Document:

Warrant to Pruchase Common Stock

 Exhibit 10.1 
 NEITHER THIS WARRANT NOR THE UNDERLYING SHARES OF COMMON STOCK HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED OR ANY STATE SECURITIES LAWS. NO SALE OR DISPOSITION MAY BE EFFECTED WITHOUT (i) AN
EFFECTIVE REGISTRATION STATEMENT RELATED THERETO, (ii) AN OPINION OF COUNSEL OR OTHER EVIDENCE, REASONABLY SATISFACTORY TO THE COMPANY, THAT SUCH REGISTRATION IS NOT REQUIRED, (iii) RECEIPT OF NO-ACTION LETTERS FROM THE APPROPRIATE
GOVERNMENTAL AUTHORITIES, OR (iv) OTHERWISE COMPLYING WITH THE PROVISIONS OF SECTION 7 OF THIS WARRANT. 
 BAKBONE SOFTWARE
INCORPORATED 
 WARRANT TO PURCHASE 4,425,126 SHARES 
 OF COMMON STOCK 
 THIS CERTIFIES THAT, for value received, SUN MICROSYSTEMS, INC.
(“Sun”) and its assigns are entitled to subscribe for and purchase up to 4,425,126 shares of the fully paid and nonassessable Common Stock (as adjusted pursuant to Section 4 hereof, the “Shares”) of
BakBone Software Incorporated, a Canadian corporation (the “Company”), at the price of $1.78 per share (such price and such other price as shall result, from time to time, from the adjustments specified in
Section 4 hereof is herein referred to as the “Warrant Price”), subject to the provisions and upon the terms and conditions hereinafter set forth. As used herein, the term “Common Stock” shall mean the
Company’s Common Stock, no par value, or any stock into or for which such Common Stock may hereafter be converted or exchanged prior to or concurrent with the exercise of this Warrant. As used herein, (a) the term “Date of
Grant” shall mean April 18, 2007, and (b) the term “Other Warrants” shall mean any warrant issued upon transfer or partial exercise of this Warrant or issued in respect of this Warrant pursuant to
Section 4 hereof. The term “Warrant” as used herein shall be deemed to include Other Warrants unless the context clearly requires otherwise. 
 This Warrant is being issued pursuant to a Technology Development and License Agreement dated as of December 18, 2006 (the “TDLA”) between Sun and BakBone Software, Inc., a California corporation
and a wholly owned subsidiary of the Company (the “Subsidiary”). All capitalized terms used but not otherwise defined herein shall have the meaning ascribed to such terms in the TDLA. 
 1. Exercisability. 
 (a) Vesting of Shares. The number of Shares of Common Stock issuable pursuant to this Warrant shall be dependent on the achievement of certain milestones as set forth below and subject to adjustment pursuant to Section 4
hereof. A portion of the Shares shall become exercisable on the Initial Vesting Date (as defined below) and the remaining Shares shall vest as follows: 
 (i) The Initial Vesting Date. 20% of the total number of Shares shall become exercisable on the Initial Vesting Date. 

 (ii) Second Vesting Date. 26-2/3% of the total number of Shares shall become
exercisable on the Second Vesting Date (as defined below), provided that the cumulative License Fees payable under the TDLA for all periods through the first anniversary of the Initial Vesting Date are at least $5,000,000. 
 (iii) Third Vesting Date. 26-2/3% of the total number of Shares shall become exercisable on the Third Vesting Date (as defined
below), provided that the cumulative License Fees payable under the TDLA for all periods through the second anniversary of the Initial Vesting Date are at least $10,000,000. 
 (iv) Fourth Vesting Date. 26-2/3% of the total number of Shares (with any remaining fractions rounded up) shall become exercisable
on the Fourth Vesting Date (as defined below), provided that the cumulative License Fees payable under the TDLA for all periods through the third anniversary of the Initial Vesting Date are at least $15,000,000. 
 (b) Acceleration of Vesting. In the event of a Change of Control, 25% of all then unvested Shares shall become immediately
exercisable. In the event Sun terminates the TDLA due to a material breach by the Subsidiary that is not cured as provided in Section 9.2 of the TDLA, all then unvested Shares shall become immediately exercisable. 
 (c) Definitions. 
 (i) A “Change of Control” of the Company shall mean each and all of the following occurrences: 
 (1) The stockholders of the Company approve a merger or consolidation of the Company with any other corporation, other than a merger or consolidation which would result in the voting securities of the Company
outstanding immediately prior thereto continuing to represent (either by remaining outstanding or by being converted into voting securities of the surviving entity or its parent company) more than fifty percent (50%) of the total voting power
represented by the voting securities of the Company or such surviving entity, or its parent company, outstanding immediately after such merger or consolidation, or the stockholders of the Company approve a plan of complete liquidation of the Company
or an agreement for the sale or disposition by the Company of all or substantially all the Company’s assets. 
 (2) The
stockholders of the Subsidiary approve a merger or consolidation of the Subsidiary with any other corporation, other than a merger or consolidation which would result in the voting securities of the Subsidiary outstanding immediately prior thereto
continuing to represent (either by remaining outstanding or by being converted into voting securities of the surviving entity or its parent company) more than fifty percent (50%) of the total voting power represented by the voting securities of
the Subsidiary or such surviving entity, or its parent company, outstanding immediately after such merger or consolidation, or the stockholders of the Subsidiary approve a plan of complete liquidation of the Subsidiary or an agreement for the sale
or disposition by the Company or the Subsidiary of all or substantially all the Subsidiary’s assets or capital stock. 
  

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 (3) The acquisition by any person as the “beneficial owner” (as defined in
Rule 13d-3 of the Securities Exchange Act of 1934, as amended), directly or indirectly, of securities of the Company representing fifty percent (50%) or more of the total voting power represented by the Company’s then outstanding voting
securities. 
 (4) The acquisition by any person (other than the Company or any direct or indirect subsidiary of the Company)
as the “beneficial owner” (as defined in Rule 13d-3 of the Securities Exchange Act of 1934, as amended), directly or indirectly, of securities of the Subsidiary representing fifty percent (50%) or more of the total voting power
represented by the Subsidiary’s then outstanding voting securities. 
 (5) A change in the composition of the Board of
Directors of the Company as a result of which fewer than a majority of the directors are “Incumbent Directors.” “Incumbent Directors” shall mean directors who either (A) are directors of the Company as of the date hereof or
(B) are elected, or nominated for election, to the Board of Directors with the affirmative votes (either by a specific vote or by approval of the proxy statement of the Company in which such person is named as a nominee for election as a
director without objection to such nomination) of at least three-quarters of the Incumbent Directors at the time of such election or nomination (but shall not include an individual whose election or nomination is in connection with an actual or
threatened proxy contest relating to the election of directors of the Company). 
 (ii) The “Fourth Vesting
Date” shall be the date that Sun receives an undisputed invoice under Section 7.1 of the TDLA with respect to the Royalty and Support Fees Report for the quarter ending on the third anniversary of the Initial Vesting Date. 

(iii) The “Initial Vesting Date” shall mean the last day of the calendar quarter during which Sun notifies the
Subsidiary of the General Availability of the Base Technology. 
 (iv) “License Fees” shall mean the amounts
owed to the Subsidiary by Sun under the TLDA. 
 (v) The “Second Vesting Date” shall be the date that Sun
receives an undisputed invoice under Section 7.1 of the TDLA with respect to the Royalty and Support Fees Report for the quarter ending on the first anniversary of the Initial Vesting Date. 
 (vi) The “Third Vesting Date” shall be the date that Sun receives an undisputed invoice under Section 7.1 of the
TDLA with respect to the Royalty and Support Fees Report for the quarter ending on the second anniversary of the Initial Vesting Date. 
 (d) Exercise Period. As to each portion hereof that vests in accordance with Section 1(a) above, this Warrant shall be exercisable, in whole or in part, during the term commencing on the date of
vesting and ending on the date that is ten years after the Date of Grant. 
  

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 2. Exercise of Warrant. 
 (a) Method of Exercise; Payment. Subject to Section 1 hereof, the purchase right represented by this Warrant may be
exercised by the holder hereof, in whole or in part and from time to time, at the election of the holder hereof, by (a) the surrender of this Warrant (with the notice of exercise substantially in the form attached hereto as
Exhibit A-1 duly completed and executed) at the principal office of the Company and by the payment to the Company, by certified or bank check, or by wire transfer to an account designated by the Company (a “Wire
Transfer”) of an amount equal to the then applicable Warrant Price multiplied by the number of Shares then being purchased, or (b) if in connection with a registered public offering of the Company’s securities, the surrender of
this Warrant (with the notice of exercise form attached hereto as Exhibit A-2 duly completed and executed) at the principal office of the Company together with notice of arrangements reasonably satisfactory to the Company for payment to the
Company either by certified or bank check or by Wire Transfer from the proceeds of the sale of shares to be sold by the holder in such public offering of an amount equal to the then applicable Warrant Price per share multiplied by the number of
Shares then being purchased or (c) exercise of the “net issuance” right provided for in Section 2(b) hereof. The person or persons in whose name(s) any certificate(s) representing the Shares shall be issuable upon exercise
of this Warrant shall be deemed to have become the holder(s) of record of, and shall be treated for all purposes as the record holder(s) of, the shares represented thereby (and such shares shall be deemed to have been issued) immediately prior to
the close of business on the date or dates upon which this Warrant is exercised. In the event of any exercise of the rights represented by this Warrant, certificates for the shares of stock so purchased shall be delivered to the holder hereof as
soon as practicable and, if requested by the holder of this Warrant, the Company shall cause its transfer agent to deliver the certificate representing Shares issued upon exercise of this Warrant to a broker or other person (as directed by the
holder exercising this Warrant) within the time period required to settle any trade made by the holder after exercise of this Warrant. 
 (b) Right to Convert Warrant into Stock; Net Issuance. 
 (i) Right to Convert.
In addition to and without limiting the rights of the holder under the terms of this Warrant, the holder shall have the right to convert this Warrant or any portion thereof (the “Conversion Right”) into shares of Common Stock as
provided in this Section 2(b) in connection with or following a Change of Control that occurs during the term of this Warrant. Upon exercise of the Conversion Right with respect to a particular number of shares subject to this Warrant
(the “Converted Warrant Shares”), the Company shall deliver to the holder (without payment by the holder of any exercise price or any cash or other consideration) that number of shares of fully paid and nonassessable Common Stock as
is determined according to the following formula: 
  

			
	 X =
	  	B - A
		  	   Y

  

							
	 Where:
	  	X	  	=	  	the number of shares of Common Stock that may be issued to the holder

  

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		  	Y	  	=	  	the fair market value of one share of Common Stock
				
		  	A	  	=	  	the aggregate Warrant Price of the specified number of Converted Warrant Shares immediately prior to the exercise of the Conversion Right (i.e., the number of Converted Warrant Shares
multiplied by the Warrant Price)
				
		  	B	  	=	  	the aggregate fair market value of the specified number of converted Warrant Shares (i.e., the number of Converted Warrant Shares multiplied by the fair market value of one Converted
Warrant Shares)

 No fractional shares shall be issuable upon exercise of the Conversion Right, and, if the number
of shares to be issued determined in accordance with the foregoing formula is other than a whole number, the Company shall pay to the holder an amount in cash equal to the fair market value of the resulting fractional share on the Conversion Date
(as hereinafter defined). For purposes of Section 9 of this Warrant, shares issued pursuant to the Conversion Right shall be treated as if they were issued upon the exercise of this Warrant. 
 (ii) Method of Exercise. The Conversion Right may be exercised by the holder in connection with or following a Change of Control by
the surrender of this Warrant at the principal office of the Company together with a written statement in the form of Exhibit A-3 hereto specifying that the holder thereby intends to exercise the Conversion Right and indicating the number of
shares subject to this Warrant which are being surrendered (referred to in Section 2(b)(i) hereof as the Converted Warrant Shares) in exercise of the Conversion Right. Such conversion shall be effective upon the closing of such Change of
Control (the “Conversion Date”). Certificates for the shares issuable upon exercise of the Conversion Right and, if applicable, a new warrant evidencing the balance of the shares remaining subject to this Warrant, shall be issued as
of the Conversion Date and shall be delivered to the holder as soon as practicable, but in no event later than 30 days following the Conversion Date. 
 (iii) Determination of Fair Market Value. For purposes of this Section 2(b), “fair market value” of a share of Common Stock as of a particular date (the Determination
Date”) shall mean: 
 (1) The average of the closing bid and asked prices of the Common Stock quoted Toronto Stock
Exchange or in the Over-the-Counter Market Summary or the closing price quoted on the Nasdaq Stock Market or any other exchange on which the Common Stock is listed, whichever is applicable, for the ten trading days prior to the date of determination
of fair market value. 
 (2) If the Common Stock is not traded Over-the-Counter or on the Nasdaq Stock Market, Toronto Stock
Exchange or any other exchange, fair market value of the Common Stock per share shall be the highest price per share which the Company could obtain from a willing buyer for shares sold by the Company from authorized but unissued shares of Common
Stock as such price shall be agreed by the parties hereto, or if agreement cannot be 

  

