Document:

Certificate of Designation, Preferences and Rights of Series A Preferred Stock

 Exhibit 4.1 
 BLUE COAT SYSTEMS, INC. 
 CERTIFICATE OF DESIGNATION, PREFERENCES AND RIGHTS 
 OF SERIES A PREFERRED STOCK 
 (Pursuant
to Section 151(g) of the General Corporation 
 Law of the State of Delaware.) 
 BLUE COAT SYSTEMS, INC., a corporation organized and existing under the laws of the State of Delaware (the “Company”), DOES HEREBY
CERTIFY THAT, pursuant to authority conferred upon the board of directors of the Company (the “Board”) by the Amended and Restated Certificate of Incorporation of the Company, as amended (the “Certificate of
Incorporation”), the Board, at a meeting held on June 22, 2006, adopted the following resolutions authorizing the issuance of Series A Preferred Stock of the Company, which resolutions are still in full force and effect and are not in
conflict with any provisions of the Certificate of Incorporation or the Bylaws of the Company: 
 RESOLVED, that pursuant to authority vested
in the Board by the Certificate of Incorporation, the Board does hereby establish a series of preferred stock of the Company from the Company’s authorized class of 10,000,000 shares of $0.0001 par value preferred shares (“Preferred
Stock”), such series to consist of 42,060 shares, which number may be decreased (but not below the number of shares thereof then outstanding) from time to time by the Board, and does hereby fix and state the voting rights, designation,
powers, preferences and relative participating, optional or other special rights and the qualifications, limitations or restrictions thereof, as follows: 
 1. Definitions. Unless otherwise specified herein, the following capitalized terms shall have the meanings ascribed to them below: 
 “Affiliate” shall mean, with respect to any specified Person, any other Person that directly, or indirectly through one
or more intermediaries, Controls, is Controlled by or is under common Control with such specified Person. 
 “Acquisition” shall mean the acquisition by the Company, whether by merger, consolidation, the purchase of assets or otherwise, of another entity, or of certain businesses or assets of another entity, for at least
$18,000,000 in cash. 
 “Available Assets” shall have the meaning set forth in Section 4(a).

 “Board” shall have the meaning set forth in the Introductory Paragraph of this Certificate of Designation.

 “Certificate of Designation” shall mean this Certificate of Designation, Preferences and Rights of Series
A Preferred Stock. 
 “Certificate of Incorporation” shall have the meaning set forth in the Introductory
Paragraph of this Certificate of Designation. 

 “Change of Control” shall be deemed to have occurred (i) if any
“person” (as defined in Section 13(d)(3) of the Exchange Act) shall directly or indirectly acquire beneficial ownership (determined in accordance with Rule 13d-3 of the Exchange Act) of more than 50% of the total voting power of all
shares of the Company’s capital stock that are entitled to vote generally in elections of directors, (ii) upon consummation of a merger or consolidation of the Company into or with another Person in which the stockholders of the Company
immediately prior to the consummation of such transaction shall own less than 50% of the voting securities of the surviving Person (or the parent Person of the surviving Person where the surviving Person is wholly-owned by the parent Person)
immediately following the consummation of such transaction, or (iii) the consummation of the sale, transfer or lease (but not including a transfer or lease by pledge or mortgage to a bona fide lender) of all or substantially all of the assets
of the Company. 
 “Closing Date” shall mean June 22, 2006. 
 “Common Stock” shall mean shares the shares of the Company’s common stock, par value $0.0001 per share. 

“Company” shall have the meaning set forth in the Introductory Paragraph of this Certificate of Designation.

 “Company Redemption Date” shall have the meaning set forth in Section 5(d)(i). 
 “Company Redemption Notice” shall have the meaning set forth in Section 5(d)(i). 
 “Constituent Person” shall have the meaning set forth in Section 6(g)(i). 
 “Control” (including the terms “Controlled by” and “under common Control with”), with respect to the
relationship between or among two or more Persons, shall mean the possession, directly or indirectly, of the power to direct or cause the direction of the affairs or management of a Person, whether through the ownership of voting securities, by
contract or otherwise. 
 “Conversion Date” shall have the meaning set forth in
Section 6(c)(iii). 
 “Conversion Notice” shall have the meaning set forth in
Section 6(c)(i). 
 “Conversion Price” shall have the meaning set forth in
Section 6(a). 
 “Conversion Ratio” shall have the meaning set forth in Section 6(a).

 “DGCL” shall mean the Delaware General Corporation Law. 
 “Exchange Act” shall mean the United States Securities Exchange Act of 1934, as amended. 
  

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 “Face Amount” shall mean (i) with respect to each share of Series A
Preferred Stock, $1,000.00, and (ii) with respect to any other series of Preferred Stock, the face amount as set forth in the certificate of designations, voting rights, powers, preferences and relative participating, optional or other special
rights and the qualifications, limitations or restrictions, in each case as such amount may be proportionately adjusted to reflect any combination, consolidation, reclassification or like adjustment. 
 “Holder Redemption Date” shall have the meaning set forth in Section 5(d)(ii). 
 “Holder Redemption Notice” shall have the meaning set forth in Section 5(d)(ii). 
 “Liquidation Event” shall mean a liquidation or winding up of the Company in a single transaction or series of
transactions or a Change of Control. 
 “Liquidation Amount” shall have the meaning set forth in
Section 4(a). 
 “Market Price” shall have the meaning set forth in Section 6(f).

