Document:

Final Form of Warrant

 Exhibit 10.01 
 THE SECURITIES REPRESENTED BY THIS CERTIFICATE ARE SUBJECT TO A NOTE PURCHASE AGREEMENT DATED AS OF APRIL 20, 2008, BY AND AMONG THE ISSUER AND THE OTHER PERSONS NAMED THEREIN, AS SUCH AGREEMENT MAY BE AMENDED, RESTATED OR MODIFIED FROM
TIME TO TIME, AND MAY NOT BE TRANSFERRED, SOLD, ASSIGNED, PLEDGED, HYPOTHECATED OR OTHERWISE DISPOSED OF EXCEPT IN ACCORDANCE WITH THE PROVISIONS THEREOF, AND ANY TRANSFEREE OF THESE SECURITIES SHALL BE SUBJECT TO THE TERMS OF SUCH AGREEMENT. COPIES
OF SUCH AGREEMENT ARE MAINTAINED WITH THE CORPORATE RECORDS OF THE ISSUER AND ARE AVAILABLE FOR INSPECTION AT THE PRINCIPAL OFFICES OF THE ISSUER. 
 THE
SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR ANY STATE SECURITIES LAWS, AND MAY NOT BE OFFERED, SOLD OR TRANSFERRED EXCEPT PURSUANT TO (I) AN
EFFECTIVE REGISTRATION STATEMENT UNDER THE ACT, AND IN COMPLIANCE WITH APPLICABLE STATE SECURITIES LAWS OR (II) AN APPLICABLE EXEMPTION FROM REGISTRATION UNDER THE ACT AND UNDER APPLICABLE STATE SECURITIES LAWS. 
 BLUE COAT SYSTEMS, INC. 
 WARRANT TO PURCHASE
COMMON STOCK 
 Warrant No.: WC- 
 Number of Shares of Common
Stock:              
 Date of Issuance: June 2, 2008 (“Issuance
Date”) 
 Blue Coat Systems, Inc., a Delaware corporation (the “Company”), hereby certifies that, for good and
valuable consideration, the receipt and sufficiency of which are hereby acknowledged,             , the registered holder hereof or its permitted assigns (the
“Holder”), is entitled, subject to the terms set forth below, to purchase from the Company, at the Exercise Price (as defined below) then in effect, upon surrender of this Warrant to Purchase Common Stock (including any Warrants to
Purchase Common Stock issued in exchange, transfer or replacement hereof, the “Warrant”), at any time or times on or after the Issuance Date, but not after 11:59 p.m., New York Time, on the Expiration Date (as defined below),
                         (            ) fully paid and
nonassessable shares of Common Stock (as defined below) (the “Warrant Shares”). Except as otherwise defined herein, capitalized terms in this Warrant shall have the meanings set forth in Section 14. This Warrant is one
of the Warrants to purchase Common Stock (the “Warrants”) issued pursuant to Section 2.1 of that certain Note Purchase Agreement dated as of April 20, 2008, by and among the Company and the purchasers (the
“Purchasers”) referred to therein (the “Purchase Agreement”). 
  

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 1. EXERCISE OF WARRANT. 
 (a) Mechanics of Exercise. Subject to the terms and conditions hereof, this Warrant may be
exercised by the Holder on any day on or after the date hereof in whole or in part, by (i) delivery of a written notice, in the form attached hereto as Exhibit A (the “Exercise Notice”), of the Holder’s election to
exercise this Warrant, (ii) delivery of this Warrant (provided that the Holder shall not be required to deliver the original Warrant in order to effect an exercise hereunder if such Holder delivers a copy of this Warrant, together with a lost
document affidavit and other documentation required by Section 7(b) below), and (iii) (A) payment to the Company of an amount equal to the applicable Exercise Price multiplied by the number of Warrant Shares as to which this
Warrant is being exercised (the “Aggregate Exercise Price”) in cash or wire transfer of immediately available funds or (B) by notifying the Company that this Warrant is being exercised pursuant to a Cashless Exercise (as
defined in Section 1(d)). Execution and delivery by the Holder of an Exercise Notice with respect to less than all of the Warrant Shares shall be deemed to be a request by such Holder to cancel the original Warrant and issue a new
Warrant evidencing the right to purchase the remaining number of Warrant Shares, which request shall be satisfied by the Company pursuant to Section 7(d) below. On or before the second (2nd) Business Day following the date on which the Company has received each of the Exercise Notice, the Warrant and the Aggregate Exercise Price (or notice of a Cashless Exercise)
(the “Exercise Delivery Documents”), the Company shall transmit by facsimile an acknowledgment of confirmation of receipt of the Exercise Delivery Documents to the Holder and the Company’s transfer agent (the “Transfer
Agent”). On or before the third (3rd) Business Day following the date on which the Company has received all of the Exercise Delivery
Documents (the “Share Delivery Date”), the Company shall (X) provided that the Transfer Agent is participating in The Depository Trust Company (“DTC”) Fast Automated Securities Transfer Program, upon the
request of the Holder, credit such aggregate number of shares of Common Stock to which the Holder is entitled pursuant to such exercise to the Holder’s or its designee’s balance account with DTC through its Deposit Withdrawal Agent
Commission system which balance account shall be specified in the Exercise Notice, or (Y) if the Transfer Agent is not participating in the DTC Fast Automated Securities Transfer Program, issue and dispatch by overnight courier to the address
as specified in the Exercise Notice, a certificate, registered in the Company’s share register in the name of the Holder or its designee, for the number of shares of Common Stock to which the Holder is entitled pursuant to such exercise. Upon
delivery of the Exercise Delivery Documents or notification to the Company of a Cashless Exercise referred to in Section 1(d), the Holder shall be deemed for all corporate purposes to have become the holder of record of the Warrant
Shares with respect to which this Warrant has been exercised, irrespective of the date of delivery of the certificates evidencing such Warrant Shares. If this Warrant is submitted in connection with any exercise pursuant to this
Section 1(a) and the number of Warrant Shares represented by this Warrant submitted for exercise is greater than the number of Warrant Shares being acquired upon such exercise as specified in the Exercise Notice, then the Company shall
as soon as practicable and in no event later than five (5) Business Days after such exercise and at its own expense, issue a new Warrant (in accordance with Section 7(d)) representing the right to purchase the number of Warrant
Shares purchasable immediately prior to such exercise under this Warrant, less the number of Warrant Shares with respect to which this Warrant is exercised as specified in the Exercise Notice. No fractional shares of Common Stock are to be issued
upon the exercise of this Warrant, but rather the number of shares of Common Stock to be issued shall be rounded up to the nearest whole number. The Company shall pay any and all taxes which may be payable with respect to the issuance and delivery
of Warrant Shares upon exercise of this Warrant. 
  

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 (b) Exercise Price. For purposes of this Warrant, “Exercise Price” means $20.76
per Warrant Share, subject to adjustment as provided herein. 
 (c) Company’s Failure to Timely Deliver Securities. If within
three (3) trading days after the Company’s receipt of the Exercise Delivery Documents the Company shall fail to issue and deliver a certificate to the Holder and register such shares of Common Stock on the Company’s share register or
credit the Holder’s balance account with DTC for the number of shares of Common Stock to which the Holder is entitled upon such Holder’s exercise hereunder, and if on or after such third (3rd) trading day the Holder purchases (in an
open market transaction or otherwise) shares of Common Stock to deliver in satisfaction of a sale by the Holder of shares of Common Stock issuable upon such exercise that the Holder anticipated receiving from the Company (a
“Buy-In”), then the Company shall, within three (3) Business Days after the Holder’s request and in the Holder’s discretion, either (i) pay cash to the Holder in an amount equal to the Holder’s total
purchase price (including brokerage commissions, if any) for the shares of Common Stock so purchased (the “Buy-In Price”), at which point the Company’s obligation to deliver such certificate (and to issue such shares of Common
Stock) shall terminate, or (ii) promptly honor its obligation to deliver to the Holder a certificate or certificates representing such shares of Common Stock and pay cash to the Holder in an amount equal to the excess (if any) of the Buy-In
Price over the product of (A) such number of shares of Common Stock, times (B) the Closing Bid Price on the date of exercise. 
 (d) Cashless Exercise. Notwithstanding anything contained herein to the contrary, the Holder may, in its sole discretion, exercise this Warrant in whole or in part and, in lieu of making the cash payment otherwise contemplated to be
made to the Company upon such exercise in payment of the Aggregate Exercise Price, elect instead to receive upon such exercise the “Net Number” of shares of Common Stock determined according to the following formula (a “Cashless
Exercise”): 
 Net Number = (A x B) - (A x C) 
                 B 
 For purposes of the
foregoing formula: 
 A = the total number of shares with respect to which this Warrant is then being exercised. 
 B = the Closing Sale Price of the shares of Common Stock (as reported by Bloomberg) on the date immediately preceding the date of the Exercise Notice.

