Document:

Form of Warrant granted pursuant to Standby Commitment

 Exhibit 4.6 

NEITHER THIS WARRANT NOR THE SECURITIES ISSUABLE UPON EXERCISE THEREOF HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR QUALIFIED
UNDER ANY STATE SECURITIES LAWS. NO SALE OR DISPOSITION OF THIS WARRANT OR ANY SUCH SECURITIES MAY BE EFFECTED EXCEPT (i) PURSUANT TO EFFECTIVE REGISTRATION STATEMENTS RELATED THERETO, (ii) PURSUANT TO AN OPINION OF COUNSEL
SATISFACTORY TO THE COMPANY THAT AN APPLICABLE EXEMPTION FROM THE REGISTRATION REQUIREMENTS OF SUCH ACT AND SUCH LAWS, OR (iii) FOLLOWING RECEIPT OF NO-ACTION LETTERS FROM THE APPROPRIATE GOVERNMENTAL AUTHORITIES. 

THE TRANSFERABILITY OF THIS WARRANT IS 

RESTRICTED AS PROVIDED IN SECTION 3 

AUTHENTIDATE HOLDING CORP. 

COMMON STOCK PURCHASE WARRANT 
  

			
	Dated as of: September 23, 2009	  	No. of Warrant Shares: 400,000

For good and valuable consideration, the receipt of which is hereby acknowledged by AUTHENTIDATE HOLDING CORP., a
Delaware corporation (the “Company”), DUKE 87, LLC (the “Holder”), is hereby granted the right to purchase, at any time from and after the
23rd day of September 2009 until 5:00 P.M., New York City
time, on September 23, 2014 (the “Warrant Exercise Term”), up to FOUR HUNDRED THOUSAND (400,000) fully-paid and non-assessable shares of the Company’s Common Stock, $.001 par value per share (“Common
Stock”). This warrant (the “Warrant”) is issued by the Company pursuant to that certain Standby Commitment between the Company and the original holder dated September 22, 2009 (the “Commitment”).

  

	 	1.	Exercise of Warrant  

1.1 Exercise Price and Mechanics of Exercise. 

(a) During the Warrant Exercise Term, this Warrant shall be exercisable at a per share price of $1.20 (the
“Exercise Price”), subject to adjustment as provided in Section 2 hereof, payable in cash or by certified or official bank check in New York Clearing House funds or in accordance with Section 1.4 below. The rights
represented by this Warrant may be exercised in whole or in part at any time during the Warrant Exercise Term, upon surrender of the original of this warrant certificate with the annexed Notice of Exercise duly executed, together with payment of the
Exercise Price for the shares of Common Stock purchased, at the Company’s principal executive offices. Upon the occurrence of all of such events, the registered Holder of the Warrant shall be entitled to receive a certificate or certificates
for the shares of Common Stock so purchased (the “Warrant Shares”). 
 (b) The purchase rights
represented by this Warrant are exercisable at the option of the Holder hereof, in whole or in part (but not as to fractional shares of the Common Stock) during any period in which this Warrant may be exercised as set forth above. In the case of the
purchase of less than all the shares of Common Stock purchasable under this Warrant, the Company shall cancel this Warrant upon the surrender thereof and, upon the written request of the Holder, the Company shall execute and deliver a new Warrant of
like tenor for the balance of the shares of Common Stock purchasable hereunder. 

 (c) Certificates for Warrant Shares purchased hereunder shall be transmitted
by the transfer agent of the Company to the Holder by crediting the account of the Holder’s prime broker with the Depository Trust Company through its Deposit Withdrawal Agent Commission system if the Company is a participant in such system,
and otherwise by physical delivery to the address specified by the Holder in the Notice of Exercise within three business days from the delivery to the Company of the Notice of Exercise, surrender of this Warrant and payment of the aggregate
Exercise Price as set forth above. This Warrant shall be deemed to have been exercised on the date on which this Warrant is surrendered and payment of the Exercise Price is received by the Company. The Warrant Shares shall be deemed to have been
issued, and Holder or any other person so designated to be named therein shall be deemed to have become a holder of record of such shares for all purposes, as of the date on which all of the criteria described in the immediately preceding sentence
have occurred, irrespective of the date of delivery of such certificate or certificates, except that, if the date of such surrender and payment is a date when the stock transfer books of the Company are closed, such person shall 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. 

1.2 Transfer Taxes. The issuance of certificates for shares of Common Stock upon the exercise of this Warrant shall
be made without charge to the Holder hereof including, without limitation, any tax which may be payable in respect of the issuance thereof, and such certificates shall be issued in the name of, or in such names as may be directed by, the Holder
hereof; provided, however, that the Company shall not be required to pay any tax which may be payable in respect of any transfer involved in the issuance and delivery of such certificate in a name other than that of the Holder 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. 
 1.3 Covenants by Company. The Company covenants that it will at all times reserve
and keep available out of its authorized Common Stock, solely for the purpose of issuance upon exercise of this Warrant as herein provided, such number of shares of Common Stock as shall then be issuable upon the exercise of this Warrant. The
Company covenants that all shares of Common Stock which shall be so issuable shall be duly and validly issued and fully-paid and non-assessable. 

1.4 Cashless Exercise. If during the Warrant Exercise Term, a registration statement filed by the Company pursuant
to the Securities Act of 1933, as amended, covering the Warrant Shares that are the subject of the Exercise Notice is not available for the issuance or resale of such Warrant Shares, and the fair market value of one share of the Common Stock is
greater than the Exercise Price (at the date of calculation as set forth below), in lieu of exercising this Warrant by payment of cash or by check, the Holder may elect to exercise this Warrant in whole or in part, and upon such election receive
shares equal to the value (as determined below) of this Warrant (or the portion thereof being canceled) by surrender of this Warrant at the principal office of the Company together with the properly endorsed Notice of Exercise in which event the
Company shall issue to the Holder a number of shares of Common Stock computed using the following formula: 
 X =
Y x (A-B)/A 
  

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 where: 

X = the number of Warrant Shares to be issued to the Holder; 

Y = the number of Warrant Shares with respect to which this Warrant is being exercised; 

A = the Market Price (as defined in below) as of the Exercise Date; and 

B = the Exercise Price. 

For purposes of the above calculation, the “Market Price” of one share of Common Stock shall mean (i) the average
of the closing sales prices for the shares of Common Stock on the Nasdaq Capital Market or other trading market where such security is listed or traded as reported by Bloomberg Financial Markets (or a comparable reporting service of national
reputation selected by the Company and reasonably acceptable to the Holder if Bloomberg Financial Markets is not then reporting sales prices of such security) (collectively, “Bloomberg”) for the ten (10) consecutive trading
days immediately preceding such date, or (ii) if the Nasdaq Capital Market is not the principal trading market for the shares of Common Stock, the average of the reported sales prices reported by Bloomberg on the principal trading market for
the Common Stock during the same period, or, if there is no sales price for such period, the last sales price reported by Bloomberg for such period, or (iii) if neither of the foregoing applies, the last sales price of such security in the
over-the-counter market on the pink sheets or bulletin board for such security as reported by Bloomberg, or if no sales price is so reported for such security, the last bid price of such security as reported by Bloomberg or (iv) if fair market
value cannot be calculated as of such date on any of the foregoing bases, the fair market value shall be as determined by the Board of Directors of the Company in the exercise of its good faith judgment. 

1.5 Rule 144. For purposes of Rule 144, it is intended and acknowledged that the Warrant Shares issued in a
Cashless Exercise transaction shall be deemed to have been acquired by the Holder, and the holding period for the Warrant Shares required by Rule 144 shall be deemed to have been commenced, on the date this Warrant was originally issued by the
Company. 
  

	 	2.	Adjustments and Extraordinary Events  

2.1 Stock Dividends, Subdivisions, Reclassifications or Combinations. If during the Warrant Exercise Term, the
Company shall (A) declare a dividend or make a distribution on its Common Stock in shares of its Common Stock, (B) subdivide or reclassify the outstanding shares of Common Stock into a greater number of shares, or (C) combine or
reclassify the outstanding Common Stock into a smaller number of shares, the Exercise Price in effect at the time of the record date for such dividend or distribution or the effective date of such subdivision, combination or reclassification shall
be proportionately adjusted. Any adjustment made herein which results in a decrease (or increase) in the Exercise Price shall also effect a proportional increase (or decrease) in the number of shares of Common Stock into which this Warrant is
exercisable. Successive adjustments in the Exercise Price shall be made whenever any event specified above shall occur. 