 “Maturity Date” shall mean June 21, 2012. 
 “Non-Electing Share” shall have the meaning set forth in Section 6(g)(i). 
 “Non-Cash Assets” shall have the meaning set forth in Section 4(a). 
 “Person” shall be construed broadly and means any natural person, firm, corporation, partnership, limited liability
company, association, trust or other entity. 
 “Preferred Stock” shall have the meaning set forth in the
first resolution of this Certificate of Designation. 
 “Redemption Amount” shall have the meaning set forth
in Section 5(a). 
 “Securities Act” shall mean the United States Securities Act of 1933, as
amended. 
 “Series A Director” shall have the meaning set forth in Section 7(d). 
 “Series A Preferred Stock” shall have the meaning set forth in Section 2. 
 2. Designation of Series; Issuance, Face Amount and Rank. This series of preferred stock is hereby designated “Series A Preferred
Stock” (hereinafter the “Series A Preferred Stock”), and the number of shares which shall constitute such series shall be 42,060, which number may be decreased (but not below the number thereof then outstanding) from time to
time by the Board. The shares of Series A Preferred Stock shall be issued by the Company in certificated form for their Face Amount (as herein defined), in such amounts, at such times and to such Persons as shall be specified by the Board, from time
to time. Except as otherwise expressly set forth herein, the shares of Series A Preferred Stock shall rank prior to the shares of Common Stock and any other class of stock of the Company ranking junior to the Series A Preferred Stock with
respect to dividends, redemption, liquidation, dissolution, and winding up 

  

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of the Company. Subject to compliance with the protective provisions set forth in Section 8, but notwithstanding any other rights of the Series A
Preferred Stock, the rights, privileges, preferences and restrictions of any additional series of Preferred Stock may be subordinate to, pari passu with (including, without limitation, inclusion in provisions with respect to
liquidation and acquisition preferences, redemption and/or approval of matters by vote or written consent), or senior to any of those of the Series A Preferred Stock, any additional series of Preferred Stock or Common Stock. 
 3. Dividends. The Series A Preferred Stock shall participate equally and ratably with the holders of Common Stock in all dividends paid on
the Common Stock, when, as and if declared by the Board, out of funds of the Company legally available therefor, as if such shares of Series A Preferred Stock had been converted to shares of Common Stock immediately prior to the record date for the
payment of such dividend. In the event that full dividends, if declared, are not paid to the holders of Series A Preferred Stock and Common Stock and funds available for payment of dividends shall be insufficient to permit payment in full to holders
of all such stock of the amounts to which they are entitled, then, subject to the rights of any series of Preferred Stock that may from time to time come into existence that is senior to or on parity with the Series A Preferred Stock with respect to
dividends, the entire amount available for payment of dividends shall be distributed ratably among all holders of such stock in proportion to the full amount to which they would otherwise be respectively entitled. Notwithstanding anything contained
herein to the contrary, no dividends shall be declared by the Board or paid or set apart for payment by the Company at such time if such declaration or payment shall be restricted or prohibited by law. 
 4. Liquidation Preference. 
 (a) General. Upon a Liquidation Event, subject to the rights of any series of Preferred Stock that may from time to time come into existence that is senior to or on parity with the Series A Preferred Stock with
respect to liquidation preference, the holders of Series A Preferred Stock then outstanding shall be entitled to be paid, out of the assets of the Company available for distribution to its stockholders, whether from capital, surplus or earnings
(“Available Assets”), the greater of (x) an amount equal to the Face Amount plus an amount equal to all declared but unpaid dividends on each share, if any, or (y) the amount that would be received in connection
with such Liquidation Event if such holder’s Series A Preferred Stock were converted into fully-paid and non-assessable shares of Common Stock at the then-effective Conversion Ratio for such shares (in the aggregate, the “Liquidation
Amount”). If upon a Liquidation Event, the Available Assets shall be insufficient to pay the holders of Series A Preferred Stock the full Liquidation Amount described in clause (x) of the immediately preceding sentence, then, subject
to the rights of any series of Preferred Stock that may from time to time come into existence that is senior to or on parity with the Series A Preferred Stock with respect to liquidation preference, the holders of Series A Preferred Stock shall
share ratably in any distribution of assets according to the respective amounts which would be payable in respect of the shares held by them upon such distribution if all amounts payable on or with respect to said shares were paid in full. The
Liquidation Amount shall be paid to the holders of Series A Preferred Stock in cash; provided, however, that in the event of a Liquidation Event in which all or part of the consideration received by the Company or its stockholders
consists of assets other than cash, then the Liquidation Amount shall be paid to the holders of Series A 

  