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reached within five business days of delivery of the notice pursuant to Section 2(b)(ii) hereof, as shall be determined by a panel of appraisers.
One appraiser shall be selected by the Holder, one appraiser shall be chosen by the Company and the third appraiser shall be chosen by the first two appraisers. If the appraisers cannot reach agreement as to the fair market value on the foregoing
basis on or before the 30th day following the Holder’s notice of election pursuant to this Section 2(b), then each appraiser shall deliver its appraisal and the appraisal which is neither the highest nor the lowest shall be the fair
market value of a share of Warrant Stock. In the event that the Company fails to choose an appraiser or the three appraisers fail to deliver an appraisal on or before the 30th day after such notice, the appraisal of the appraiser selected by the
Holder shall control and shall be fair market value for the purposes of this Warrant. The cost of the appraiser selected by each party shall be borne by that party and the cost of the third appraiser shall be borne one-half by each party. In the
event that the Company does not select an appraiser or three appraisals are not received on or before the 30th day after such notice of election, the Company shall pay one-half the cost of the Holder’s appraiser. Appraisers selected under this
Section 2(b)(iii)(2) must be unaffiliated with the Holder and the Company and must have reasonable professional qualifications for the appraisal. 
 (c) Exercise Prior to Expiration. If this Warrant is not previously exercised with respect to all Shares that have become
exercisable pursuant to Section 1(c), the Company shall give notice to the Holder not less than 150 days or more than 210 days prior to the expiration of this Warrant. To the extent any portion of this Warrant which is exercisable is not
previously exercised as to all of the vested Shares subject hereto, and if the Company fails to provide the notice required by the previous sentence, and if the fair market value of one share of the Common Stock is greater than the Warrant Price
then in effect, the exercisable portion of this Warrant then expiring shall be deemed automatically exercised pursuant to Section 2(b) above (even if not surrendered) immediately before its expiration. For purposes of such automatic
exercise, the fair market value of one share of the Common Stock upon such expiration shall be determined pursuant to Section 2(b)(iii). To the extent this Warrant or any portion thereof is deemed automatically exercised pursuant to this
Section 2(c), the Company agrees to promptly notify the holder hereof of the number of Shares, if any, the holder hereof is to receive by reason of such automatic exercise. 
 3. Covenants as to Shares. The Company covenants that all Shares that may be issued upon the exercise of the rights represented by this
Warrant will, upon issuance pursuant to the terms and conditions herein, be validly issued, fully paid and nonassessable and free from all taxes, liens and charges with respect to the issue thereof. The Company covenants and agrees that during the
period within which the rights represented by this Warrant may be exercised, the Company will at all times have authorized, and reserved for the purpose of the issue upon exercise of the purchase rights evidenced by this Warrant, a sufficient number
of shares of its Common Stock to provide for the exercise of the rights represented by this Warrant. The Company further covenants and agrees that the Company will from time to time take all such action as may be requisite to assure that the stated
or par value per share of Common Stock is at all times equal to or less than the then effective Warrant Price per share of Common Stock issuable upon exercise of this Warrant. If and so long as the Common Stock issuable upon the exercise of the
rights represented by this Warrant is listed on any national securities exchange or quotation system, the Company will, if permitted by the rules of such exchange or quotation system, use its best efforts to list and keep listed on such exchange or
quotation system, upon official notice of issuance, all shares of such capital stock. 
  

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 4. Adjustment of Warrant Price and Number of Shares. The number and kind of securities
purchasable upon the exercise of this Warrant and the Warrant Price shall be subject to adjustment from time to time upon the occurrence of certain events, as follows: 
 (a) Reclassification or Merger. In case of any reclassification or change of securities of the class issuable upon exercise of this
Warrant (other than a change in par value, or from par value to no par value, or from no par value to par value, or as a result of a subdivision or combination), or in case of any merger of the Company with or into another corporation (other than a
merger with another corporation in which the Company is the acquiring and the surviving corporation and which does not result in any reclassification or change of outstanding securities issuable upon exercise of this Warrant), or in case of any sale
of all or substantially all of the assets of the Company (each, a “Reorganization”), the Company, or such successor or purchasing corporation, as the case may be, shall duly execute and deliver to the holder of this Warrant a new
Warrant (in form and substance satisfactory to the holder of this Warrant), or the Company shall make appropriate provision without the issuance of a new Warrant, so that the holder of this Warrant shall have the right to receive upon exercise of
this Warrant, at a total purchase price not to exceed that payable upon the exercise of the exercisable but unexercised portion of this Warrant, and in lieu of the shares of Common Stock theretofore issuable upon exercise of this Warrant, the kind
and amount of shares of stock, other securities, money and property receivable upon such reclassification, change or merger by a holder of the number of shares of Common Stock then purchasable under this Warrant. Such new Warrant shall provide for
adjustments that shall be as nearly equivalent as may be practicable to the adjustments provided for in this Section 4. The provisions of this subparagraph (a) shall similarly apply to successive reclassifications, changes, mergers
and transfers. 
 (b) Subdivision or Combination of Shares. If the Company at any time while this Warrant remains
outstanding and unexpired shall subdivide or combine its outstanding shares of Common Stock, the Warrant Price shall be proportionately decreased and the number of Shares issuable hereunder shall be proportionately increased in the case of a
subdivision or and the Warrant Price shall be proportionately increased and the number of Shares issuable hereunder shall be proportionately decreased in the case of a combination. 
 (c) Stock Dividends and Other Distributions. If the Company at any time while this Warrant is outstanding and unexpired shall
(i) pay a dividend with respect to its Common Stock payable in Common Stock, then the Warrant Price shall be adjusted, from and after the date of determination of shareholders entitled to receive such dividend or distribution, to that price
determined by multiplying the Warrant Price in effect immediately prior to such date of determination by a fraction (A) the numerator of which shall be the total number of shares of Common Stock outstanding immediately prior to such dividend or
distribution, and (B) the denominator of which shall be the total number of shares of Common Stock outstanding immediately after such dividend or distribution; or (ii) make any other distribution with respect to Common Stock, including a
distribution of shares of any subsidiary of the Company (except any distribution specifically provided for in Sections 4(a) and 4(b)), then, in each such case, provision 

  

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shall be made by the Company such that the holder of this Warrant shall receive upon exercise of this Warrant a proportionate share of any such dividend or
distribution as though it were the holder of the Shares as of the record date fixed for the determination of the shareholders of the Company entitled to receive such dividend or distribution. 
 (d) Adjustment of Number of Shares. Upon each adjustment in the Warrant Price, the number of Shares purchasable hereunder shall be
adjusted, to the nearest whole share, to the product obtained by multiplying the number of Shares purchasable immediately prior to such adjustment in the Warrant Price by a fraction, the numerator of which shall be the Warrant Price immediately
prior to such adjustment and the denominator of which shall be the Warrant Price immediately thereafter. 
 5. Notice of Certain
Events. 
 (a) Whenever the Warrant Price or the number of Shares purchasable hereunder shall be adjusted pursuant to
Section 4 hereof, the Company shall make a certificate signed by its chief financial officer setting forth, in reasonable detail, the event requiring the adjustment, the amount of the adjustment, the method by which such adjustment was
calculated, and the Warrant Price and the number of Shares purchasable hereunder after giving effect to such adjustment, and shall cause copies of such certificate to be mailed to the holder of this Warrant at such holder’s last known address.

 (b) In the event of: 
 (i) any taking by the Company of a record of the holders of Common Stock for the purpose of determining the holders thereof who are entitled to receive any dividend, distribution, or other right, 
 (ii) an underwritten registered public offering subject to the Holder’s rights as set forth in Section 1.2 of Exhibit C
(a “Public Offering”), or 
 (iii) a Reorganization; 
 then and in each such event the Company will mail to the Holder hereof a notice (i) specifying, if known, the date on which any such record is to be taken for the
purpose of such dividend, distribution or right, and stating, if known, the amount and character of such dividend, distribution or right, (ii) specifying the date on which the Public Offering is anticipated to close, if known, or
(iii) specifying the anticipated date on which any Reorganization is to close, and, if known, the time, if any is to be fixed, as to which the holders of record of Common Stock shall be entitled to exchange their shares for securities or other
property deliverable on such Reorganization. The Company shall give such notice to the Holder at least twenty business days prior to the record date or closing date specified therein, as the case may be. 
 6. Fractional Shares. No fractional shares of Common Stock will be issued in connection with any exercise hereunder, but in lieu of such
fractional shares the Company shall make a cash payment therefor based on the fair market value of the Common Stock (as determined under Section 2(b) above) on the date of exercise. 
  

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 7. Compliance with Securities Act; Disposition of Warrant or Shares of Common Stock.

 (a) Representations of Holder. The holder of this Warrant, by acceptance hereof, agrees that this Warrant, and the
Shares to be issued upon exercise hereof are being acquired for investment and that such holder will not offer, sell or otherwise dispose of this Warrant, or any Shares except under circumstances which will not result in a violation of the
Securities Act of 1933, as amended (the “Securities Act”) or any applicable state securities laws. In addition, in connection with the issuance of this Warrant, the holder specifically represents to the Company by acceptance of this
Warrant as follows: 
 (i) The holder is aware of the Company’s business affairs and financial condition, and has
acquired information about the Company sufficient to reach an informed and knowledgeable decision to acquire this Warrant. The holder is acquiring this Warrant for its own account for investment purposes only and not with a view to, or for the
resale in connection with, any “distribution” thereof in violation of the Securities Act. 
 (ii) The holder
understands that this Warrant has not been registered under the Securities Act in reliance upon a specific exemption therefrom, which exemption depends upon, among other things, the bona fide nature of the holder’s investment intent as
expressed herein. 
 (iii) The holder further understands that this Warrant must be held indefinitely unless subsequently
registered under the Securities Act and qualified under any applicable state securities laws, or unless exemptions from registration and qualification are otherwise available. The holder is aware of the provisions of Rule 144, promulgated under the
Securities Act. 
 (iv) The holder is an “accredited investor” as such term is defined in Rule 501 of
Regulation D promulgated under the Securities Act. 
 (b) Disposition of Warrant or Shares. With respect to any
offer, sale or other disposition of this Warrant or any Shares acquired pursuant to the exercise of this Warrant prior to registration of such Warrant or Shares, the holder hereof agrees to give written notice to the Company prior thereto,
describing briefly the manner thereof, together with a written opinion of such holder’s counsel, or other evidence, if reasonably satisfactory to the Company, to the effect that such offer, sale or other disposition may be effected without
registration or qualification (under the Securities Act as then in effect or any federal or state securities law then in effect) of this Warrant or the Shares and indicating whether or not under the Securities Act certificates for this Warrant or
the Shares 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 opinion or
other evidence, the Company, as promptly as practicable but no later than 15 days after receipt of the written notice, shall notify such holder that such holder may sell or otherwise dispose of this Warrant or such Shares, all in accordance with the
terms of the notice delivered to the Company. If a determination has been made pursuant to this Section 7(b) that the opinion of counsel for the holder or other evidence is not reasonably satisfactory to the Company, the Company shall so
notify the holder promptly with 

  

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details thereof after such determination has been made. Notwithstanding the foregoing, this Warrant or such Shares may, as to such federal laws, be offered,
sold or otherwise disposed of in accordance with Rule 144 under the Securities Act, 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 have been satisfied. Each certificate representing this Warrant or the Shares thus transferred (except a transfer pursuant to Rule 144) shall bear a legend as to the applicable restrictions on transferability in order to ensure
compliance with such laws, unless in the aforesaid 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) Applicability of Restrictions. Neither any restrictions of any legend described in this
Warrant nor the requirements of Section 7(b) above shall apply to any transfer or grant of a security interest in this Warrant (or the Shares obtainable upon exercise thereof) or any part hereof (i) to a partner of the holder if the
holder is a partnership or to a member of the holder if the holder is a limited liability company, (ii) to a partnership of which the holder is a partner or a limited liability company of which the holder is a member, or (iii) to any
affiliate of the holder if the holder is a corporation; provided, however, in any such transfer, if applicable, the transferee shall on the Company’s request agree in writing to be bound by the terms of this Warrant as if an original
holder hereof. 
 8. Rights as Shareholders; Information. No holder of this Warrant, as such, shall be entitled to vote or
receive dividends or be deemed the holder of Common Stock or any other securities which may at any time be issuable upon the exercise hereof for any purpose, nor shall anything contained herein be construed to confer upon the holder of this Warrant,
as such, any of the rights of a shareholder of the Company or any right to vote for the election of directors or upon any matter submitted to shareholders at any meeting thereof, or to receive notice of meetings, or to receive dividends or
subscription rights or otherwise until this Warrant shall have been exercised and the Shares purchasable upon the exercise hereof shall have become deliverable, as provided herein. Notwithstanding the foregoing, the Company will transmit to the
holder of this Warrant such information, documents and reports as are generally distributed to the holders of any class or series of the securities of the Company concurrently with the distribution thereof to the shareholders: provided, that the
filing by the Company of any such materials on the EDGAR system of the SEC shall be deemed to satisfy the Company’s obligation to deliver such material to the holder of this Warrant. 
 9. Registration Rights. The holder of this Warrant shall be entitled to the rights set forth on Exhibit C attached hereto (the
“Rights Addendum”). In the event (a) the Company determines to register the sale of additional shares of its Common Stock under the securities laws of Canada or any province or territory of Canada, or (b) the Company’s
Common Stock is re-listed and trading in its Common Stock re-commences on the Toronto Stock Exchange, Holder shall be entitled to receive substantially similar registration rights to those granted under the Rights Addendum to such registration in
Canada to the extent necessary to provide Holder with liquidity on the Toronto Stock Exchange Similar to that provided by the Rights Addendum in the United States, pursuant to the securities laws or regulations of Canada and such province or
territory of Canada, and Holder and the Company agree to negotiate in good faith with respect to the terms thereof. 
  