2.2 Reorganization, Reclassification, Merger, Consolidation or Disposition of Assets. If during the Warrant
Exercise Term (i) the Company shall reorganize its capital, reclassify its capital stock, consolidate or merge with or into another corporation (where the Company is not the surviving corporation or where there is a change in or distribution
with 
  

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respect to the Common Stock of the Company); (ii) any tender offer or exchange offer (whether by the Company or another individual or entity) is completed pursuant to which holders of Common
Stock are permitted to tender or exchange their shares for other securities, cash or property; (iii) the Company shall sell, transfer or otherwise dispose all or substantially all of its property, assets or business to another corporation and,
pursuant to the terms of such reorganization, reclassification, merger, consolidation, tender or exchange offer, or disposition of assets, shares of common stock of the successor or acquiring corporation, or any cash, shares of stock or other
securities or property of any nature whatsoever (including warrants or other subscription or purchase rights) in addition to or in lieu of common stock of the successor or acquiring corporation (“Other Property”), are to be received
by or distributed to the holders of Common Stock of the Company, then the Holder shall have the right thereafter to receive, upon exercise of this Warrant, the number of shares of common stock of the successor or acquiring corporation or of the
Company, if it is the surviving corporation, and Other Property receivable upon or as a result of such reorganization, reclassification, merger, consolidation, tender or exchange offer, or disposition of assets by a Holder of the number of shares of
Common Stock for which this Warrant is exercisable immediately prior to such event. In case of any such reorganization, reclassification, merger, tender or exchange offer, consolidation or disposition of assets (“Extraordinary
Transaction”), the successor or acquiring corporation (if other than the Company) shall expressly assume the due and punctual observance and performance of each and every covenant and condition of this Warrant to be performed and observed
by the Company and all the obligations and liabilities hereunder, subject to such modifications as may be deemed appropriate (as determined in good faith by resolution of the Board of Directors of the Company) in order to provide for adjustments of
Warrant Shares for which this Warrant is exercisable which shall be as nearly equivalent as practicable to the adjustments provided for in this Section 2.2. As soon as commercially practicable following the Extraordinary Transaction, the
successor or acquiring corporation (if other than the Company), shall deliver to Holder a new warrant in repacement of this Warrant consistent with the provisions referenced in the immediately preceding sentence against receipt by such successor or
acquiring corporation of the original of this Warrant. For purposes of this Section 2.2, “common stock of the successor or acquiring corporation” shall include stock of such corporation of any class which is not preferred as to
dividends or assets over any other class of stock of such corporation and which is not subject to redemption and shall also include any evidences of indebtedness, shares of stock or other securities which are convertible into or exchangeable for any
such stock, either immediately or upon the arrival of a specified date or the happening of a specified event and any warrants or other rights to subscribe for or purchase any such stock. The foregoing provisions of this Section 2.2 shall
similarly apply to successive reorganizations, reclassifications, mergers, tender or exchange offers, consolidations or disposition of assets. 

2.3 Notice of Adjustment. Whenever the number of Warrant Shares or number or kind of securities or other property
purchasable upon the exercise of this Warrant or the Exercise Price is adjusted in accordance with this Section 2, as herein provided, the Company shall give prior written notice thereof to the Holder of at least 15 days prior to the date on
which the Company closes its books or takes a record for determining the particular event, which notice shall state the number of Warrant Shares (and other securities or property) purchasable upon the exercise of this Warrant and the Exercise Price
of such Warrant Shares (and other securities or property) after such adjustment, setting forth a brief statement of the facts requiring such adjustment and setting forth the computation by which such adjustment was made. 

 

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	 	3.	Restrictions on Transfer  

(a) The Holder acknowledges that he has been advised by the Company that this Warrant and the Warrant Shares issuable upon
exercise thereof (collectively the “Securities”) have not been registered under the Securities Act of 1933, as amended (the “Securities Act”), that the Warrant is being issued, and the shares issuable upon exercise
of the Warrant will be issued, on the basis of the statutory exemption provided by section 4(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 contained herein. The Holder acknowledges that he has been informed by the Company of, or is otherwise familiar with, the nature of the limitations imposed by the Securities Act
and the rules and regulations thereunder on the transfer of securities. In particular, 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, and the Company has no obligations or intention to so register the Securities except as may otherwise
be provided herein, 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 Securities 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 Warrant and Warrant Shares must be held indefinitely
unless a subsequent disposition thereof is registered under the Securities Act or registered or qualified under any applicable state securities or “blue-sky” laws or is exempt from registration and/or qualification. The Holder has no need
for liquidity in its investment in the Company, and is able to bear the economic risk of such investment for an indefinite period and to afford a complete loss thereof. The Holder is an “accredited investor” as such term is defined in Rule
501 (the provisions of which are known to the Holder) promulgated under the Act. 
 The Holder acknowledges that the securities
shall bear the following legend: 
 “THESE SECURITIES HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933. SUCH
SECURITIES MAY NOT BE SOLD OR OFFERED FOR SALE, TRANSFERRED, HYPOTHECATED OR OTHERWISE ASSIGNED IN THE ABSENCE OF AN EFFECTIVE REGISTRATION STATEMENT WITH RESPECT THERETO UNDER SUCH ACT OR AN OPINION OF COUNSEL TO THE COMPANY THAT AN EXEMPTION FROM
REGISTRATION FOR SUCH SALE, OFFER, TRANSFER, HYPOTHECATION OR OTHER ASSIGNMENT IS AVAILABLE UNDER SUCH ACT.” 

(b) Disposition of Warrant or shares of Common Stock issuable on exercise of the Warrant. With respect to
any offer, sale or other disposition of this Warrant or any shares of Common Stock acquired pursuant to the exercise of this Warrant prior to registration of such Warrant or shares of Common Stock, the Holder agrees to give written notice to the
Company prior thereto, describing briefly the manner thereof, together with evidence, reasonably satisfactory to the Company (which shall include such representation of the transferee regarding investment intent as the Company may request, to the
effect that such offer, sale or other disposition may be effected without registration or qualification (under the Act as then in effect or any federal or state securities law then in effect) of this Warrant or such shares of Common Stock and
indicating whether or not under the Act certificates for this Warrant or such shares of Common Stock to be sold or otherwise disposed of require any restrictive legend as to applicable restrictions on transferability in order to ensure compliance
with such law. Upon 
  

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receiving such written notice and reasonably satisfactory evidence, the Company, as promptly as practicable but no later than seven (7) days after receipt of the written notice, shall notify
the Holder that the Holder may sell or otherwise dispose of this Warrant or such shares of Common Stock, all in accordance with the terms of the notice delivered to the Company. If the Company determines that the evidence is not reasonably
satisfactory to the Company, the Company shall so notify the Holder promptly with details thereof after such determination has been made. Notwithstanding the foregoing, any shares of Common Stock issued upon exercise of this Warrant or such
shares of Common Stock may be offered, sold or otherwise disposed of in accordance with Rule 144 under the Act and in compliance with the applicable statutory resale restrictions imposed by Canadian securities laws, provided that the Company
shall have been furnished with such information as the Company may reasonably request to provide a reasonable assurance that the provisions of Rule 144 and the applicable Canadian resale restrictions imposed by the Canadian securities laws have
been satisfied. Each certificate representing this Warrant or the shares of Common Stock thus transferred shall bear a legend as to the applicable restrictions on transferability in order to ensure compliance with such laws, unless pursuant to
an opinion of counsel for the Holder, such legend is not required in order to ensure compliance with such laws. The Company may issue stop transfer instructions to its transfer agent in connection with such restrictions. 