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Preferred Stock in such non-cash assets (“Non-Cash Assets”) and cash, if any, such that the amount of Non-Cash Assets as a percentage of the
total amount of Non-Cash Assets and cash received by the holders of Series A Preferred Stock upon such Liquidation Event and, if any amount is paid to the holders of Common Stock upon such Liquidation Event, the holders of Common Stock is, as nearly
as practicable, the same. Subject to the rights of the holders of any series of Preferred Stock that rank senior to or on parity with the Series A Preferred Stock with respect to liquidation preference, after payment has been made in full to the
holders of the Series A Preferred Stock, holders of securities ranking junior to the Series A Preferred Stock (including the Common Stock) shall, subject to the respective terms and provisions (if any) applying thereto, be entitled to receive any
and all assets remaining to be paid or distributed, and the holders of Series A Preferred Stock shall not be entitled to share therein. 
 (b) Valuation of Non-Cash Assets. In any Liquidation Event, if the holders of Series A Preferred Stock are to be paid in Non-Cash Assets or if the proceeds of such Liquidation Event are Non-Cash Assets,
the value of such Non-Cash Assets will be deemed their fair market value as determined below. 
 (i) The method of valuation
of Non-Cash Assets that are securities not subject to investment letter or other restrictions on free marketability is as follows: 
 (A) If traded on a securities exchange or through The Nasdaq Stock Market, the value shall be deemed to be the average of the closing prices of the securities on such exchange or system over the twenty (20) trading day period ending
three (3) trading days prior to the closing of the Liquidation Event; 
 (B) If actively traded over-the-counter, the
value shall be deemed to be the average of the closing bid or sale prices (whichever is applicable) over the twenty (20) trading day period ending three (3) trading days prior to the closing of the Liquidation Event; and 
 (C) If there is no active public market, the value shall be the fair market value thereof, as mutually determined by the Board and the
holders of at least a majority of the then-outstanding shares of Series A Preferred Stock. 
 (ii) The method of valuation of
Non-Cash Assets that are securities subject to investment letter or other restrictions on free marketability (other than restrictions arising solely by virtue of a stockholder’s status as an affiliate or former affiliate) shall be to make an
appropriate discount from the market value determined as above in (i) (A), (B) or (C) to reflect the approximate fair market value thereof, as mutually determined by the Board and the holders of at least a majority of the
then-outstanding shares of Series A Preferred Stock, voting together as a separate class. 
 (iii) The fair market value of
all Non-Cash Assets other than securities shall be as mutually determined by the Board and the holders of at least a majority of the then-outstanding shares of Series A Preferred Stock, voting together as a separate class. 
 (iv) In the event of a Change of Control, the foregoing methods for valuing Non-Cash Assets to be distributed to holders of Series A
Preferred Stock in 

  

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connection with the Change of Control shall, upon approval by the holders of at least a majority of the then-outstanding shares of Series A Preferred Stock,
voting together as a separate class, of the definitive agreements governing the Change of Control, be superseded by any determination of such value set forth in the definitive agreements governing the Change of Control. 
 (c) Notice Required. Written notice of any voluntary or involuntary Liquidation Event, stating the payment date and the place where the
distributable amount shall be payable, shall be given by mail, postage prepaid, not less than fifteen (15) days prior to the Liquidation Event stated therein, to the holders of record of the Series A Preferred Stock at their respective
addresses as the same shall then appear on the books of the Company. 
 5. Redemption. 
 (a) Mandatory Redemption at Maturity. Upon the Maturity Date, subject to the rights of any series of Preferred Stock that may from
time to time come into existence that is senior to or on a parity with the Series A Preferred Stock with respect to mandatory redemption rights, the Company shall redeem all (but not less than all) of the shares of Series A Preferred Stock then
outstanding. Upon such date, each holder of shares of Series A Preferred Stock shall have the right to receive in respect of each share owned by such holder a sum in cash equal to the Face Amount plus an amount equal to all declared but
unpaid dividends on each share, if any (the “Redemption Amount”). 
 (b) Company Optional Redemption. In the
event that the Company does not close an Acquisition within one hundred fifty (150) days after the Closing Date, the Company may at its option redeem, in whole or in part, out of funds legally available therefor, the outstanding shares of
Series A Preferred Stock by providing written notice to the holders thereof pursuant to Section 5(d)(i) below. The redemption shall take place at any time after the expiration of such one hundred fifty (150) day period and within
one hundred eighty (180) days after the Closing Date and shall be at a price equal to the current Redemption Amount. In the case of a redemption of less than all of the shares of Series A Preferred Stock at the time outstanding, the shares to
be redeemed shall be selected pro rata or by lot as reasonably determined by the Board to be equitable. 
 (c)
Holder Optional Redemption. In the event that the Company does not close an Acquisition within one hundred fifty (150) days after the Closing Date, at the election of a holder of Series A Preferred Stock, the Company shall redeem, out of
funds legally available therefor, the number of outstanding shares of Series A Preferred Stock held by such holder and identified by such holder in a written notice to the Company pursuant to Section 5(d)(ii) below. The redemption shall
take place at any time after the expiration of such one hundred fifty (150) day period and within one hundred eighty (180) days after the Closing Date at a price equal to the current Redemption Amount. 
 (d) Redemption Mechanics. 
 (i) Company Redemption Notice. Notice of any redemption pursuant to Sections 5(a) or 5(b) (a “Company Redemption Notice”) shall be sent by or on behalf 

  

