as a result of such Fundamental Transaction by a holder of the number of shares of Common Stock for which this Debenture is
convertible immediately prior to such Fundamental Transaction (without regard to any limitation in Section 4(d) and Section 4(e) on the conversion of this Debenture). For purposes of any such conversion, the determination of the Conversion
Price shall be appropriately adjusted to apply to such Alternate Consideration based on the amount of Alternate Consideration issuable in respect of one (1) share of Common Stock in such Fundamental Transaction, and the Company shall apportion
the Conversion Price among the Alternate Consideration in a reasonable manner reflecting the relative value of any different components of the Alternate Consideration. If holders of Common Stock are given any choice as to the securities, cash or
property to be received in a Fundamental Transaction, then the Holder shall be given the same choice as to the Alternate Consideration it receives upon any conversion of this Debenture following such Fundamental Transaction. The Company shall cause
any successor entity in a Fundamental Transaction in which the Company is not the survivor (the “Successor Entity”) to assume in writing all of the obligations of the Company under this Debenture and the other Transaction Documents
in accordance with the provisions of this Section 5(d). Upon the occurrence of any such Fundamental Transaction, the Successor Entity shall succeed to, and be substituted for (so that from and after the date of such Fundamental Transaction, the
provisions of this Debenture and the other Transaction Documents referring to the “Company” shall refer instead to the Successor Entity), and may exercise every right and power of the Company and shall assume all of the obligations of the
Company under this Debenture and the other Transaction Documents with the same effect as if such Successor Entity had been named as the Company herein. 

(e) Calculations. All calculations under this Section 5 shall be made to the nearest cent or the nearest 1/100th of a share, as
the case may be. For purposes of this Section 5, the number of shares of Common Stock deemed to be issued and outstanding as of a given date shall be the sum of the number of shares of Common Stock (excluding any treasury shares of the Company)
issued and outstanding. 
 (f) Notice to the Holder. 

(i) Adjustment to Conversion Price. Whenever the Conversion Price is adjusted pursuant to any provision of this Section 5, the
Company shall promptly deliver to each Holder a notice setting forth the Conversion Price after such adjustment and setting forth a brief statement of the facts requiring such adjustment. 

(ii) Notice to Allow Conversion by Holder. If (A) the Company shall declare a dividend (or any other distribution in whatever
form) on the Common Stock, (B) the Company shall declare a special nonrecurring cash dividend on or a redemption of the Common Stock, (C) the approval of any stockholders of the Company shall be required in connection with any
reclassification of the Common Stock, any consolidation or merger to which the Company is a party, any sale or transfer of all or substantially all of the assets of the Company, or any compulsory share exchange whereby the Common Stock is converted
into other securities, cash or property or (D) the Company shall authorize the voluntary or involuntary dissolution, liquidation or winding up of the affairs of the Company, then, in each case, the Company shall cause to be filed at each office
or agency maintained for the purpose of conversion of this Debenture, and shall cause to be delivered to the Holder at its last address as it shall appear upon the Debenture Register, at least ten (10) calendar days prior to the applicable
record or effective date hereinafter specified, a notice stating (x) the date on which a record is to be taken for the purpose of such dividend, distribution, redemption, rights or warrants, or if a record is not to be taken, the date as of
which the holders of the Common Stock of record to be entitled to such dividend, distributions, redemption, rights or warrants are to be determined or (y) the date on which such reclassification,


  
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consolidation, merger, sale, transfer or share exchange is expected to become effective or close, and the date as of which it is expected that holders of the Common Stock of record shall be
entitled to exchange their shares of the Common Stock for securities, cash or other property deliverable upon such reclassification, consolidation, merger, sale, transfer or share exchange, provided that the failure to deliver such notice or any
defect therein or in the delivery thereof shall not affect the validity of the corporate action required to be specified in such notice. To the extent that any notice provided hereunder constitutes, or contains, material, non-public information
regarding the Company, the Company shall not be required to provide such notice until such time as it makes public disclosure of such event, at which point it shall simultaneously with its public disclosure, provide notice to the Holder. The Holder
shall remain entitled to convert this Debenture during the period commencing on the date of such notice through the effective date of the event triggering such notice except as may otherwise be expressly set forth herein. 

Section 6. Redemption. 