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 10. Representations and Warranties. The Company represents and warrants to the holder of
this Warrant as follows: 
 (a) This Warrant has been duly authorized and executed by the Company and is a valid and binding
obligation of the Company enforceable in accordance with its terms, subject to laws of general application relating to bankruptcy, insolvency and the relief of debtors and the rules of law or principles at equity governing specific performance,
injunctive relief and other equitable remedies; 
 (b) The Shares have been duly authorized and reserved for issuance by the
Company and, when issued in accordance with the terms hereof will be validly issued, fully paid and non-assessable; 
 (c) The
execution and delivery of this Warrant are not, and the issuance of the Shares upon exercise of this Warrant in accordance with the terms hereof will not be, inconsistent with the Company’s articles of incorporation or bylaws (collectively, the
“Charter Documents”), do not and will not contravene any law, governmental rule or regulation, judgment or order applicable to the Company, and do not and will not conflict with or contravene any provision of, or constitute a
default under, any indenture, mortgage, contract or other instrument of which the Company is a party or by which it is bound or require the consent or approval of, the giving of notice to, the registration or filing with or the taking of any action
in respect of or by, any Federal, state, local or foreign government authority or agency or other person, except for the filing of notices pursuant to federal or state securities laws, which filings will be effected by the time required thereby;

 (d) There are no actions, suits, audits, investigations or proceedings pending or, to the knowledge of the Company,
threatened against the Company in any court or before any governmental commission, board or authority which, if adversely determined, will have a material adverse effect on the ability of the Company to perform its obligations under this Warrant;

 (e) True and correct copies of the Charter Documents as in effect on the date hereof are attached hereto as Exhibit
B. 
 (f) All shares of Series A convertible preferred stock are convertible into Common Stock on a 1-to-1 basis. The
number of shares of Common Stock of the Company outstanding on the date hereof, on a fully-diluted basis (assuming the conversion of all outstanding convertible securities and the exercise of all outstanding options and warrants) is equal to
88,502,529 shares, 64,542,358 of which are Common Stock, 5,567,171 of which are options to purchase Common Stock, 18,000,000 of which are Series A convertible preferred stock, 300,000 of which are restricted stock units, 13,000 of which are shares
of Common Stock held by Employee Benefit Trust and 80,000 of which are warrants to purchase Common Stock. 
 11. Modification and
Waiver. This Warrant and any provision hereof may be changed, waived, discharged or terminated only by an instrument in writing signed by the party against which enforcement of the same is sought. 
  

 -11- 

 12. Notices. Any notice, request, communication or other document required or permitted to
be given or delivered to the holder hereof or the Company shall be delivered, or shall be sent by reputable overnight courier service, certified or registered mail, postage prepaid with return receipt requested, to the initial holder at the address
set forth below, to any subsequent holder at its address as shown on the books of the Company or to the Company at the address set forth below. 
 If to the initial holder: 
 Sun Microsystems, Inc. 
 Attn: Business Affairs 
 Program Coordinator 
 16 Network Circle UMPK16-226 
 Menlo Park,
CA 94025 
 investment_admin@sun.com 
 with a cc to: 
 Sun Microsystems, Inc. 
 10 Network Circle 
 Menlo Park, CA 94025

 Attention: General Counsel 
 If
to the Company: 
 BakBone Software Incorporated 
 Attn: Legal Department 
 Manager Intellectual Property & Contracts 
 9540 Towne Centre Drive, Suite 100 
 San
Diego, CA 92121 
 Each of the foregoing parties shall be entitled to specify a different address by giving five days’ advance written
notice as aforesaid to the other parties. All such notices and communications shall be deemed to have been received (i) in the case of personal delivery, on the date of such delivery and (ii) in the case of mailing, on the third business
day following the date of such mailing. 
 13. Binding Effect on Successors. This Warrant shall be binding upon any corporation
succeeding the Company by merger, consolidation or acquisition of all or substantially all of the Company’s assets, and all of the obligations of the Company relating to the Shares issuable upon the exercise or conversion of this Warrant shall
survive the exercise, conversion and termination of this Warrant and all of the covenants and agreements of the Company shall inure to the benefit of the successors and assigns of the holder hereof. 
 14. Lost Warrants or Stock Certificates. The Company covenants to the holder hereof that, upon receipt of evidence reasonably satisfactory
to the Company of the loss, theft, destruction 

  

 -12- 

 
or mutilation of this Warrant or any stock certificate and, in the case of any such loss, theft or destruction, upon receipt of an indemnity reasonably
satisfactory to the Company, or in the case of any such mutilation upon surrender and cancellation of such Warrant or stock certificate, the Company will make and deliver a new Warrant or stock certificate, of like tenor, in lieu of the lost,
stolen, destroyed or mutilated Warrant or stock certificate. 
 15. Descriptive Headings. The descriptive headings of the
several paragraphs of this Warrant are inserted for convenience only and do not constitute a part of this Warrant. The language in this Warrant shall be construed as to its fair meaning without regard to which party drafted this Warrant. 

16. Governing Law. This Warrant shall be construed and enforced in accordance with, and the rights of the parties shall be governed by,
the laws of the State of California. 
 17. Survival of Representations, Warranties and Agreements. All representations and
warranties of the Company and the holder hereof contained herein shall survive the Date of Grant, the exercise or conversion of this Warrant (or any part hereof) or the termination or expiration of rights hereunder. All agreements of the Company and
the holder hereof contained herein shall survive indefinitely until, by their respective terms, they are no longer operative. 
 18.
Remedies. In case any one or more of the covenants and agreements contained in this Warrant shall have been breached, the holders hereof (in the case of a breach by the Company), or the Company (in the case of a breach by a holder),
may proceed to protect and enforce their or its rights either by suit in equity and/or by action at law, including, but not limited to, an action for damages as a result of any such breach and/or an action for specific performance of any such
covenant or agreement contained in this Warrant. 
 19. No Impairment of Rights. The Company will not, by amendment of its
Charter Documents or through any other means, avoid or seek to avoid the observance or performance of any of the terms of this Warrant, but will at all times in good faith assist in the carrying out of all such terms and in the taking of all such
action as may be necessary or appropriate in order to protect the rights of the holder of this Warrant against impairment. 
 20.
Severability. The invalidity or unenforceability of any provision of this Warrant in any jurisdiction shall not affect the validity or enforceability of such provision in any other jurisdiction, or affect any other provision of this
Warrant, which shall remain in full force and effect. 
 21. Recovery of Litigation Costs. If any legal action or other
proceeding is brought for the enforcement of this Warrant, or because of an alleged dispute, breach, default, or misrepresentation in connection with any of the provisions of this Warrant, the successful or prevailing party or parties shall be
entitled to recover reasonable attorneys’ fees and other costs incurred in that action or proceeding, in addition to any other relief to which it or they may be entitled. 
 [Remainder of page intentionally left blank] 
  

 -13- 

 22. Entire Agreement; Modification. This Warrant constitutes the entire agreement between
the parties pertaining to the subject matter contained in it and supersedes all prior and contemporaneous agreements, representations, and undertakings of the parties, whether oral or written, with respect to such subject matter. 
  

			
	BAKBONE SOFTWARE INCORPORATED
		
	By:	 	  
	Title:	 	  

  

 -14- 

 EXHIBIT A-1 
 NOTICE OF EXERCISE 
 To: BakBone Software Incorporated (the “Company”) 
 1. The undersigned hereby elects to purchase
                     shares of Common Stock of the Company pursuant to the terms of the attached Warrant. 
 2. The undersigned elects to exercise the attached Warrant by means of a cash payment and tenders herewith payment of the purchase price of such shares
in full. The undersigned represents that the aforesaid shares are being acquired for the account of the undersigned for investment and not with a view to, or for resale in connection with, the distribution thereof and that the undersigned has no
present intention of distributing or reselling such shares, all except as in compliance with applicable securities laws. The undersigned represents that it is an “accredited investor” as such term is defined in Rule 501 of Regulation D
promulgated under the Securities Act of 1933, as amended. 
 3. Please issue a certificate or certificates representing said shares in the
name of the undersigned or in such other name or names as are specified below: 
  

	
	  
	(Name)
	
	  
	
	  
	(Address)

  

	
	
	   
	Name of Holder
	
	   
	Signature of Authorized Signatory
	
	   
	Name and Title of Signatory

 Date:                                 
  

 - 1 - 

 EXHIBIT A-2 
 NOTICE OF EXERCISE 
 To: BakBone Software Incorporated (the “Company”) 
 1. Contingent upon and effective immediately prior to the closing (the “Closing”) of the Company’s public offering contemplated by
the Registration Statement on Form S-    , filed,                 , 200    , the undersigned hereby elects
to purchase                      shares of Common Stock of the Company pursuant to the terms of the attached Warrant: 
 2. The undersigned elects to exercise the attached Warrant by means of a cash payment. The undersigned has instructed the custodian for the selling
shareholders to deliver to the Company $                     or, if less, the net proceeds due the undersigned from the sale of shares in the
aforesaid public offering. If such net proceeds are less than the purchase price for such shares, the undersigned agrees to deliver the difference to the Company prior to the Closing. The undersigned represents that the aforesaid shares are being
acquired for the account of the undersigned for investment and not with a view to, or for resale in connection with, the distribution thereof and that the undersigned has no present intention of distributing or reselling such shares, all except as
in compliance with applicable securities laws. The undersigned represents that it is an “accredited investor” as such term is defined in Rule 501 of Regulation D promulgated under the Securities Act of 1933, as amended. 
 3. Please issue a certificate or certificates representing said shares in the name of the undersigned or in such other name or names as are specified
below and deliver to the custodian for the selling shareholders: 
  

	
	  
	(Name)
	
	  
	
	  
	(Address)

  

	
	
	   
	Name of Holder
	
	   
	Signature of Authorized Signatory
	
	   
	Name and Title of Signatory

 Date:                                 
  

 - 2 - 

 EXHIBIT A-3 
 NOTICE OF EXERCISE 
 To: BakBone Software Incorporated (the “Company”) 
 1. Contingent upon and effective upon the closing of a Change in Control that occurs during the term of the attached Warrant, the undersigned hereby
elects to purchase                      shares of Common Stock of the Company pursuant to the terms of the attached Warrant. 
 2. The undersigned elects to exercise the attached Warrant and tenders herewith payment of the exercise price in full, together with all applicable
transfer taxes, if any, by means of a cashless exercise, such that payment shall take the form of the cancellation of such number of shares of Common Stock of the Company as is necessary, in accordance with the formula set forth in subsection 2(b),
to exercise this Warrant with respect to the above number of shares of Common Stock purchasable pursuant to the cashless exercise procedure set forth in subsection 2(b). 
 3. Please issue a certificate or certificates representing said shares in the name of the undersigned or in such other name or names as are specified below: 
  

	
	  
	(Name)
	
	  
	
	  
	(Address)

  

	
	
	   
	Name of Holder
	
	   
	Signature of Authorized Signatory
	
	   
	Name and Title of Signatory

 Date:                                 
  

 - 3 - 

 EXHIBIT B 
 CHARTER DOCUMENTS 
 [WILL FOLLOW SEPARATELY] 
  

 - 4 - 

 EXHIBIT C 
 ADDITIONAL RIGHTS 
 SECTION 1. Registration Rights 
 1.1 Certain Definitions 
 As used in
this Exhibit C, the following terms shall have the following respective meanings: 
 “Commission” shall mean the Securities and Exchange Commission or any other federal agency at the time administering the Securities Act. 
 “Exchange Act” shall mean the Securities Exchange Act of 1934, as amended, or any similar federal statute, and the
rules and regulations of the Commission thereunder, all as the same shall be in effect at the time. 
 “Form
S-3” means such form under the Securities Act as in effect on the date hereof or any successor or similar registration form under the Securities Act subsequently adopted by the SEC which permits inclusion or incorporation of substantial
information by reference to other documents filed by the Company with the SEC. 
 “Holder” shall mean
the Holder and any person holding or having the right to acquire Registrable Securities to whom the rights under this Agreement have been transferred in accordance with Section 1.12 hereof. 
 “Initial Public Offering” shall mean the firm commitment underwritten first public offering of Common Stock by the
Company to the public following the date hereof pursuant to a registration statement (other than Form S-8 or S-4 or successors to such forms) filed with, and declared effective by, the Commission under the Securities Act. 
 The terms “register”, “registered” and “registration” refer to a
registration effected by preparing and filing a registration statement in compliance with the Securities Act, and the declaration or ordering of the effectiveness of such registration statement. 
 “Registrable Securities” means the Warrant Stock or other securities issued or issuable with respect to the
Warrant Stock upon any stock split, stock dividend or other distribution, recapitalization or similar event, or any Common Stock otherwise issued or issuable with respect to the Warrant Stock; provided, however, that shares of Common Stock or
other securities shall only be treated as Registrable Securities if and so long as they have not been (A) sold to or through a broker or dealer or underwriter in a public distribution or a public securities transaction, or (B) sold in a
transaction exempt from the registration and prospectus delivery requirements of the Securities Act under Section 4(1) thereof so that all transfer restrictions and restrictive legends with respect thereto are removed upon the consummation of
such sale. 
  

 - 1 - 

 “Registration Expenses” shall mean all expenses incurred by the
Company in complying with Sections 1.2, 1.3 and 1.4 hereof, including, without limitation, all registration, qualification and filing fees, printing expenses, escrow fees, fees and disbursements of counsel for the Company,
reasonable fees and disbursements not to exceed $50,000 of a single special counsel for the Holders, blue sky fees and expenses, and the expense of any special audits incident to or required by any such registration (but excluding the compensation
of regular employees of the Company which shall be paid in any event by the Company). 
 “Rule 144”
shall mean Rule 144 promulgated by the Commission pursuant to the Securities Act, as such Rule may be amended from time to time, or any similar rule or regulation hereafter adopted by the Commission having substantially the same effect as such Rule.