 

	 	4.	Piggyback Registration Rights. 

4.1 Registration. If at any time during the Warrant Exercise Term, the Company shall determine to prepare and file
with the Commission a registration statement under the Securities Act of 1933, as amended (the “Securities Act”) relating to an offering for its own account or the account of others under the Securities Act of any of its equity
securities, other than (i) that certain registration statement on Form S-3 with the SEC File No. 333-161220 or (ii) a registration statement on Form S-4 or Form S-8 (each as promulgated under the Securities Act) or their then
equivalents relating to equity securities to be issued solely in connection with any acquisition of any entity or business or equity securities issuable in connection with the stock option or other employee benefit plans, then the Company shall send
to each holder of this Warrant (a “Holder”) a written notice of such determination and, if within fifteen (15) days after the date of such notice, any such Holder shall so request in writing, the Company shall include in such
registration statement all or any part of such Warrant Shares which such Holder requests to be registered, subject to customary underwriter cutbacks applicable to all holders of registration rights, provided that if at any time after giving written
notice of its intention to register any securities and prior to the effective date of the registration statement filed in connection with such registration, the Company shall determine for any reason not to register or to delay registration of such
securities, the Company may, at its election, give written notice of such determination to such Holder and, thereupon, (A) in the case of a determination not to register, shall be relieved of its obligation to register any Warrant Shares in
connection with such registration (but not from its obligation to pay expenses in accordance with Section 4.5 hereof), and (B) in the case of a determination to delay registering, shall be permitted to delay registering any Warrant
Shares being registered pursuant to this Section 4(a) for the same period as the delay in registering such other securities. Notwithstanding the foregoing, the Company shall not be required to register any Warrant Shares pursuant to this
Section 4(a) that are eligible for resale pursuant to Rule 144(b) promulgated under the Securities Act or that are the subject of a then effective registration statement. For the purpose of the foregoing, inclusion of the Warrant Shares by the
Holder in a registration statement under a condition that the offer and/or sale of such Warrant Shares not commence until a date not to exceed 90 days from the effective date of such registration statement shall be deemed to be in compliance with
this sub-paragraph. 
  

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 4.2 Exceptions. The Company shall have no obligation to include
Warrant Shares of any Holder in a registration statement pursuant to this Section 4, unless and until such Holder (i) in connection with any underwritten offering, agrees to enter into an underwriting agreement, a custody agreement and
power of attorney and any other customary documents required in an underwritten offering all in customary form and containing customary provisions and (ii) shall have furnished the Company with all information and statements about or pertaining
to such Holder in such reasonable detail and on such timely basis as is reasonably deemed by the Company to be legally required with respect to the preparation of the registration statement. 

4.3 Procedures. The foregoing registration rights shall be contingent on the Holders furnishing the Company with
such appropriate information (relating to the intentions of such Holders) as the Company shall reasonably request in writing. Each Holder agrees to furnish to the Company a completed selling security holder questionnaire in such form as is provided
by the Company to the Holder not less than two business days prior to date on which the Company files the registration statement (the “Filing Date”). The Company shall not be required to include the Warrant Shares of a Holder in a
registration statement for any Holder who fails to furnish to the Company a fully completed questionnaire at least two business days prior to the Filing Date. The Company may require each selling Holder to furnish to the Company a certified
statement as to the number of shares of Common Stock beneficially owned by such Holder and, if required by the Commission, the natural persons thereof that have voting and dispositive control over the Shares. Following the effective date of such
registration, the Company shall upon the request of any owner of Warrants and/or Warrant Shares forthwith supply such number of prospectuses meeting the requirements of the Securities Act as shall be requested by such owner to permit such Holder to
make a public offering of all Warrant Shares from time to time offered or sold to such Holder, provided that such Holder shall from time to time furnish the Company with such appropriate information (relating to the intentions of such Holder) as the
Company shall request in writing. The Company shall also use its best efforts to qualify the Warrant Shares for sale in such states as such Holder shall reasonably designate. The Company may withdraw the registration at any time. 

4.4 Indemnity. The Company shall indemnify and hold harmless each such Holder and each underwriter, if any, within
the meaning of the Securities Act, who may purchase from or sell for any such Holder any Warrant Shares from and against any and all losses, claims, damages and liabilities caused by any untrue statement or alleged untrue statement of a material
fact contained in the Registration Statement or any post-effective amendment thereto or any registration statement under the Securities Act or any prospectus included therein required to be filed or furnished by reason of this Section 4 or
caused by any omission or alleged omission to state therein a material fact required to be stated therein or necessary to make the statements therein not misleading except insofar as such losses, claims, damages or liabilities are caused by any such
untrue statement or alleged untrue statement or omission or alleged omission based upon information furnished or required to be furnished in writing to the Company by such Holder or underwriter expressly for use therein, which indemnification shall
include each person, if any, who controls any such underwriter within the meaning of the Securities Act; provided, however, that the Company shall not be obliged so to indemnify any such Holder or underwriter or controlling person unless such Holder
or underwriter shall at the same time agree to indemnify the Company, its directors, each officer signing the related registration statement and each person, if any, who controls the Company within the meaning of the Securities Act, from and against
any and all losses, claims, damages and liabilities caused by any untrue statement or alleged untrue statement of a material fact contained in any registration statement or any prospectus required to be filed or furnished by reason of this
Section 4 or caused by any omission to state therein a 
  

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material fact required to be stated therein or necessary to make the statements therein not misleading insofar as such losses, claims, damages or liabilities are caused by any untrue statement or
alleged untrue statement or omission based upon information furnished in writing to the Company by any such Holder or underwriter expressly for use therein. 

4.5. Registration Expenses. The Holder thereof shall pay all transfer taxes, if any, relating to the sale of its
shares, any registration fees, underwriting discounts or commissions or the equivalent thereof applicable to the sale of its shares and the fees of his own counsel. Other than as described in the preceding sentence, the Company shall pay all
expenses incident to the registration of the Warrant Shares by the Company, including, without limitation, all registration and filing fees, fees and expenses of compliance with securities or blue sky laws, underwriting discounts, fees and expenses
(other than any Holder’s portion of any underwriting discounts or commissions or the equivalent thereof), printing expenses, messenger and delivery expenses, and reasonable fees and expenses of counsel for the Company and the independent
certified public accountants and other persons retained by the Company. 
  

	 	5.	Exercise Limitations. 

(a) A Holder shall not have the right to exercise any portion of this Warrant to the extent that after giving effect to
such issuance after exercise, such Holder (together with such Holder’s affiliates), as set forth on the applicable Notice of Exercise, would beneficially own in excess of 4.99% of the number of shares of the Common Stock outstanding immediately
after giving effect to such issuance. For purposes of the foregoing sentence, the number of shares of Common Stock beneficially owned by such Holder and its affiliates shall include the number of shares of Common Stock issuable upon exercise of this
Warrant with respect to which the determination of such sentence is being made, but shall exclude the number of shares of Common Stock which would be issuable upon (A) exercise of the remaining, nonexercised portion of this Warrant beneficially
owned by such Holder or any of its affiliates and (B) exercise or conversion of the unexercised or nonconverted portion of any other securities of the Company (including, without limitation, any other shares of Common Stock or Warrants) subject
to a limitation on conversion or exercise analogous to the limitation contained herein beneficially owned by such Holder or any of its affiliates. Except as set forth in the preceding sentence, for purposes of this Section 4, beneficial
ownership shall be calculated in accordance with Section 13(d) of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), it being acknowledged by a Holder that the Company is not representing to such Holder that
such calculation is in compliance with Section 13(d) of the Exchange Act and such Holder is solely responsible for any schedules required to be filed in accordance therewith. 

(b) To the extent that the limitation contained in this Section 5 applies, the determination of whether this
Warrant is exercisable (in relation to other securities owned by such Holder) and of which a portion of this Warrant is exercisable shall be in the sole discretion of a Holder, and the submission of a Notice of Exercise shall be deemed to be each
Holder’s determination of whether this Warrant is exercisable (in relation to other securities owned by such Holder) and of which portion of this Warrant is exercisable, in each case subject to such aggregate percentage limitation, and the
Company shall have no obligation to verify or confirm the accuracy of such determination. For purposes of this Section 5, in determining the number of outstanding shares of Common Stock, a Holder may rely on the number of outstanding
shares of Common Stock as reflected in (x) the Company’s most recent Form 10-Q or Form 10-K, as the case may be, (y) a more recent public announcement by the Company or (z) any other 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 

 

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Trading Days confirm orally and in writing to such 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 Warrant, by such Holder or its affiliates since the date as of which such number of outstanding shares of Common Stock was reported. The provisions of
this Section 5 may be waived by such Holder, at the election of such Holder, upon not less than 61 days’ prior notice to the Company, and the provisions of this Section 5 shall continue to apply until such 61st day (or
such later date, as determined by such Holder, as may be specified in such notice of waiver). 
  