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of the Company at least ten (10) but not more than thirty (30) days prior to the date specified for redemption in such notice (the “Company
Redemption Date”), by first class mail, postage prepaid, to all holders of record of shares of Series A Preferred Stock at their last address as they shall appear on the books of the Company; provided that with respect to a
redemption made pursuant to Section 5(a), no failure to give such notice or any defect therein or in the mailing thereof shall affect the validity of the proceedings for the redemption of any shares of Series A Preferred Stock. In
addition to any information required by law, such Company Redemption Notice shall state (A) whether such redemption is being made pursuant to the mandatory redemption provision set forth in Section 5(a) or the optional redemption
provision set forth in Section 5(b), (B) the Company Redemption Date, (C) the aggregate number of shares of Series A Preferred Stock to be redeemed and, if less than all of the outstanding shares of Series A Preferred Stock are
to be redeemed, then the number of such shares to be redeemed from the applicable holder and (D) the place or places where certificates for such shares are to be surrendered for payment. 
 (ii) Holder Redemption Notice. Notice of any redemption pursuant to Section 5(c) (a “Holder Redemption
Notice”) shall be sent by or on behalf of a holder of Series A Preferred Stock at least ten (10) but not more than thirty (30) days prior to the date specified for redemption in such notice (the “Holder Redemption
Date”), by first class mail, postage prepaid, to the Company. The Holder Redemption Notice shall state (A) the Holder Redemption Date and (B) the aggregate number of shares of Series A Preferred Stock to be redeemed for such
holder. 
 (iii) Redemption Payment. The Company shall redeem the shares of each holder of Series A Preferred Stock
being redeemed pursuant to this Section 5 by making the applicable cash payments to such holder in respect of each share owned by such holder and being redeemed. 
 (iv) Retirement of Shares. Any shares of Series A Preferred Stock redeemed pursuant to the provisions of this Section 5
shall be retired and given the status of authorized and unissued Preferred Stock, undesignated as to series, subject to reissuance by the Company as shares of Preferred Stock of one or more series, as may be determined from time to time by the
Board. 
 (v) Surplus Under DGCL. On the Maturity Date, the liquidation preference of any shares of capital stock of
the Company shall not be included in “total liabilities” in connection with determining “surplus” under the DGCL. 
 6.
Conversion. 
 (a) Optional Conversion. Each share of Series A Preferred Stock shall be convertible, at
any time and from time to time at the option of the holder thereof, into the number of fully paid and non-assessable shares of Common Stock equal to the Face Amount of such share of Series A Preferred Stock divided by the appropriate Conversion
Price. The initial “Conversion Price” per share of Series A Preferred Stock shall be $17.525 and shall be subject to adjustment from time to time as set forth in Section 6(g). The number of shares of Common 

  

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Stock into which each share of Series A Preferred Stock is convertible, after taking into account any such adjustments, is hereinafter referred to as the
“Conversion Ratio.” Upon any decrease or increase in the Conversion Price as described in Section 6(g), the Conversion Ratio shall be appropriately increased or decreased. The date and time the right to convert shares of
Series A Preferred Stock will terminate shall be at the close of business on the day immediately preceding the Maturity Date (unless the Company shall default in making the payment of the Redemption Amount due on the Maturity Date, in which case the
right of the holder to convert its whole shares of Series A Preferred Stock shall terminate on the date the payment of the Redemption Amount is made and such shares of Series A Preferred Stock are redeemed). 
 (b) Automatic Conversion. Each share of Series A Preferred Stock shall be automatically converted into fully-paid, non-assessable
shares of Common Stock at the then effective Conversion Ratio for such share upon the approval of the holders of at least a majority of the then-outstanding Series A Preferred Stock, voting as a separate class. 
 (c) Conversion Mechanics. 
 (i) In order to exercise the conversion privilege pursuant to Section 6(a), a holder of the shares of Series A Preferred Stock to be converted shall surrender the certificate representing such shares at
the office of the Company, with a written notice of election to convert completed and signed, specifying the number of shares to be converted (the “Conversion Notice”). Unless the shares issuable on conversion are to be issued in
the same name as the name in which such shares of Series A Preferred Stock are registered, each share surrendered for conversion shall be accompanied by instruments of transfer, in form satisfactory to the Company, duly executed by the holder or the
holder’s duly authorized attorney and an amount sufficient to pay any transfer or similar tax. 
 (ii) As promptly as
practicable after the surrender by the holder of the certificates for shares of Series A Preferred Stock for conversion pursuant to Section 6(a), the Company shall issue and deliver to such holder or on the holder’s written order to
the holder’s transferee a certificate or certificates for, or make or cause to be made a book-entry notation of, the whole number of shares of Common Stock issuable upon conversion. 
 (iii) Each conversion shall be deemed to have been effected on the Conversion Date. The “Conversion Date” shall mean (A),
in the case of an optional conversion pursuant to Section 6(a), immediately prior to the close of business on the first date on which both the certificates for shares of Series A Preferred Stock were surrendered and the Conversion Notice
was received by the Company and (B) in the case of an automatic conversion pursuant to Section 6(b), on the date and at such time determined by the approval of the holders of at least a majority of the then-outstanding Series A
Preferred Stock, which time and date may be conditional on the occurrence of any event. The Person in whose name or names any certificate or certificates for shares of Common Stock are issuable upon such conversion shall be deemed to have become the
holder of record of the shares of Common Stock represented thereby on the Conversion Date, and such conversion shall be into a number of shares of Common Stock equal to 

  