 C = the Exercise Price then in effect for the applicable Warrant Shares at the time of such exercise. 
  

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 (e) Disputes. In the case of a dispute as to the determination of the Exercise Price or the
arithmetic calculation of the Warrant Shares, the Company shall promptly issue to the Holder the number of Warrant Shares that are not disputed and resolve such dispute thereafter. 
 (f) Pro Rata Exercise. Without limiting the remedies set forth herein, in the event that the Company receives an Exercise Notice from more than
one holder of Warrants for the same Share Delivery Date and the Company can honor for exercise some, but not all, of such portions of the Warrants submitted for exercise, the Company, subject to the restrictions in this Warrant, shall honor for
exercise from each holder of Warrants electing to have Warrants exercised on such date a pro rata amount of such holder’s portion of its Warrants submitted for exercise based on the number of Warrant Shares to be issued upon exercise on such
date by such holder relative to the aggregate number of Warrant Shares to be issued upon exercise on such date. In the event of a dispute as to the number of shares of Common Stock issuable to the Holder in connection with a exercise of this
Warrant, the Company shall issue to the Holder the number of shares of Common Stock not in dispute and resolve such dispute thereafter. 
 2. ADJUSTMENT
OF EXERCISE PRICE AND NUMBER OF WARRANT SHARES. The Exercise Price and the number of Warrant Shares shall be adjusted from time to time as follows: 
 (a) Stock Dividends and Stock Splits. If the Company, at any time after the Issuance Date: (i) pays a stock dividend or otherwise makes a distribution or distributions, payable on shares of Common Stock in
shares of Common Stock or in any securities of the Company or any of its Subsidiaries which would entitle the holder thereof to acquire at any time Common Stock, including, without limitation, any debt, preferred stock, rights, options, warrants or
other instrument that is at any time convertible into or exercisable or exchangeable for, or otherwise entitles the holder thereof to receive, Common Stock; (ii) subdivides outstanding shares of Common Stock into a larger number of shares;
(iii) combines (including by way of a reverse stock split) outstanding shares of Common Stock into a smaller number of shares; or (iv) issues, in the event of a reclassification of shares of the Common Stock, any shares of capital stock of
the Company, then the Exercise Price shall be multiplied by a fraction of which the numerator shall be the number of shares of Common Stock (excluding any treasury shares of the Company) outstanding immediately prior to such event and of which the
denominator shall be the number of shares of Common Stock outstanding immediately after such event. Any adjustment made pursuant to this Section 2(a) shall become effective immediately after the distribution date of any such dividend or
distribution and shall become effective immediately after the effective date in the case of a subdivision, combination or re-classification. 
 (b) Subsequent Rights Offerings. If the Company, at any time after the Issuance Date, issues rights, options or warrants to all holders of Common Stock, such issuance will also be granted to the Holder on an as-exercised basis
without the Holder having to exercise this Warrant in order to be entitled to such issuance. 
 (c) Other Dividends. If the Company,
at any time after the Issuance Date, pays a dividend or otherwise makes a distribution or distributions of cash or other assets (other than any dividend or distribution described in Section 2(a) or Section 2(d)), such
dividend will also be granted to the Holder on an as-exercised basis (without regard to any limitations) without the Holder having to exercise this Warrant in order to be entitled to such issuance. 
  

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 (d) Fundamental Transactions. If, at any time after the Issuance Date, (i) the Company
effects any merger or consolidation of the Company with or into another Person, (ii) the Company effects any sale of all or substantially all of its assets in one transaction or a series of related transactions to any Person other than a wholly
owned Subsidiary, or (iii) the Company effects any reclassification of the Common Stock or any compulsory share exchange, in each case as a result of which the Common Stock is effectively converted into or exchanged for other securities, cash
or property (in any such case, a “Fundamental Transaction”), then, upon any subsequent exercise of this Warrant, the Holder shall have the right to receive, for each share of Common Stock that would have been issuable upon exercise
of this Warrant immediately prior to the occurrence of such Fundamental Transaction, the same kind and amount of securities, cash or property as it would have been entitled to receive upon the occurrence of such Fundamental Transaction if it had
been, immediately prior to such Fundamental Transaction, the holder of one (1) share of Common Stock (the “Alternate Consideration”); provided, however, that if the Fundamental Transaction is a transaction wherein
all of the holders of all of the securities (including the holders of shares of Common Stock) of the Company receive only cash in exchange for all such securities, then the Holder of this Warrant, upon consummation of such Fundamental Transaction,
shall receive an amount of cash (if any) equal to the amount which the Holder would have been entitled to receive had this Warrant been exercised in accordance with Section 1(d) hereof immediately prior to such Fundamental Transaction
(and, upon receipt by the Holder of any such cash (or, if no such cash is payable, upon the consummation of the Fundamental Transaction), this Warrant shall be deemed canceled). If the Fundamental Transaction causes the Common Stock to be converted
into the right to receive more than a single type of consideration (determined based in part upon any form of stockholder election), the Alternate Consideration into which the Warrants will be exercisable will be deemed to be the weighted average of
the types and amounts of consideration received by the holders of Common Stock that affirmatively make such election. To the extent necessary to effectuate the foregoing provisions, any Successor Entity shall issue to the Holder a new Warrant
consistent with the foregoing provisions and evidencing the Holder’s right to exercise such Warrant into Alternate Consideration. The terms of any agreement pursuant to which a Fundamental Transaction is effected shall include terms requiring
any such successor or surviving entity to comply with the provisions of this Section 2(d) and ensuring that this Warrant (or any such replacement security) will be similarly adjusted upon any subsequent transaction analogous to a
Fundamental Transaction. 
 (e) Adjustment of Exercise Price upon Certain Self-Tenders. If the Company at any time or from time to
time on or after the Issuance Date makes a payment of cash or other consideration to the holders of the Common Stock in respect of a tender offer or exchange offer, other than an odd-lot offer, and the value of the sum of (i) the aggregate cash
and other consideration paid for such Common Stock, and (ii) any other consent or other fees paid to holders of Common Stock in respect of such tender offer or exchange offer expressed as an amount per share of Common Stock validly tendered or
exchanged pursuant to such tender offer or exchange offer, exceeds the Volume Weighted Average Price of the Common Stock on the Trading Day immediately prior to the date any such tender offer or exchange offer is first publicly announced (the
“Tender Announcement Date”), then the Exercise Price shall be adjusted in accordance with the following formula: 
 R’
= R x           O x P    
                        F + (P x O’) 
  