	 	6.	Exchange and Replacement of Warrant Certificates. 

6.1 Exchanges. This Warrant Certificate is exchangeable without expense, upon the surrender hereof by the
registered Holder at the principal executive office of the Company, for a new Warrant Certificate of like tenor and date representing in the aggregate the right to purchase the same number of Warrant Shares in such denominations as shall be
designated by the Holder thereof at the time of such surrender. 
 6.2 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. 
  

	 	7.	Elimination of Fractional Interests. 

The Company shall not be required to issue certificates representing fractions of the shares of Common Stock and shall not
be required to issue scrip or pay cash in lieu of fractional interests, it being the intent of the parties that all fractional interests shall be eliminated by rounding any fraction up or down to the nearest whole number of shares of Common Stock.

  

	 	8.	Rights of Warrant Holders. 

Nothing contained in this Agreement shall be construed as conferring upon the Holder any rights whatsoever as a
stockholder of the Company, either at law or in equity, including without limitation, or Holders the right to vote or to consent or to receive notice as a stockholder in respect of any meetings of stockholders for the election of directors the right
to receive dividends or any other matter. 
  

	 	9.	Miscellaneous. 

9.1 Successors and Assigns. All the covenants and agreements made by the Company in this Warrant shall bind its
successors and assigns. This Warrant shall be for the sole and exclusive benefit of the Holder and nothing in this Warrant shall be construed to confer upon any person other than the Holder any legal or equitable right, remedy or claim hereunder.

 9.2 Acceptance. Receipt of this Warrant by the Holder shall constitute acceptance of and agreement to
all of the terms and conditions contained herein. 
  

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 9.3 No Recourse. No recourse shall be had for any claim based hereon
or otherwise in any manner in respect hereof, against any incorporator, stockholder, officer or director, past, present or future, of the Company or of any predecessor corporation, whether by virtue of any constitutional provision or statute or rule
of law, or by the enforcement of any assessment or penalty or in any other manner, all such liability being expressly waived and released by the acceptance hereof and as part of the consideration for the issue hereof. 

9.4 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. 
 9.5
Notices. All notices required or permitted hereunder shall be in writing and shall be deemed effectively given: (a) upon personal delivery to the party to be notified, (b) when sent by confirmed telex or facsimile if sent during normal
business hours of the recipient, if not, then on the next business day, (c) five days after having been sent by registered or certified mail, return receipt requested, postage prepaid, or (d) one day after deposit with a nationally
recognized overnight courier, specifying next day delivery, with written verification of receipt. All communications shall be sent to the Company at the address listed on the signature page hereto and to Holder at the applicable address set forth on
the applicable signature page to the Subscription Agreement or at such other address as the Company or Holder may designate by ten (10) days advance written notice to the other parties hereto. 

9.6 Governing Law. The provisions of this Warrant shall in all respects be constructed according to, and the rights
and liabilities of the parties hereto shall in all respects be governed by, the laws of the State of New York. This Warrant shall be deemed a contract made under the laws of the State of New York and the validity of this Warrant and all rights and
liabilities hereunder shall be determined under the laws of said State. 
 9.7 Headings. The headings of
the Sections of this Warrant are inserted for convenience only and shall not be deemed to constitute a part of this Warrant. 

Signature page to Common Stock Purchase Warrant follows. 

 

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 IN WITNESS WHEREOF, AUTHENTIDATE HOLDING CORP. has, as of the date first set forth above,
caused this Warrant to be executed in its corporate name by its officer, and its seal to be affixed hereto. 
 October 8, 2010 

 

			
	AUTHENTIDATE HOLDING CORP.
		
	By:	 	 
		 	Name: O’Connell Benjamin
		 	Title:   President
	
	 Connell Corporate Center

300 Connell Drive, 5th Floor
 Berkeley Heights,
NJ 07922

  

 - 11 - 

 NOTICE OF EXERCISE 

 

	TO:	AUTHENTIDATE HOLDING CORP. 

	 	Connell Corporate Center 

	 	300 Connell Drive, 5th Floor 

	 	Berkeley Heights, NJ 07922 

	 	Attention: Chief Financial Officer 

The undersigned Holder hereby irrevocably elects to exercise the right to purchase
                         shares of Common Stock covered by this Warrant according to the conditions hereof and herewith
makes full payment of the Exercise Price of such shares. 
 The undersigned, by marking the box following this sentence,
indicates his or her intention to exercise                      shares covered by this Warrant on a cashless basis in accordance with the
terms of this Warrant: € 
 Kindly deliver to the undersigned a certificate representing the Shares. 

INSTRUCTIONS FOR DELIVERY 
  

			
	Name:
                                         
                                         
                                         
                                   	  	
	(please typewrite or print in block letters)	  
		
	Address:
                                         
                                         
                                         
                              	  	
		
	Tax I.D. No. or Social Security No.:
                                         
                                         
                   	  	

 If such number of shares shall not be all the shares purchasable upon the exercise of the Warrants
evidenced by this Warrant, a new warrant certificate for the balance of such Warrants remaining unexercised shall be registered in the name of and delivered to: 
  

			
	Name:
                                         
                                         
                                         
                                   	  	
	(please typewrite or print in block letters)	  
		
	Address:
                                         
                                         
                                         
                              	  	
		
	Tax I.D. No. or Social Security No.:
                                         
                                         
                   	  	

			
		
	Dated:
                                         
                                         
         	  	

			
		
	Signature
                                         
                                         
                      	  	

 STATE OF                 )

 COUNTY OF             ) ss: 

On this      day of             , before me
personally came                 , to me known, who being by me duly sworn, did depose and say that he resides at
                    , that he is the holder of the foregoing instrument and that he executed such instrument and duly acknowledged to me that
he executed the same. 
  

	
	  
	Notary Public

  

 - 12 - 

 [FORM OF ASSIGNMENT] 

(To be executed by the registered holder if such holder 

desires to transfer the Warrant Certificate.) 

FOR VALUE RECEIVED, the undersigned Holder of this Warrant hereby sells, assigns and transfers the foregoing Warrant and all rights
evidenced thereby to 
  

					
	Name:	 		 	  
		 		 	(Please Print)
			
	Address:	 		 	 
		 		 	(Please Print)
			
	Tax ID No.:	 		 	 

 and does hereby irrevocably constitute and
appoint                                 , Attorney, to transfer the within
Warrant Certificate on the books of Authentidate Holding Corp., with full power of substitution. 
 NOTE: The signature to this Assignment Form
must correspond with the name as it appears on the face of the Warrant, without alteration or enlargement or any change whatever. Officers of corporations and those acting in a fiduciary or other representative capacity should file proper evidence
of authority to assign the foregoing Warrant. 
  

									
					
	Dated:	 	__________________	 		 	Holder:	 	 
				
		 		 		 	 
		 		 		 	(Print Name)
				
		 		 		 	 
		 		 		 	(Signature)

 STATE OF
                        ) 

COUNTY OF                     ) ss: 

On this      day of
                    , before me personally came
                    , to me known, who being by me duly sworn, did depose and say that he resides at
                    , that he is the holder of the foregoing instrument and that he executed such instrument and duly acknowledged to me that
he executed the same. 
  

					
			
	 	 		 	  
		 		 	Notary Public

  

 - 13 -Form of Warrant granted to consultant

 Exhibit 4.7 

NEITHER THIS WARRANT NOR THE SECURITIES ISSUABLE UPON EXERCISE THEREOF HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR QUALIFIED
UNDER ANY STATE SECURITIES LAWS. NO SALE OR DISPOSITION OF THIS WARRANT OR ANY SUCH SECURITIES MAY BE EFFECTED EXCEPT (i) PURSUANT TO EFFECTIVE REGISTRATION STATEMENTS RELATED THERETO, (ii) PURSUANT TO AN OPINION OF COUNSEL
SATISFACTORY TO THE COMPANY THAT AN APPLICABLE EXEMPTION FROM THE REGISTRATION REQUIREMENTS OF SUCH ACT AND SUCH LAWS, OR (iii) FOLLOWING RECEIPT OF NO-ACTION LETTERS FROM THE APPROPRIATE GOVERNMENTAL AUTHORITIES. 