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the product of the number of shares of Series A Preferred Stock surrendered times the Conversion Ratio in effect on the Conversion Date. All shares of Common
Stock delivered upon conversion of the Series A Preferred Stock will upon delivery be duly and validly issued and fully paid and non-assessable, free of all liens and charges and not subject to any preemptive rights. Upon the surrender of
certificates representing shares of Series A Preferred Stock, such shares shall no longer be deemed to be outstanding and all rights of a holder with respect to such shares surrendered for conversion shall immediately terminate except the right to
receive Common Stock and other amounts payable pursuant to this Section 6; provided, however, that in the case of an automatic conversion pursuant to Section 6(b), each outstanding shares of Series A Preferred
Stock shall be converted automatically into a share of Common Stock on the Conversion Date without any further action by the holder of such share and whether or not the certificates representing such shares are surrendered to the Company;
provided, further, that the Company shall not be obligated to issue certificates evidencing shares of Common Stock issuable upon such automatic conversion unless either the certificates representing the shares of Series A Preferred
Stock are surrendered to the Company. 
 (iv) Except as provided above and in Section 6(g), the Company shall make
no payment or adjustment for declared but unpaid dividends on shares of Series A Preferred Stock on conversion of such shares or for dividends in cash on the shares of Common Stock issued upon such conversion. 
 (d) Issuance of Shares. 
 (i) The Company shall at all times reserve and keep available, free from preemptive rights, such number of its authorized but unissued shares of Common Stock as may be required to effect conversions of the Series A
Preferred Stock. The Company shall from time to time in accordance with the DGCL increase the authorized amount of its Common Stock if at any time the number of shares of Common Stock remaining unissued and available for issuance shall not be
sufficient to permit conversion of the Preferred Stock in accordance with any applicable conversion provisions applicable to such Preferred Stock. 
 (ii) Prior to the delivery of any securities that the Company is obligated to deliver upon conversion of the Series A Preferred Stock, the Company shall comply with all applicable federal and state laws and
regulations which require action by the Company. The Company will list such shares on each national securities exchange or automated quotation system on which the Common Stock is listed or quoted. 
 (e) Transfer Taxes. The Company shall pay any and all issuance, delivery and transfer taxes in respect of the issuance or delivery
of shares of Common Stock on conversion of the Series A Preferred Stock pursuant hereto. However, if any such certificate is to be issued in a name other than that of the holder of the shares of Series A Preferred Stock converted, the Person or
Persons requesting the issuance thereof shall pay to the Company the amount of any tax payable in respect of any transfer involved in such issuance or shall establish to the satisfaction of the Company that such tax has been paid. 
  

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 (f) Fractional Shares. In connection with the conversion of any shares of Series A
Preferred Stock, no fractions of shares of Common Stock shall be issued. In lieu thereof the Company shall pay a cash adjustment in respect of such fractional interest in an amount equal to such fractional interest multiplied by the Market Price on
the day on which such shares of Series A Preferred Stock are deemed to have been converted. The “Market Price” shall be (i) if the Common Stock is then traded on a national securities exchange or The Nasdaq Stock Market (or a
similar national quotation system), then the value shall be computed based on the closing price on such exchange or system on such day, (ii) if the Common Stock is actively traded over-the-counter, then the value shall be computed based on the
closing price on such day, and (iii) if there is no public market for the Common Stock, then the value shall be computed based on fair market value thereof, as determined in good faith by the Board on such day. 
 (g) Adjustments. 
 (i) If the Company at any time after the date of issue of the Series A Preferred Stock (A) declares a dividend or makes a distribution on Common Stock payable in Common Stock, (B) subdivides or splits the
outstanding Common Stock, (C) combines or reclassifies the outstanding Common Stock into a smaller number of shares, (D) issues any shares of its capital stock in a reclassification of Common Stock (including any such reclassification in
connection with a consolidation or merger in which the Company is the continuing corporation), or (E) consolidates with, merges with or into or is converted into any other Person, the Conversion Price in effect at the time of the record date
for such dividend or distribution or of the effective date of such subdivision, split, combination, consolidation, conversion, merger or reclassification shall be adjusted so that the conversion of the Series A Preferred Stock after such time shall
entitle the holder to receive the aggregate number of shares of Common Stock or other securities of the Company (or shares of any security into which such shares of Common Stock have been combined, consolidated, converted, merged or reclassified
pursuant to Sections 6(g)(i)(C), 6(g)(i)(D) or 6(g)(i)(E)) which, if this Series A Preferred Stock had been converted immediately prior to such time, such holder would have owned upon such conversion and been entitled to receive
by virtue of such dividend, distribution, subdivision, split, combination, consolidation, conversion, merger or reclassification, assuming such holder of Common Stock (x) is not a Person with which the Company consolidated or into which the
Company merged or which merged into the Company or to which such recapitalization, sale or transfer was made, as the case may be (a “Constituent Person”), or an affiliate of a Constituent Person and (y) failed to exercise any
rights of election as to the kind or amount of securities, cash and other property receivable upon such reclassification, consolidation, conversion, merger, recapitalization, sale or transfer (provided, however, that if the kind or
amount of securities, cash and other property receivable upon such reclassification, consolidation, conversion, merger, recapitalization, sale or transfer is not the same for each share of Common Stock held immediately prior to such
reclassification, consolidation, conversion, merger, recapitalization, sale or transfer by other than a Constituent Person or an affiliate thereof and in respect of which such rights of election shall not have been exercised (the
“Non-Electing Share”), then for the purpose of this Section 6(g) the kind and amount of securities, cash and other property receivable upon such reclassification, consolidation, conversion, merger, recapitalization, sale
or transfer by each Non-Electing Share shall be 

  