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 For purposes of the foregoing formula: 
 R = the Exercise Price in effect at the expiration time of the tender offer or exchange offer that is the subject of this Section 2(d) (the
“Expiration Time”); 
 R’ = the Exercise Price in effect immediately after the Expiration Time; 
 F = the fair market value (as determined by the Company’s Board of Directors in the exercise of their fiduciary duties with the concurrence of the
Required Holders) of the aggregate value of all cash and any other consideration paid or payable for Common Stock validly tendered or exchanged (including any consent or other fees) and not withdrawn prior to the Expiration Time (the
“Purchased Shares”); 
 O’ = the number of shares of Common Stock outstanding immediately after the Expiration Time,
excluding any Purchased Shares; 
 O = the number of shares of Common Stock outstanding immediately after the Expiration Time, including any
Purchased Shares; and 
 P = the Volume Weighted Average Price of the Common Stock on the Trading Day next succeeding the Tender Announcement
Date. 
 Such decrease, if any, shall become effective immediately upon the opening of business on the day next succeeding the Expiration
Time. In the event that the Company is obligated to purchase shares pursuant to any tender offer or exchange offer, but the Company is prevented by applicable law from effecting any such purchases or all such purchases are rescinded, the Exercise
Price shall again be adjusted to the Exercise Price that would then be in effect if such tender or exchange offer had not been made. If the application of this Section 2(e) to any tender or exchange offer would result in an increase in
the Exercise Price, no adjustment shall be made for such tender or exchange offer under this Section 2(e). The Company shall not effect any transaction described in this Section 2(e) if such transaction would have the effect
of setting the Exercise Price at an amount that would cause the exercise in full of the exercise rights set forth in this Warrant to result in a violation of NASD Rules or any listing standards applicable to the Company. 
 (f) Calculations. All calculations under this Section 2 shall be made to the nearest cent or the nearest 1/100th of a share, as the
case may be. No adjustment shall be made to the Exercise Price unless such adjustment would require a change of at least 1% in the Exercise Price. Any adjustment that would otherwise be required to be made shall be carried forward and taken into
account in any subsequent adjustment or in connection with any exercise of the Warrants. For purposes of this Section 2, the number of shares of Common Stock deemed to be issued and outstanding as of a given date shall be the sum of the
number of shares of Common Stock (excluding any treasury shares of the Company) issued and outstanding. 
  

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 3. INTENTIONALLY OMITTED. 
 4. FUNDAMENTAL TRANSACTIONS. 
 (a) The Company shall not enter into or be party to a Fundamental Transaction unless the
Successor Entity assumes in writing all of the obligations of the Company under this Warrant, the Purchase Agreement, the Registration Rights Agreements (as defined in the Purchase Agreement) and the other Transaction Documents (as defined in the
Purchase Agreement) in accordance with the provisions of this Section 4 pursuant to written agreements, including agreements to deliver to each holder of Warrants in exchange for such Warrants a security of the Successor Entity evidenced
by a written instrument substantially similar in form and substance to the Warrants, including, without limitation, having a number of warrant shares equal to the warrant shares of the Warrants held by such holder, having substantially identical
exercise rights as the Warrants (and, as applicable, reflecting any adjustments pursuant to Section 2(d)). Upon the occurrence of any Fundamental Transaction, the Successor Entity shall succeed to, and be substituted for (so that from
and after the date of such Fundamental Transaction, the provisions of this Warrant referring to the “Company” shall refer instead to the Successor Entity), and may exercise every right and power of the Company and shall assume all of the
obligations of the Company under this Warrant with the same effect as if such Successor Entity had been named as the Company herein. The provisions of this Section 4 shall apply similarly and equally to successive Fundamental
Transactions and shall be applied without regard to any limitations on the exercise of this Warrant. 
 5. NONCIRCUMVENTION. The Company hereby
covenants and agrees that the Company will not, by amendment of its charter, bylaws or through any reorganization, transfer of assets, consolidation, merger, scheme of arrangement, dissolution, issue or sale of securities, or any other voluntary
action, avoid or seek to avoid the observance or performance of any of the terms of this Warrant, and will at all times in good faith carry out all the provisions of this Warrant and take all action as may be required to protect the rights of the
Holder. Without limiting the generality of the foregoing, the Company (i) shall not increase the par value of any shares of Common Stock receivable upon the exercise of this Warrant above the Exercise Price then in effect, (ii) shall take
all such actions as may be necessary or appropriate in order that the Company may validly and legally issue fully paid and nonassessable shares of Common Stock upon the exercise of this Warrant, and (iii) shall, so long as any of the Warrants
are outstanding, take all action necessary to reserve and keep available out of its authorized and unissued shares of Common Stock, solely for the purpose of effecting the exercise of the Warrants, one hundred five percent (105%) of the number
of shares of Common Stock as shall from time to time be necessary to effect the exercise of the Warrants then outstanding (without regard to any limitations on exercise). 
 6. WARRANT HOLDER NOT DEEMED A STOCKHOLDER. Except as otherwise specifically provided herein, the Holder, solely in such Person’s capacity as a holder of this Warrant, shall not be entitled to vote or
receive dividends or be deemed the holder of share 

  

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capital of the Company for any purpose, nor shall anything contained in this Warrant be construed to confer upon the Holder, solely in such Person’s
capacity as the Holder of this Warrant, any of the rights of a shareholder of the Company or any right to vote, give or withhold consent to any corporate action (whether any reorganization, issue of stock, reclassification of stock, consolidation,
merger, conveyance or otherwise), receive notice of meetings, receive dividends or subscription rights, or otherwise, prior to the issuance to the Holder of the Warrant Shares which such Person is then entitled to receive upon the due exercise of
this Warrant. In addition, nothing contained in this Warrant shall be construed as imposing any liabilities on the Holder to purchase any securities (upon exercise of this Warrant or otherwise) or as a shareholder of the Company, whether such
liabilities are asserted by the Company or by creditors of the Company. 
 7. REISSUANCE OF WARRANTS. 
 (a) Transfer of Warrant. If this Warrant is to be transferred, the Holder shall surrender this Warrant to the Company, whereupon the Company will
forthwith issue and deliver upon the order of the Holder a new Warrant (in accordance with Section 7(d)), registered as the Holder may request, representing the right to purchase the number of Warrant Shares being transferred by the
Holder and, if less than the total number of Warrant Shares then underlying this Warrant is being transferred, a new Warrant (in accordance with Section 7(d)) to the Holder representing the right to purchase the number of Warrant Shares
not being transferred. 
 (b) Lost, Stolen or Mutilated Warrant. Upon receipt by the Company of evidence reasonably satisfactory to
the Company of the loss, theft, destruction or mutilation of this Warrant, and, in the case of loss, theft or destruction, of any indemnification undertaking by the Holder to the Company in customary form and, in the case of mutilation, upon
surrender and cancellation of this Warrant, the Company shall execute and deliver to the Holder a new Warrant (in accordance with Section 7(d)) representing the right to purchase the Warrant Shares then underlying this Warrant.

 (c) Exchangeable for Multiple Warrants. This Warrant is exchangeable, upon the surrender hereof by the Holder at the principal
office of the Company, for a new Warrant or Warrants (in accordance with Section 7(d)) representing in the aggregate the right to purchase the number of Warrant Shares then underlying this Warrant, and each such new Warrant will
represent the right to purchase such portion of such Warrant Shares as is designated by the Holder at the time of such surrender; provided, however, that no Warrants for fractional shares of Common Stock shall be issued. 
 (d) Issuance of New Warrants. Whenever the Company is required to issue a new Warrant pursuant to the terms of this Warrant, such new Warrant
(i) shall be of like tenor with this Warrant, (ii) shall represent, as indicated on the face of such new Warrant, the right to purchase the Warrant Shares then underlying this Warrant (or in the case of a new Warrant being issued pursuant
to Section 7(a) or Section 7(c), the Warrant Shares designated by the Holder which, when added to the number of shares of Common Stock underlying the other new Warrants issued in connection with such issuance, does not exceed
the number of Warrant Shares then underlying this Warrant), (iii) shall have an issuance date, as indicated on the face of such new Warrant which is the same as the Issuance Date, and (iv) shall have the same rights and conditions as this
Warrant. 
  

