Document:

EX-4.1

 Exhibit 4.1 

THIS NOTE HAS NOT BEEN REGISTERED UNDER THE FEDERAL OR ANY STATE SECURITIES LAWS AND MAY NOT BE SOLD, TRANSFERRED OR HYPOTHECATED IN ABSENCE OF AN EFFECTIVE
REGISTRATION STATEMENT UNDER SUCH LAWS AS MAY BE APPLICABLE OR, AN OPINION OF COUNSEL THAT AN EXEMPTION FROM SUCH APPLICABLE LAWS EXIST. 

NOTE 
  

					
	 $100,000
				Issuance Date: February 17, 2015
			Maturity Date: 180 days from the Issuance Date, subject to Extensions

 FOR VALUE RECEIVED, Authentidate Holding Corp., a Delaware corporation (the “Borrower”), with its
principal offices located at 300 Connell Drive, Fifth Floor, Berkeley Heights, N.J. 07922, hereby promises to pay to the order of
                     (the “Holder”) with its principal offices at
                                         
                       , or at such other address as the Holder designates in writing to the Borrower, the principal sum of One Hundred
Thousand Dollars ($100,000) (the “Principal Amount”), on the Maturity Date. 
 This Promissory Note (“Note”) has been
executed and issued pursuant to the terms of a Securities Purchase Agreement between the Borrower and the Holder dated of even date herewith (the “Purchase Agreement”) pursuant to which the Holder acquired this Note and common stock
purchase warrants. Unless otherwise separately defined herein, all capitalized terms used in this Note shall have the same meaning as is set forth in the Purchase Agreement. This Note is a direct obligation of the Borrower and ranks senior to all
Indebtedness issued by the Company after the date of this Note, other than Permitted Indebtedness, in accordance with the Purchase Agreement under the terms set forth herein. This Note is junior in right of payment as to a $200,000 secured
promissory note issued by the Borrower on January 29, 2015. 
 1. Interest on this Note shall be computed at an annual rate of eight
percent (8%), payable in arrears on the Maturity Date at which time all accrued and unpaid interest shall be immediately due and payable. All computations of interest payable hereunder shall be on the basis of a 365-day year and actual days elapsed
in the period for which such interest is payable. Accrued interest on the outstanding principal amount shall be due and payable on the Maturity Date in cash. While in default, this Note shall bear interest at the rate of 16% per annum, or such
maximum rate of interest allowable under the laws of the State of New York, if less. Payments of all amounts due hereunder shall be made in lawful money of the United States. 

2. The “Maturity Date” of this Note shall be 180 days from the Issuance Date. The Holder at its sole discretion, may elect to extend
the Maturity Date by an additional 90 days (an “Extension”); provided that the Holder shall give written notice to the Borrower at least 30 days before such Maturity Date. The Holder will have the right to elect up to two
Extensions. Upon the election by the Holder to extend the Maturity Date of this Note, the Maturity Date shall automatically be amended to be the date that is 90 days following the initial Maturity Date, or in the case of a second Extension, 180 days
following the initial Maturity Date. 

  
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 Payment of the Principal Amount of this Note shall be made upon the surrender of this Note to the
Borrower, at its chief executive office (or such other office within the United States as shall be designated by the Borrower to the Holder hereof) (the “Designated Office”), in such coin or currency of the United States of America
as at the time of payment shall be legal tender for the payment of public and private debts. If the Maturity Date (or any Extension of such Maturity Date) shall be a Saturday or a Sunday or shall be a legal holiday in the State of New York,
then such action may be taken or such right may be exercised on the next succeeding day not a legal holiday. 
 3. Upon the
occurrence and continuation of an Event of Default, the Holders of at least 50.1% of the Principal Amount of this Note (the “Majority Holders”), by written notice to the Borrower, may declare due and payable the entire unpaid balance of
this Note then outstanding, together with accrued interest thereon, if any. For purposes of this Note, an “Event of Default” shall consist of any of the following events: 

(a) The Borrower shall fail to pay any portion of the Principal Amount of this Note when the same becomes due and payable, whether at the
Maturity Date or at any accelerated date of maturity or at any other date fixed for payment, and such default continues for 15 days or more. 

(b) The Borrower shall voluntarily commence any case, proceeding or other action under any existing or future law of any jurisdiction,
domestic or foreign, relating to bankruptcy, insolvency, or relief of debtors, seeking to have an order for relief entered with respect to it, or seeking to adjudicate it as bankrupt or insolvent, or seeking other relief with respect to its debts;
or a court shall enter an order for relief or any such adjudication or appointment, which case, proceeding or action or order, adjudication, or appointment, as the case may be, remains undismissed, undischarged or unbonded for a period of 60 days,
then, or any time thereafter during the continuance of any of such events. 
 (c) A final judgment for money damages or order for the
payment of money damages in excess of One Hundred Thousand Dollars ($100,000) (exclusive of amounts covered by insurance) shall be entered against the Borrower, which has not been vacated or stayed within 45 days of entry. 

(d) Any material representation or warranty of the Borrower herein shall prove to have been false in any material respect upon the date when
made. 
 (e) The occurrence of a default (after giving effect to any grace periods or rights to cure held by the Borrower) under any
material indebtedness of the Borrower resulting from other than the failure to timely pay interest or principal of such indebtedness which results in the acceleration of the maturity of such indebtedness. 