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deemed to be the kind and amount so receivable per share by a plurality of the Non-Electing Shares). Such adjustment shall be made successively whenever any
event listed above shall occur. If a record date is fixed for any dividend or distribution referred to in Section 6(g)(i)(A) but such dividend or distribution is not so made, the Conversion Price shall again be adjusted to be the Conversion
Price which would then be in effect if such record date had not been fixed. 
 (ii) All calculations under this
Section 6(g) shall be made to the nearest four decimal points. 
 (iii) If, at any time as a result of the
provisions of this Section 6(g), holders of Series A Preferred Stock upon subsequent conversion shall become entitled to receive any shares of capital stock of the Company other than Common Stock, the number of such other shares so
receivable upon conversion of this Series A Preferred Stock shall thereafter be subject to adjustment from time to time in a manner and on terms as nearly equivalent as practicable to the provisions contained herein. 
 (h) No Impairment. The Company will not, by amendment of this Certificate of Designation or the Certificate of Incorporation or
through any reorganization, transfer of assets, consolidation, merger, 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 to be observed or performed
hereunder by the Corporation, but will at all times assist in the carrying out of all the provisions of this Section 6 and in the taking of all such action as may be necessary or appropriate in order to protect the conversion rights of
the holders of the Series A Preferred Stock against impairment. 
 7. Voting Rights. 
 (a) Preferred Stock. Each holder of Series A Preferred Stock shall be entitled to the number of votes equal to the number of shares
of Common Stock into which the shares of Series A Preferred Stock held by such holder could be converted as of the record date. The holders of shares of Series A Preferred Stock shall be entitled to vote on all matters on which the Common Stock
shall be entitled to vote. Holders of Series A Preferred Stock shall be entitled to notice of any stockholders’ meeting in accordance with the Bylaws of the Company. Fractional votes shall not, however, be permitted and any fractional voting
rights resulting from the above formula (after aggregating all shares into which shares of Preferred Stock held by each holder could be converted), shall be disregarded. 
 (b) Restricted Class Voting. Other than as provided herein or required by law, the holders of Series A Preferred Stock and the
holders of Common Stock shall vote together as a single class. 
 (c) No Series Voting. Other than as provided herein
or required by law, there shall be no series voting. 
 (d) Election of Directors. Until the date that is one
(1) year after the Closing Date, the holders of at least a majority of the then-outstanding Series A Preferred Stock, voting as a separate class, shall be entitled to elect one (1) director to the Board on the Closing Date and 

  

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at each meeting or pursuant to each consent of the Company’s stockholders for the election of directors (the “Series A Director”).
The Series A Director shall only be removed by the holders of at least a majority of the then-outstanding Series A Preferred Stock, voting as a separate class. 
 8. Protective Provisions. As long as any of the Series A Preferred Stock shall be issued and outstanding, the Company shall not, without first obtaining the approval (by vote or written consent as
provided by law) of the holders of at least a majority of the then-outstanding Series A Preferred Stock, voting as a separate class: 
 (a) alter or change the rights, privileges, preferences and restrictions of the Series A Preferred Stock in a manner adverse to the holders thereof, by merger, consolidation or otherwise; or 
 (b) amend or waive any provisions of the Corporation’s Certificate of Incorporation in a manner adverse to the holders of the
outstanding shares of Series A Preferred Stock; provided, however, that the mere authorization, creation and issuance of any additional series of Preferred Stock with rights, privileges, preferences and restrictions subordinate to,
pari passu with or senior to any of those of the Series A Preferred Stock shall not require approval of holders of at least a majority of the then-outstanding Series A Preferred Stock pursuant to this Section 8(b).

 Except as expressly required under law, on any matter on which holders of Series A Preferred Shares shall be entitled to
vote under this Section 8, such holders shall be entitled to one vote per share. 
 9. No Sinking Fund. No sinking
fund shall be established for the retirement or redemption of shares of Series A Preferred Stock. 
 10. Preemptive or Subscription
Rights. No holder of shares of Series A Preferred Stock shall have any preemptive or subscription rights in respect of any securities of the Company that may be issued. 
 11. No Other Rights. The shares of Series A Preferred Stock shall not have any designations, preferences or relative, participating,
optional or other special rights except as expressly set forth in the Company’s Certificate of Incorporation, this Certificate or as otherwise required by law. 
 RESOLVED, FURTHER, that the Secretary of the Company be, and he hereby is, authorized, empowered and directed to execute an Certificate of
Designation, Preferences and Rights of Series A Preferred Stock and that such Certificate be delivered to and filed with the Secretary of State of the State of Delaware pursuant to the provisions of Section 103 and Section 151(g) of the
DGCL, both as amended. 
 * * * * * 
  

 12 

 IN WITNESS WHEREOF, Blue Coat Systems, Inc. has caused this Certificate of Designation to be executed by
its duly authorized officer as of June 22, 2006. 
  

			
	 BLUE COAT SYSTEMS, INC.

		
	 By:
	 	 /s/ Brian NeSmith

		 	 Brian NeSmith
 President and Chief Executive OfficerSeries A Preferred Stock Purchase Agreement