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 8. NOTICES. Whenever notice is required to be given under this Warrant, unless otherwise provided herein, such
notice shall be given as follows: 
 If to the Company: 
 Blue Coat Systems, Inc. 
 420 North Mary Avenue 
 Sunnyvale, California 94085 
 Attention: Betsy
Bayha 
 Facsimile No.: (408) 220-2175 
 with a copy to: 
 Davis Polk & Wardwell 
 1600 El Camino Real 
 Menlo Park, California
94025 
 Attention: William M. Kelly 
        Sarah K. Solum 
 Facsimile No.: (650) 752-2112 
                (650) 752-3611 
 If to the Holder: 
 To its address and
facsimile number set forth in Section 8.11 of the Purchase Agreement, with copies to such Holders representatives as set forth in that same section, 
 or to such other address and/or facsimile number and/or to the attention of such other Person as the recipient party has specified by written notice given to each other party five (5) days prior to the effectiveness of such change.
Without limiting the generality of the foregoing, the Company will give written notice to the Holder (i) promptly upon any adjustment of the Conversion Price, setting forth in reasonable detail, and certifying, the calculation of such
adjustment and (ii) at least ten (10) days prior to the date on which the Company closes its books or takes a record (A) with respect to any dividend or distribution upon the Common Stock, (B) with respect to any pro rata
subscription offer to holders of Common Stock or (C) for determining rights to vote with respect to any Fundamental Transaction, dissolution or liquidation, provided in each case that such information shall be made known to the public prior to
or in conjunction with such notice being provided to the Holder. 
 9. AMENDMENT AND WAIVER. Except as otherwise provided herein, the provisions of
this Warrant may be amended and the Company may take any action herein prohibited, or omit to perform any act herein required to be performed by it, only if the Company has obtained the written consent of the Required Holders; provided that
no such action may increase the exercise price of any Warrant or decrease the number of shares or class of stock obtainable upon exercise of any Warrant without the written consent of the Holder. No such amendment shall be effective to the extent
that it applies to less than all of the holders of the Warrants then outstanding. 
  

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 10. GOVERNING LAW. This Warrant shall be governed by and construed and enforced in accordance with, and all
questions concerning the construction, validity, interpretation and performance of this Warrant shall be governed by, the internal laws of the State of New York, without giving effect to any choice of law or conflict of law provision or rule
(whether of the State of New York or any other jurisdictions) that would cause the application of the laws of any jurisdictions other than the State of New York. 
 11. CONSTRUCTION; HEADINGS. This Warrant shall be deemed to be jointly drafted by the Company and all the Purchasers and shall not be construed against any person as the drafter hereof. The headings of this Warrant are for
convenience of reference and shall not form part of, or affect the interpretation of, this Warrant. 
 12. REMEDIES, OTHER OBLIGATIONS, BREACHES AND
INJUNCTIVE RELIEF. The remedies provided in this Warrant with respect to the Company’s failure to comply with the terms of this Warrant shall be cumulative and in addition to all other remedies available under the Purchase Agreement, the
Notes, this Warrant, the Registration Rights Agreements and the other Transaction Documents, at law or in equity (including a decree of specific performance and/or other injunctive relief), and nothing herein shall limit the right of the Holder to
pursue actual damages for any failure by the Company to comply with the terms of this Warrant. The Company acknowledges that a breach by it of its obligations hereunder will cause irreparable harm to the Holder and that the remedy at law for any
such breach may be inadequate. The Company therefore agrees that, in the event of any such breach or threatened breach, the holder of this Warrant shall be entitled, in addition to all other available remedies, to an injunction restraining any
breach, without the necessity of showing economic loss and without any bond or other security being required. 
 13. TRANSFER. This Warrant may be
offered for sale, sold, transferred or assigned without the consent of the Company, except that if such sale, transfer or assignment is for less than 90,000 Warrant Shares) or such lesser number of Warrant Shares then covered by this Warrant and is
not to a Permitted Transferee (as defined in the Purchase Agreement), then the consent of the Company shall be required. 
 14. CERTAIN DEFINITIONS.
For purposes of this Warrant, the following terms shall have the following meanings: 
 (a) “Bloomberg” means Bloomberg
Financial Markets. 
 (b) “Business Day” means any day other than Saturday, Sunday or other day on which commercial banks in
The City of New York are authorized or required by law to remain closed. 
 (c) “Closing Bid Price” and “Closing
Sale Price” means, for any security as of any date, the last closing bid price and last closing trade price, respectively, for such security on the Principal Market, as reported by Bloomberg, or, if the Principal Market begins to operate on
an 

  

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extended hours basis and does not designate the closing bid price or the closing trade price, as the case may be, then the last bid price or last trade
price, respectively, of such security prior to 4:00 p.m., New York Time, as reported by Bloomberg, or, if the Principal Market is not the principal securities exchange or trading market for such security, the last closing bid price or last trade
price, respectively, of such security on the principal securities exchange or trading market where such security is listed or traded as reported by Bloomberg, or if the foregoing do not apply, the last closing bid price or last trade price,
respectively, of such security in the over-the-counter market on the electronic bulletin board for such security as reported by Bloomberg, or, if no closing bid price or last trade price, respectively, is reported for such security by Bloomberg, the
average of the bid prices, or the ask prices, respectively, of any market makers for such security as reported in the “pink sheets” by Pink Sheets LLC (formerly the National Quotation Bureau, Inc.). If the Closing Bid Price or the Closing
Sale Price cannot be calculated for a security on a particular date on any of the foregoing bases, the Closing Bid Price or the Closing Sale Price, as the case may be, of such security on such date shall be the fair market value as mutually
determined by the Company and the Holder. All such determinations shall be appropriately adjusted for any stock dividend, stock split, stock combination or other similar transaction during the applicable calculation period. 
 (d) “Common Stock” means (i) the Company’s shares of Common Stock, par value $0.001 per share, and (ii) any share capital
into which such Common Stock shall have been changed or any share capital resulting from a reclassification of such Common Stock. 
 (e)
“Eligible Market” means the Principal Market, The New York Stock Exchange, Inc., the American Stock Exchange, The Nasdaq Stock Market or another national securities exchange or quotation system. 
 (f) “Expiration Date” means June 2, 2013 or, if such date falls on a day other than a Business Day or on which trading does not
take place on the Principal Market (a “Holiday”), the next date that is not a Holiday. 
 (g) “NASD” means
the National Association of Securities Dealers, Inc., currently known as the Financial Industry Regulatory Authority, Inc. 
 (h)
“Note” means any Senior Convertible Note issued pursuant to the Purchase Agreement. 
 (i) “Parent Entity”
of a Person means an entity that, directly or indirectly, controls the applicable Person. 
 (j) “Person” means an
individual, a limited liability company, a partnership, a joint venture, a corporation, a trust, an unincorporated organization, any other entity and a government or any department or agency thereof. 
 (k) “Principal Market” means the Nasdaq Global Select Market. 
 (l) “Registration Rights Agreement” means that certain registration rights agreement by and among the Company and the Purchasers.

  

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 (m) “Required Holders” means the holders of the Warrants representing at least 67% of
shares of Common Stock underlying the Warrants then outstanding. 
 (n) “Subsidiaries” of any Person means another Person,
an amount of the voting securities, other voting rights or voting partnership interests of which is sufficient to elect at least a majority of its board of directors or other governing body (or, if there are no such voting interests, 50% or more of
the equity interests of which) is owned directly or indirectly by such first Person. 
 (o) “Successor Entity” means the
Person (or, if so elected by the Required Holders, the Parent Entity) formed by, resulting from or surviving any Fundamental Transaction or the Person (or, if so elected by the Required Holders, the Parent Entity) with which such Fundamental
Transaction shall have been entered into. 
 (p) “Trading Day” means any day on which the Common Stock is traded on the
Principal Market, or, if the Principal Market is not the principal trading market for the Common Stock, then on the principal securities exchange or securities market on which the Common Stock is then traded; provided that “Trading
Day” shall not include any day on which the Common Stock is scheduled to trade on such exchange or market for less than four hours or any day that the Common Stock is suspended from trading during the final hour of trading on such exchange
or market (or if such exchange or market does not designate in advance the closing time of trading on such exchange or market, then during the hour ending at 4:00:00 p.m., New York Time, or such other time as such exchange or market publicly
announces shall be the closing time of trading). 
 (q) “Volume Weighted Average Price” means, for any security as of any
date, the dollar volume-weighted average price for such security on the Principal Market during the period beginning at 9:30:01 a.m., New York Time (or such other time as the Principal Market publicly announces is the official open of trading), and
ending at 4:00:00 p.m., New York Time (or such other time as the Principal Market publicly announces is the official close of trading) as reported by Bloomberg through its “Volume at Price” functions, or, if the foregoing does not apply,
the dollar volume-weighted average price of such security in the over-the-counter market on the electronic bulletin board for such security during the period beginning at 9:30:01 a.m., New York Time (or such other time as such market publicly
announces is the official open of trading), and ending at 4:00:00 p.m., New York Time (or such other time as such market publicly announces is the official close of trading) as reported by Bloomberg. If the Volume Weighted Average Price cannot be
calculated for a security on a particular date on any of the foregoing bases, the Volume Weighted Average Price of such security on such date shall be the fair market value as mutually determined by the Company’s Board of Directors and the
holder. All such determinations to be appropriately adjusted for any stock dividend, stock split, stock combination or other similar transaction during the applicable calculation period. 
 [Signature Page Follows] 
  

 12 

 IN WITNESS WHEREOF, the Company has caused this Warrant to Purchase Common Stock to be duly executed as
of the Issuance Date set out above. 
  