(f) The Borrower shall liquidate, dissolve, terminate or suspend its business operations. 

  
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 (g) The Borrower shall have a change in control, provided, however that each such event may be
waived by the Holder. A “change of control” means the occurrence of any of the following events: (i) any consolidation or merger of the Borrower in which the Borrower is not the continuing or surviving corporation or pursuant to which
shares of stock of the Borrower would be converted into cash, securities or other property, other than a consolidation or merger of the Borrower in which holders of its common stock immediately prior to the consolidation or merger have substantially
the same proportionate ownership of common stock of the surviving corporation immediately after the consolidation or merger as immediately before; (ii) a sale, lease, exchange or other transfer (in one transaction or a series of related
transactions) of all or substantially all the assets of the Borrower; or (iii) the purchase by any person (as defined in Section 13(d) of the Securities Exchange Act of 1934), corporation or other entity, other than the Borrower or a
wholly owned subsidiary of the Borrower, of shares pursuant to a tender or exchange offer, to acquire any stock of the Borrower (or securities convertible into stock) for cash, securities or any other consideration provided that, after consummation
of the offer, such person, group, corporation or other entity is the beneficial owner (as defined in Rule 13d-3), directly or indirectly, of 50% or more of the outstanding stock of the Borrower. 

(h) The Borrower shall breach any material covenant contained in the Purchase Agreement other than failure to make a payment of principal or
interest and such breach continues for a period of 30 days after written notice of such failure has been given to the Borrower by the Majority Holders. 

Nothing in this Section 3 is intended to restrict the Holder’s rights under any of the Transaction Documents or at law, and the
Holder may exercise all such rights and remedies as and when they are available. 
 The Majority Holders may, on behalf of the Holders of
all of the Notes, rescind and annul a declaration of an Event of Default, and its consequences if: (1) all existing Events of Default (other than pursuant to Section 3(a) of this Note) have been remedied, cured or waived, and (2) the
rescission would not conflict with any judgment or decree of a court of competent jurisdiction. 
 4. Prepayment. The Borrower may not prepay this
Note in whole or in part at any time without the Holder’s prior written consent; provided, however, the Holder may elect to require the Borrower to prepay the Note as provided for in Section 6.2 of the Purchase Agreement. In
addition, upon the exercise of an Extension, than at any time and from time to time prior to the Maturity Date, upon no less than 20 days’ written notice by the Borrower to the Holder (the “Prepayment Notice”), all or a portion of the
then outstanding Notes may be redeemed by the Borrower by payment of the Principal Amount (or portion thereof) to be redeemed at the end of such 20-day notice period (the “Redemption Amount”). The last day of such 20 day notice period
shall be the “Redemption Date”. Provided the Borrower tenders the Redemption Amount on the Redemption Date, the Principal Amount of the Note noticed for prepayment shall, after the Redemption Date, be reduced by the Redemption Amount and
thereafter represent only the right to receive, on the Maturity Date, the difference between the initial Principal Amount of this Note and the Redemption Amount. 

  
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 5. Transferability; Loss and Replacement. 

(a) This Note has not been registered under the Securities Act, or the securities laws of any state or other jurisdiction. Neither this
Note nor any interest or participation herein may be reoffered, sold, assigned, transferred, pledged, encumbered or otherwise disposed of (a “Transfer”) in the absence of registration under the Securities Act and any applicable
state securities laws, or unless (i) such transaction is exempt from, or not subject to, registration under the Securities Act or the securities laws of any state or other jurisdiction and (ii) is made in compliance with applicable federal
and state statutory resale restrictions, if any. The Holder by its acceptance of this Note agrees that it shall not offer, sell, assign, transfer, pledge, encumber or otherwise dispose of this Note or any portion thereof or interest therein
other than in a minimum denomination of $50,000 principal amount (or any integral multiple of $10,000 in excess thereof) and then (other than with respect to a Transfer pursuant to a registration statement that is effective at the time of such
Transfer) only (a) to the Borrower, (b) to an affiliate of the Holder, (c) to a Person it reasonably believes to be an “accredited investor” within the meaning of Rule 501(a) under the Securities Act, or
(d) pursuant to a transaction in compliance with Rule 144 or Rule 144A under the Securities Act, and in the case of (b), (c) and (d) above in which the transferor furnishes the Borrower with such certifications, legal opinions or
other information as the Borrower may reasonably request to confirm that such transfer is being made pursuant to an exemption from, or in a transaction not subject to, the registration requirements of the Securities Act as applicable.