 “Rule 415” shall mean Rule 415 promulgated by the Commission pursuant to the Securities Act, as
such Rule may be amended from time to time, or any similar rule or regulation hereafter adopted by the Commission having substantially the same effect as such Rule. 
 “Securities Act” shall mean the Securities Act of 1933, as amended, or any similar federal statute and the rules
and regulations of the Commission thereunder, all as the same shall be in effect at the time. 
 “Selling
Expenses” shall mean all underwriting discounts, selling commissions and stock transfer taxes applicable to the securities registered by the Holders. 
 “Warrant” shall mean the Warrant to purchase the Common Stock of the Company to which this Exhibit C is
attached. 
 “Warrant Stock” shall mean the Common Stock issued or issuable upon exercise of the
Warrant. 
 1.2 Company Registration 
 (a) Notice of Registration. If at any time or from time to time the Company shall determine to register any of its securities, either for its own account or the account of a security holder or holders,
other than (x) a registration relating solely to employee benefit plans or (y) a registration relating solely to a Commission Rule 145 transaction, the Company will: 
 (i) promptly give to each Holder written notice thereof, and 
 (ii) include in such registration (and any related qualification under blue sky laws or other compliance), and in any underwriting
involved therein, all the Registrable Securities that have been acquired upon exercise of the Warrant or that are then exercisable under the Warrant specified in a written request or requests made within 15 days after receipt of such written notice
from the Company by any Holder. 
  

 - 2 - 

 (b) Underwriting. If the registration of which the Company gives notice is
for a registered public offering involving an underwriting, the Company shall so advise the Holder as a part of the written notice given pursuant to Section 1.2(a)(i). In such event, the right of any Holder to registration pursuant to
Section 1.2 shall be conditioned upon such Holder’s participation in such underwriting and the inclusion of Registrable Securities in the underwriting, to the extent requested, to the extent provided herein. The Holder shall
(together with the Company and the other holders distributing their securities through such underwriting (the “Other Participating Holders”)) enter into an underwriting agreement in customary form with the managing underwriter
selected for such underwriting by the Company. Notwithstanding any other provision of this Section 1.2, if the managing underwriter determines that marketing factors require a limitation of the number of shares to be underwritten, the
managing underwriter may limit the number of Registrable Securities to be included in the registration and underwriting, on a pro rata basis based on the total number of securities (including, without limitation, Registrable Securities) requested to
be registered pursuant to registration rights granted to the Holder and the Other Participating Holders by the Company; provided, however, that the right of the underwriters to exclude shares (including Registrable Securities) from the
registration and underwriting as described above shall be restricted so that the number of Registrable Securities included in any such registration is not reduced below 25% of the shares included in the registration, except for a registration
relating to the Company’s Initial Public Offering from which all Registrable Securities may be excluded. If the Holder or any Other Participating Holder disapproves of the terms of any such underwriting, it, he or she may elect to withdraw
therefrom by written notice to the Company and the managing underwriter. Any securities excluded or withdrawn from such underwriting shall be withdrawn from such registration. 
 (c) Right to Terminate Registration. The Company shall have the right to terminate or withdraw any registration initiated by
it under this Section 1.2 prior to the effectiveness of such registration, whether or not any Holder has elected to include securities in such registration. 
 1.3 Resale Registration Rights. 
 (a) In case the Company shall receive from any
Holder or Holders a written request or requests that the Company effect a registration and any related qualification or compliance with respect to all or a part of the Registrable Securities owned by such Holder or Holders, for an offering to be
made on a delayed or continuous basis pursuant to Rule 415, and the Company is eligible to register such Registrable Securities on Form S-3, the Company will: 
 (i) promptly give written notice of the proposed registration, and any related qualification or compliance, to all other Holders of
Registrable Securities; and 
 (ii) as soon as reasonably practicable, effect such registration and all such qualifications
and compliances as may be so requested and as would permit or facilitate the sale and distribution of all or such portion of such Holder’s or Holders’ Registrable Securities as are specified in such request, together with all or such
portion of the Registrable Securities of any other Holder or Holders, joining in such request as are specified in a written request given within 15 days after receipt of such written notice from the Company; provided, however, that the
Company shall not be obligated to effect any such registration, qualification or compliance pursuant to this Section 1.3(a): 
 (A) if the Company is not eligible to register the Registrable Securities on Form S-3 or Form S-3 is not otherwise available for such offering by the Holders; 
  

 - 3 - 

 (B) if the Holders, together with the holders of any other securities of the Company
entitled to inclusion in such registration, propose to sell Registrable Securities and such other securities (if any) at an aggregate price to the public of less than $1,000,000; 
 (C) during the period starting with the date of filing of, and ending on the date 180 days following the effective date of the
registration statement pertaining to a public offering; provided that the Company makes reasonable good efforts to cause such registration statement to become effective; 
 (D) if within 15 days of receipt of a written request from a Holder or Holders pursuant to Section 1.3(a), the Company gives
notice to the Holders of the Company’s intention to make a public offering within 60 days; or 
 (E) if the Company
shall furnish to the Holders a certificate signed by the Chairman of the Board of Directors or President of the Company stating that in the good faith judgment of the Board of Directors of the Company, it would be seriously detrimental to the
Company and its stockholders for such Form S-3 registration to be effected at such time, in which event the Company shall have the right to defer the filing of the Form S-3 registration statement for a period of not more than 60 days after receipt
of the request of the Holder or Holders under this Section 2.4; provided, that such right to delay a request under this Section 1.3(a)(ii)(E), Section 1.3(b)(ii)(G) or Section 1.4(c)(vi) (the “Delay
Provisions”) shall be exercised by the Company not more than once in any 12-month period. 
 (b) In case the Company
shall receive from any Holder or Holders a written request or requests that the Company effect a registration and any related qualification or compliance with respect to all or a part of the Registrable Securities owned by such Holder or Holders,
for an offering to be made on a delayed or continuous basis pursuant to Rule 415, and the Company is not eligible to register such Registrable Securities on Form S-3, the Company will: 
 (i) promptly give written notice of the proposed registration, and any related qualification or compliance, to all other Holders of
Registrable Securities; and 
 (ii) as soon as reasonably practicable, effect such registration on Form S-1 and effect all
such qualifications and compliances as may be so requested and as would permit or facilitate the sale and distribution of all or such portion of such Holder’s or Holders’ Registrable Securities as are specified in such request, together
with all or such portion of the Registrable Securities of any other Holder or Holders, joining in such request as are specified in a written request given within 15 days after receipt of such written notice from the Company; provided,
however, that the Company shall not be obligated to effect any such registration, qualification or compliance pursuant to this Section 1.3(b): 
 (A) for any Registrable Securities that are not fully vested and then-issuable pursuant to the Warrant; 
  

 - 4 - 

 (B) prior to the date that the Company has filed its Annual Report on Form 10-K for the
fiscal year ended March 31, 2007; 
 (C) if such Registrable Securities may be sold by the Holders pursuant to Rule
144(k), as determined by counsel to the Company pursuant to a written opinion letter to such effect, addressed and reasonably acceptable to the Company’s transfer agent and the affected Holders; 
 (D) if the Holders of such Registrable Securities do not intend to sell or distribute such Registrable Securities within 90 days of the
effectiveness of such registration statement pursuant to such registration statement; 
 (E) if the Holders, together with
the holders of any other securities of the Company entitled to inclusion in such registration, propose to sell Registrable Securities and such other securities (if any) at an aggregate price to the public of less than $1,000,000; 
 (F) during the period starting with the date of filing of, and ending on the date 180 days following the effective date of the
registration statement pertaining to a public offering; provided that the Company makes reasonable good efforts to cause such registration statement to become effective; 
 (G) if within 15 days of receipt of a written request from a Holder or Holders pursuant to Section 1.3(a), the Company gives notice
to the Holders of the Company’s intention to make a public offering within 60 days; or 
 (H) if the Company shall
furnish to the Holders a certificate signed by the Chairman of the Board of Directors or President of the Company stating that in the good faith judgment of the Board of Directors of the Company, it would be seriously detrimental to the Company and
its stockholders for such Form S-1 registration to be effected at such time, in which event the Company shall have the right to defer the filing of the Form S-1 registration statement for a period of not more than 60 days after receipt of the
request of the Holder or Holders under this Section 2.4; provided, that such right to delay a request under any of the Delay Provisions shall be exercised by the Company not more than once in any 12-month period. 
 (c) The Company shall be required to keep a registration statement on Form S-3 effected pursuant to Section 1.3(a) effective
until such date that is the earlier of one year from the date of effectiveness of such registration statement or the date when all of the Registrable Securities registered thereunder shall have been publicly sold by the Holders. The Company shall be
required to keep a registration statement on Form S-1 effected pursuant to Section 1.3(b) effective until such date that is the earlier of three months from the date of effectiveness of such registration statement or the date when all of
the Registrable Securities registered thereunder shall have been publicly sold by the Holders; provided, however, that the Company shall be permitted to withdraw the Registrable Securities and re-register the registration statement on
Form S-3 at such time as such form becomes available to the Company, in which case the Company shall be required to keep such registration statement on Form S-3 effective until such date that is the earlier 

  

 - 5 - 

 
of one year from the date of effectiveness of such registration statement or the date when all of the Registrable Securities registered thereunder shall have
been publicly sold by the Holders. 
 (d) Subject to the foregoing, the Company shall file a Form S-1 or Form S-3
registration statement, as applicable, covering the Registrable Securities and other securities so requested to be registered as soon as reasonably practicable after receipt of the request or requests of the Holders. Registrations effected pursuant
to this Section 1.3 shall not be counted as registrations effected pursuant to Sections 1.2 or 1.4, respectively. 
 1.4 Demand Registration 
 (a) If at any time after the Fourth Vesting Date (as such term is defined in the
Warrant) the Company shall receive from the Holders holding or having the right to acquire a majority of the Registrable Securities held by the Holders and their permitted assigns (the “Initiating Holders”) a written request that
the Company file a registration statement under the Securities Act covering the registration of such Registrable Securities, the Company will, within 15 days of the receipt thereof, (i) give written notice of such request to all Holders, and
(ii) use its reasonable best efforts to effect, as soon as reasonably practicable, such registration and all such qualifications and compliances as may be so requested and as would permit or facilitate the sale and distribution of all or such
portion of such Holder’s or Holders’ Registrable Securities as are specified in such request, together with all or such portion of the Registrable Securities of any other Holder or Holders, joining in such request as are specified in a
written request given within 15 days after receipt of such written notice from the Company. 
 (b) If the Initiating Holders
intend to distribute the Registrable Securities covered by their request by means of an underwriting, they shall so advise the Company as a part of their request made pursuant to this Section 1.4, and the Company shall include such
information in the written notice referred to in Section 1.4(a). In such event, the right of any Holder to include its Registrable Securities in such registration shall be conditioned upon such Holder’s participation in such
underwriting and the inclusion of such Holder’s Registrable Securities in the underwriting to the extent provided herein. All Holders proposing to distribute their securities through such underwriting shall enter into an underwriting agreement
in customary form with the underwriter or underwriters selected for such underwriting by a majority in interest of the Initiating Holders (which underwriter or underwriters shall be reasonably acceptable to the Company). Notwithstanding any other
provision of this Section 1.4, if the underwriter advises the Company that marketing factors require a limitation of the number of securities to be underwritten then the Company shall so advise all Holders which would otherwise be
underwritten pursuant hereto, and the number of shares that may be included in the underwriting shall be allocated to the Holders on a pro rata basis based on the number of Registrable Securities held by all such Holders (including the
Initiating Holders). Any Registrable Securities excluded or withdrawn from such underwriting shall be withdrawn from the registration. 
 (c) The Company shall not be required to effect a registration pursuant to this Section 1.4: 
 (i) for any Registrable Securities that are not fully vested and then-issuable pursuant to the Warrant; 
  

 - 6 - 

 (ii) if the registration does not cover at least 20% of the Registrable Securities, or if
the anticipated aggregate offering price, net of underwriting discounts and commissions, would not exceed $5,000,000; 
 (iii)
after the Company has effected two registrations pursuant to Section 1.2, Section 1.3 or Section 1.4, and such registrations have been declared or ordered effective; 
 (iv) during the period starting with the date of filing of, and ending on the date 90 days following the effective date of the
registration statement pertaining to a public offering; provided that the Company makes reasonable good faith efforts to cause such registration statement to become effective; 
 (v) if within 15 days of receipt of a written request from Initiating Holders pursuant to Section 1.4(a), the Company gives
notice to the Holders of the Company’s intention to make a public offering within 60 days; or 
 (vi) if the Company
shall furnish to Holders requesting a registration statement pursuant to this Section 1.4, a certificate signed by the Chairman of the Board of the Company stating that in the good faith judgment of the Board of Directors of the Company,
it would be seriously detrimental to the Company and its stockholders for such registration statement to be effected at such time, in which event the Company shall have the right to defer such filing for a period of not more than 60 days after
receipt of the request of the Initiating Holders; provided that such right to delay a request under any of the Delay Provisions shall be exercised by the Company not more than once in any 12-month period. 
 1.5 Expenses of Registration. Except as specifically provided herein, all Registration Expenses incurred in connection with any registration,
qualification or compliance pursuant to Section 1.2 or any registration under Section 1.3 or Section 1.4 herein shall be borne by the Company. All Selling Expenses incurred in connection with any registrations
hereunder, shall be borne by the holders of the securities so registered pro rata on the basis of the number of shares so registered. 
 1.6 Registration Procedures. In the case of each registration, qualification or compliance effected by the Company pursuant to this Exhibit C, the Company will: 
 (a) Prepare and file with the Commission a registration statement with respect to such securities and use its best efforts to cause such
registration statement to become and remain effective until the distribution described in the registration statement has been completed, but in no event longer than 90 days. 
 (b) Prepare and file with the Commission such amendments and supplements to such registration statement and the prospectus used in
connection with such registration statement as may be necessary to comply with the provisions of the Securities Act with respect to the disposition of all securities covered by such registration statement. 
 (c) Furnish to the Holders participating in such registration and to the underwriters, if any, of the securities being registered such
reasonable number of copies of the registration 

  

 - 7 - 

 
statement, preliminary prospectus, final prospectus and such other documents as such underwriters may reasonably request in order to facilitate the public
offering of such securities. 
 (d) Use its best efforts to register and qualify the securities covered by such registration
statement under such other securities or Blue Sky laws of such jurisdictions as shall be reasonably requested by the Holders; provided that the Company shall not be required in connection therewith or as a condition thereto to qualify to do business
or to file a general consent to service of process in any such states or jurisdictions, unless the Company is already subject to service in such jurisdiction and except as may be required by the Securities Act. 
 (e) In the event of any underwritten public offering, enter into and perform its obligations under an underwriting agreement, in usual and
customary form, with the managing underwriter of such offering. Each Holder participating in such underwriting shall also enter into and perform its obligations under such an agreement. 
 (f) Notify each Holder of Registrable Securities covered by such registration statement at any time when a prospectus relating thereto is
required to be delivered under the Act of the happening of any event as a result of which the prospectus included in such registration statement, as then in effect, includes an untrue statement of a material fact or omits to state a material fact
required to be stated therein or necessary to make the statements therein not misleading in the light of the circumstances then existing. 
 (g) Cause all such Registrable Securities registered pursuant hereunder to be listed on each securities exchange or other trading market on which similar securities issued by the Company are then listed. 