 Exhibit 10.1 
 SERIES A PREFERRED STOCK PURCHASE AGREEMENT 
 This SERIES A PREFERRED STOCK PURCHASE AGREEMENT
(this “Agreement”) dated June 22, 2006, is entered into by and among Blue Coat Systems, Inc., a Delaware corporation (the “Company”), and each of the parties set forth on Schedule A attached hereto
(each, an “Investor” and, collectively, the “Investors”). 
 THE PARTIES TO THIS AGREEMENT enter
into this Agreement on the basis of the following facts, intentions and understandings: 
 WHEREAS, concurrently with the execution
and delivery of this Agreement, the Company and Network Appliance, Inc., a Delaware corporation (“Seller”), have entered into an Asset Purchase Agreement, dated as of the date hereof (including all license agreements, transition
services agreements and other agreements and instruments entered into in connection therewith on or after the date hereof, the “Asset Purchase Documents”), pursuant to which the Company will purchase certain assets and assume
certain liabilities of Seller (the “Acquisition”); and 
 WHEREAS, upon the terms and subject to the conditions
hereof, the Investors desire to make an investment in the Company for the purpose of, among other things, providing funding for the Acquisition. 
 NOW THEREFORE, in consideration of the mutual promises made herein and other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties hereto, intending to be legally bound, agree as
follows: 
 Section 1. Authorization. 
 The Company has authorized (a) the sale and issuance of up to 42,060 shares of the Company’s Series A Preferred Stock, par value $0.0001 per share (the “Series A Preferred Shares”), having
the rights, privileges, preferences and restrictions set forth in the Certificate of Designation, Preferences and Rights of Series A Preferred Stock, in the form attached hereto as Exhibit A (the “Certificate of Designation”)
and (b) reserved up to 2,400,000 shares of the Company’s common stock, par value $0.0001 per share (the “Common Stock”), for issuance upon conversion of the Series A Preferred Shares (the “Conversion
Shares”). 
 Section 2. Purchase and Sale of Securities. 
 In consideration of and upon the basis of the representations, warranties and agreements and subject to the terms and conditions set forth in this
Agreement, each Investor agrees to purchase from the Company and the Company agrees to sell to each Investor on the Closing Date (as defined in Section 3 hereof), the number of Series A Preferred Shares set forth opposite such Investor’s
name on Schedule A attached hereto for a price per share equal to $1,000.00 (the “Private Placement”). For purposes of this Agreement, the “Purchase Price” shall mean $42,060,000.00, representing the total
purchase price for all Series A Preferred Shares purchased pursuant to this Agreement. 

 Section 3. Closing. 
 (a) The closing of the sale of the Series A Preferred Shares (the “Closing”) shall take place upon the satisfaction or,
if applicable, waiver of the conditions set forth in Sections 8 and 9 hereof, or at such other date and time as the Investors purchasing a majority of the Series A Preferred Shares sold pursuant to this Agreement (the “Majority
Investors”) and the Company shall mutually agree (such date and time being referred to herein as the “Closing Date”). At or prior to the Closing, the Majority Investors shall receive confirmation (which confirmation may be
telephonic) from Computershare, the Company’s transfer agent, that the Investors shall be listed as a record owner of the Series A Preferred Shares that the Investors are purchasing pursuant to this Agreement. At the Closing, each Investor will
pay the Purchase Price for the Investor’s shares by check or wire transfer of immediately available funds. 
 (b) As soon
as reasonably practicable, the Company shall deliver to each Investor a certificate representing the Series A Preferred Shares that each Investor is purchasing, duly registered on the books of the Company in the name of such Investor. 
 Section 4. Use of Proceeds. 
 The
Company shall use the Purchase Price for general corporate purposes; provided, however, that up to $24,000,000 of the Purchase Price may be used by the Company for any acquisition by the Company of another entity, whether by merger,
consolidation, the purchase of assets or otherwise, or of certain businesses or assets of another entity, including the Acquisition. 
 Section 5. Representations and Warranties of the Company. 
 Except as otherwise specifically described in (i) the
Company’s annual report on Form 10-K for the year ended April 30, 2005, the Company’s quarterly reports on Form 10-Q for the quarterly periods ended July 31, 2005, October 31, 2005 and January 31, 2006 and any
current reports on Form 8-K filed subsequent to the date of filing of the Form 10-K for the year ended April 30, 2005 and through the date of this Agreement with the Securities and Exchange Commission (the “SEC”) by the Company
(including the information incorporated by reference therein, the “SEC Documents”), or (ii) a Schedule of Exceptions (the “Schedule of Exceptions”), provided to each Investor and its counsel on the date hereof,
each of which qualify the following representations and warranties in their entirety, the Company hereby represents and warrants to each Investor as follows: 
 (a) Organization, Good Standing and Qualification. The Company is a corporation duly organized, validly existing and in good
standing under the laws of the State of Delaware and has all requisite corporate power and authority to carry on its business as presently conducted. The Company is duly qualified to transact business and is in good standing in each jurisdiction in
which the failure to so qualify would have a material adverse effect on the business, properties, financial condition or operating results of the Company, as such business is presently conducted. Each Significant Subsidiary (as defined in the
Securities Exchange Act of 1934, as amended (the “Exchange Act”)) of the Company is duly organized, validly existing and in good standing under the laws of its respective jurisdiction and has all requisite corporate power and
authority to carry on its business as presently conducted, except where the failure to 

  