					
	BLUE COAT SYSTEMS, INC.
		
	By:	 	 
		 	Name:	 	
		 	Title:	 	

  

 13 

 EXHIBIT A 
 EXERCISE NOTICE 
 TO BE EXECUTED BY THE REGISTERED HOLDER TO EXERCISE THIS 
 WARRANT TO PURCHASE COMMON STOCK 
 BLUE COAT
SYSTEMS, INC. 
 TO: CHIEF FINANCIAL OFFICER 
 The undersigned holder hereby exercises the right to purchase                      of the shares of Common Stock (“Warrant
Shares”) of Blue Coat Systems, Inc., a Delaware corporation (the “Company”), evidenced by the attached Warrant to Purchase Common Stock (the “Warrant”). Capitalized terms used herein and not otherwise
defined shall have the respective meanings set forth in the Warrant. 
 1. Form of Exercise Price. The Holder intends that payment of
the Exercise Price shall be made as: 
  

	 	 ̈	                     a “Cash Exercise” with respect to
                     Warrant Shares; and/or 

  

	 	 ̈	                     a “Cashless Exercise” with
respect to                      Warrant Shares. 

 2. Payment of Exercise Price. In the event that the holder has elected a Cash Exercise with respect to some or all of the Warrant Shares to be
issued pursuant hereto, the holder shall pay the Aggregate Exercise Price in the sum of $                     to the Company in
accordance with the terms of the Warrant. 
 3. Delivery of Warrant Shares. The Company shall deliver to the holder
                     Warrant Shares in accordance with the terms of the Warrant. 
 4. Accredited Investor. The undersigned certifies to the Company that as of the date hereof, it is an “accredited investor” as that term
is defined in Rule 501(a) of Regulation D. 
 Date:              ,          
  

	
	  
	Name of Registered Holder

  

					
	By: 	 	 
		 	Name: 	 	
		 	Title: 	 	

 Exhibit A-1 

 ACKNOWLEDGMENT 
 The Company hereby acknowledges this Exercise Notice and hereby directs [TRANSFER AGENT] to issue the above indicated number of shares of Common Stock in accordance with the Transfer Agent Instructions dated
[            ] [__], 200[_] from the Company and acknowledged and agreed to by [TRANSFER AGENT]. 
  

					
	 BLUE COAT SYSTEMS, INC.

		
	By: 	 	 
		 	Name: 	 	
		 	Title: 	 	

 Exhibit A-2Registration Rights Agreement

 Exhibit 10.02 
 REGISTRATION RIGHTS AGREEMENT 
 This
REGISTRATION RIGHTS AGREEMENT (this “Agreement”) is made as of the 2nd day of June, 2008, by and between Blue Coat Systems, Inc., a
Delaware corporation (the “Company”), and the investors listed on Schedule A attached hereto (the “Investors” and, each individually, an “Investor”). 
 THE PARTIES TO THIS AGREEMENT enter into this Agreement on the basis of the following facts, intentions and understandings: 
 WHEREAS, the Company, Francisco Partners II, L.P. and Manchester Securities Corp. are parties to that certain Note Purchase Agreement dated as of
April 20, 2008 (the “Purchase Agreement”); 
 WHEREAS, pursuant to the Purchase Agreement, the Company will issue to
the Investors $40,000,000 aggregate principal amount of its Zero Coupon Senior Convertible Notes due 2013 (the “Notes”); 
 WHEREAS, pursuant to the Purchase Agreement, the Company will issue to the Investors 192,678 Warrants to Purchase Common Stock (the “Warrants”); and 
 WHEREAS, in order to induce Francisco Partners II, L.P. to enter into the Purchase Agreement and in order to induce the Investors to purchase the Notes
and the Warrants from the Company pursuant to the Purchase Agreement, the Investors and the Company hereby agree that this Agreement shall govern certain of the rights of the Investors to cause the Company to register (i) the shares of common
stock, par value $0.0001 per share (the “Common Stock”), of the Company issued or issuable upon conversion of the Notes (such issued or issuable shares of Common Stock being referred to as the “Conversion Shares”)
and (ii) the shares of Common Stock issued or issuable upon exercise of the Warrants (such issued or issuable shares of Common Stock being referred to as the “Warrant Shares”). 
 NOW, THEREFORE, the parties hereby agree as follows: 
 Section 1. Registration Rights. The Company covenants and agrees as follows: 
 1.1 Definitions. For purposes of
this Section 1: 
 (a) The term “1934 Act” means the Securities Exchange Act of 1934, as amended.

 (b) The term “Act” means the Securities Act of 1933, as amended. 
 (c) The term “Anniversary Date” means the first anniversary of the date of this Agreement. 
 (d) The term “Form S-3” means such form under the Act as in effect on the date hereof or any successor registration form
under the Act subsequently adopted by the SEC. 

 (e) The term “Form S-4” means such form under the Act as in effect on
the date hereof or any successor registration form under the Act subsequently adopted by the SEC. 
 (f) The term
“Holder” means any person owning or having the right to acquire Registrable Securities or any assignee thereof in accordance with Section 1.10 hereof. 
 (g) The terms “register,” “registered,” and “registration” refer to a registration in
compliance with the Act effected by preparing and filing a registration statement or similar document in compliance with the Act, and the declaration or ordering of effectiveness of such registration statement or document. 
 (h) The term “Other Registrable Securities” means any securities of the Company (A) that are issued by the Company
in connection with a financing, merger or acquisition transaction occurring subsequent to the date of the Purchase Agreement and (B) that have been granted registration rights by the Company in connection with such transaction. 
 (i) The term “Registrable Securities” means (i) the Conversion Shares and the Warrant Shares and (ii) any
Common Stock of the Company issued as (or issuable upon the conversion or exercise of any warrant, right or other security that is issued as) a dividend or other distribution with respect to, or in exchange for, or in replacement of, the shares
referenced in the preceding clause (i) above, excluding in all cases, however, any Registrable Securities sold by a person in a transaction in which the rights under this Section 1 are not assigned. 
 (j) The “number of shares of Registrable Securities” outstanding shall be determined by the number of shares of Common
Stock outstanding that are, and the number of shares of Common Stock issuable pursuant to then exercisable or convertible securities that are, Registrable Securities. 
 (k) The “number of shares of Other Registrable Securities” outstanding shall be determined by the number of shares of
Common Stock outstanding that are, and the number of shares of Common Stock issuable pursuant to then exercisable or convertible securities that are, Other Registrable Securities. 
 (l) The term “Rule 144” shall mean Rule 144 under the Act. 
 (m) The term “SEC” shall mean the Securities and Exchange Commission. 
 1.2 Piggyback Registration. 
 (a) If (but without any obligation to do so) the Company proposes to register (including for this purpose a registration effected by the Company for stockholders other than the Holders) any of its capital stock or other securities under the
Act in connection with the public offering of such securities (other than a registration relating solely to the sale of securities of participants in a Company stock plan, a registration effected on Form S-4 or a registration on any form that does
not include substantially the same information as would be required to be included in a registration statement covering the sale of the Registrable Securities), the Company shall, at such time, give each Holder written notice of such registration.
Upon the written request of each Holder given within twenty (20) days after delivery of such notice by the Company in accordance with Section 2.6, the Company shall, subject to the provisions of Section 1.2(c), use all commercially
reasonable efforts to cause to be registered under the Act all of the Registrable Securities that each such Holder requests to be registered. 
  