(b) The Transfer of this Note is registrable on the books of the Borrower upon surrender of this Note for registration of Transfer at the
Borrower’s designated office, duly endorsed by, or accompanied by a written instrument of transfer in form satisfactory to the Borrower duly executed by, the Holder hereof or such Holder’s attorney duly authorized in writing, and thereupon
one or more new Notes, of authorized denominations and for the same aggregate principal amount, will be issued to the designated transferee or transferees. Prior to due presentation of this Note for registration of Transfer, the Borrower and
any agent of the Borrower may treat the Person in whose name this Note is registered as the owner thereof for all purposes, whether or not this Note be overdue, and neither the Borrower nor any such agent shall be affected by notice to the contrary.
Upon presentation of this Note for registration of Transfer at the Borrower’s designated office accompanied by (i) certification by the transferor that such Transfer is in compliance with the terms hereof and (ii) by a written
instrument of Transfer in a form approved by the Borrower executed by the Holder, in person or by the Holder’s attorney thereunto duly authorized in writing, and including the name, address and telephone and fax numbers of the transferee and
name of the contact person of the transferee, such Note shall be transferred on the Note Register, and a new Note of like tenor and bearing the same legends shall be issued in the name of the transferee and sent to the transferee at the address and
c/o the contact person so indicated. Transfers and exchanges of Notes shall be subject to such additional restrictions as are set forth in the legends on the Notes and to such additional reasonable regulations as may be prescribed by the
Borrower as specified herein. Successive registrations of Transfers as aforesaid may be made from time to time as desired, and each such registration shall be noted on the Note register. 

(c) Upon receipt by the Borrower of evidence reasonably satisfactory to it of the loss, theft, destruction or mutilation of this Note, and in
the case of loss, theft or destruction, receipt 

  
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of indemnity reasonably satisfactory to the Borrower and upon surrender and cancellation of this Note, if mutilated, the Borrower will deliver a new Note of like tenor and dated as of such
cancellation, in lieu of such Note. 
 6. Miscellaneous. 

(a) All makers and endorsers now or hereafter becoming parties hereto jointly and severally waive demand, presentment, notice of non-payment
and protest. 
 (b) Neither this Note nor any term hereof may be amended or waived orally or in writing, except that any term of this Note
and the other Notes may be amended and the observance of any term of this Note and the other Notes may be waived (either generally or in a particular instance and either retroactively or prospectively), and such amendment or waiver shall be
applicable to all of the Notes, upon the approval of the Borrower and the Majority Holders; provided, however, that any amendment that would (i) reduce the principal amount of any Note, (ii) reduce the percentage in aggregate principal
amount of Notes outstanding necessary to modify or amend the Notes; or (iii) modify this Section shall, in each case, require the approval of the holder of each Note to which such amendment shall apply. 

(c) This Note and the rights and obligations of the Holder and of the undersigned shall be governed and construed in accordance with the laws
of the State of New York. 
 (d) Upon the occurrence and during the continuance of an Event of Default under this Note, the Borrower shall,
upon demand, pay to the Holder the amount of any and all reasonable costs and expenses (including reasonable attorneys’ fees) that Holder may incur in connection with the enforcement or collection of this Note. 

(e) No failure or delay on the part of the Holders hereof in the exercise of any power, right or privilege hereunder shall operate as a waiver
thereof, nor shall any single or partial exercise of any such power, right or privilege preclude other or further exercise thereof or of any other right, power or privilege. All rights and remedies existing hereunder are cumulative to, and not
exclusive of, any rights or remedies. 
 (f) The Borrower hereby, to the fullest extent permitted by applicable law, waives presentment,
demand, notice (including without limitation notice of default (except as otherwise specifically set forth herein), notice of protest, notice of intention to accelerate maturity, notice of acceleration of maturity and notice of nonpayment or
dishonor), protest and all other demands and notices in connection with delivery, acceptance, performance, default, acceleration or enforcement of or under this Note, and the bringing of suit and diligence in taking any action to collect amounts
owing hereunder or in proceeding against any of the rights and properties securing payment hereof, and is directly and primarily liable for the amount of all sums owing or to be owing hereon. No extension of the time for the payment of this Note
made by agreement with any person now or hereafter liable for the payment of this Note shall operate to release, discharge, modify, change or affect the original liability of the Borrower under this Note. 

(g) To the extent that Holder receives any payment on account of any of Borrower’s obligations under this Note, and any such payment(s)
or any part thereof are 

  
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subsequently invalidated, declared to be fraudulent or preferential, set aside, subordinate and/or required to be repaid to a trustee, receiver or any other person or entity under any bankruptcy
act, state or federal law, common law or equitable cause, then, to the extent of such payment(s) received, the Borrower’s obligations or part thereof intended to be satisfied shall be revived and continue in full force and effect, as if such
payment(s) had not been received by the Holder and applied on account of Borrower’s obligations. 
 (h) All notices, offers, acceptance
and any other acts under this Note (except payment) shall be in writing, and shall be sufficiently given if delivered to the addressees in person, by FedEx or similar receipted next business day delivery, or by facsimile or email delivery followed
by overnight next business day delivery to the Borrower at the address set forth above (or such other address as the Borrower may by notice to the Holder may designate from time to time) and to the Holder at the address set forth above (or such
other address as the Holder by notice to the Borrower may designate from time to time). Time shall be counted to, or from, as the case may be, the date of delivery. 

[Signature Page Follows] 

  
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 IN WITNESS WHEREOF, the Borrower has caused this Note to be executed as of the Issuance Date. 

 

			
	BORROWER:
	
	AUTHENTIDATE HOLDING CORP.
		