(a) Optional Redemption at Election of Company. Subject to the provisions of this Section 6(a), at any time after Original Issue
Date and from time to time, the Company may deliver a notice to the Holder (an “Optional Redemption Notice” and the date such notice is deemed delivered hereunder, the “Optional Redemption Notice Date”) of its
irrevocable election to redeem some or all of the then outstanding principal amount of this Debenture for cash in an amount equal to the Optional Redemption Amount on the 20th Trading Day
following the Optional Redemption Notice Date (such date, the “Optional Redemption Date,” such 20 Trading Day period, the “Optional Redemption Period” and such redemption, the “Optional
Redemption”). The Optional Redemption Amount is payable in full on the Optional Redemption Date. The Company covenants and agrees that it will honor all Notices of Conversion tendered from the time of delivery of the Optional Redemption
Notice through 5:00 p.m. (New York time) on the business day immediately preceding the Optional Redemption Date. The Company’s determination to pay an Optional Redemption in cash shall be applied ratably to all of the holders of the then
outstanding Debentures based on their (or their predecessor’s) initial purchases of Debentures pursuant to the Purchase Agreement. Unless a Holder elects to convert its Debentures prior to the time and date specified above, each Holder shall,
prior to 5:00 p.m. (New York time) on the Optional Redemption Date, return any and all original Debentures to be redeemed to the Company (or such other place at set forth in the Optional Redemption Notice) and such certificates shall be duly
endorsed or assigned either to the Company or in blank. 
 (b) Mandatory Redemption. Commencing on the date that shall be three
(3) months after the first date on which the outstanding aggregate principal amount of Debentures is at least $3.0 million (excluding any Debentures issued upon the cancellation of Prior Notes, as defined in the Purchase Agreement) (the
“Collateral Set-aside Date”), and on a monthly basis thereafter (each, a “Collateral Sweep Date”), the Holder may deliver a notice to the Company within five (5) Trading Days from any Collateral Sweep Date (a
“Mandatory Redemption Notice” and the date such notice is deemed delivered hereunder, the “Mandatory Redemption Notice Date”) of its irrevocable election to cause the Company to redeem such portion of the then
outstanding principal amount of this Debenture (and accrued interest thereon) for cash in an amount equal to the Mandatory Redemption Amount on the 5th Trading Day following the Mandatory
Redemption Notice Date (such date, the “Mandatory Redemption Date” and such redemption, the “Mandatory Redemption”). The Mandatory Redemption Notice shall specify the principal amount of Debentures to be redeemed.
The Mandatory Redemption Amount is payable in full on the Mandatory Redemption Date. Any Mandatory Redemption shall be applied ratably to all Holders that submit a Mandatory Redemption based on their (or their predecessor’s) initial purchases
of Debentures pursuant to the Purchase Agreement. The Company hereby agrees to publicly disclose the payment of any Mandatory Redemption Amount within four Trading Days from the Mandatory Redemption Date. On or before the Collateral Set-aside Date,
the Company agrees to (i) establish a collection account (the 

  
 13 








 
“Designated Account”) with a reputable, third-party banking institution (the “Institution”) and (ii) deposit into the Designated Account cash in an amount equal to
the Mandatory Redemption Amount for the most recent month ended prior to the Collateral Set-aside Date. In establishing the Designated Account, the Institution shall be instructed to hold the funds deposited therein as an escrow agent in accordance
with the provisions of this Debenture. Thereafter, while the aggregate outstanding principal amount of all Debentures issued under the Purchase Agreement is at least $500,000, on a monthly basis, the Company shall, on or before the third Trading Day
of each such month, deposit additional cash amounts into the Designated Account in an amount equal to the Mandatory Redemption Amount for the most recent month ended. To the extent that the Holder does not deliver a Mandatory Redemption Notice to
the Company by a given Collateral Sweep Date, the Company shall be permitted to instruct the Institution to release the funds on deposit in the Designated Account for the Mandatory Redemption of such Holder’s Debenture for such month to the
Company and the Company may use those funds for its general working capital and business operations. 
 (c) Redemption Procedure. The
payment of cash pursuant to an Optional Redemption or a Mandatory Redemption shall be payable on the Optional Redemption Date or Mandatory Redemption Date. If any portion of the payment pursuant to an Optional Redemption or Mandatory Redemption
shall not be paid by the Company by the applicable due date, interest shall accrue thereon at an interest rate equal to the lesser of 18% per annum or the maximum rate permitted by applicable law until such amount is paid in full.
Notwithstanding anything herein contained to the contrary, if any portion of an Optional Redemption Amount in connection with an Optional Redemption remains unpaid after such date, the Holder may elect, by written notice to the Company given at any
time thereafter, to invalidate such Optional Redemption, ab initio, and, with respect to the Company’s failure to honor the Optional Redemption, the Company shall have no further right to exercise such Optional Redemption.