(h) Provide a transfer agent and registrar for all Registrable Securities registered pursuant hereunder and a CUSIP number for all such
Registrable Securities, in each case not later than the effective date of such registration. 
 (i) Use its best efforts to
furnish, at the request of any Holder requesting registration of Registrable Securities pursuant to the terms of this Exhibit C, on the date that such Registrable Securities are delivered to the underwriters for sale in connection with a
registration pursuant to this Exhibit C, if such securities arc being sold through underwriters, an opinion, dated such date, of the counsel representing the Company for the purposes of such registration, in form substance as is customarily
given to underwriters in an underwritten public offering, addressed to the underwriters and to the Holders requesting registration of Registrable Securities. 
 1.7 Indemnification 
 (a) The Company will indemnify each Holder, each of its officers
and directors and partners, and each person controlling such Holder within the meaning of Section 15 of the Securities Act, with respect to which registration, qualification or compliance has been effected pursuant to this Exhibit C, and
each underwriter, if any, and each person who controls any underwriter within the meaning of Section 15 of the Securities Act, against all actual out-of-pocket expenses, claims, losses, damages or liabilities (or actions in respect thereof),
including any of the foregoing incurred in any litigation or in settlement of any litigation, commenced or threatened, arising out of or based on any untrue statement (or alleged untrue statement) of a material fact 

  

 - 8 - 

 
contained in any registration statement, prospectus, preliminary prospectus, offering circular or other document, or any amendment or supplement thereto,
incident to any such registration, qualification or compliance, or based on any omission (or alleged omission) to state therein a material fact required to be stated therein or necessary to make the statements therein, in light of the circumstances
in which they were made, not misleading, or any violation or any alleged violation by the Company of the Securities Act or the Exchange Act or any state securities law, or of any rule or regulation promulgated under any of the foregoing applicable
to the Company in connection with any such registration, qualification or compliance, and the Company will reimburse each such Holder, each of its officers and directors, and each person controlling such Holder, each such underwriter and each person
who controls any such underwriter, for any legal and any other actual out-of-pocket expenses reasonably incurred in connection with investigating, preparing or defending any such claim, loss, damage, liability or action, as such expenses are
incurred; provided, however, that the indemnity agreement contained in this Section 1.7(a) shall not apply to amounts paid in settlement of any such matter if the settlement is effected without the consent of the Company, which
consent shall not be unreasonably withheld; and provided further that the Company will not be liable in any such case to the extent that any such claim, loss, damage, liability or expense arises out of or is based on any untrue statement or omission
or alleged untrue statement or omission, made in reliance upon and in conformity with written information furnished to the Company by such Holder, controlling person or underwriter specifically for use therein. 
 (b) Each Holder will, if Registrable Securities held by such Holder are included in the securities as to which such registration,
qualification or compliance is being effected, indemnify the Company, each of its directors and officers, each underwriter, if any, of the Company’s securities covered by such a registration statement, each person who controls the Company or
such underwriter within the meaning of Section 15 of the Securities Act, and each other such Holder, each of its officers and directors and each person controlling such Holder within the meaning of Section 15 of the Securities Act, against
all actual out-of-pocket expenses, claims, losses, damages and liabilities (or actions in respect thereof), including any of the foregoing incurred in settlement of any litigation, commenced or threatened, arising out of or based on any untrue
statement (or alleged untrue statement) of a material fact contained in any such registration statement, prospectus, offering circular or other document, or any amendment or supplement thereto, incident to any such registration, qualification or
compliance, or based on any omission (or alleged omission) to state therein a material fact required to be stated therein, in light of the circumstances in which they were made, or necessary to make the statements therein not misleading, and will
reimburse the Company, such Holders, such directors, officers, persons, underwriters or control persons for any legal and any other actual out-of-pocket expenses reasonably incurred in connection with investigating or defending any such claim, loss,
damage, liability or action, as such expenses are incurred, in each case to the extent, but only to the extent, that such untrue statement (or alleged untrue statement) or omission (or alleged omission) is made in such registration statement,
prospectus, offering circular or other document in reliance upon and in conformity with written information furnished to the Company by such Holder specifically for use therein; provided, however, that the indemnity agreement contained in
this Section 1.7(b) shall not apply to amounts paid in settlement of any matter if the settlement is effected without the consent of the Holder, which consent shall not be unreasonably withheld; and provided, further, that the
maximum liability of each selling Holder under this Section 1.7(b) shall be equal to the net proceeds to such selling Holder as a result of such registration and offering. 
  

 - 9 - 

 (c) Each party entitled to indemnification under this Section 1.7 (the
“Indemnified Party”) shall give notice to the party required to provide indemnification (the “Indemnifying Party”) promptly after such Indemnified Party has actual knowledge of any claim as to which indemnity may be
sought, and shall permit the Indemnifying Party to assume the defense of any such claim or any litigation resulting therefrom, provided that counsel for the Indemnifying Party, who shall conduct the defense of such claim or litigation, shall be
approved by the Indemnified Party (whose approval shall not unreasonably be withheld), and the Indemnified Party may participate in such defense at such party’s expense; provided, however, that an Indemnified Party (together with all
other Indemnified Parties which may be represented without conflict by one counsel) shall have the right to retain one separate counsel, with the reasonable fees and expenses of such counsel to be paid by the Indemnifying Party, if representation of
such Indemnified Party by the counsel retained by the Indemnifying Party would be inappropriate due to actual or potential differing interests between such Indemnified Party and any other party represented by such counsel in such proceeding. The
failure of any Indemnified Party to give notice as provided herein shall not relieve the Indemnifying Party of its obligations under this Section 1.7 unless the failure to give such notice is materially prejudicial to an Indemnifying
Party’s ability to defend such action. No Indemnifying Parry, in the defense of any such claim or litigation, shall, except with the consent of each Indemnified Party (not to be unreasonably withheld), consent to entry of any judgment or enter
into any settlement which does not include as an unconditional term thereof the giving by the claimant or plaintiff to such Indemnified Party of a release from all liability in respect to such claim or litigation. 
 (d) If the indemnification provided for in this Section 1.7 is held by a court of competent jurisdiction to be unavailable to
an indemnified party with respect to any loss, liability, claim, damage, or expense referred to therein, then the indemnifying party, in lieu of indemnifying such indemnified party hereunder, shall contribute to the amount paid of payable by such
indemnified party as a result of such loss, liability, claim, damage, or expense in such proportion as is appropriate to reflect the relative fault of the indemnifying party on the one hand and of the indemnified party on the other in connection
with the statements or omissions that resulted in such loss, liability, claim, damage, or expense as well as any other relevant equitable considerations; provided, however, that, in no event shall any contribution by a Holder under this
Section 1.7(d) exceed the net proceeds from the offering received by such Holder, except in the case of willful fraud by such Holder. The relative fault of the indemnifying party and of the indemnified party shall be determined by
reference to, among other things, whether the untrue or alleged untrue statement of a material fact or the omission to state a material fact relates to information supplied by the indemnifying party or by the indemnified party and the parties’
relative intent, knowledge, access to information, and opportunity to correct or prevent such statement or omission. 
 (e)
The obligations of the Company and Holders under this Section 1.7 shall survive the completion of any offering of Registrable Securities in a registration statement under this Section 1, and otherwise. 
 1.8 Information by Holder. The Holder or Holders of Registrable Securities included in any registration shall furnish to the Company such
information regarding such Holder or Holders, the Registrable Securities held by them and the distribution proposed by such Holder or Holders as the Company may request in writing and as shall be required in connection with any registration,
qualification or compliance referred to in this Exhibit C. 
  

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 1.9 Rule 144 Reporting. With a view to making available the benefits of certain rules and
regulations of the Commission which may at any time permit the sale of the Common Stock to the public without registration, after the Company files with the Commission its Annual Report on Form 10-K for the fiscal year ended March 31, 2007, the
Company agrees to use its best efforts to (a) make and keep public information available, as those terms are understood and defined in Rule 144 under the Securities Act, (b) file with the Commission in a timely manner all reports and
other documents required of the Company under the Exchange Act (at any time after it has become subject to such reporting requirements), and (c) so long as the Holder owns any Registrable Securities, to furnish to the Holder forthwith upon
request a written statement by the Company as to its compliance with the reporting requirements of Rule 144 and of the Exchange Act, a copy of the most recent annual or quarterly report of the Company, and such other reports and documents of
the Company and other information in the possession of or reasonably obtainable by the Company as the Holder may reasonably request in availing itself of any rule or regulation of the Commission allowing the Holder to sell any such securities
without registration. 
 1.10 Limitation on Subsequent Registration Rights. After the date of this Agreement, the Company shall not,
without the prior written consent of the Holders holding a majority of the Registrable Securities held by the Holders and then outstanding, enter into any agreement with any holder or prospective holder of any securities of the Company that would
allow such holder or prospective holder to (a) include such securities in any registration filed under this Exhibit C, unless under the terms of such agreement, such holder or prospective holder may include such securities in any such
registration only to the extent that the inclusion of his securities will not reduce the amount of the Registrable Securities of the Holders which is included, or (b) make a demand registration to the Company. 
 1.11 Transfer of Registration Rights. The rights to cause the Company to register securities granted to the Holder under this Exhibit C may be
assigned to a transferee or assignee in connection with any transfer or assignment of Registrable Securities by the Holder (together with any affiliate); provided, however, that (a) such transfer may otherwise be effected in accordance
with applicable securities laws, (b) notice of such assignment is given to the Company, and (c) such transferee or assignee agrees to be bound by the terms and conditions of this Exhibit C. 
 1.12 Termination of Rights. The rights of any particular Holder to cause the Company to register securities under Sections 1.2, 1.3
and 1.4 shall terminate with respect to such Holder on the earlier of (a) the tenth anniversary of the Grant Date of the Warrant, (b) the later of (x) the one year anniversary of a Change of Control and (y) the one year
anniversary of the Fourth Vesting Date, and (c) such time as Rule 144 or another similar exemption under the Securities Act is available for the sale of all such Holders’ securities during a three (3)-month period without
registration. 
  

 - 11 -Employment Agreement with Benjamin Bulkley

 EXHIBIT 10.1 
 ALLSCRIPTS, INC. 
 EMPLOYMENT AGREEMENT 
 THIS EMPLOYMENT AGREEMENT, (this “Agreement”) is effective as of this 24th day of April, 2007, by and between Allscripts LLC, a
limited liability corporation organized and existing under the laws of the State of Delaware, with its principal place of business at 222 Merchandise Mart Plaza, Chicago, Illinois 60654 (“Company”) and Benjamin E. Bulkley
(“Executive”). 
 RECITALS 
 WHEREAS, Company desires to employ Executive as its Chief Operating Officer; and 
 WHEREAS,
Executive desires to be employed by Company in the aforesaid capacity. 
 NOW THEREFORE, in consideration of the foregoing premises,
of the mutual agreements and covenants contained herein and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties agree as follows: 
 AGREEMENT 
  

	1.	Employment. 

 Company hereby agrees to
employ Executive, and Executive hereby accepts employment, as Chief Operating Officer of Company, pursuant to the terms of this Agreement. Executive shall have the duties and responsibilities and perform such administrative and managerial services
of that position as are set forth in the bylaws of Company (the “Bylaws”) or as shall be delegated or assigned to Executive by the Chief Executive Officer of Company (the “CEO”) from time to time. Executive shall
report to the CEO and carry out his responsibilities hereunder on a full-time basis for and on behalf of Company; provided that Executive shall be entitled to devote time to personal investments and civic and charitable activities, personal
education and development, so long as such activities do not interfere with or conflict with Executive’s duties hereunder. Notwithstanding the foregoing, Executive agrees that, during the term of this Agreement, Executive shall not act as an
officer of any entity other than Company without the prior written consent of Company. 
  