IN ADDITION, THE SECURITIES ISSUABLE UPON EXERCISE OF THIS WARRANT ARE SUBJECT TO A LOCK-UP AGREEMENT SET FORTH BELOW, RESTRICTING ANY SALE OF SUCH
UNDERLYING SECURITIES IN ACCORDANCE WITH THE PROVISIONS CONTAINED HEREIN. 
 THE TRANSFERABILITY OF THIS WARRANT IS 

 RESTRICTED AS PROVIDED IN SECTION 3 

Warrant No. 2010-1 
 Number of Shares of
Common Stock: 100,000 
 AUTHENTIDATE HOLDING CORP. 

COMMON STOCK PURCHASE WARRANT 

For good and valuable consideration, the receipt of which is hereby acknowledged by AUTHENTIDATE HOLDING CORP., a
Delaware corporation (the “Company”), WOLFE, AXELROD, WEINBERGER ASSOCIATES, LLC (the “Holder”), is hereby granted the right to purchase, at any time from and after the
2nd day of August 2010 (the “Issue Date”)
until 5:00 P.M., New York City time, on August 2, 2015 (the “Warrant Exercise Term”), up to ONE HUNDRED THOUSAND (100,000) fully-paid and non-assessable shares of the Company’s Common Stock, $.001 par value per share
(“Common Stock”) subject to and in accordance with the vesting provisions set forth below in Section 1.1. In addition, the Warrant Exercise Term may automatically be reduced in accordance with the provisions of
Section 1.2, below. 
  

	 	1.	Exercise of Warrant  

1.1 Exercise Price, Vesting and Mechanics of Exercise. 

(a) During the Warrant Exercise Term, this Warrant shall be exercisable at a per share price of $0.70 (the
“Exercise Price”), subject to adjustment as provided in Section 2 hereof, payable in cash or by certified or official bank check in New York Clearing House funds. Subject to the vesting conditions set forth below, the rights
represented by this Warrant may be exercised in whole or in part at any time during the Warrant Exercise Term, upon surrender of the original of this warrant certificate with the annexed Notice of Exercise duly executed, together with payment of the
Exercise Price for the shares of Common Stock purchased at the Company’s principal executive offices. Upon the occurrence of all of such events, the registered Holder of the Warrant shall be entitled to receive a certificate or certificates for
the shares of Common Stock so purchased (the “Warrant Shares”). This warrant (the “Warrant”) has been issued by the Company pursuant to that certain Retainer Agreement (the “Agreement”) between the
Company and the original Holder dated July 26, 2010 and is subject to the certain vesting, forfeiture and other 

 
provisions as set forth below and in the Agreement. This Warrant may be exercised by the Holder as to the whole or any lesser number of an aggregate of the Warrant Shares covered hereby in
accordance with the vesting requirements set forth in Section 1.1(b) of this Warrant. 

(b) Commencing on the Issue Date, and provided Holder is performing services to the Company pursuant
to the Agreement, this Warrant may be exercised to purchase Warrant Shares in monthly increments of
1/12th of the total number of Warrant Shares on each 30
day anniversary of the Issue Date during the first 12 months of the Warrant Exercise Term. Following the first anniversary of the Issue Date, this Warrant shall be exercisable for all of the Warrant Shares covered by this Warrant until the
expiration of the Warrant Exercise Term or such earlier date as set forth in Section 1.2 of this Warrant and Section 6 of the Agreement. 

(c) The purchase rights represented by this Warrant are exercisable at the option of the Holder hereof, in whole or in
part (but not as to fractional shares of the Common Stock) during any period in which this Warrant may be exercised as set forth above. In the case of the purchase of less than all the shares of Common Stock purchasable under this Warrant, the
Company shall cancel this Warrant upon the surrender thereof and, upon the written request of the Holder, the Company shall execute and deliver a new Warrant of like tenor for the balance of the shares of Common Stock purchasable hereunder.

 1.2 Early Termination of Warrant Exercise Term. In the event that (a) the original Holder
determines to terminate the Agreement for any reason other than as described in Sections 6(i) or 6(ii) of the Agreement, or (b) the Company determines to terminate the Agreement for the reasons described in Section 6(ii) of the
Agreement, than this Warrant shall only be exercisable for that number of Warrant Shares that were vested as of such termination date and further provided that in such event, the Warrant Exercise Term shall immediately be reduced, without any
further action by either party, to be equal to a period of 90 days from the date of termination. 
 1.3
Delivery of Warrant Shares. Certificates for Warrant Shares purchased hereunder shall be transmitted by the transfer agent of the Company to the Holder by physical delivery to the address specified by the Holder in the Notice of Exercise within
three business days from the delivery to the Company of the Notice of Exercise, surrender of this Warrant and payment of the aggregate Exercise Price as set forth above. This Warrant shall be deemed to have been exercised on the date on which this
Warrant is surrendered and payment of the Exercise Price is received by the Company. The Warrant Shares shall be deemed to have been issued, and Holder or any other person so designated to be named therein shall be deemed to have become a holder of
record of such shares for all purposes, as of the date on which all of the criteria described in the immediately preceding sentence have occurred, irrespective of the date of delivery of such certificate or certificates, except that, if the date of
such surrender and payment is a date when the stock transfer books of the Company are closed, such person shall 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. 
 1.4 Transfer Taxes. The issuance of certificates for shares of Common Stock upon the exercise
of this Warrant shall be made without charge to the Holder hereof of any Federal and state stamp, original issue or similar taxes which may be payable in respect of the issue of any Warrant Share. Certificates representing Warrant Shares shall be
issued in the name of, or in such names as may be directed by, the Holder hereof; provided, however, that the Company shall not be required to pay any tax which may be payable in respect of any transfer involved in the issuance and delivery of such
certificate in a name other than that of the Holder 
  

 - 2 - 

 
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. 
 1.5 Covenants
by Company. The Company covenants that it will at all times reserve and keep available out of its authorized Common Stock, solely for the purpose of issuance upon exercise of this Warrant as herein provided, such number of shares of Common Stock
as shall then be issuable upon the exercise of this Warrant. The Company covenants that all shares of Common Stock which shall be so issuable shall be duly and validly issued and fully-paid and non-assessable. 

 

	 	2.	Adjustments and Extraordinary Events  

2.1 Stock Dividends, Subdivisions, Reclassifications or Combinations. If during the Warrant Exercise Term, the
Company shall (A) declare a dividend or make a distribution on its Common Stock in shares of its Common Stock, (B) subdivide or reclassify the outstanding shares of Common Stock into a greater number of shares, or (C) combine or
reclassify the outstanding Common Stock into a smaller number of shares, the Exercise Price in effect at the time of the record date for such dividend or distribution or the effective date of such subdivision, combination or reclassification shall
be proportionately adjusted. Any adjustment made herein which results in a decrease (or increase) in the Exercise Price shall also effect a proportional increase (or decrease) in the number of shares of Common Stock into which this Warrant is
exercisable. Successive adjustments in the Exercise Price shall be made whenever any event specified above shall occur. 