 2 

 (b) 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. The expenses of such withdrawn registration shall be borne by the Company in
accordance with Section 1.6 hereof. 
 (c) In connection with any offering involving an underwriting of shares of the
Company’s capital stock, the Company shall not be required under this Section 1.2 to include any of the Holders’ securities in such underwriting unless they accept the terms of the underwriting as reasonably agreed upon between the
Company and the underwriters selected by the Company (or by other persons entitled to select the underwriters) and enter into an underwriting agreement in customary form with such underwriters, and then only in such quantity as the underwriters
determine in their sole discretion will not jeopardize the success of the offering by the Company. If the total amount of securities, including Registrable Securities and Other Registrable Securities, requested by stockholders to be included in such
offering exceeds the amount of securities sold other than by the Company that the underwriters determine in their sole discretion is compatible with the success of the offering, then the Company shall be required to include in the offering only that
number of such securities, including Registrable Securities, that the underwriters determine in their sole discretion will not jeopardize the success of the offering. In no event shall (i) any Registrable Securities and Other Registrable
Securities be excluded from such offering unless all other stockholders’ securities (other than Registrable Securities and Other Registrable Securities) have been first excluded or (ii) the amount of Registrable Securities and Other
Registrable Securities included in the offering be reduced below twenty percent (20%) of the total amount of securities included in such offering. 
 In the event that less than all of the Registrable Securities and Other Registrable Securities requested to be registered can be included in such offering, then the number of Registrable Securities included in the
offering shall equal the total number of Registrable Securities and Other Registrable Securities included in the offering, as determined pursuant to the immediately preceding paragraph, multiplied by a fraction (i) the numerator of which is the
number of Registrable Securities then held by all Holders that request to include Registrable Securities in the offering and (ii) the denominator of which is the sum of the number of Registrable Securities then held by all Holders that request
to include Registrable Securities in the offering and the number of Other Registrable Securities then held by all holders of Other Registrable Securities that request to include Other Registrable Securities in the offering. The number of Registrable
Securities included in the offering pursuant to the immediately preceding sentence shall be apportioned pro rata among the selling Holders based on the number of Registrable Securities held by all selling Holders or in such other proportions as
shall mutually be agreed to by all such selling Holders. For purposes of the preceding sentence concerning apportionment, for any selling stockholder that is a Holder of Registrable Securities and that is a venture capital fund, private equity fund,
partnership or corporation, the affiliated venture capital funds, private equity funds, partners, retired partners and stockholders of such Holder, or the estates and family members of any such partners and retired partners and any trusts for the

  

 3 

 
benefit of any of the foregoing persons shall be deemed to be a single “selling Holder,” and any pro rata reduction with respect to such
“selling Holder” shall be based upon the aggregate amount of Registrable Securities owned by all such related entities and individuals. 
 1.3 Shelf Registration. 
 (a) As soon as reasonably practicable, but in no event later than one hundred
twenty (120) days after the date hereof, the Company will prepare and file with the SEC a registration statement on Form S-3 for the purpose of registering under the Securities Act all of the Registrable Securities for resale by, and for the
account of, the Holders as selling stockholders thereunder (the “Shelf Registration Statement”). The Shelf Registration Statement shall permit the Holders to offer and sell, on a delayed or continuous basis pursuant to Rule 415
under the Securities Act, any and all of the Registrable Securities. The Company agrees to use commercially reasonable efforts to cause the Shelf Registration Statement to become effective as promptly as practicable thereafter, but in any event no
later than one hundred eighty (180) days after the date hereof. 
 (b) The Company shall be required to keep the Shelf
Registration Statement effective until such date that is the earlier of (i) the date as of which all of the Holders may sell all of the Registrable Securities without restriction pursuant to Rule 144 promulgated under the Act or (ii) the
date when all of the Registrable Securities registered thereunder shall have been sold pursuant to the Shelf Registration Statement, Rule 144 or another transaction in which the purchaser receives securities that do not bear any legends and are
freely-tradable. Thereafter, the Company shall be entitled to withdraw the Shelf Registration Statement and the Holders shall have no further right to offer or sell any of the Registrable Securities pursuant to the Shelf Registration Statement (or
any prospectus relating thereto). 
 1.4 Obligations of the Company. Whenever required under this Section 1 to effect the
registration of any Registrable Securities, except as otherwise expressly provided herein, the Company shall, as expeditiously as reasonably possible: 
 (a) prepare and file with the SEC a registration statement with respect to such Registrable Securities and use all commercially reasonable efforts to cause such registration statement to become and remain effective;

 (b) prepare and file with the SEC 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 Act with respect to the disposition of all Registrable Securities covered by such registration statement; 
 (c) furnish to the Holders such number of copies of a prospectus, including a preliminary prospectus, in conformity with the requirements
of the Act, and such other documents as they may reasonably request in order to facilitate the disposition of Registrable Securities owned by them; 
 (d) use all commercially reasonable 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; 

 

 4 

 (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; 
 (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 to this
Section 1 to be listed on each securities exchange and trading system on which similar securities issued by the Company are then listed; and 
 (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. 
 Notwithstanding the provisions of this Section 1, the Company shall be entitled to postpone or suspend the filing,
effectiveness or use of, or trading under, any registration statement during any period when (i) the Company is not eligible to use Form S-3, (ii) the SEC or The Nasdaq Stock Market requests that the Company amend or supplement the Shelf
Registration Statement or the prospectus included therein or requests additional information relating thereto, (iii) the SEC or The Nasdaq Stock Market issues a stop order or similar order suspending the effectiveness or restricting the use of
the Shelf Registration Statement or initiates proceedings to issue a stop order or similar order, (iv) the Board of Directors of the Company in good faith determines that the Shelf Registration Statement, the prospectus included therein, any
amendment or supplement thereto or any document incorporated or deemed to be incorporated therein contains 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 light of the circumstances then existing; provided, however, that the Company uses commercially reasonable efforts to prepare and file with the SEC such amendments and supplements to the such registration statement or
amendment as shall be reasonably necessary to cure such untrue statement or omission, or (v) the Board of Directors of the Company in good faith determines that the failure to so postpone or suspend would require disclosure of material
nonpublic information that, if disclosed at such time, would be materially harmful to the interests of the Company and its stockholders; provided, however, that during any such period all executive officers and directors of the Company and all
stockholders of the Company with similar registration rights are also prohibited from selling securities of the Company; provided, further, however, that such postponement or suspension (A) shall not exceed a period of forty-five (45) days
and (B) shall be exercised by the Company not more than twice in any twelve (12) month period (for a maximum of ninety (90) days within any such twelve (12) month period), provided that the second period of postponement or
suspension within any twelve (12) month period shall not commence less than sixty (60) days after the end of the first period of postponement or suspension within any such twelve (12) month period. 
  

 5 

 In the event of the suspension of effectiveness of any registration statement pursuant to this
Section 1.4, the applicable time period during which such registration statement is to remain effective shall be extended by that number of days equal to the number of days the effectiveness of such registration statement was suspended.

 1.5 Information from Holder. It shall be a condition precedent to the obligations of the Company to take any action pursuant to
this Section 1 with respect to the Registrable Securities of any selling Holder that such Holder shall furnish to the Company such information regarding itself, the Registrable Securities held by it, and the intended method of disposition of
such securities as shall be reasonably required to effect the registration of such Holder’s Registrable Securities. 
 1.6 Expenses
of Registration. All expenses (other than (i) underwriting discounts and commissions relating to the Registrable Securities that are being sold by the Holders and (ii) fees of any counsel for the selling Holders) that are incurred in
connection with registrations, filings or qualifications pursuant to Sections 1.2 and 1.3, including (without limitation) all registration, filing and qualification fees, printers’ and accounting fees and fees and disbursements of counsel for
the Company shall be borne by the Company. 
 1.7 Delay of Registration. No Holder shall have any right to obtain or seek an
injunction restraining or otherwise delaying any such registration as the result of any controversy that might arise with respect to the interpretation or implementation of this Section 1. 
 1.8 Indemnification. In the event any Registrable Securities are included in a registration statement under this Section 1: 
 (a) To the extent permitted by law, the Company will indemnify and hold harmless each Holder, the partners, officers, directors and
stockholders of each Holder, legal counsel and accountants for each Holder, any underwriter (as defined in the Act) for such Holder and each person, if any, who controls such Holder or underwriter within the meaning of the Act or the 1934 Act,
against any losses, claims, damages or liabilities (joint or several) to which they may become subject under the Act, the 1934 Act, any state securities laws or any rule or regulation promulgated under the Act, the 1934 Act or any state securities
laws, insofar as such losses, claims, damages, or liabilities (or actions in respect thereof) arise out of or are based upon any of the following statements, omissions or violations (collectively a “Violation”): (i) any untrue
statement or alleged untrue statement of a material fact contained in such registration statement, including any preliminary prospectus or final prospectus contained therein or any amendments or supplements thereto, (ii) the omission or alleged
omission to state in such registration statement a material fact required to be stated therein, or necessary to make the statements therein not misleading or (iii) any violation or alleged violation by the Company of the Act, the 1934 Act, any
state securities laws or any rule or regulation promulgated under the Act, the 1934 Act or any state securities laws, and the Company will reimburse each such Holder, underwriter, controlling person or other aforementioned person for any legal or
other expenses reasonably incurred by them in connection with investigating or defending any such 