 Section 7. Negative Covenants. As long as any portion of this Debenture remains outstanding, unless the holders of a
Majority in Interest shall have otherwise given prior written consent, the Company shall not, and shall not permit any of the Subsidiaries to, directly or indirectly: 

(a) other than Permitted Indebtedness, enter into, create, incur, assume, guarantee or suffer to exist any indebtedness for borrowed money of
any kind, including, but not limited to, a guarantee, on or with respect to any of its property or assets now owned or hereafter acquired or any interest therein or any income or profits therefrom; 

(b) other than Permitted Liens, enter into, create, incur, assume or suffer to exist any Liens of any kind, on or with respect to any of its
property or assets now owned or hereafter acquired or any interest therein or any income or profits therefrom; 
 (c) repay, repurchase or
offer to repay, repurchase or otherwise acquire more than a de minimis number of shares of its Common Stock or Common Stock Equivalents other than as to (i) the Conversion Shares or Warrant Shares as permitted or required under the
Transaction Documents and (ii) repurchases of Common Stock or Common Stock Equivalents pursuant to employee, director or consultant repurchase plans or similar agreements; or 

(d) prepay any Indebtedness, other than the Debentures if on a pro-rata basis and other than pursuant to payments of Permitted Indebtedness.
For purposes of clarity, nothing herein shall restrict or limit the Company’s payment of the principal amount of, or interest on, the Prior Notes (as defined in the Purchase Agreement) in accordance with the terms of such Prior Notes. 

Section 8. Events of Default 

  
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 (a) “Event of Default” means, wherever used herein, any of the following events
(whatever the reason for such event and whether such event shall be voluntary or involuntary or effected by operation of law or pursuant to any judgment, decree or order of any court, or any order, rule or regulation of any administrative or
governmental body): 
 (i) Reserved; 

(ii) the effectiveness of the applicable Registration Statement lapses for any reason (including, without limitation, the
issuance of a stop order) or such Registration Statement (or the prospectus contained therein) is unavailable to any holder of Registrable Securities (as defined in the Registration Rights Agreement) for sale of all of such holder’s Registrable
Securities in accordance with the terms of the Registration Rights Agreement, and (I) such lapse or unavailability continues for a period of five (5) consecutive days or for more than an aggregate of ten (10) days in any 365-day
period (in addition to days during an Allowable Delay (as defined in the Registration Rights Agreement)) and (II) any such holder does not then have the right to sell all of such holder’s Registrable Securities without restriction pursuant to
Rule 144 (including, without limitation, volume limitations); 
 (iii) the suspension from trading or the failure of the
Common Stock to be trading or listed (as applicable) on the Trading Market for a period of five (5) consecutive days or for more than an aggregate of ten (10) days in any 365-day period; 

(iv) the Company’s (A) failure to cure a Conversion Failure or a Delivery Failure (as defined in the Warrants) by
delivery of the required number of shares of Common Stock within five (5) Trading Days after the applicable Conversion Date or exercise date (as the case may be) or (B) notice, written or oral, to any holder of the Debentures or Warrants,
including, without limitation, by way of public announcement or through any of its agents, at any time, of its intention not to comply, as required, with a request for conversion of any Debentures into shares of Common Stock that is requested in
accordance with the provisions of the Debentures, other than pursuant to Section 4(d) or a request for exercise of any Warrants for Warrant Shares in accordance with the provisions of the Warrants, other than pursuant to Section 2(i)(i) of
the Warrants; 
 (v) Reserved; 

(vi) the Company’s or any Subsidiary’s failure to pay to the Holder any amount of Principal, Interest, late charges
or other amounts when and as due under this Debenture (including, without limitation, the Company’s or any Subsidiary’s failure to pay any redemption payments or amounts hereunder) or any other Transaction Document (as defined in the
Purchase Agreement) or any other agreement, document, certificate or other instrument delivered in connection with the transactions contemplated hereby and thereby, except, in the case of a failure to pay Interest, late charges or other amounts when
and as due, in which case only if such failure remains uncured for a period of at least fifteen (15) days; 
 (vii) the
Company fails to remove any restrictive legend on any certificate or any shares of Common Stock issued to the Holder upon conversion or exercise (as the case may be) of any Securities acquired by the Holder under the Purchase Agreement (including
this Debenture) as and when required by such Securities or the Purchase Agreement, unless otherwise then prohibited by applicable federal securities laws, and any such failure remains uncured for at least five (5) Trading Days; 