2.2 Reorganization, Reclassification, Merger, Consolidation or Disposition of Assets. If during the Warrant
Exercise Term (i) the Company shall reorganize its capital, reclassify its capital stock, consolidate or merge with or into another corporation (where the Company is not the surviving corporation or where there is a change in or distribution
with respect to the Common Stock of the Company); (ii) any tender offer or exchange offer (whether by the Company or another individual or entity) is completed pursuant to which holders of Common Stock are permitted to tender or exchange their
shares for other securities, cash or property; (iii) the Company shall sell, transfer or otherwise dispose of all or substantially all of its property, assets or business to another corporation and, pursuant to the terms of such reorganization,
reclassification, merger, consolidation, tender or exchange offer, or disposition of assets, shares of common stock of the successor or acquiring corporation, or any cash, shares of stock or other securities or property of any nature whatsoever
(including warrants or other subscription or purchase rights) in addition to or in lieu of common stock of the successor or acquiring corporation (“Other Property”), are to be received by or distributed to the holders of Common
Stock of the Company, then the Holder shall have the right thereafter to receive, upon exercise of this Warrant, the number of shares of common stock of the successor or acquiring corporation or of the Company, if it is the surviving corporation,
and Other Property receivable upon or as a result of such reorganization, reclassification, merger, consolidation, tender or exchange offer, or disposition of assets by a Holder of the number of shares of Common Stock for which this Warrant is
exercisable immediately prior to such event. In case of any such reorganization, reclassification, merger, tender or exchange offer, consolidation or disposition of assets (“Extraordinary Transaction”), the successor or acquiring
corporation (if other than the Company) shall expressly assume the due and punctual observance and performance of each and every covenant and condition of this Warrant to be performed and observed by the Company and all the obligations and
liabilities hereunder, subject to such modifications as may be deemed appropriate (as determined in good faith by resolution of the Board of Directors of the Company) 

 

 - 3 - 

 
in order to provide for adjustments of Warrant Shares for which this Warrant is exercisable which shall be as nearly equivalent as practicable to the adjustments provided for in this
Section 2.2. As soon as commercially practicable following the Extraordinary Transaction, the successor or acquiring corporation (if other than the Company), shall deliver to Holder a new warrant in repacement of this Warrant consistent
with the provisions referenced in the immediately preceding sentence against receipt by such successor or acquiring corporation of the original of this Warrant. For purposes of this Section 2.2, “common stock of the successor or
acquiring corporation” shall include stock of such corporation of any class which is not preferred as to dividends or assets over any other class of stock of such corporation and which is not subject to redemption and shall also include any
evidences of indebtedness, shares of stock or other securities which are convertible into or exchangeable for any such stock, either immediately or upon the arrival of a specified date or the happening of a specified event and any warrants or other
rights to subscribe for or purchase any such stock. The foregoing provisions of this Section 2.2 shall similarly apply to successive reorganizations, reclassifications, mergers, tender or exchange offers, consolidations or disposition of
assets. 
 2.3 Notice of Adjustment. Whenever the number of Warrant Shares or number or kind of securities
or other property purchasable upon the exercise of this Warrant or the Exercise Price is adjusted in accordance with this Section 2, as herein provided, the Company shall give prior written notice thereof to the Holder of at least 15 days prior
to the date on which the Company closes its books or takes a record for determining the particular event, which notice shall state the number of Warrant Shares (and other securities or property) purchasable upon the exercise of this Warrant and the
Exercise Price of such Warrant Shares (and other securities or property) after such adjustment, setting forth a brief statement of the facts requiring such adjustment and setting forth the computation by which such adjustment was made. 

 

	 	3.	Restrictions on Transfer  

(a) The Holder acknowledges that he has been advised by the Company that this Warrant and the Warrant Shares issuable upon
exercise thereof (collectively the “Securities”) have not been registered under the Securities Act of 1933, as amended (the “Securities Act”), that the Warrant is being issued, and the shares issuable upon exercise
of the Warrant will be issued, on the basis of the statutory exemption provided by section 4(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 contained herein. The Holder acknowledges that he has been informed by the Company of, or is otherwise familiar with, the nature of the limitations imposed by the Securities Act
and the rules and regulations thereunder on the transfer of securities. In particular, 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, and the Company has no obligations or intention to so register the Securities except as may otherwise
be provided herein, 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 Securities 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 Warrant and Warrant Shares must be held indefinitely
unless a subsequent disposition thereof is registered under the Securities Act or registered or qualified under any applicable state securities or “blue-sky” laws or is exempt from 

 

 - 4 - 

 
registration and/or qualification. The Holder has no need for liquidity in its investment in the Company, and is able to bear the economic risk of such investment for an indefinite period and to
afford a complete loss thereof. The Holder is an “accredited investor” as such term is defined in Rule 501 (the provisions of which are known to the Holder) promulgated under the Act. 

The Holder acknowledges that the securities shall bear the following legend: 

“THESE SECURITIES HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933. SUCH SECURITIES MAY NOT BE SOLD OR OFFERED FOR SALE,
TRANSFERRED, HYPOTHECATED OR OTHERWISE ASSIGNED IN THE ABSENCE OF AN EFFECTIVE REGISTRATION STATEMENT WITH RESPECT THERETO UNDER SUCH ACT OR AN OPINION OF COUNSEL TO THE COMPANY THAT AN EXEMPTION FROM REGISTRATION FOR SUCH SALE, OFFER, TRANSFER,
HYPOTHECATION OR OTHER ASSIGNMENT IS AVAILABLE UNDER SUCH ACT.” 
 (b) Disposition of Warrant or
Warrant Shares. With respect to any offer, sale or other disposition of this Warrant or any shares of Common Stock acquired pursuant to the exercise of this Warrant prior to registration of such Warrant or shares of Common Stock, the Holder
agrees to give written notice to the Company prior thereto, describing briefly the manner thereof, together with evidence, reasonably satisfactory to the Company (which shall include such representation of the transferee regarding investment intent
as the Company may request, to the effect that such offer, sale or other disposition may be effected without registration or qualification under the Act as then in effect or any federal or state securities law then in effect) of this Warrant or such
shares of Common Stock and indicating whether or not under the Act certificates for this Warrant or such shares of Common Stock to be sold or otherwise disposed of require any restrictive legend as to applicable restrictions on transferability in
order to ensure compliance with such law. Upon receiving such written notice and reasonably satisfactory evidence, the Company, as promptly as practicable but no later than seven (7) days after receipt of the written notice, shall notify
the Holder that the Holder may sell or otherwise dispose of this Warrant or such shares of Common Stock, all in accordance with the terms of the notice delivered to the Company. If the Company determines that the evidence is not reasonably
satisfactory to the Company, the Company shall so notify the Holder promptly with details thereof after such determination has been made. Notwithstanding the foregoing, any shares of Common Stock issued upon exercise of this Warrant or such
shares of Common Stock may be offered, sold or otherwise disposed of in accordance with Rule 144 under the Act and in compliance with the applicable statutory resale restrictions imposed by applicable securities laws, provided that the Company
shall have been furnished with such information as the Company may reasonably request to provide a reasonable assurance that the provisions of Rule 144 and the applicable resale restrictions imposed by the securities laws have been
satisfied. Each certificate representing this Warrant or the shares of Common Stock thus transferred shall bear a legend as to the applicable restrictions on transferability in order to ensure compliance with such laws, unless pursuant to an
opinion of counsel for the Holder, such legend is not required in order to ensure compliance with such laws. The Company may issue stop transfer instructions to its transfer agent in connection with such restrictions. 

(c) Lock-up of Warrant Shares. Notwithstanding anything else set forth in this Warrant, with respect to the
Warrant Shares, commencing on each incremental vesting date of the Warrant Shares and ending on the one year anniversary of each such incremental vesting date (each such one (1) year period pertaining to vested Warrant Shares is referred to

  

 - 5 - 

 
herein as the “Lock-Up Period”), the Holder shall not, directly or indirectly, through an “affiliate”, “associate” (as such terms are defined in the General
Rules and Regulations under the Securities Act of 1933, as amended (the “Securities Act”)), a family member or otherwise (a) sell, transfer, assign, offer, pledge, contract to sell, transfer or assign, sell any option or contract to
purchase, purchase any option or contract to sell, transfer or assign, grant any option, right or warrant to purchase, or otherwise transfer, assign or dispose of, directly or indirectly (either privately or publicly pursuant to Rule 144 of the
General Rules and Regulations under the Securities Act, or otherwise), any of the Warrant Shares, or (b) enter into any swap or other arrangement that transfers or assigns to another person or entity, in whole or in part, any of the economic
benefits, obligations or other consequences of any nature of ownership of the Warrant Shares, whether any such transaction is to be settled by delivery of the Warrant Shares in cash or otherwise. In the event the Holder exercises all or any portion
of this Warrant for Warrant Shares during the Lock-up Period, the Holder agrees that the certificates representing such Warrant Shares shall bear a legend substantially as follows: 

“THE SECURITIES REPRESENTED BY THIS CERTIFICATE ARE SUBJECT TO CERTAIN RESTRICTIONS AGAINST RESALE AS SET FORTH IN THAT CERTAIN
WARRANT, DATED AS OF AUGUST 13, 2010, AS MAY BE AMENDED OR MODIFIED FROM TIME TO TIME.” 
  