	By:		 /s/ William A. Marshall

	Name:		William A. Marshall
	Title:		Chief Financial Officer

  
 7EX-4.2

 Exhibit 4.2 

THIS WARRANT AND THE UNDERLYING SHARES OF COMMON STOCK HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933 (THE “SECURITIES ACT”), OR ANY
OTHER SECURITIES LAWS, HAVE BEEN TAKEN FOR INVESTMENT, AND MAY NOT BE SOLD OR TRANSFERRED OR OFFERED FOR SALE OR TRANSFER UNLESS A REGISTRATION STATEMENT UNDER THE SECURITIES ACT AND OTHER APPLICABLE SECURITIES LAWS WITH RESPECT TO SUCH SECURITIES
IS THEN IN EFFECT, OR IN THE OPINION OF COUNSEL TO THE ISSUER OF THESE SECURITIES, SUCH REGISTRATION UNDER THE SECURITIES ACT AND OTHER APPLICABLE SECURITIES LAWS IS NOT REQUIRED. 

 

	
	Issuance Date: February 17, 2015 (the “Issuance Date”)

 WARRANT FOR THE PURCHASE OF SHARES OF 

COMMON STOCK OF AUTHENTIDATE HOLDING CORP. 

THIS IS TO CERTIFY that, for value received,
                        , its successors and assigns (the “Holder”), is entitled to purchase, subject to the terms and
conditions hereinafter set forth, 80,000 shares of Authentidate Holding Corp, a Delaware corporation (the “Company”) common stock, $0.001 par value per share (“Common Stock”), and to receive certificates for the Common Stock so
purchased. The shares of Common Stock issuable upon exercise of this Warrant may be referred to herein as the “Warrant Shares”. The exercise price of this Warrant is $1.01 per share, subject to adjustment as provided below (the
“Exercise Price”). This Warrant is one of the Warrants issued by the Company pursuant to that certain Securities Purchase Agreement dated as of the Issuance Date (the “Purchase Agreement”) pursuant to which the Company has
offered and sold to the purchasers named therein certain promissory notes (the “Note”) and this Warrant. 
 1. Exercise Period
and Vesting. To the extent vested (in accordance with the provisions described below) this Warrant shall be exercisable at any time by the Holder beginning on the first business day following the six-month anniversary of the date listed above
(the “Initial Exercise Date”), and ending at 5:00 p.m., New York, New York time, five years from the Issuance Date (the “Exercise Period”). This Warrant will terminate automatically and immediately upon the expiration of the
Exercise Period. 
 From and after the date on which this Warrant may first be exercised, this Warrant may be exercised to purchase Warrant
Shares as follows: (i) an aggregate of 6,665 Warrant Shares shall be vested as of the day that is the one month anniversary of the Issuance Date and (ii) thereafter, provided that the Note has not been repaid in full, the remaining Warrant
Shares shall vest in equal increments of 6,667 Warrant Shares on each of the next five (5) successive monthly anniversary dates of the Issuance Date. Following the day that is the 180th
anniversary date of the Issuance Date, this Warrant shall be exercisable for all of the 40,000 Warrant Shares covered by this Warrant until the expiration of the Exercise Period or such earlier date as set forth elsewhere in this Warrant. If the
Note is extended for one or both of the 90 day extension periods described therein (each, an “Extension Period”), then a maximum of an additional 20,000 shares shall vest 

 
over each applicable 90 day Extension Period as follows: (i) an aggregate of 6,666 Warrant Shares shall be vested as of the day that is the one month anniversary of the commencement of each
Extension Period, and (ii) thereafter, provided that the Note has not been repaid in full, the remaining Warrant Shares eligible to vest during such Extension Period shall vest in equal monthly increments of 6,667 Warrant Shares on each of the
two and three month anniversary dates of the commencement of an applicable Extension Period. Upon the payment by the Company of the entire principal amount of the Note for any reason, no additional Warrant Shares shall vest. 

2. Exercise of Warrant. 

(a) Subject to the vesting provisions specified above, this Warrant may be exercised, in whole or in part, at any time and from time to time
during the Exercise Period. Such exercise shall be accomplished by tender to the Company of an amount equal to the Exercise Price multiplied by the number of underlying shares being purchased (the “Purchase Price”), by wire transfer or by
certified check or bank cashier’s check drawn on a United States bank in immediately available U.S. funds, payable to the order of the Company. As a condition of exercise, the Holder shall where applicable execute a customary investment letter
and accredited investor questionnaire. The Holder’s right to exercise this Warrant is subject to compliance with any applicable laws and rules including Section 5 of the Securities Act of 1933. 

(b) Upon receipt of the Purchase Price in Section 2(a), together with presentation and surrender to the Company of this Warrant with an
executed subscription form in substantially the form attached hereto as Exhibit A (the “Subscription”), the Company will deliver to the Holder, as promptly as possible, a certificate or certificates representing the shares of
Common Stock so purchased, registered in the name of the Holder or its transferee (as permitted under Section 3 below). With respect to any exercise of this Warrant, the Holder will for all purposes be deemed to have become the holder of record
of the number of shares of Common Stock purchased hereunder on the date a properly executed Subscription and payment of the Purchase Price is received by the Company (the “Exercise Date”), irrespective of the date of delivery of the
certificate evidencing such shares, except that, if the date of such receipt is a date on which the stock transfer books of the Company are closed, such person will be deemed to have become the holder of such shares at the close of business on the
next succeeding date on which the stock transfer books are open. Fractional shares of Common Stock will not be issued upon the exercise of this Warrant. In lieu of any fractional shares that would have been issued but for the immediately preceding
sentence, the Holder will be entitled to receive cash equal to the current market price of such fraction of a share of Common Stock on the trading day immediately preceding the Exercise Date. In the event this Warrant is exercised in part, the
Company shall issue a new Warrant to the Holder covering the aggregate number of shares of Common Stock as to which this Warrant remains exercisable for. The Company acknowledges and agrees that this Warrant was issued on the Issuance Date. The
issuance of Warrant Shares upon exercise of this Warrant shall be made without charge to Holder for any issuance tax in respect thereof or other cost incurred by the Company in connection with such exercise and the related issuance of Warrant Shares
(other than any transfer taxes resulting from the issuance of Warrant Shares to any person other than Holder). 