  

 6 

 
loss, claim, damage, liability or action as such expenses are incurred; provided, however, that the indemnity agreement contained in this subsection l.8(a)
shall not apply to amounts paid in settlement of any such loss, claim, damage, liability or action if such settlement is effected without the consent of the Company (which consent shall not be unreasonably withheld), nor shall the Company be liable
to a person claiming indemnification in any such case for any such loss, claim, damage, liability or action to the extent that it arises out of or is based upon a Violation that occurs in reliance upon and in conformity with written information
furnished expressly for use in connection with such registration by such Holder, underwriter, controlling person or other aforementioned person that is claiming indemnification; provided, further, however, that the foregoing indemnity agreement with
respect to any preliminary prospectus shall not inure to the benefit of any such Holder or underwriter or other aforementioned person, or any person controlling such Holder or underwriter, from whom the person asserting any such losses, claims,
damages or liabilities purchased shares in the offering, if a copy of the most current prospectus was not sent or given by or on behalf of such Holder or underwriter or other aforementioned person to such person, if required by law to have been so
delivered, at or prior to the written confirmation of the sale of the shares of such person, and if the prospectus (as so amended or supplemented) would have cured the defect giving rise to such loss, claim, damage or liability. 
 (b) To the extent permitted by law, each selling Holder will, severally and not jointly, indemnify and hold harmless the Company, each of
its directors, each of its officers who has signed the registration statement, each person, if any, who controls the Company within the meaning of the Act, legal counsel and accountants for the Company, any underwriter, any other Holder selling
securities in such registration statement and any controlling person of any such underwriter or other Holder, against any losses, claims, damages or liabilities (joint or several) to which any of the foregoing persons may become subject, under the
Act, the 1934 Act, any state securities laws or any rule or regulation promulgated under the Act, the 1934 Act or any state securities laws, insofar as such losses, claims, damages or liabilities (or actions in respect thereto) arise out of or are
based upon any Violation, in each case to the extent (and only to the extent) that such Violation occurs in reliance upon and in conformity with written information furnished by such Holder expressly for use in connection with such registration; and
each such Holder will reimburse any person intended to be indemnified pursuant to this subsection l.8(b) for any legal or other expenses reasonably incurred by such person in connection with investigating or defending any such loss, claim, damage,
liability or action as such expenses are incurred; provided, however, that the indemnity agreement contained in this subsection l.8(b) shall not apply to amounts paid in settlement of any such loss, claim, damage, liability or action if such
settlement is effected without the consent of the Holder (which consent shall not be unreasonably withheld), and provided that in no event shall any indemnity under this subsection l.8(b) exceed the net proceeds from the offering received by such
Holder. 
 (c) Promptly after receipt by an indemnified party under this Section 1.8 of notice of the commencement of any
action (including any governmental action), such indemnified party will, if a claim in respect thereof is to be made against any indemnifying party under this Section 1.8, deliver to the indemnifying party a written notice of the commencement
thereof and the indemnifying party shall have the right to participate in and, to the extent the indemnifying party so desires, jointly with any other indemnifying party similarly noticed, to assume the defense thereof with counsel mutually
satisfactory to the parties; provided, however, 

  

 7 

 
that an indemnified party (together with all other indemnified parties that may be represented without conflict by one counsel) shall have the right to
retain one separate counsel, with the fees and expenses 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 to deliver written notice to the indemnifying party within a reasonable time of the commencement of any such action, if
prejudicial to its ability to defend such action, shall relieve such indemnifying party of liability to the indemnified party under this Section 1.8 to the extent of such prejudice, but the omission to so deliver written notice to the
indemnifying party will not relieve it of any liability that it may have to any indemnified party otherwise than under this Section 1.8. 
 (d) If the indemnification provided for in this Section 1.8 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 herein, then the indemnifying party, in lieu of indemnifying such indemnified party hereunder, shall contribute to the amount paid or 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 the indemnified party on the other hand 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 no contribution by any Holder, when combined with any amounts paid by such Holder pursuant to Section 1.8(b), shall exceed the net proceeds from the
offering received by such Holder. The relative fault of the indemnifying party and 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 or
alleged 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) Notwithstanding the foregoing, to the extent that the provisions on indemnification and
contribution contained in the underwriting agreement entered into by any Holder claiming indemnification in connection with an underwritten public offering are in conflict with the foregoing provisions, the provisions in the underwriting agreement
shall control with respect to such Holder. 
 (f) The obligations of the Company and Holders under this Section 1.8 shall
survive the completion of any offering of Registrable Securities in a registration statement under this Section 1 and otherwise. 
 1.9
Reports Under the 1934 Act. With a view to making available to the Holders the benefits of Rule 144 and any other rule or regulation of the SEC that may at any time permit a Holder to sell securities of the Company to the public without
registration beginning on the Anniversary Date, the Company agrees, to: 
 (a) make and keep public information available, as
those terms are understood and defined in Rule 144, at all times on and after the Anniversary Date; 
  

 8 

 (b) file with the SEC in a timely manner all reports and other documents required of the
Company under the Act and the 1934 Act after the date hereof; 
 (c) not later than the Anniversary Date, file with the SEC
all reports and other documents required of the Company under the Act and the 1934 Act for the 12 months preceding the Anniversary Date; and 
 (d) furnish to any Holder on and after the Anniversary Date, so long as the Holder owns any Registrable Securities, forthwith upon request (i) a written statement by the Company that it has complied with the
reporting requirements of Rule 144, (ii) a copy of the most recent annual or quarterly report of the Company and such other reports and documents so filed by the Company, and (iii) such other information as may be reasonably requested to
avail any Holder of any rule or regulation of the SEC that permits the selling of any such securities without registration on or after the Anniversary Date. 
 1.10 Assignment of Registration Rights. The rights to cause the Company to register Registrable Securities pursuant to this Section 1 may be assigned (but only with all related obligations) by a Holder to
any transferee or assignee of such securities, including any transferee or assignee that (i) is a subsidiary, parent, partner, limited partner, retired partner or stockholder of a Holder, or (ii) is a Holder’s family member or trust
for the benefit of an individual Holder, provided: (a) the Company is, within a reasonable time after such transfer, furnished with written notice of the name and address of such transferee or assignee and the securities with respect to which
such registration rights are being assigned; (b) such transferee or assignee agrees in writing to be bound by and subject to the terms and conditions of this Agreement; and (c) such assignment shall be effective only if immediately
following such transfer the further disposition of such securities by the transferee or assignee is restricted under the Act. 
 1.11
Limitations on Subsequent Registration Rights. From and after the date of this Agreement, the Company shall not, without the prior written consent of the Holders of a majority of the Registrable Securities, 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 receive registration rights that are senior to the registration rights held by the Holders. For avoidance of doubt, any registration
rights (other than with respect to a registration relating solely to the sale of securities of participants in a Company stock plan, a registration effected on Form S-4 or a registration on any form that does not include substantially the same
information as would be required to be included in a registration statement covering the sale of the Registrable Securities) that allow a holder or prospective holder of securities of the Company to register any securities of the Company, or include
any securities of the Company in a registered offering, without affording a pari passu right of registration or inclusion to the Holders shall be deemed to be registration rights senior to the registration rights held by the Holders. 
 1.12 Termination of Registration Rights. No Holder shall be entitled to exercise any right provided for in this Section 1 (i) after
three (3) years following the date of this Agreement, (ii) as to any Holder, such earlier time after the date of this Agreement during which such Holder (A) can sell all shares held by it in compliance with Rule 144 and without
restriction thereunder or (B) holds one percent (1%) or less of the Company’s outstanding Common Stock and all Registrable Securities held by such Holder (together with any affiliate of the Holder with whom 

  

 9 

 
such Holder must aggregate its sales under Rule 144) can be sold in any three (3) month period without registration in compliance with Rule 144 and
without restriction thereunder or (iii) after such time at which such Holder receives freely-tradable securities in connection with any consolidation, reorganization or merger of the Company with or into any other corporation or corporations or
a sale, conveyance, or other disposition of all or substantially all of the Company’s property or business. 
 Section 2. Miscellaneous.