  
 15 








 (viii) the occurrence of any default under, redemption of or acceleration prior
to maturity of any Indebtedness of the Company or any of its Subsidiaries, other than in any amount not in excess of an aggregate of $150,000; 

(ix) bankruptcy, insolvency, reorganization or liquidation proceedings or other proceedings for the relief of debtors shall be
instituted by or against the Company or any Subsidiary and, if instituted against the Company or any Subsidiary by a third party, shall not be dismissed within sixty (60) days of their initiation 

(x) the commencement by the Company or any Subsidiary of a voluntary case or proceeding under any applicable federal, state or
foreign bankruptcy, insolvency, reorganization or other similar law or of any other case or proceeding to be adjudicated a bankrupt or insolvent, or the filing by it of a petition seeking reorganization or relief under any applicable federal, state
or foreign law, or the making by it of an assignment for the benefit of creditors, or the execution of a composition of debts, or the occurrence of any other similar federal, state or foreign proceeding, or the admission by it in writing of its
inability to pay its debts generally as they become due, or the taking of corporate action by the Company or any Subsidiary in furtherance of any such action; 

(xi) the entry by a court of (i) a decree, order, judgment or other similar document in respect of the Company or any
Subsidiary of a voluntary or involuntary case or proceeding under any applicable federal, state or foreign bankruptcy, insolvency, reorganization or other similar law or (ii) a decree, order, judgment or other similar document adjudging the
Company or any Subsidiary as bankrupt or insolvent, or approving as properly filed a petition seeking liquidation, reorganization, arrangement, adjustment or composition of or in respect of the Company or any Subsidiary under any applicable federal,
state or foreign law or (iii) a decree, order, judgment or other similar document appointing a custodian, receiver, liquidator, assignee, trustee, sequestrator or other similar official of the Company or any Subsidiary or of any substantial
part of its property, or ordering the winding up or liquidation of its affairs, and the continuance of any such decree, order, judgment or other similar document or any such other decree, order, judgment or other similar document unstayed and in
effect for a period of sixty (60) consecutive days; 
 (xii) a final judgment or judgments for the payment of money
aggregating in excess of $150,000 are rendered against the Company and/or any of its Subsidiaries and which judgments are not, within forty-five (45) days after the entry thereof, bonded, discharged or stayed pending appeal, or are not
discharged within thirty (30) days after the expiration of such stay; provided, however, any judgment which is covered by insurance or an indemnity from a credit worthy party shall not be included in calculating the $150,000 amount set forth
above so long as the Company provides the Holder a written statement from such insurer or indemnity provider (which written statement shall be reasonably satisfactory to the Holder) to the effect that such judgment is covered by insurance or an
indemnity and the Company or such Subsidiary (as the case may be) will receive the proceeds of such insurance or indemnity within forty-five (45) days of the issuance of such judgment; 

(xiii) the Company and/or any Subsidiary, individually or in the aggregate, either (i) fails to pay, when due, or within
any applicable grace period, any payment with respect to any Indebtedness in excess of $150,000 due to any third party (other than, with respect to unsecured Indebtedness only, payments contested by the Company and/or such Subsidiary (as the case
may be) in good faith by proper proceedings and with respect to which adequate reserves have been set aside for the payment thereof in accordance with 

  
 16 








 
GAAP) or is otherwise in breach or violation of any agreement for monies owed or owing in an amount in excess of $150,000, which breach or violation permits the other party thereto to declare a
default or otherwise accelerate amounts due thereunder, or (ii) suffer to exist any other circumstance or event that would, with or without the passage of time or the giving of notice, result in a default or event of default under any agreement
binding the Company or any Subsidiary, which default or event of default would or is likely to have a material adverse effect on the business, assets, operations (including results thereof), liabilities, properties, condition (including financial
condition) or prospects of the Company or any of its Subsidiaries, individually or in the aggregate; 
 (xiv) other than as
specifically set forth in another clause of this Section 8(a), the Company or any Subsidiary breaches, in any material respect, any representation, warranty, covenant or other term or condition of any Transaction Document (including, without
limitation, the Security Agreement (as defined in the Purchase Agreement) and the Subsidiary Guarantees (as defined in the Securities Purchase Agreement)) (subject to any grace or cure periods provided therein), except, in the case of a breach of a
covenant or other term or condition that is curable, only if such breach remains uncured for a period of ten (10) consecutive Trading Days after notice of breach from Holder or fifteen (15) consecutive Trading Days from when the Company
became aware of such breach (in each case, subject to any grace or cure period provided therein); 
 (xv) Reserved; 