	2.	Effective Date and Term. 

 The initial term
of Executive’s employment by Company under this Agreement shall commence as of April 24, 2007 (the “Effective Date”) and shall continue in effect for a term of one (1) year, unless earlier terminated as provided herein.
Thereafter, the Company may elect to renew this Agreement upon the expiration of the initial term or any renewal term by providing written notice of renewal to Executive at least ninety (90) days prior to the expiration of the then current
term. If such notice is not provided, Executive must notify Company that Company failed to provide a notice of renewal. If Company does not cure such failure within five (5) business days, this Agreement will terminate at the expiration of the
then current term. If 

  

 - 1 - 

 Company elects not to renew this Agreement at the end of the initial term or any renewal term, such nonrenewal shall be
treated as a termination of the Employment Period without cause by Company for the limited purpose of determining the payments and benefits available to Executive (i.e., Executive shall be entitled to the severance/benefits set forth in
Section 4.5.1). If Executive elects not to renew this Agreement, the same shall not constitute a termination of the Employment Period without cause and Executive shall be entitled to receive the severance/benefits set forth in
Section 4.5.5. As used herein, the term “Employment Period” shall mean the period from the Effective Date until the termination of the Agreement (i) for non-renewal pursuant to this Section 2, or
(ii) pursuant to Section 4 herein. 
  

	3.	Compensation and Benefits. 

 In
consideration for the services Executive shall render under this Agreement, Company shall provide or cause to be provided to Executive the following compensation and benefits: 
 3.1 Base Salary. During the Employment Period, Company shall pay to Executive an annual base salary at a rate of four hundred thousand
dollars ($400,000) per annum, subject to all appropriate federal and state withholding taxes, which base salary shall be payable in accordance with Company’s normal payroll practices and procedures. Executive’s base salary shall be
reviewed annually prior to the beginning of each Fiscal Year (as defined below) during the Employment Period by the CEO or the Board of Directors of Company (the “Board”), or a committee of the Board, and may be increased in the
sole discretion of the CEO, Board, or such committee of the Board, based on Executive’s performance during the preceding Fiscal Year. For purposes of this Agreement, the term “Fiscal Year” shall mean the fiscal year of the
Company, commencing on January 1 of each year and ending on December 31. Executive’s base salary, as such base salary may be increased annually hereunder, is hereinafter referred to as the “Base Salary.” After
Executive has been employed for a period of six (6) months by the Company, the CEO shall review the performance of Executive and the Company and determine if any adjustment in said salary is merited, in the sole discretion of the CEO.

 3.2 Performance Bonus. Executive shall be eligible to receive a cash bonus in accordance with this Section 3.2. Payment
of the Performance Bonus, if any, will be subject to the sole discretion of the CEO, Board or a committee of the Board, and the amount of any such Performance Bonus will be determined by, and based upon criteria selected by, the CEO, Board or such
committee. Based upon the foregoing exercise of discretion, Executive’s target Performance Bonus, if any, shall be 50% of his/her salary, but may, based on performance, exceed such amount. The Performance Bonus shall be payable on or before
April 30 of the year immediately succeeding the Fiscal Year for which such Performance Bonus was earned; provided, however, that if the applicable Company (or Parent) objectives are based upon Company’s (or Parent’s) annual audited
financial statements, and if, on April 30 of the applicable year such financial statements have not yet been issued, the Performance Bonus, if any, shall be payable promptly upon the issuance of such financial statements. Notwithstanding the
foregoing, Company agrees to pay Executive the amount of Fifty Thousand Dollars ($50,000) as the minimum bonus with respect to his employment with the Company during 2007 at such time as Performance Bonuses are paid for said year in the manner set
forth above. After Executive has been employed for a period of six (6) months by the Company, the CEO shall 
  

 - 2 - 

 review the performance of Executive and the Company and determine if any adjustment in said minimum bonus is merited, in
the sole discretion of the CEO. 
 3.3 Benefits. During the Employment Period and as otherwise provided hereunder,
Executive shall be entitled to the following: 
 3.3.1 Vacation. Executive shall be entitled to twenty
(20) business days per Fiscal Year of paid vacation, such vacation time not to be cumulative (i.e., vacation time not taken in any Fiscal Year shall not be carried forward and used in any subsequent Fiscal Year). 
 3.3.2 Participation in Benefit Plans. Executive shall be entitled to health and/or dental benefits, including immediate
coverage for Executive and his eligible dependents, which are generally available to Company’s senior executive employees and as provided by Company in accordance with its group health insurance plan coverage. In addition, Executive shall be
entitled to participate in any profit sharing plan, retirement plan, group life insurance plan or other insurance plan or medical expense plan maintained by the Company for its senior executives generally, in accordance with the general eligibility
criteria therein. 
 3.3.3 Physical Examination. Executive shall be entitled to receive reimbursement for the
cost of one general physical examination per twelve (12) month period during the term of the Agreement from a physician chosen by Executive in his reasonable discretion. 
 3.3.4 Perquisites. Executive shall be entitled to such other benefits and perquisites that are generally available to
Company’s senior executive employees and as provided in accordance with Company’s plans, practices, policies and programs for senior executive employees of Company. 
 3.3.5 Indemnification. Executive shall be entitled to indemnification (including immediate advancement of all legal fees
with respect to any claim for indemnification) and directors’ and officers’ insurance coverage, to the extent made available to other senior executives, in accordance with the Bylaws and all other applicable policies and procedures of
Company. 
 3.4 Expenses. Company shall reimburse Executive for proper and necessary expenses incurred by Executive in the
performance of his duties under this Agreement from time to time upon Executive’s submission to Company of invoices of such expenses in reasonable detail and subject to all standard policies and procedures of Company with respect to such
expenses. In addition, Executive shall be reimbursed for expenses associated with his relocation to the Chicago area as set forth on Appendix A. 
 3.5 Stock Awards. Executive shall be eligible to participate in any applicable stock bonus, stock option, or similar plan implemented by Company and generally available to its senior executive employees, including, without
limitation, Company’s Amended and Restated 1993 Stock Incentive Plan approved by the Board and Company’s shareholders on or about June 7, 1999 (the “Plan”) for the grant of options to Executive as approved by the
Board. Executive will receive restricted shares of Company stock with a value of $600,000. The award of these shares is subject to the approval of Company’s Compensation Committee, at its next scheduled 
  

 - 3 - 

 
meeting subsequent to the execution of this agreement. Therefore the number of shares will not be determined until the grant date. The shares will vest over
a 4 year period and be subject to a separate agreement that is customary for such grants. 
  

	4.	Termination of the Agreement Prior To the Expiration. 

 This Agreement and the Employment Period of Executive may be terminated at any time as follows (the effective date of such termination hereinafter referred to as the “Termination Date”): 

4.1 Termination upon Death or Disability of Executive. 
 4.1.1 This Agreement and the Employment Period shall terminate immediately upon the death of Executive. In such event, all rights
of Executive and/or Executive’s estate (or named beneficiary) shall cease except for the right to receive payment of the amounts set forth in Section 4.5.4 of the Agreement. 
 4.1.2 Company may terminate this Agreement and the Employment Period upon the disability of Executive. For purposes of this
Agreement, Executive shall be deemed to be “disabled” if Executive, as a result of illness or incapacity, shall be unable to perform substantially his required duties for a period of three (3) consecutive months or for any aggregate
period of three (3) months in any six (6) month period. In the event of a dispute as to whether Executive is disabled, Company may refer Executive to a licensed practicing physician of Company’s choice, and Executive agrees to submit
to such tests and examination as such physician shall deem appropriate to determine Executive’s capacity to perform the services required to be performed by Executive hereunder. In such event, the parties hereby agree that the decision of such
physician as to the disability of Executive’s shall be final and binding on the parties. Any termination of the Agreement under this Section 4.1.2 shall be effected without any adverse affect on Executive’s rights to receive benefits
under any disability policy of Company, but shall not be treated as a termination without cause. 
 4.2 Termination by Company for
Cause. Company may terminate this Agreement and the Employment Period for Cause (as defined herein) upon written notice to Executive, which termination shall be effective on the date specified by Company in such notice; provided however,
that Executive shall have a period of ten (10) days (or such longer period not to exceed 30 days as would be reasonably required for Executive to cure such action or inaction) after the receipt of the written notice from Company to cure the
particular action or inaction, to the extent a cure is possible. For purposes of this Agreement, the term “Cause” shall mean: 
 4.2.1 The willful or grossly negligent failure by Executive to perform his duties and obligations hereunder in any material respect, other than any such failure resulting from the disability of Executive;

 4.2.2 Executive’s conviction of a crime or offense involving the property of Company, or any crime or offense
constituting a felony or involving fraud or moral turpitude; provided that, in the event that Executive is arrested or indicted for a crime or offense related to any of the foregoing, then Company may, at its option, place Executive on paid leave of
absence, pending the final outcome of such arrest or indictment; 
  

 - 4 - 

 4.2.3 Executive’s violation of any law, which violation is materially and
demonstrably injurious to the operations or reputation of Company; or 
 4.2.4 Executive’s material violation of
any generally recognized policy of Company, Executive’s refusal to follow the lawful directions of the Board, or Executive’s insubordination to his supervisor. 
 Notwithstanding the foregoing, any notice and lapse of time period provided in this Section 4.2 shall not be required with respect to any event or circumstance which is the same or substantially the same as an
event or circumstance with respect to which notice and an opportunity to cure has been given within the previous six (6) months. 
 4.3 Termination without Cause. Either party may terminate this Agreement and the Employment Period without cause upon thirty (30) days prior written notice to the other party. If Company elects not to renew this Agreement
at the end of the initial term or any renewal term, such nonrenewal shall be treated as a termination of the Employment Period without cause by Company for the limited purpose of determining the payments and benefits available to Executive (i.e.,
Executive shall be entitled to the severance/benefits set forth in Section 4.5.1). 
 4.4 Termination by Executive for
Constructive Discharge. 
 4.4.1 Executive may terminate this Agreement and the Employment Period, in
accordance with the process set forth below, a result of a Constructive Discharge. For purposes of this Agreement “Constructive Discharge” shall mean: 
  

	 	(i)	a failure of Company to meet its obligations in any material respect under this Agreement, including, but not limited to, any reduction in or failure to pay the Base Salary;

  

	 	(ii)	a material diminution in or other substantial adverse alteration in the nature or scope of Executive’s responsibilities with Company; 

  

	 	(iii)	Executive has been asked to relocate his principal place of business to a location that is more than fifty (50) miles from Company’s offices located in Chicago,
Illinois; or 

  

	 	(iv)	there has been a Change of Control of Company. 

 4.4.2 For purposes of this Agreement, a “Change of Control” shall mean any one of the following events (references to “shares” or “common stock” shall be deemed to include
the membership interests of Company): 
  

	 	(i)	the acquisition by any person or group of beneficial ownership of stock possessing more than thirty percent (30%) of the outstanding securities of Company which
generally entitle the holder thereof to vote for the election of directors (“Voting Power”), except that (a) no such person or group shall be deemed to own beneficially (1) any securities acquired directly from
Company pursuant to a written agreement with Company, or (2) any 

  

 - 5 - 

	 	    	securities held by the Company or a subsidiary of Company (“Subsidiary”), or any employee benefit plan (or related trust) of Company or a Subsidiary; and
(b) no Change in Control shall be deemed to have occurred solely by reason of any such acquisition by a corporation with respect to which, after such acquisition, more than sixty percent (60%) of the then outstanding shares of
common stock of such corporation and the Voting Power of such corporation are then beneficially owned, directly or indirectly, by the persons who were the beneficial owners of the stock and Voting Power of Company immediately before such
acquisition, in substantially the same proportions as their ownership immediately before such acquisition; or 

  

	 	(ii)	the individuals who constitute the Board as of the date of this Agreement (the “Incumbent Board”) cease for any reason other than their deaths to constitute
at least a majority of the Board; provided that any individual who becomes a director after the date of this Agreement whose election or nomination for election by Company’s stockholders was approved by a vote of at least two-thirds
(2/3) of the directors then comprising the Incumbent Board shall be considered, for purposes of this section, as though such individual were a member of the Incumbent Board, but excluding, for this purpose, any such individual whose initial
assumption of office is in connection with an actual or threatened election contest relating to the election of the directors of Company (as such terms are used in Rule 14a-11 under the 1934 Act); or 

  

	 	(iii)	Company effects: (a) a merger, reorganization or consolidation of Company with respect to which the individuals and entities who were the respective beneficial
owners of the shares of common stock and Voting Power of Company immediately before such merger, reorganization or consolidation do not, immediately after such merger, reorganization or consolidation, beneficially own, directly or indirectly, more
than sixty percent (60%) of, respectively, the then outstanding shares of common stock and the Voting Power of the corporation resulting from such merger, reorganization, or consolidation; (b) a liquidation or dissolution of
Company; or (c) a sale or other disposition of all or substantially all of the assets of Company. 