	 	4.	Piggyback Registration Rights. 

4.1 Registration. If at any time during the Warrant Exercise Term, the Company shall determine to prepare and file
with the Commission a registration statement under the Securities Act of 1933, as amended (the “Securities Act”) relating to an offering for its own account or the account of others under the Securities Act of any of its equity
securities, other than a registration statement on Form S-4 or Form S-8 (each as promulgated under the Securities Act) or their then equivalents relating to equity securities to be issued solely in connection with any acquisition of any entity or
business or equity securities issuable in connection with the stock option or other employee benefit plans, then the Company shall send to each holder of this Warrant (a “Holder”) a written notice of such determination and, if
within fifteen (15) days after the date of such notice, any such Holder shall so request in writing, the Company shall include in such registration statement all or any part of such Warrant Shares which such Holder requests to be registered,
subject to customary underwriter cutbacks applicable to all holders of registration rights, provided that if at any time after giving written notice of its intention to register any securities and prior to the effective date of the registration
statement filed in connection with such registration, the Company shall determine for any reason not to register or to delay registration of such securities, the Company may, at its election, give written notice of such determination to such Holder
and, thereupon, (A) in the case of a determination not to register, shall be relieved of its obligation to register any Warrant Shares in connection with such registration (but not from its obligation to pay expenses in accordance with
Section 4.5 hereof), and (B) in the case of a determination to delay registering, shall be permitted to delay registering any Warrant Shares being registered pursuant to this Section 4(a) for the same period as the delay in
registering such other securities. Notwithstanding the foregoing, the Company shall not be required to register any Warrant Shares pursuant to this Section 4(a) that are eligible for resale pursuant to Rule 144(b) promulgated under the
Securities Act or that are the subject of a then effective registration statement. For the purpose of the foregoing, inclusion of the Warrant Shares by the Holder in a registration statement under a condition that the offer and/or sale of such
Warrant Shares not commence until a date not to exceed the greater of (i) the expiration of the Lock-Up Period with respect to the Warrant Shares or (ii) 90 days from the effective date of such registration statement shall be deemed to be
in compliance with this sub-paragraph. 
  

 - 6 - 

 4.2 Exceptions. The Company shall have no obligation to include
Warrant Shares of any Holder in a registration statement pursuant to this Section 4, unless and until such Holder (i) in connection with any underwritten offering, agrees to enter into an underwriting agreement, a custody agreement and
power of attorney and any other customary documents required in an underwritten offering all in customary form and containing customary provisions and (ii) shall have furnished the Company with all information and statements about or pertaining
to such Holder in such reasonable detail and on such timely basis as is reasonably deemed by the Company to be legally required with respect to the preparation of the registration statement. 

4.3 Procedures. The foregoing registration rights shall be contingent on the Holders furnishing the Company with
such appropriate information (relating to the intentions of such Holders) as the Company shall reasonably request in writing. Each Holder agrees to furnish to the Company a completed selling security holder questionnaire in such form as is provided
by the Company to the Holder not less than two business days prior to date on which the Company files the registration statement (the “Filing Date”). The Company shall not be required to include the Warrant Shares of a Holder in a
registration statement for any Holder who fails to furnish to the Company a fully completed questionnaire at least two business days prior to the Filing Date. The Company may require each selling Holder to furnish to the Company a certified
statement as to the number of shares of Common Stock beneficially owned by such Holder and, if required by the Commission, the natural persons thereof that have voting and dispositive control over the Shares. Following the effective date of such
registration, the Company shall upon the request of any owner of Warrants and/or Warrant Shares forthwith supply such number of prospectuses meeting the requirements of the Securities Act as shall be requested by such owner to permit such Holder to
make a public offering of all Warrant Shares from time to time offered or sold to such Holder, provided that such Holder shall from time to time furnish the Company with such appropriate information (relating to the intentions of such Holder) as the
Company shall request in writing. The Company shall also use its best efforts to qualify the Warrant Shares for sale in such states as such Holder shall reasonably designate. The Company may withdraw the registration at any time. 

4.4 Indemnity. The Company shall indemnify and hold harmless each such Holder and each underwriter, if any, within
the meaning of the Securities Act, who may purchase from or sell for any such Holder any Warrant Shares from and against any and all losses, claims, damages and liabilities caused by any untrue statement or alleged untrue statement of a material
fact contained in the Registration Statement or any post-effective amendment thereto or any registration statement under the Securities Act or any prospectus included therein required to be filed or furnished by reason of this Section 4 or
caused by any omission or alleged omission to state therein a material fact required to be stated therein or necessary to make the statements therein not misleading except insofar as such losses, claims, damages or liabilities are caused by any such
untrue statement or alleged untrue statement or omission or alleged omission based upon information furnished or required to be furnished in writing to the Company by such Holder or underwriter expressly for use therein, which indemnification shall
include each person, if any, who controls any such underwriter within the meaning of the Securities Act; provided, however, that the Company shall not be obliged so to indemnify any such Holder or underwriter or controlling person unless such Holder
or underwriter shall at the same time agree to indemnify the Company, its directors, each officer signing the related registration statement and each person, if any, who controls the Company within the meaning of the Securities Act, from and against
any and all losses, claims, damages and liabilities caused by any untrue statement or alleged untrue statement of a material fact contained in any registration statement or any prospectus required to be filed or furnished by reason of this
Section 4 or caused by any omission to state therein a 
  

 - 7 - 

 
material fact required to be stated therein or necessary to make the statements therein not misleading insofar as such losses, claims, damages or liabilities are caused by any untrue statement or
alleged untrue statement or omission based upon information furnished in writing to the Company by any such Holder or underwriter expressly for use therein. 

4.5. Registration Expenses. The Holder thereof shall pay all transfer taxes, if any, relating to the sale of its
shares, any registration fees, underwriting discounts or commissions or the equivalent thereof applicable to the sale of its shares and the fees of his own counsel. Other than as described in the preceding sentence, the Company shall pay all
expenses incident to the registration of the Warrant Shares by the Company, including, without limitation, all registration and filing fees, fees and expenses of compliance with securities or blue sky laws, underwriting discounts, fees and expenses
(other than any Holder’s portion of the expenses, including any underwriting discounts or commissions or the equivalent thereof), printing expenses, messenger and delivery expenses, and reasonable fees and expenses of counsel for the Company
and the independent certified public accountants and other persons retained by the Company. 
  

	 	5.	Exercise Limitations. 

(a) A Holder shall not have the right to exercise any portion of this Warrant to the extent that after giving effect to
such issuance after exercise, such Holder (together with such Holder’s affiliates), as set forth on the applicable Notice of Exercise, would beneficially own in excess of 4.99% of the number of shares of the Common Stock outstanding immediately
after giving effect to such issuance. For purposes of the foregoing sentence, the number of shares of Common Stock beneficially owned by such Holder and its affiliates shall include the number of shares of Common Stock issuable upon exercise of this
Warrant with respect to which the determination of such sentence is being made, but shall exclude the number of shares of Common Stock which would be issuable upon (A) exercise of the remaining, nonexercised portion of this Warrant beneficially
owned by such Holder or any of its affiliates and (B) exercise or conversion of the unexercised or nonconverted portion of any other securities of the Company (including, without limitation, any other shares of Common Stock or Warrants) subject
to a limitation on conversion or exercise analogous to the limitation contained herein beneficially owned by such Holder or any of its affiliates. Except as set forth in the preceding sentence, for purposes of this Section 4, beneficial
ownership shall be calculated in accordance with Section 13(d) of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), it being acknowledged by a Holder that the Company is not representing to such Holder that
such calculation is in compliance with Section 13(d) of the Exchange Act and such Holder is solely responsible for any schedules required to be filed in accordance therewith. 