 2.1 Successors and Assigns. Except as otherwise provided herein, the terms and conditions of this Agreement shall inure to the
benefit of and be binding upon the respective successors and permitted assigns of the parties (including transferees of any shares of Registrable Securities). Nothing in this Agreement, express or implied, is intended to confer upon any party other
than the parties hereto or their respective successors and assigns any rights, remedies, obligations or liabilities under or by reason of this Agreement, except as expressly provided in this Agreement. 
 2.2 Governing Law. This Agreement shall be governed by and construed under the laws of the State of Delaware as applied to agreements among
Delaware residents entered into and to be performed entirely within Delaware. 
 2.3 Counterparts. This Agreement may be executed in
two or more counterparts, each of which shall be deemed an original, but all of which together shall constitute one and the same instrument. 
 2.4 Remedies. Each Investor shall be entitled to enforce its rights under this Agreement specifically to recover damages and costs (including reasonable attorney’s fees) for any breach of any provision of this Agreement and to
exercise all other rights existing in its favor. The parties hereto agree and acknowledge that money damages are not an adequate remedy for any breach of the provisions of this Agreement and that the Investors are entitled to specific performance
and/or other injunctive relief (without posting any bond or deposit) in order to enforce or prevent any violations of the provisions of this Agreement. 
 2.5 Titles and Subtitles. The titles and subtitles used in this Agreement are used for convenience only and are not to be considered in construing or interpreting this Agreement. 
 2.6 Notices. All notices, requests, consents and other communications hereunder shall be in writing; shall be mailed (a) if within the
domestic United States, by first-class registered or certified airmail, by nationally recognized overnight express courier, postage prepaid, or by facsimile or (b) if delivered to or from outside the United States, by International Federal
Express or facsimile; shall be deemed given: (i) if delivered by first-class registered or certified mail domestic, three business days after so mailed, (ii) if delivered by nationally recognized overnight carrier, one business day after
so mailed, (iii) if delivered by International Federal Express, two business days after so mailed or (iv) if delivered by facsimile, upon electronic confirmation of receipt; and shall be delivered as addressed as follows: 
 (a) if to the Company, to: 
 Blue Coat Systems, Inc. 
 420 North Mary Avenue 
 Sunnyvale, California 94085 
 Attention: Betsy E. Bayha, Esq. 
 Phone: (408) 220-2200 
 Telecopy:
(408) 220-2157 
  

 10 

 (b) with a copy mailed to: 
 Davis Polk & Wardwell 
 1600 El
Camino Real 
 Menlo Park, California 94025 
 Phone: (650) 752-2000 
 Telecopy: (650) 752-2111 
 Attention: William M. Kelly, Esq. 
                   Sarah K. Solum, Esq. 
 (c) if to the Investors, at the addresses set forth on Schedule A attached hereto, or at such other address or addresses as may have been furnished to the Company in writing. 
 2.7 Expenses. If any action at law or in equity is necessary to enforce or interpret the terms of this Agreement, the prevailing party shall be
entitled to reasonable attorneys’ fees, costs and necessary disbursements in addition to any other relief to which such party may be entitled. 
 2.8 Entire Agreement; Amendments and Waivers. This Agreement and the Purchase Agreement constitute the full and entire understanding and agreement among the parties with regard to the subjects hereof. Any term of this Agreement may
be amended and the observance of any term of this Agreement may be waived (either generally or in a particular instance and either retroactively or prospectively) only with the written consent of the Company and the holders of a majority of the
then-outstanding Registrable Securities; provided, however, that any such amendment or waiver that adversely effects any Investor in a different manner than any other holder of Registrable Securities shall also require approval of such Investor. Any
amendment or waiver effected in accordance with this paragraph shall be binding upon each holder of any Registrable Securities, each future holder of all such Registrable Securities, and the Company. Each Holder acknowledges that by the operation of
this Section 2.8, the holders of a majority of the then-outstanding Registrable Securities will have the right and power to diminish or eliminate all rights of such Holder under this Agreement. 
 2.9 Severability. If one or more provisions of this Agreement are held to be unenforceable under applicable law, such provision(s) shall be
excluded from this Agreement and the balance of this Agreement shall be interpreted as if such provision(s) were so excluded and shall be enforceable in accordance with its terms. 
 2.10 Aggregation of Stock. All shares of Registrable Securities held or acquired by affiliated entities (including affiliated venture capital
funds) or persons shall be aggregated together for the purpose of determining the availability of any rights under this Agreement. 
  

 11 

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

			
	BLUE COAT SYSTEMS, INC.
		
	By:	 	/s/ Brian NeSmith
		 	 Name: Brian NeSmith
 Title: President & CEO

 SIGNATURE PAGE TO THE BLUE COAT SYSTEMS, INC. 
 REGISTRATION RIGHTS AGREEMENT 

			
	INVESTORS
	
	FRANCISCO PARTNERS II, L.P.
		
	By:	 	 FRANCISCO PARTNERS GP II, L.P.
 its General Partner

		
	By:	 	 FRANCISCO PARTNERS GP II MANAGEMENT, LLC
 its General
Partner

		
	By:	 	/s/ Keith B. Geeslin
		 	 Name: Keith B. Geeslin
 Title: Managing
Member

 SIGNATURE PAGE TO THE BLUE COAT SYSTEMS, INC. 
 REGISTRATION RIGHTS AGREEMENT 

			
	INVESTORS
	
	FRANCISCO PARTNERS PARALLEL FUND II, L.P.
		
	By:	 	 FRANCISCO PARTNERS GP II, L.P.
 its General Partner

		
	By:	 	 FRANCISCO PARTNERS GP II MANAGEMENT, LLC
 its General
Partner

		
	By:	 	/s/ Keith B. Geeslin
		 	 Name: Keith B. Geeslin
 Title: Managing
Member

 SIGNATURE PAGE TO THE BLUE COAT SYSTEMS, INC. 
 REGISTRATION RIGHTS AGREEMENT 

 Schedule A 
 INVESTORS 
  

					
	 Investor
	  	 Investor’s Address
 and Facsimile Number
	  	 Investor’s Representative’s Address and
Facsimile No.

	Francisco Partners II, L.P	  	 Francisco Partners II, L.P
 One Letterman
Drive
 Building C, Suite 410
 San Francisco, CA 94129

Attention: Mr. Keith Geeslin
 Phone: (415) 418-2900
 Telecopy: (415) 418-2999
	  	 O’Melveny & Myers LLP
 Embarcadero Center
West
 275 Battery Street, Suite 2600
 San Francisco, CA 94111

 Attention: Michael J. Kennedy, Esq.
                   C. Brophy Christensen, Esq.
 Phone: (415) 984-8700
 Telecopy: (415) 984-8701

			
	 Francisco Partners Parallel
 Fund II,
L.P.
	  	
 Francisco Partners Parallel
 Fund
II, L.P.
 One Letterman Drive
 Building C, Suite 410

San Francisco, CA 94129
 Attention: Mr. Keith Geeslin
 Phone: (415) 418-2900
 Telecopy: (415) 418-2999
	  	 O’Melveny & Myers LLP
 Embarcadero Center
West
 275 Battery Street, Suite 2600
 San Francisco, CA 94111

 Attention: Michael J. Kennedy, Esq.
                   C. Brophy Christensen, Esq.
 Phone: (415) 984-8700
 Telecopy: (415) 984-8701

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