 3. Transferability and Exchange. 

(a) This Warrant, and the Common Stock issuable upon the exercise hereof, may not be sold, transferred, pledged or hypothecated unless the
Company shall have been provided with an opinion of counsel reasonably satisfactory to the Company that such transfer is not in violation of the Securities Act of 1933 (the “Securities Act”), and any applicable state securities laws.
Subject to the satisfaction of this condition, this Warrant and the underlying shares of Common Stock if not eligible to be sold under Rule 144 of the Securities Act shall be transferable from time to time by the Holders upon written notice to the
Company. If this Warrant is transferred, in whole or in part, the Company may request the transferee to sign an investment letter and shall, upon surrender of this Warrant to the Company, deliver to each transferee a new Warrant evidencing the
rights of such transferee to purchase the number of shares of Common Stock that such transferee is entitled to purchase pursuant to such transfer. The Company may place a legend similar to the legend at the top of this Warrant on any replacement
Warrant and on each certificate representing shares issuable upon exercise of this Warrant or any replacement Warrants. Only registered Holder may enforce the provisions of this Warrant against the Company. A transferee of the original registered
Holder becomes a registered Holder only upon delivery to the Company of the original Warrant and an original Assignment, substantially in the form set forth in Exhibit B attached hereto. 

(b) This Warrant is exchangeable upon its surrender by the Holder to the Company for new Warrants of like tenor and date representing in the
aggregate the right to purchase the number of shares purchasable hereunder, each of such new Warrants to represent the right to purchase such number of shares as may be designated by the Holder at the time of such surrender (not to exceed the
aggregate number of shares underlying this Warrant). 
 4. Adjustments to Exercise Price and Number of Shares Subject to Warrant. The
Exercise Price and the number of shares of Common Stock purchasable upon the exercise of this Warrant are subject to adjustment from time to time upon the occurrence of any of the events specified in this Section 4. For the purpose of this
Section 4, “Common Stock” means shares now or hereafter authorized of any class of common stock of the Company, however designated, that has the right to participate in any distribution of the assets or earnings of the Company without
limit as to per share amount (excluding, and subject to any prior rights of, any class or series of preferred stock). 
 (a) In case the
Company shall (i) pay a dividend or make a distribution in shares of Common Stock to holders of shares of Common Stock, (ii) subdivide its outstanding shares of Common Stock into a greater number of shares, (iii) combine its
outstanding shares of Common Stock into a smaller number of shares, or (iv) issue by reclassification of its shares of Common Stock other securities of the Company, then the Exercise Price in effect at the time of the record date for such
dividend or on the effective date of such subdivision, combination or reclassification, and/or the number and kind of securities issuable on such date, shall be proportionately adjusted so that the Holder of the Warrant thereafter exercised shall be
entitled to receive the aggregate number and kind of shares of Common Stock (or such other securities other than Common Stock) of the Company, at the same aggregate Exercise Price, that, if such Warrant had been exercised immediately prior to such
date, the Holder would have owned upon such exercise and been entitled to receive by virtue of such dividend, distribution, subdivision, 

 
combination or reclassification. It is agreed that the adjustments provided for in this Section 4(a) will be made with the intent and, as nearly as practicable, the effect that neither the
percentage of the total equity of the Company obtainable on exercise of this Warrants, nor the total exercise price payable for such percentage upon exercise, will be affected by any event described in this Section 4(a). Such adjustment shall
be made successively whenever any event listed above shall occur. 
 (b) If securities of the Company or securities of any subsidiary of the
Company are distributed pro rata to holders of Common Stock, such number of securities will be distributed to the Holder or its assignee upon exercise of its rights hereunder as such Holder or assignee would have been entitled to if this Warrant had
been exercised prior to the record date for such distribution. The provisions with respect to adjustment of the Common Stock provided in this Section 4 will also apply to the securities to which the Holder or its assignee is entitled
under this Section 4(c). 
 (c) Notwithstanding any provision herein to the contrary, no adjustment in the Exercise Price shall
be required unless such adjustment would require an increase or decrease of at least 1% in the Exercise Price; provided, however, that any adjustments which by reason of this Section 4(c) are not required to be made shall be
carried forward and taken into account in any subsequent adjustment. All calculations under this Section 4 shall be made to the nearest cent or the nearest one-hundredth of a share, as the case may be. 