(xvi) any material provision of any Transaction Document (including, without limitation, the Security Agreement and the
Guarantees) shall at any time for any reason (other than pursuant to the express terms thereof or such provision has been performed in full or waived by the relevant party) cease to be valid and binding on or enforceable against the parties thereto,
or a proceeding shall be commenced by the Company or any Subsidiary or any governmental authority having jurisdiction over any of them, seeking to establish the invalidity or unenforceability thereof, or the Company or any Subsidiary shall deny in
writing that it has any liability or obligation purported to be created under any Transaction Document (including, without limitation, the Security Agreement and the Guarantees); 

(xvii) the Security Agreement shall for any reason fail or cease to create a separate valid and perfected and, except to the
extent permitted by the terms hereof or thereof, first priority Lien on the Collateral (as defined in the Security Agreement) in favor of the Collateral Agent; or 

(xviii) any material damage to, or loss, theft or destruction of, any material portion of the Collateral, whether or not
insured, which causes, for more than thirty (30) consecutive days, the cessation or substantial curtailment of revenue producing activities at any facility of the Company or any Subsidiary, if any such event or circumstance could have a
Material Adverse Effect. 
 (b) Remedies upon Event of Default. 

(i) If an Event of Default occurs and is continuing with respect to any of the Debentures, the Holder may declare all of the then outstanding
Principal of this Debenture and all other Debentures held by the Holder, including any Interest, to be due and payable immediately, except that in the case of an Event of Default arising from events described in clauses (v), (vi) and/or
(vii) of Section 8(a), this Debenture shall become due and payable automatically without further action or 

  
 17 








 
notice. In the event of such acceleration, the amount due and owing to the Holder shall be 110% of the outstanding Principal of the Debentures held by the Holder (plus all accrued and unpaid
Interest and late charges, if any). The Holder’s remedies under this Debenture shall be cumulative. 
 Section 9.
Miscellaneous. 
 (a) Notices. Any and all notices or other communications or deliveries to be provided by the Holder
hereunder, including, without limitation, any Notice of Conversion, shall be in writing and delivered personally, by facsimile, or sent by a nationally recognized overnight courier service, addressed to the Company, at the address set forth above,
or such other facsimile number or address as the Company may specify for such purposes by notice to the Holder delivered in accordance with this Section 9(a). Any and all notices or other communications or deliveries to be provided by the
Company hereunder shall be in writing and delivered personally, by facsimile, or sent by a nationally recognized overnight courier service addressed to each Holder at the facsimile number or address of the Holder appearing on the books of the
Company, or if no such facsimile number or address appears on the books of the Company, at the principal place of business of such Holder, as set forth in the Purchase Agreement. Any notice or other communication or deliveries hereunder shall be
deemed given and effective on the earliest of (i) the date of transmission, if such notice or communication is delivered via facsimile at the facsimile number set forth on the signature pages attached hereto prior to 5:30 p.m. (New York City
time) on any date, (ii) the next Trading Day after the date of transmission, if such notice or communication is delivered via facsimile at the facsimile number set forth on the signature pages attached hereto on a day that is not a Trading Day
or later than 5:30 p.m. (New York City time) on any Trading Day, (iii) the second Trading Day following the date of mailing, if sent by U.S. nationally recognized overnight courier service or (iv) upon actual receipt by the party to whom
such notice is required to be given. 
 (b) Absolute Obligation. Except as expressly provided herein, no provision of this Debenture
shall alter or impair the obligation of the Company, which is absolute and unconditional, to pay the principal of, liquidated damages and accrued interest, as applicable, on this Debenture at the time, place, and rate, and in the coin or currency,
herein prescribed. This Debenture is a direct debt obligation of the Company. This Debenture ranks pari passu with all other Debentures now or hereafter issued under the terms set forth herein. 