(b) To the extent that the limitation contained in this Section 5 applies, the determination of whether this
Warrant is exercisable (in relation to other securities owned by such Holder) and of which a portion of this Warrant is exercisable shall be in the sole discretion of a Holder, and the submission of a Notice of Exercise shall be deemed to be each
Holder’s determination of whether this Warrant is exercisable (in relation to other securities owned by such Holder) and of which portion of this Warrant is exercisable, in each case subject to such aggregate percentage limitation, and the
Company shall have no obligation to verify or confirm the accuracy of such determination. For purposes of this Section 5, in determining the number of outstanding shares of Common Stock, a Holder may rely on the number of outstanding
shares of Common Stock as reflected in (A) the Company’s most recent Form 10-Q or Form 10-K, as the case may be, (B) a more recent public announcement by the Company or (C) any other 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 

 

 - 8 - 

 
trading days confirm orally and in writing to such 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 Warrant, by such Holder or its affiliates since the date as of which such number of outstanding shares of Common Stock was reported. The provisions of
this Section 5 may be waived by such Holder, at the election of such Holder, upon not less than 61 days’ prior notice to the Company, and the provisions of this Section 5 shall continue to apply until such 61st day (or
such later date, as determined by such Holder, as may be specified in such notice of waiver). 
  

	 	6.	Exchange and Replacement of Warrant Certificates. 

6.1 Exchanges. This Warrant Certificate is exchangeable without expense, upon the surrender hereof by the
registered Holder at the principal executive office of the Company, for a new Warrant Certificate of like tenor and date representing in the aggregate the right to purchase the same number of Warrant Shares in such denominations as shall be
designated by the Holder thereof at the time of such surrender. 
 6.2 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. 
  

	 	7.	Elimination of Fractional Interests. 

The Company shall not be required to issue certificates representing fractions of the shares of Common Stock and shall not
be required to issue scrip or pay cash in lieu of fractional interests, it being the intent of the parties that all fractional interests shall be eliminated by rounding any fraction up or down to the nearest whole number of shares of Common Stock.

  

	 	8.	Rights of Warrant Holders. 

Nothing contained in this Agreement shall be construed as conferring upon the Holder any rights whatsoever as a
stockholder of the Company, either at law or in equity, including without limitation, or Holders the right to vote or to consent or to receive notice as a stockholder in respect of any meetings of stockholders for the election of directors the right
to receive dividends or any other matter. 
  

	 	9.	Miscellaneous. 

9.1 Successors and Assigns. All the covenants and agreements made by the Company in this Warrant shall bind its
successors and assigns. This Warrant shall be for the sole and exclusive benefit of the Holder and nothing in this Warrant shall be construed to confer upon any person other than the Holder any legal or equitable right, remedy or claim hereunder.

 9.2 Acceptance. Receipt of this Warrant by the Holder shall constitute acceptance of and agreement to
all of the terms and conditions contained herein. 
  

 - 9 - 

 9.3 No Recourse. No recourse shall be had for any claim based hereon
or otherwise in any manner in respect hereof, against any incorporator, stockholder, officer or director, past, present or future, of the Company or of any predecessor corporation, whether by virtue of any constitutional provision or statute or rule
of law, or by the enforcement of any assessment or penalty or in any other manner, all such liability being expressly waived and released by the acceptance hereof and as part of the consideration for the issue hereof. 

9.4 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. 
 9.5
Notices. All notices required or permitted hereunder shall be in writing and shall be deemed effectively given: (a) upon personal delivery to the party to be notified, (b) when sent by confirmed telex or facsimile if sent during normal
business hours of the recipient, if not, then on the next business day, (c) five days after having been sent by registered or certified mail, return receipt requested, postage prepaid, or (d) one day after deposit with a nationally
recognized overnight courier, specifying next day delivery, with written verification of receipt. All communications shall be sent to the Company at the address listed on the signature page hereto and to Holder at the applicable address set forth on
the applicable signature page to the Subscription Agreement or at such other address as the Company or Holder may designate by ten (10) days advance written notice to the other parties hereto. 

9.6 Governing Law. The provisions of this Warrant shall in all respects be constructed according to, and the rights
and liabilities of the parties hereto shall in all respects be governed by, the laws of the State of New York. This Warrant shall be deemed a contract made under the laws of the State of New York and the validity of this Warrant and all rights and
liabilities hereunder shall be determined under the laws of said State. 
 9.7 Headings. The headings of
the Sections of this Warrant are inserted for convenience only and shall not be deemed to constitute a part of this Warrant. 

Signature page to Common Stock Purchase Warrant follows. 

 

 - 10 - 

 IN WITNESS WHEREOF, AUTHENTIDATE HOLDING CORP. has caused this Warrant to be executed in its
corporate name by its officer, and its seal to be affixed hereto. 
 Dated: August 13, 2010 

 

			
	AUTHENTIDATE HOLDING CORP.
		
	By:	 	 
		 	 Name: O’Connell Benjamin

Title:   President

	
	 Connell Corporate Center

300 Connell Drive, 5th Floor
 Berkeley Heights,
NJ 07922

  

 - 11 - 

 NOTICE OF EXERCISE 

 

	TO:	AUTHENTIDATE HOLDING CORP. 

	 	Connell Corporate Center 

	 	300 Connell Drive, 5th Floor 

	 	Berkeley Heights, NJ 07922 

	 	Attention: Chief Financial Officer 

The undersigned Holder hereby irrevocably elects to exercise the right to purchase
                         shares of Common Stock covered by this Warrant according to the conditions hereof and herewith
makes full payment of the Exercise Price of such shares. 
 Kindly deliver to the undersigned a certificate representing the
Shares. 
 INSTRUCTIONS FOR DELIVERY 
  

			
	Name:
                                         
                                         
                                         
                                   	  	
	(please typewrite or print in block letters)	  
		
	Address:
                                         
                                         
                                         
                              	  	
		
	Tax I.D. No. or Social Security No.:
                                         
                                         
                   	  	

 If such number of shares shall not be all the shares purchasable upon the exercise of the Warrants
evidenced by this Warrant, a new warrant certificate for the balance of such Warrants remaining unexercised shall be registered in the name of and delivered to: 
  

			
	Name:
                                         
                                         
                                         
                                   	  	
	(please typewrite or print in block letters)	  
		
	Address:
                                         
                                         
                                         
                              	  	
		
	Tax I.D. No. or Social Security No.:
                                         
                                         
                   	  	

			
		
	Dated:
                                         
                                         
         	  	

			
		
	Signature
                                         
                                         
                      	  	

 STATE OF                 )

 COUNTY OF             ) ss: 

On this      day of
                    , before me personally came             , to me known,
who being by me duly sworn, did depose and say that he resides at                         , that he is the holder of the
foregoing instrument and that he executed such instrument and duly acknowledged to me that he executed the same. 
  

	
	  
	Notary Public

  

 - 12 - 

 [FORM OF ASSIGNMENT] 

(To be executed by the registered holder if such holder 

desires to transfer the Warrant Certificate.) 

FOR VALUE RECEIVED, the undersigned Holder of this Warrant hereby sells, assigns and transfers the foregoing Warrant and all rights
evidenced thereby to 
  

					
	Name:	 		 	  
		 		 	(Please Print)
			
	Address:	 		 	 
		 		 	(Please Print)
			
	Tax ID No.:	 		 	 

 and does hereby irrevocably constitute and
appoint                                 , Attorney, to transfer the within
Warrant Certificate on the books of Authentidate Holding Corp., with full power of substitution. 
 NOTE: The signature to this Assignment Form
must correspond with the name as it appears on the face of the Warrant, without alteration or enlargement or any change whatever. Officers of corporations and those acting in a fiduciary or other representative capacity should file proper evidence
of authority to assign the foregoing Warrant. 
  

									
					
	Dated:	 	__________________	 		 	Holder:	 	 
				
		 		 		 	 
		 		 		 	(Print Name)
				
		 		 		 	 
		 		 		 	(Signature)

 STATE OF
                        ) 

COUNTY OF                     ) ss: 

On this      day of
                , before me personally came                 , to me known,
who being by me duly sworn, did depose and say that he resides at                         , that he is the holder of the
foregoing instrument and that he executed such instrument and duly acknowledged to me that he executed the same. 
  

					
			
	 	 		 	  
		 		 	Notary Public

  

 - 13 -

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