(d) Intentionally omitted. 
 (e)
If the Company merges or consolidates into or with another corporation or entity, or if another corporation or entity merges into or with the Company (excluding such a merger in which the Company is the surviving or continuing corporation and which
does not result in any reclassification, conversion, exchange, or cancellation of the outstanding shares of Common Stock), or if all or substantially all of the assets or business of the Company are sold or transferred to another corporation,
entity, or person, then, as a condition to such consolidation, merger, or sale (any a “Transaction”), lawful and adequate provision shall be made whereby the Holder shall have the right from and after the Transaction to receive, upon
exercise of this Warrant and upon the terms and conditions specified herein and in lieu of the shares of the Common Stock that would have been issuable if this Warrant had been exercised immediately before the Transaction, such shares of stock,
securities, or assets as the Holder would have owned immediately after the Transaction if the Holder have exercised this Warrant immediately before the effective date of the Transaction. 

(f) In case any event shall occur as to which the other provisions of this Section 4 are not strictly applicable but the failure to make
any adjustment would not fairly protect the purchase rights represented by this Warrant in accordance with the essential intent and principles hereof, then, in each such case, the Company shall effect such adjustment, on a basis consistent with the
essential intent and principles established in this Section 4, as may be necessary to preserve, without dilution, the purchase rights represented by this Warrant. 

5. No Registration Rights. Issuance of this Warrant and the Warrant Shares (together, the “Securities”) have not been
registered under the Securities Act. The Holder 

 
acknowledges that the Warrant is being issued, and the Warrant Shares will be issued, on the basis of the statutory exemption provided by section 4(a)(2) of the Securities Act relating to
transactions by an issuer not involving any public offering, and that the Company’s reliance upon this statutory exemption is based in part upon the representations made by the Holder. The Holder agrees that no sale, assignment or transfer of
the Securities shall be valid or effective, and the Company shall not be required to give any effect to any such sale, assignment or transfer, unless (i) the sale, assignment or transfer of the Securities is registered under the Securities Act,
or (ii) the Securities are sold, assigned or transferred in accordance with all the requirements and limitations of Rule 144 under the Securities Act or such sale, assignment, or transfer is otherwise exempt from registration under the
Securities Act. The Holder represents and warrants that he has acquired this Warrant and will acquire the Warrant Shares for his own account for investment and not with a view to the sale or distribution thereof or the granting of any participation
therein, and that he has no present intention of distributing or selling to others any of such interest or granting any participation therein. The Holder acknowledges that the Securities must be held indefinitely unless a subsequent disposition
thereof is registered under the Securities Act or registered or qualified under any applicable state securities laws or is exempt from registration and/or qualification. The Holder is able to bear the economic risk of such investment and to afford a
complete loss thereof and is an “accredited investor” as such term is defined in Rule 501 (the provisions of which are known to the Holder) promulgated under the Securities Act. 

When exercised, the stock certificates shall bear the following legend: 

“The securities represented by this certificate have not been registered under the Securities Act of 1933 (the “Securities
Act”), and may not be offered for sale or sold except pursuant to (i) an effective registration statement under the Securities Act, or (ii) an opinion of counsel to the issuer of these securities that an exemption from registration
under the Securities Act is available. 
 6. Reservation of Shares. The Company agrees at all times to reserve and hold available out
of its authorized but unissued shares of Common Stock the number of shares of Common Stock issuable upon the full exercise of this Warrant. The Company further covenants and agrees that all shares of Common Stock that may be delivered upon the
exercise of this Warrant will, upon delivery, be fully paid and nonassessable and free from all taxes, liens and charges with respect to the purchase thereof hereunder. 

7. Notices to Holder. Upon any adjustment of the Exercise Price pursuant to Section 4, the Company shall promptly thereafter cause
to be given to the Holder written notice of such adjustment. Such notice shall include the Exercise Price (and/or the number of shares of Common Stock issuable upon the exercise of this Warrant) after such adjustment, and shall set forth in
reasonable detail the Company’s method of calculation and the facts upon which such calculations were based. Where appropriate, such notice shall be given in advance and included as a part of any notice required to be given under the other
provisions of this Section 7. 
 In the event of (a) any fixing by the Company of a record date with respect to the holders of any
class of securities of the Company for the purpose of determining which of such holders are entitled to dividends or other distributions, or any rights to subscribe for, purchase or 