(c) Lost or Mutilated Debenture. If this Debenture shall be mutilated, lost, stolen or destroyed, the Company shall execute and
deliver, in exchange and substitution for and upon cancellation of a mutilated Debenture, or in lieu of or in substitution for a lost, stolen or destroyed Debenture, a new Debenture for the principal amount of this Debenture so mutilated, lost,
stolen or destroyed, but only upon receipt of evidence of such loss, theft or destruction of such Debenture, and of the ownership hereof, reasonably satisfactory to the Company. 

(d) Governing Law. All questions concerning the construction, validity, enforcement and interpretation of this Debenture shall be
governed by and construed and enforced in accordance with the internal laws of the State of New York, without regard to the principles of conflict of laws thereof. Each party agrees that all legal proceedings concerning the interpretation,
enforcement and defense of the transactions contemplated by any of the Transaction Documents (whether brought against a party hereto or its respective Affiliates, directors, officers, shareholders, employees or agents) shall be commenced in the
state and federal courts sitting in the City of New York, Borough of Manhattan (the “New York Courts”). Each party hereto hereby irrevocably submits to the exclusive jurisdiction of the New York Courts for the adjudication of any
dispute hereunder or in connection herewith or with any transaction contemplated hereby or discussed herein (including with respect to the enforcement of any of the Transaction Documents), and hereby irrevocably waives, and agrees not to assert in
any suit, action or proceeding, any claim that it is not personally subject to the jurisdiction of such New York Courts, or 

  
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such New York Courts are improper or inconvenient venue for such proceeding. Each party hereby irrevocably waives personal service of process and consents to process being served in any such
suit, action or proceeding by mailing a copy thereof via registered or certified mail or overnight delivery (with evidence of delivery) to such party at the address in effect for notices to it under this Debenture and agrees that such service shall
constitute good and sufficient service of process and notice thereof. Nothing contained herein shall be deemed to limit in any way any right to serve process in any other manner permitted by applicable law. Each party hereto hereby irrevocably
waives, to the fullest extent permitted by applicable law, any and all right to trial by jury in any legal proceeding arising out of or relating to this Debenture or the transactions contemplated hereby. 

(e) Waiver. Any waiver by the Company or the Holder of a breach of any provision of this Debenture shall not operate as or be construed
to be a waiver of any other breach of such provision or of any breach of any other provision of this Debenture. The failure of the Company or the Holder to insist upon strict adherence to any term of this Debenture on one or more occasions shall not
be considered a waiver or deprive that party of the right thereafter to insist upon strict adherence to that term or any other term of this Debenture on any other occasion. Any waiver by the Company or the Holder must be in writing. 

(f) Severability. If any provision of this Debenture is invalid, illegal or unenforceable, the balance of this Debenture shall remain
in effect, and if any provision is inapplicable to any Person or circumstance, it shall nevertheless remain applicable to all other Persons and circumstances. If it shall be found that any interest or other amount deemed interest due hereunder
violates the applicable law governing usury, the applicable rate of interest due hereunder shall automatically be lowered to equal the maximum rate of interest permitted under applicable law. 

(g) Next Business Day. Whenever any payment or other obligation hereunder shall be due on a day other than a Business Day, such payment
shall be made on the next succeeding Business Day. 
 (h) Headings. The headings contained herein are for convenience only, do not
constitute a part of this Debenture and shall not be deemed to limit or affect any of the provisions hereof. 
 (i) Secured
Obligation. The obligations of the Company under this Debenture are secured by certain assets of the Company pursuant to the Security Agreement, dated as of the date of the Purchase Agreement, between the Company and the Secured Parties (as
defined therein). 
 (j) Dispute Resolution. In the case of a dispute as to the determination of the Conversion Price, the Closing
Bid Price, the Closing Sale Price or fair market value (as the case may be) or the arithmetic calculation of the Conversion Rate or the applicable Optional Redemption Amount or Mandatory Redemption Amount (as the case may be), the Company or the
Holder (as the case may be) shall submit the disputed determinations or arithmetic calculations (as the case may be) via facsimile (i) within two (2) Business Days after receipt of the applicable notice giving rise to such dispute to the
Company or the Holder (as the case may be) or (ii) if no notice gave rise to such dispute, at any time after the Holder learned of the circumstances giving rise to such dispute (including, without limitation, as to whether any issuance or sale
or deemed issuance or sale was an issuance or sale or deemed issuance or sale of Excluded Securities). If the Holder and the Company are unable to agree upon such determination or calculation within two (2) Business Days of such disputed
determination or arithmetic calculation (as the case may be) being submitted to the Company or the Holder (as the case may be), then the Company shall, within two (2) Business Days, submit via facsimile (a) the disputed determination of
the Conversion Price, the Closing Bid Price, the Closing Sale Price or fair market value (as the case may be) to an independent, reputable investment bank selected by the Company and approved by the Holder or (b) the