 4.4.3 For purpose of the foregoing definition, the terms “beneficially owned” and “beneficial ownership” and “person” shall have the meanings ascribed to them in SEC rules 13d-5(b) under the 1934 Act,
and “group” means two or more persons acting together in such a way to be deemed a person for purposes of Section 13(d) of the 1934 Act. 
 4.4.4 In the event of a Constructive Discharge other than as a result of a
Change in Control, Executive shall have the right to terminate this Agreement and receive the benefits set forth in Section 4.5.1 below, upon delivery of written notice to Company no later than the close of business on the sixtieth
(60th) day following the effective date of a Constructive Discharge; provided, however, that such termination
shall not be effective until the expiration of ten (10)

  

 - 6 - 

 
days after receipt by Company of such written notice and Company has not cured such Constructive Discharge within the 10-day period. If Company so effects a
cure, the Constructive Discharge notice shall be deemed rescinded and of no force or effect. Notwithstanding the foregoing, such notice and lapse of time shall not be required with respect to any event or circumstance which is the same or
substantially the same as an event or circumstance with respect to which notice and an opportunity to cure has been given within the previous six (6) months. The effective date of a Constructive Discharge shall be: (i) in the event
of a Constructive Discharge under Section 4.4.1(i) or (ii), the effective date of the event giving rise to the Constructive Discharge; or (ii) in the event of a Constructive Discharge under Section 4.4.1(iii), the date on which
Executive receives notice of the request to relocate. 
 4.4.5 In the event of a Constructive Discharge as a result of
a Change of Control, Executive shall have the right to terminate this Agreement and receive the benefits set forth in Section 4.5.2 upon delivery of written notice to Company no later than twelve (12) months following the effective date of
the Change of Control. 
  
 4.5 Rights upon
Termination. Upon termination of this Agreement and the Employment, the following shall apply: 
 4.5.1
Termination by Company Without Cause or for Constructive Discharge. If Company terminates the Employment Period without Cause, or if Executive terminates the Employment Period as a result of a Constructive Discharge, Executive shall be
entitled to receive payment of any Base Salary amounts that have accrued but have not been paid as of the Termination Date, and the unpaid Performance Bonus, if any, with respect to the Fiscal Year preceding the Fiscal Year in which the Termination
Date occurs (such Performance Bonus, if any, to be determined in the manner that it would have been determined, and payable at the time it would have been payable, under Section 3.2 had there been no termination of the Employment Period). In
addition, subject to Section 4.5.2, below, Company shall be obligated to pay Executive (or provide Executive with) the following benefits as severance: 
  

	 	(i)	during the first twelve (12) months of the term of this agreement, one month’s salary for each month of service up to a maximum of twelve (12) months shall be
payable; subsequent to the first anniversary of this agreement, one (1) year of Executive’s Base Salary, payable in twelve (12) equal monthly installments commencing on the Termination Date, equal to Executive’s annual Base
Salary in effect immediately prior to the Termination Date, such amount to be payable regardless of whether Executive obtains other employment and is compensated therefor (but, in all events for purposes of this section, only so long as Executive is
not in violation of Section 5 hereof); 

  

	 	(ii)	 the Performance Bonus for the Fiscal Year in which the Termination Date occurs that would have been payable under Section 3.2 had there been no termination of
the Employment Period (such Performance Bonus to be determined in the manner it would have been determined under Section 3.2 had there been no termination of the Employment Period), payable in twelve (12) equal monthly installments
commencing on the fifteenth day 

  

 - 7 - 

	 	 
of the first full month following the Termination Date. Any Performance Bonus payable with respect to the Fiscal Year in which the Termination Date occurs
shall be paid in accordance with Section 3.2; 

  

	 	(iii)	continuation of Executive’s then current enrollment (including family enrollment, if applicable) in all health and/or dental insurance benefits set forth in Section 3.2.2
for a period of twelve (12) months following the Termination Date, with Executive’s contribution to such plans as if Executive were employed by Company (and in such a manner as to not jeopardize Executive’s qualification for such
insurance, and which may require that such benefits be provided pursuant to COBRA), such contributions to be paid by Executive in the same period (e.g., monthly, bi-weekly, etc.) as all other employees of Company; provided, however that Company may
terminate such coverage if payment from Executive is not made within ten (10) days of the date on which Executive receives written notice from Company that such payment is due; and provided, further, that such benefits may be discontinued
earlier to the extent that Executive becomes entitled to comparable benefits from a subsequent employer; 

  

	 	(iv)	outplacement services, in an amount up to ten thousand dollars ($10,000), paid to Executive on exit; and 

  

	 	(v)	any stock options or other awards granted to Executive pursuant to Section 3.5 that have not vested as of the Termination Date shall vest in full upon the Termination Date,
except as otherwise stated in such award. 

 4.5.2 Additional Severance Upon Termination for Change of
Control. If Executive terminates the Employment Period pursuant to Section 4.4 by reason of a Change of Control, then Executive shall be entitled to receive the compensation and benefits described in Section 4.5.1 (except for those
benefits described in Sections 4.5.1(i) and (ii)) and the following additional benefits as severance: 
  

	 	(i)	payment in a lump sum of an amount equal to the product of Executive’s Base Salary in effect as of the Termination Date multiplied by 2; and 

  

	 	(ii)	a lump sum payment of Performance Bonus equal to the target Performance Bonus that would have been received by Executive during the Fiscal Year in which the Change of Control
occurs, multiplied by 2. 

 4.5.3 Termination With Cause by Company or Without Cause by Executive.
If Company terminates the Employment Period with Cause, or if Executive terminates the Employment Period other than as a result of a Constructive Discharge or a non-renewal under Section 2, Company shall be obligated to pay Executive
(i) any Base Salary amounts that have accrued but have not been paid as of the Termination Date; and (ii) the unpaid Performance Bonus, if any, with respect to the Fiscal Year preceding the Fiscal Year in which the
Termination 

  

 - 8 - 

 
Date occurs (such Performance Bonus, if any, to be determined in the manner it would have been determined, and payable at the time it would have been
payable, under Section 3.2 had there been no termination of the Employment Period). No other amounts shall be payable. 
 4.5.4 Termination Upon Death or Disability. If the Employment Period is terminated because of the death or disability of Executive, Company shall be obligated to pay Executive or, if applicable, Executive’s estate, the
following amounts: (i) earned but unpaid Base Salary; (ii) the unpaid Performance Bonus, if any, with respect to the Fiscal Year preceding the Fiscal Year in which the Termination Date occurs (such Performance Bonus, if any,
to be determined in the manner it would have been determined, and payable at the time it would have been payable, under Section 3.2 had there been no termination of the Employment Period); and (iii) the amount of Executive’s
Performance Bonus, if any, for the Fiscal Year in which the Termination Date occurs that would have been payable under Section 3.2 had there been no termination of the Employment Period (such Performance Bonus, if any, to be determined in the
manner it would have been determined under Section 3.2 had there been no termination of the Employment Period), payable as follows: (a) fifty percent (50%) of such Performance Bonus shall be paid on the Termination Date; and
(b) the remaining fifty percent (50%) shall be paid in twelve (12) equal monthly installments commencing on the fifteenth day of the first full month following the Termination Date. Any Performance Bonus payable with respect to
the Fiscal Year in which the Termination Date occurs shall be paid in accordance with Section 3.2. 
 4.5.5
Termination for Non-Renewal by Executive. If the Employment Period is terminated by reason of a non-renewal by Executive under Section 2, then Executive shall be entitled to receive payment of any Base Salary amounts that have accrued
but have not been paid as of the Termination Date, and the unpaid Performance Bonus, if any, with respect to the Fiscal Year preceding the Fiscal Year in which the Termination Date occurs (such Performance Bonus, if any, to be determined in the
manner that it would have been determined, and payable at the time it would have been payable, under Section 3.2 had there been no termination of the Employment Period). No other amounts shall be payable. 
 4.6 Effect of Notice of Termination. Any notice of termination by Company, whether for Cause or without cause, may specify that,
during the notice period, Executive need not attend to any business on behalf of Company. 
  

	5.	Noncompetition and Confidentiality. 

 5.1 Covenant Not to Compete. During the Employment Period and for a period of two (2) years after the expiration or earlier termination of the Employment Period (other than a termination by Company without Cause or
a termination by Executive for Constructive Discharge), Executive shall not, (i) directly or indirectly act in concert or conspire with any person employed by Company in order to engage in or prepare to engage in or to have a financial
or other interest in any business which is a Direct Competitor (as defined below); or (ii) serve as an employee, agent, partner, shareholder, director or consultant for, or in any other capacity participate, engage or have a financial or
other interest in any business which is a Direct Competitor (provided, however, that notwithstanding anything to the contrary contained in this Agreement, Executive may own up to two percent (2%) of the outstanding shares of the capital stock
of a company whose securities are registered under Section 12 of the Securities Exchange 

  

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Act of 1934). For purposes of this Agreement, the term “Direct Competitor” shall mean any person or entity engaged in the business of
marketing or providing within the continental United States prescription products or services for pharmacy benefit management products or services including, without limitation, prepackaged prescription products or services, point of care pharmacy
dispensing systems, point of care decision support or clinical software for physicians, mail service pharmacy products or services, or pharmaceuticals or pharmaceutical delivery systems. Notwithstanding the foregoing, Direct Competitor shall not
include (or preclude Executive from employment with) (i) a pharmaceutical, biotech or medical device company or (ii) a subsidiary or separately reported business unit of a Direct Competitor which subsidiary or business unit is not itself a
Direct Competitor (and Executive remains in full compliance with Section 5.3 below). 
 5.2 No Solicitation of
Employees. During the Employment Period and for a period of two (2) years following the expiration or earlier termination of the Employment Period for any reason, Executive shall not, directly or indirectly, whether for its own account
or for the account of any other individual or entity, (i) employ, hire or solicit for employment, or attempt to employ, hire or solicit for employment, any Employee (as defined below), (ii) divert or attempt to divert,
directly or indirectly, or otherwise interfere in a material fashion with or circumvent Company’s relationship with, any Employees, or (iii) induce or attempt to induce, directly or indirectly, any Employee to terminate his or her
employment or other business relationship with Company. For purposes of this Section 5.2, “Employee” shall mean any person who is or was employed by Company during the Employment Period; provided, however, that “Employee”
shall not include any person (a) whose employment with Company was terminated by Company without cause, or (b) who was not employed by Company at any time during the six (6) month period immediately prior to the
Termination Date. A hiring pursuant to a general solicitation (and without the involvement or knowledge of Executive) which is responded to by an Employee shall not be precluded hereunder for anyone who is below the level of Vice President of
Company. 
 5.3 Confidential Information. Company has advised Executive, and Executive acknowledges, that it is the
policy of Company to maintain as secret and confidential all Protected Information (as defined below), and that Protected Information has been and will be developed at substantial cost and effort to Company. Executive shall not at any time, directly
or indirectly divulge, furnish or make accessible to any person, firm, corporation, association or other entity (otherwise than as may be required in the regular course of Executive’s employment), nor use in any manner, either during the
Employment Period or after the termination of the Employment Period for any reason, any Protected Information, or cause any such information of Company to enter the public domain, except as required by law or court order. “Protected
Information” means trade secrets, confidential and proprietary business information of Company, and any other information of Company, including but not limited to, customer lists (including potential customers), sources of supply,
processes, plans, materials, pricing information, internal memoranda, marketing plans, internal policies, and products and services which may be developed from time to time by the company and its agents or employees, including Executive; provided,
however, that information that is in the public domain (other than as a result of a breach of this Agreement), approved for release by Company or lawfully obtained from third parties who are not bound by a confidentiality agreement with Company, is
not Protected Information. 
  

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 5.4 Injunctive Relief. Executive acknowledges and agrees that the restrictions imposed upon
him by this Section 5 and the purpose for such restrictions are reasonable and are designed to protect the Protected Information and the continued success of Company without unduly restricting Executive’s future employment by others.
Furthermore, Executive acknowledges that in view of the Protected Information of Company which Executive has or will acquire or has or will have access to and the necessity of the restriction contained in this Section 5, any violation of the
provisions of this Section 5 would cause irreparable injury to Company and its successors in interest with respect to the resulting disruption in their operations. By reason of the foregoing, Executive consents and agrees that if he violates
any of the provisions of this Section 5, the company and its successors in interest, as the case may be, shall be entitled, in addition to any other remedies that they may have, including monetary damages, to an injunction to be issued by a
court of competent jurisdiction, restraining Executive from committing or continuing any violation of this Section 5. 
  