 
otherwise acquire any shares of capital stock of any class or any other securities or property, or to receive any other right, (b) any capital reorganization of the Company, or
reclassification or recapitalization of the capital stock of the Company or any transfer of all or substantially all of the assets or business of the Company to, or consolidation or merger of the Company with or into, any other entity or person, or
(c) any voluntary or involuntary dissolution or winding up of the Company, then and in each such event the Company will give the Holder a written notice specifying, as the case may be (i) the record date for the purpose of such dividend,
distribution, or right, and stating the amount and character of such dividend, distribution, or right; or (ii) the date on which any such reorganization, reclassification, recapitalization, transfer, consolidation, merger, conveyance,
dissolution, liquidation, or winding up is to take place and the time, if any is to be fixed, as of which the holders of record of Common Stock (or such capital stock or securities receivable upon the exercise of this Warrant) shall be entitled to
exchange their shares of Common Stock (or such other stock securities) for securities or other property deliverable upon such event. Notwithstanding anything else in this Section 7 to the contrary, however, if the date on which the Company is
obliged to provide any notice hereunder to the Holders is prior to a public announcement relating to the events set forth and on such date the Company’s securities are traded or quoted on any recognized national securities exchange or quotation
system, then such notice shall be provided to each Holder simultaneously with the notice provided to the Company’s common stockholders. Failure to give such notice, or any defect therein, shall not, however, affect the legality or validity of
any such action. 
 8. No Rights as a Shareholder. This Warrant does not entitle the Holder to any voting rights or other rights as a
shareholder of the Company, nor to any other rights whatsoever except the rights herein set forth. 
 9. Additional Covenants of the
Company. For so long as the Common Stock is listed for trading or trades on any national securities exchange including, the Company shall, upon issuance of any shares for which this Warrant is exercisable, at its expense, promptly obtain and
maintain the listing or qualifications for trading of such shares. 
 The Company shall comply with the reporting requirements of Sections
13 and 15(d) of the Securities Exchange Act of 1934 for so long as and to the extent that such requirements apply to the Company. 
 The
Company shall not, by amendment of its Certificate of Incorporation or through any reorganization, transfer of assets, consolidation, merger, dissolution, issuance or sale of securities, or any other voluntary action, avoid or seek to avoid the
observance or performance of any of the terms of this Warrant. Without limiting the generality of the foregoing, the Company (a) shall comply with Section 6 of this Warrant and have available sufficient shares of Common Stock to be issued
from time to time upon exercise of this Warrant, (b) will not increase the par value of any shares of Common Stock issuable upon exercise of this Warrant above the amount payable therefor upon such exercise, and (c) will take all such
actions as may be necessary or appropriate in order that the Company may validly and legally issue fully paid and nonassessable stock. 

10. Successors and Assigns. This Agreement shall be binding upon and inure to the benefit of the Company, the Holder and their
respective successors and permitted assigns. 

 11. Notices. The Company agrees to maintain a ledger of the ownership of this Warrant (the
“Ledger”). Any notice hereunder shall be given by FedEx or other overnight delivery service for delivery on the next business day if to the Company, at its principal executive office and, if to the Holder, to his address shown in the
Ledger of the Company; provided, however, that either the Company or the Holder may at any time on three days’ written notice to the other designate or substitute another address where notice is to be given. Notice shall be deemed
given and received after a FedEx or other overnight delivery service is delivered to the carrier. 
 12. Severability. Every
provision of this Warrant is intended to be severable. If any term or provision hereof is illegal or invalid for any reason whatsoever, such illegality or invalidity shall not affect the remainder of this Warrant. 

13. Governing Law. This Warrant shall be governed by and construed in accordance with the laws of the State of New York without giving
effect to the principles of choice of laws thereof. 
 14. Entire Agreement. This Warrant (including the Exhibits attached hereto)
constitutes the entire understanding between the Company and the Holder with respect to the subject matter hereof, and supersedes all prior negotiations, discussions, agreements and understandings relating to such subject matter. 

15. Waivers and Amendments. No course of dealing between the Company and the Holder hereof shall operate as a waiver of any right of
any Holder hereof, and no delay on the part of the Holder in exercising any right hereunder shall so operate. This Warrant may be amended or waived only by a written instrument executed by the Company and the Holder hereof. Any amendment shall be
endorsed upon this Warrant, and all future Holders shall be bound thereby. 
 16. Loss, Destruction, Etc. Upon receipt by the Company
of evidence reasonably satisfactory to it of the loss, theft, destruction or mutilation of this Warrant Certificate, and, in case of loss, theft or destruction, of indemnity or security reasonably satisfactory to it, and reimbursement to the Company
of all reasonable expenses incidental thereto, and upon surrender and cancellation of the Warrants, if mutilated, the Company will make and deliver a new Warrant of like tenor, in lieu thereof and any such lost, stolen, destroyed or mutilated
warrant shall thereupon become void. 
 17. Acceptance. Receipt of this Warrant by the Holder shall constitute acceptance of and
agreement to all of the terms and conditions contained herein. 
 [Remainder of Page Intentionally Left Blank] 

[Signature Page Follows] 

 [Signature Page To Warrant] 

IN WITNESS WHEREOF, the Company has caused this Warrant to be executed by its duly authorized officer as of the date first set forth above.

  

			
	AUTHENTIDATE HOLDING CORP.
		
	By:		 /s/ William A. Marshall

	Name:		William A. Marshall
	Title:		Chief Financial Officer

 Exhibit A to the Warrant 

SUBSCRIPTION FORM 
 (To be Executed by the
Holder to Exercise the Rights To Purchase Common Stock Evidenced by the Within Warrant) 
 Section 1 - Please complete the following:

  

	 	•	 	I am exercising my right to purchase all of the shares of Common Stock which I am entitled to purchase under this warrant. The number of shares of Common Stock is
                . 

  

	 	•	 	I am exercising my right to purchase                 shares of Common Stock, and request that the Company deliver to me or as I shall
designate below a new Warrant representing the right to purchase                 shares of Common Stock. 

I am making payment of the full exercise price for such shares at an Exercise Price per share of $        as provided
for in such Warrant. The total exercise price payable is $        . Such payment takes the form of (check applicable box or boxes): 
  

	 	 ̈	$            in certified or official bank check payable to the order of the Company; or 

 

	 	 ̈	$            by wire transfer of immediately available funds 

I request that a certificate for the Common Stock be issued in the name of the undersigned and be delivered to the undersigned at the address stated below. If
the Common Stock is not all of the shares purchasable pursuant to the Warrant, I request that a new Warrant of like tenor for the balance of the remaining shares purchasable thereunder be delivered to me at the address stated below. 