  
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disputed arithmetic calculation of the Conversion Rate or the applicable Optional Redemption Amount or Mandatory Redemption Amount (as the case may be) to an independent, outside accountant
selected by the Company. The Company shall cause at its expense the investment bank or the accountant (as the case may be) to perform the determinations or calculations (as the case may be) and notify the Company and the Holder of the results no
later than ten (10) Business Days from the time it receives such disputed determinations or calculations (as the case may be). Such investment bank’s or accountant’s determination or calculation (as the case may be) shall be binding
upon all parties absent demonstrable error. 
 ********************* 

(Signature Page Follows)  

  
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 IN WITNESS WHEREOF, the Company has caused this Debenture to be duly executed by a duly
authorized officer as of the date first above indicated. 
  

			
	AUTHENTIDATE HOLDING CORP.
		
	By:	 	  

		 	Name: Ian C. Bonnet
		 	Title: Chief Executive Officer
	
	Facsimile No. for delivery of Notices:                         



  
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 ANNEX A 

NOTICE OF CONVERSION 
 The
undersigned hereby elects to convert principal under the 9% Senior Secured Convertible Debenture due June    , 2016 of Authentidate Holding Corp., a Delaware corporation (the “Company”), into shares of common
stock (the “Common Stock”), of the Company according to the conditions hereof, as of the date written below. If shares of Common Stock are to be issued in the name of a person other than the undersigned, the undersigned will pay all
transfer taxes payable with respect thereto and is delivering herewith such certificates and opinions as reasonably requested by the Company in accordance therewith. No fee will be charged to the holder for any conversion, except for such transfer
taxes, if any. 
 By the delivery of this Notice of Conversion the undersigned represents and warrants to the Company that its ownership of
the Common Stock does not exceed the amounts specified under Section 4 of this Debenture, as determined in accordance with Section 13(d) of the Exchange Act. 

The undersigned agrees to comply with the prospectus delivery requirements under the applicable securities laws in connection with any
transfer of the aforesaid shares of Common Stock. 
 Conversion calculations: 
  

	
	 Date to Effect
Conversion:                                       
                                         
                                         
                                     

	
	 Principal Amount of Debenture
to be Converted:                                    
                                         
                                       


	
	 Number of shares of Common Stock
to be issued:                                     
                                         
                                    

	
	
Signature:                          
                                         
                                         
                                         
                                         


	
	
Name:                           
                                         
                                         
                                         
                                         
     

	
	 Address for Delivery of Common Stock Certificates:  

	
	
                            
                                         
                                         
                                         
                                         
                  

	
	
                            
                                         
                                         
                                         
                                         
                  

	
	 Or

	
	 DWAC Instructions:

	
	 Broker
No:                                        
                                         
                                         
                                         
                         

	
	 Account
No:                                        
                                         
                                         
                                         
                      



  
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 Schedule 1 

CONVERSION SCHEDULE 
 The 9% Senior Secured
Convertible Debenture due on June     , 2016 in the original principal amount of $                    is issued by Authentidate
Holding Corp. This Conversion Schedule reflects conversions made under Section 4 of the above referenced Debenture. 
 Dated:
                                         
                      
  

							
	 Date of Conversion

(or for first entry,
 Original Issue
Date)
	 	 Amount of

Conversion
	 	 Aggregate

Principal
 Amount

Remaining
 Subsequent to

Conversion
 (or original

Principal
 Amount)
	 	 Company Attest

	  
	 	  
	 	  
	 	  

	  
	 	  
	 	  
	 	  

	  
	 	  
	 	  
	 	  

	  
	 	  
	 	  
	 	  

	  
	 	  
	 	  
	 	  

	  
	 	  
	 	  
	 	  

	  
	 	  
	 	  
	 	  

	  
	 	  
	 	  
	 	  

	  
	 	  
	 	  
	 	  

	  
	 	  
	 	  
	 	  



  
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