	6.	Certain Additional Payments by Company. 

 Company agrees that: 
 6.1 Anything in this Agreement to the contrary notwithstanding, in the event it shall be determined
that any payment or distribution by Company to or for the benefit of Executive (whether paid or payable or distributed or distributable pursuant to the terms of this Agreement or otherwise, but determined without regard to any additional payments
required under this Section 6) (a “Payment”) would be subject to the excise tax imposed by Section 4999 of the Code or if any interest or penalties are incurred by Executive with respect to such excise tax (such excise
tax, together with any such interest and penalties, being hereafter collectively referred to as the “Excise Tax”), then Executive shall be entitled to receive an additional payment (a “Gross-Up Payment”) in an
amount such that after payment by Executive of all taxes (including interest or penalties imposed with respect to such taxes), including, without limitation, any income taxes (and any interest and penalties imposed with respect thereto) and Excise
Tax imposed upon the Gross-Up Payment, Executive retains an amount of the Gross-Up Payment equal to the Excise Tax imposed upon the Payment. 
 6.2 Subject to the provisions of Section 6.3, below, all determinations required to be made under this Section 6, including whether and when a Gross-Up Payment is required and the amount of such Gross-Up Payment and the
assumptions to be utilized in arriving at such determination, shall be made by the accounting firm which is then serving as the auditors for Company (the “Accounting Firm”), which shall provide detailed supporting calculations both
to Company and Executive within fifteen (15) business days of the receipt of notice from Executive that there has been a Payment, or such earlier time as is requested by Company. In the event that the Accounting Firm is serving as accountant or
auditor for the individual, entity, or group effecting the Change in Control, Executive shall appoint another nationally recognized accounting firm to make the determinations required hereunder (which accounting firm shall then be referred to as the
Accounting Firm hereunder). All fees and expenses of the Accounting Firm shall be borne solely by Company. Any Gross-Up Payment, as determined pursuant to this Section 6, shall be paid by Company to Executive within five (5) days of the
receipt of the Accounting Firm’s determination. If the Accounting Firm determines that no Excise Tax is payable by Executive, it shall furnish Executive with a written opinion that failure to report the 
  

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 Excise Tax on Executive’s applicable federal income tax return would not result in the imposition of a negligence or
similar penalty. Any good faith determination by the Accounting Firm shall be binding upon Company and Executive. As a result of the uncertainty in the application of Section 4999 of the Code at the time of the initial determination by the
Accounting Firm hereunder, it is possible that Gross-Up Payments which will not have been made by Company should have been made (“Underpayment”), consistent with the calculations required to be made hereunder. In the event that
Company exhausts its remedies pursuant to Section 6.3, below, and Executive thereafter is required to make a payment of any Excise Tax, the Accounting Firm shall determine the amount of the Underpayment that has occurred and any such
Underpayment shall be promptly paid by Company to or for the benefit of Executive. 
 6.3 Executive shall notify Company in writing of
any claim by the Internal Revenue Service that, if successful, would require the payment by Company of a Gross-Up Payment. Such notification shall be given as soon as practicable but no later than fifteen (15) business days after Executive is
informed in writing of such claim and shall apprise Company of the nature of such claim and the date on which such claim is requested to be paid. Executive shall not pay such claim prior to the expiration of the thirty (30) day period following
the date on which Executive gives such notice to the company (or such shorter period ending on the date that any payment of taxes with respect to such claim is due). If Company notifies Executive in writing prior to the expiration of such period
that it desires to contest such claim, Executive shall: 
 6.3.1 Give Company any information reasonably requested by
Company relating to such claim; 
 6.3.2 Take such action in connection with contesting such claim as Company shall
reasonably request in writing from time to time, including, without limitation, accepting legal representation with respect to such claim by an attorney reasonably selected by Company; 
 6.3.3 Cooperate with Company in good faith in order effectively to contest such claim; and 
 6.3.4 Permit Company to participate in any proceedings relating to such claim; 
 provided, however, that Company shall bear and pay directly all costs and expenses (including additional interest and penalties) incurred in connection with such contest
and shall indemnify and hold Executive harmless, on an after-tax basis, for any Excise Tax or income tax (including interest and penalties with respect thereto) imposed as a result of such representation and payment of costs an expenses. Without
limiting the foregoing provisions of this Section 6.3, the company shall control all proceedings taken in connection with such contest and, at its sole option, may pursue or forego any and all administrative appeals, proceedings, hearings and
conferences with the taxing authority in respect of such claim and may, at its sole option, either direct Executive to pay the tax claimed and sue for a refund or contest the claim in any permissible manner; and Executive agrees to prosecute such
contest to a determination before any administrative tribunal, in a court of initial jurisdiction and in one or more appellate courts, as Company shall determine; provided further, however, that if Company directs Executive to pay such claim and sue
for a refund, Company shall advance the amount of such payment to Executive on an interest-free basis ad shall indemnify and hold Executive harmless, on an after- 
  

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 tax basis, from any Excise Tax or income tax (including interest or penalties with respect thereto) imposed with respect
to such advance or with respect to any imputed income with respect to such advance; and further provided that any extension of the statute of limitations relating to payment of taxes for the taxable year of Executive with respect to which such
contested amount is claimed to be due is limited solely to such contested amount. further more, Company’s control of the contest shall be limited to issues with respect to which a Gross-Up Payment would be payable hereunder and Executive shall
be entitled to settle or contest, as the case may be, any other issue raised by the Internal Revenue Service or any other taxing authority. 
 If, after the receipt by Executive of an amount advanced by Company pursuant to Section 6.3 above, Executive becomes entitled to receive any refund with respect to such claim, Executive shall (subject to Company’s complying with
the requirements of said interest paid or credited thereon, after taxes applicable thereto). If, after the receipt by Executive of an amount advanced by Company pursuant to said Section 6.3, a determination is made that Executive shall not be
entitled to any refund with respect to such claim and Company does not notify Executive in writing of its intent to contest such denial of refund prior to the expiration of thirty (30) days after such determination, then such advance shall be
forgiven and shall not be required to be repaid; and the amount of such advance shall offset, to the extent thereof, the amount of the Gross-Up Payment required to be paid. 
  

	7.	No Set-Off or Mitigation. 

 The
Company’s obligation to make the payments provided or in this Agreement and otherwise to perform its obligations hereunder shall not be affected by any set-off, counterclaim, recoupment, defense or other claim, right or action which the Company
may have against Executive or others. In no event shall Executive be obligated to seek other employment or take any other action by way of mitigation of the amounts payable to Executive under any of the provisions of this Agreement and, except as
otherwise provided herein, such amounts shall not be reduced whether or not Executive obtains other employment. 
  

	8.	Payment of Certain Expenses. 

 Company agrees
to pay promptly as incurred, to the fullest extent permitted by law, all legal fees and expenses which Executive may reasonably incur as a result of any contest by Company, Executive or others of the validity or enforceability of, or liability
under, any provision of the Agreement (including as a result of any contest initiated by Executive about the amount of any payment due pursuant to this Agreement), plus in each case interest on any delayed payment at the applicable federal rate
provided for in Section 7872(f)(2)(A) of the Code; provided, however, that Company shall not be obligated to make such payment with respect to any contest in which Company prevails over Executive. 
  

	9.	Indemnification. 

 To the fullest extent
permitted by law, Company shall indemnify Executive (including the advancement of expenses) for any judgments, fines, amounts paid in settlement and reasonable expenses, including attorney’s fees, incurred by Executive in connection with the

  

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defense or any lawsuit or other claim to which Executive is made a party by reason of being an officer, director or employee of Company or any of its
Subsidiaries. 
  

	10.	Miscellaneous. 

 10.1 Valid
Obligation. This Agreement has been duly authorized, executed and delivered by Company and has been duly executed and delivered by Executive and is a legal, valid and binding obligation of Company and of Executive, enforceable in accordance
with its terms. 
 10.2 No Conflicts. Executive represents and warrants that the performance by him of his duties hereunder
will not violate, conflict with, or result in a breach of any provision of, any agreement to which he/she is a party. 
 10.3
Applicable Law. This Agreement shall be construed in accordance with the laws of the State of Illinois, without reference to Illinois’ choice of law statutes or decisions. 
 10.4 Severability. The provisions of this Agreement shall be deemed severable, and the invalidity or unenforceability of any one ore more
of the provisions hereof shall not affect the validity or enforceability of any other provision. In the event any clause of this Agreement is deemed to be invalid, the parties shall endeavor to modify that clause in a manner which carries out the
intent of the parities in executing this Agreement. 
 10.5 No Waiver. The waiver of a breach of any provision of this
Agreement by any party shall not be deemed or held to be a continuing waiver of such breach or a waiver of any subsequent breach of any provision of this Agreement or as nullifying the effectiveness of such provision, unless agreed to in writing by
the parties. 
 10.6 Notices. 
 All demands, notices, requests, consents and other communications required or permitted under this Agreement shall be in writing and shall be personally delivered or sent by facsimile machine (with a confirmation copy
sent by one of the other methods authorized in this Section), or by commercial overnight delivery service, to the parties at the addresses set forth below: 
  

					
	To Company:	 	Allscripts, Inc.	  	
		 	222 Merchandise Mart Plaza, Suite 2024	  	
		 	Chicago, Illinois 60654	  	
		 	Attention: Chief Executive Officer	  	
		 		  	
		 	with a copy to:	  	
		 	General Counsel	  	
		 		  	
		 		  	
	To Executive:	 	at current address on file with the Company	  	

  

 - 14 - 

 Notices shall be deemed given upon the earliest to occur of (i) receipt by the party to whom such notice is
directed, if hand delivered; (ii) if sent by facsimile machine, on the day (other than a Saturday, Sunday or legal holiday in the jurisdiction to which such notice is directed) such notice is sent if sent (as evidenced by the facsimile
confirmed receipt) prior to 5:00 p.m. Central Time and, if sent after 5:00 p.m. Central Time, on the day (other than a Saturday, Sunday or legal holiday in the jurisdiction to which such notice is directed) after which such notice is sent; or
(iii) on the first business day (other than a Saturday, Sunday or legal holiday in the jurisdiction to which such notice is directed) following the day the same is deposited with the commercial carrier if sent by commercial overnight
delivery service. Each party, by notice duly given in accordance therewith may specify a different address for the giving of any notice hereunder. 
 10.7 Assignment of Agreement. This Agreement shall be binding upon and inure to the benefit of Executive and Company, their respective successors and permitted assigns and Executive’s heirs and personal
representatives. Neither party may assign any rights or obligations hereunder to any person or entity without the prior written consent of the other party. This Agreement shall be personal to Executive for all purposes. 
 10.8 Entire Agreement; Amendments. Except as otherwise provided herein, this Agreement contains the entire understanding between the
parties, and there are no other agreements or understandings between the parties with respect to Executive’s employment by Company and his obligations thereto. Executive acknowledges that he is not relying upon any representations or warranties
concerning his employment by Company except as expressly set forth herein. No amendment or modification to the Agreement shall be valid except by a subsequent written instrument executed by the parties hereto. 
 10.9 Dispute Resolution and Arbitration. The following procedures shall be used in the resolution of disputes: 
 10.9.1 Dispute. In the event of any dispute or disagreement between the parties under this Agreement, the disputing party
shall provide written notice to the other party that such dispute exists. The parties will then make a good faith effort to resolve the dispute or disagreement. If the dispute is not resolved upon the expiration of fifteen (15) days from the
date a party receives such notice of dispute, the entire matter shall then be submitted to arbitration as set forth in Section 8.9.2. 
 10.9.2 Arbitration. If the dispute or disagreement between the parties has not been resolved in accordance with the provisions of Section 8.9.1 above, then any such controversy or claim arising out
of or relating to this Agreement, or the breach thereof, shall be settled by arbitration to be held in Chicago, Illinois, in accordance with the employment dispute resolution rules of the American Arbitration Association then in effect. Any decision
rendered herein shall be final and binding on each of the parties and judgement may be entered thereon in the appropriate state or federal court. The arbitrators shall be bound to strict interpretation and observation of the terms of this Agreement.
The company shall pay the costs of arbitration. 
 10.10 Survival. The provisions of Sections 4.5, 5, 8 and 9 of this
Agreement shall survive the expiration or earlier termination of the Agreement. 
  

 - 15 - 

 10.11 Headings. Section headings used in this Agreement are for convenience of
reference only and shall not be used to construe the meaning of any provision of this Agreement. 
 10.12 Counterparts.
This Agreement may be executed in counterparts, each of which shall be deemed an original, but both of which together shall constitute one and the same instrument. 
 [Signature page follows] 
  

 - 16 - 

 IN WITNESS WHEREOF, the parties have executed this Agreement as of the date and year first above
written. 
  

			
	ALLSCRIPTS, INC.
		
	By:	 	/s/ Lee Shapiro
		
	Name:	 	Lee Shapiro
		
	Title:	 	President
	
	EXECUTIVE:
	
	/s/ Benjamin E. Bulkley
	 Benjamin E. Bulkley

  
  
  

 - 17 - 

 Appendix A – Relocation Expenses 
 Executive shall have the opportunity to work with a relocation service selected by the Company at Company’s expense. The following costs are also reimbursed under this Agreement: 
  

	 	•	 	 Commission in connection with the sale of Executive’s current home 

	 	•	 	 Expenses in connection with the purchase of a new home in the Chicago area by Executive: 

  

			
	 Reimbursable Home Purchase Closing Costs

		
	 Discount or Origination Fees maximum 1%
	  	 State Surtax Stamps

	 Abstract/Title Search Exam
	  	 Sub-Escrow Tie-in Fee

	 Assumption Fee
	  	 Survey (if required by lender)

	 Attorney’s Fees – Lender
	  	 Tax Service Fee

	 Attorney’s Fees – Purchaser
	  	 Title Insurance—Lender’s Coverage

	 Credit Report
 Escrow Fee
	  	 Title Insurance—Owner’s Coverage
     (if required by state or local laws)

	 Lender’s Inspection Fee
 Notary Fee
	  	 Title Insurance Binder (Lender’s)
 Transfer Fee (Purchaser’s Share)

	 Wire Transfer Fees
	  	 Toxic Substance Inspection

	 Recording Fees – Deed
	  	 General Home Inspection

	 Settlement/Closing Fee
 Stamps on Deed or Mortgage
	  	 Appraisal
 Processing Fee/Document Preparation

	 Underwriting Fees
 Lender’s Closing Fees
	  	 Maximum inspection fees $500
 Flood Certificate

	 Courier/Express Mail Fees
	  	 E-Doc Fee

  

	 	•	 	 Moving costs (exceptional items require approval) 

	 	•	 	 Temporary living expenses for Executive through December 31, 2007, but if Executive’s family has joined him in the Chicago area, through April 30,
2008 

	 	•	 	 Family travel – up to 5 trips to Chicago for Executive’s family, plus 5 additional trips for Executive’s spouse. Additional travel shall be subject
to the approval of Company’s CEO. 

	 	•	 	 Incidentals – an allowance of $33,333 

	 	•	 	 Tax gross up of taxable benefits will be accommodated 

  

 - 18 -

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