In connection with the issuance of the Common Stock, I hereby represent to the Company that I am acquiring the Common Stock for my own account for investment
and not with a view to, or for resale in connection with, a distribution of the shares within the meaning of the Securities Act of 1933 (the “Securities Act”). 

I am            am not             
[please initial one] an accredited investor for at least one of the reasons on Exhibit A-1 to the Warrant. If the SEC has amended the rule defining the definition of accredited investor, I acknowledge that as a condition to exercise
the Warrant, the Company may request updated information regarding the Holder’s status as an accredited investor. My exercise of the Warrant shall be in compliance with the applicable exemptions under the Securities Act and applicable state law

 I understand that if at this time the Common Stock has not been registered under the Securities Act, I must hold such Common Stock indefinitely unless
the Common Stock is subsequently registered and qualified under the Securities Act or is exempt from such registration and qualification. I shall make no transfer or disposition of the Common Stock unless (a) such transfer or disposition can be
made without registration under the Securities Act by reason of a specific exemption from such registration and such qualification, or (b) a registration statement has been filed pursuant to the Securities Act and has been declared effective
with respect to such disposition. I agree that each certificate representing the Common Stock delivered to me shall bear substantially the same as set forth on the front page of the Warrant. 

 I further agree that the Company may place stop transfer orders with its transfer agent same effect as the above
legend. The legend and stop transfer notice referred to above shall be removed only upon my furnishing to the Company of an opinion of counsel to the Company to the effect that such legend may be removed. 

 

									
	Date:		  
				Signed:		  

					Print Name:		  

					Address:		  

					
	Date:		  
				Signed:		  

					Print Name:		  

					Address:		  

 Exhibit A-1 to the Warrant 

For Individual Investors Only: 
 1. A person who
has an individual net worth, or combined net worth (with his or her spouse) who has, in excess of $1,000,000. For purposes of this question, “net worth” means the excess of total assets at fair market value. The fair market value of my
primary residence and the indebtedness on mortgages or deeds of trust related to such residence shall be excluded unless the indebtedness exceeds the fair market value. 

2a. A person who had individual income (exclusive of any income attributable to the person’s spouse) of more than who has $200,000 in
each of the two most recently completed years and who reasonably expects to have an individual income in excess of $200,000 this year. 

2b. Alternatively, a person, who with his or her spouse, has joint income in excess of $300,000 in each applicable year. 

3. A director or executive officer of the Company. 

Other Investors: 
 4. Any bank as defined in
Section 3(a)(2) of the Securities Act of 1933 (“Securities Act”) whether acting in its individual or fiduciary capacity; any broker or dealer registered pursuant to section 15 of the Securities Exchange Act of 1934; insurance company
as defined in Section 2(13) of the Securities Act; investment company registered under the Investment Company Act of 1940 or a business development company as defined in Section 2(a)(48) of that Act; Small Business Investment Company
licensed by the U.S. Small Business Administration under Section 301(c) or (d) of the Small Business Investment Act of 1958; any plan established and maintained by a state, its political subdivisions, or any agency or instrumentality of a
state or its political subdivisions, for the benefit of its employees, if such plan has total assets in excess of $5,000,000; employee benefit plan within the meaning of Title I of the Employee Retirement Income Security Act of 1974, if the
investment decision is made by a plan fiduciary, as defined in Section 3(21) of such Act, which is either a bank, savings and loan association, insurance company, or registered investment advisor, or if the employee benefit plan has total
assets in excess of $5,000,000, or if a self-directed plan, with investment decisions made solely by persons that are accredited investors. 

5. A private business development company as defined in Section 202(a)(22) of the Investment Advisors Act of 1940. 

6. An organization described in Section 501(c)(3) of the Internal Revenue Code, corporation, Massachusetts or similar business trust or
partnership, not formed for the specific purpose of acquiring the securities offered, with total assets in excess of $5,000,000. 
 7. A
trust, with total assets in excess of $5,000,000, not formed for the specific purpose of acquiring the securities offered, whose purchase is directed by a sophisticated person as described in Rule 506(b)(2)(ii) of the Securities Act. 

8. An entity in which all of the equity owners are accredited investors. 

 Exhibit B to the Warrant 

ASSIGNMENT 
 (To be Executed by the Holder to
Effect Transfer of the Attached Warrant) 
 For Value Received
                                         hereby
sells, assigns and transfers to
                                         the
Warrant attached hereto and the rights represented thereby to purchase                  shares of Common Stock in accordance with the terms and conditions hereof, and
does hereby irrevocably constitute and appoint
                                         as
attorney to transfer such Warrant on the books of the Company with full power of substitution. 
  

									
	Dated:		  
				Signed:		  

	Please print or typewrite name and address of assignee:						Please insert Social Security or other Tax Identification Number of Assignee:

  

									
	Dated:		  
				Signed:		  

	Please print or typewrite name and address of assignee:						Please insert Social Security or other Tax Identification Number of Assignee:

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