 2 

 
be in good standing would not have a material adverse effect on the business, properties, financial condition or operating results of the Company, as such
business is presently conducted. 
 (b) Authorization. All corporate action on the part of the Company, its officers,
directors and stockholders necessary for the authorization, execution and delivery of this Agreement and the Investors’ Rights Agreement (as defined in Section 8), the performance of all obligations of the Company hereunder and thereunder,
and the authorization, issuance, sale and delivery of the Series A Preferred Shares being sold hereunder and the Common Stock being issued upon conversion thereof has been taken or will be taken prior to the Closing, and this Agreement and the
Investors’ Rights Agreement constitute valid and legally binding obligations of the Company, enforceable in accordance with their respective terms, except (i) as limited by applicable bankruptcy, insolvency, reorganization, moratorium, and
other laws of general application affecting enforcement of creditors’ rights generally and (ii) as limited by laws relating to the availability of specific performance, injunctive relief, or other equitable remedies. 
 (c) No Violation or Default. Neither the Company nor any Significant Subsidiary of the Company is in violation or default of any
provision of its certificate of incorporation, bylaws or other organizational documents, as amended, or of any judgment, order, writ, or decree by which it is bound. Neither the Company nor any Significant Subsidiary of the Company is in violation
or default of any instrument or Material Contract (as defined herein) to which it is a party or by which it is bound, or, to its knowledge, of any provision of any federal or state statute, rule or regulation applicable to the Company in which such
violation or default of such instrument, Material Contract or provision of such federal or state statute, rule or regulation applicable to the Company would have, either individually or in the aggregate, a material adverse effect on the business,
properties, financial condition or operating results of the Company, as such business is presently conducted. Neither the Company nor any Significant Subsidiary of the Company has received notice from any other party to a Material Contract that such
party intends to terminate such Material Contract. The execution, delivery and performance of this Agreement and the Investors’ Rights Agreement, and the consummation of the transactions contemplated hereby and thereby will not result in any
such violation or be in conflict with or constitute, with or without the passage of time and giving of notice, either a default under any such provision, instrument, judgment, order, writ, decree or Material Contract or an event that results in the
creation of any lien, charge or encumbrance upon any assets of the Company or any Significant Subsidiary of the Company or the suspension, revocation, impairment, forfeiture, or nonrenewal of any material permit, license, authorization, or approval
applicable to the Company, its business or operations or any of its assets or properties. For purposes of this Agreement, “Material Contract” shall mean (i) any contract to which the Company is a party that is or is required to be
filed as an exhibit to the SEC Documents and (ii) any contract to which the Company or any Significant Subsidiary is a party which is material to the business, properties, financial condition or operating results of the Company or any
Significant Subsidiary, as such business is presently conducted (a “Material Contract”). 
 (d)
Consents. No consent, approval, order or authorization of, or registration, qualification, designation, declaration or filing with, any federal, state or local governmental authority on the part of the Company is required in connection with
the consummation of the transactions contemplated by this Agreement, except (i) the filing pursuant to Regulation D promulgated by the SEC under the Securities Act of 1933, as amended (the “Securities Act”), 

  

 3 

 
which filing will be effected within 15 days of the Closing, or such other post-closing filings as may be required and (ii) such filings and/or
qualifications that may be required pursuant to the Nasdaq Marketplace Rules (the “Nasdaq Rules”), which filings and qualifications will be made on a timely basis, but in any event prior to the Closing. 
 (e) Litigation. There is no action, suit, proceeding or investigation pending or, to the Company’s knowledge, currently
threatened in writing against the Company or any subsidiary or any of their respective directors and officers that questions the validity of this Agreement or the Investors’ Rights Agreement, or the right of the Company to enter into such
agreements or to consummate the transactions contemplated hereby or thereby. There is no action, suit, proceeding or investigation pending or, to the knowledge of the Company, currently threatened in writing against the Company or any subsidiary or
any of their respective directors and officers which would have, either individually or in the aggregate, a material adverse effect on the business, properties, financial condition or operating results of the Company, as such business is presently
conducted. 
 (f) Filings. The Company has filed all forms, reports and documents required to be filed by it with the
SEC since March 31, 2005 (collectively, the “Company SEC Reports”). As of the respective dates they were filed (and if amended or superseded by a filing prior to the date of this Agreement, then on the date of such filing),
(i) the Company SEC Reports complied in all material respects with the requirements of the Securities Act or the Exchange Act, as the case may be, and the rules and regulations of the SEC thereunder applicable to such Company SEC Reports, and
(ii) none of the Company SEC Reports contained any untrue statement of a material fact or omitted to state a material fact required to be stated therein or necessary in order to make the statements made therein, in the light of the
circumstances under which they were made, not misleading. None of the Company’s subsidiaries is required to file any forms, reports or documents with the SEC. The Company has previously furnished to the Investors a complete and correct copy of
any amendments or modifications, which have not yet been filed with the SEC but which are required to be filed to any Company SEC Reports which had been filed by Company with the SEC prior to the date hereof. 
 (g) Financial Statements. The consolidated financial statements (including any notes thereto) contained in the Company SEC Reports
(i) complied as to form in all material respects with the published rules and regulations of the SEC with respect thereto, (ii) were prepared in accordance with United States generally accepted accounting principles
(“GAAP”) applied on a consistent basis throughout the periods indicated (except as may be indicated in the notes thereto or, in the case of unaudited statements, as permitted by Form 10-Q or 8-K promulgated by the SEC) and
(iii) each presented fairly, in all material respects, the consolidated financial position of the Company and its consolidated subsidiaries as of the respective dates thereof and for the respective periods indicated therein, except as otherwise
noted therein (subject, in the case of unaudited statements, to normal and recurring year-end adjustments which were not and are not expected, individually or in the aggregate, to have a material adverse effect on the business, properties, financial
condition or operating results of the Company, as such business is presently conducted). The Company does not intend to correct or restate, nor, to the Company’s knowledge, is there any basis for any correction or restatement of, any aspect of
any of the consolidated financial statements contained in the Company SEC Reports. The 

  

 4 

 
Company has not had any material disagreement with any of its auditors regarding accounting matters or policies during any of its past three full years or
during the current fiscal year-to-date which disagreements would require disclosure to the Company’s Board of Directors. The books and records of the Company and each subsidiary have been, and are being maintained in all material respects in
accordance with applicable legal and accounting requirements and the consolidated financial statements contained in the Company SEC Reports are consistent with such books and records. 
 (h) Internal Controls. The Company and each of its subsidiaries has established and maintains, adheres to and enforces a system of
internal accounting and disclosure controls which are effective in providing assurance regarding the reliability of financial reporting and the preparation of financial statements in accordance with GAAP (including the consolidated financial
statements contained in the Company SEC Reports), including policies and procedures that (i) require the maintenance of records that in reasonable detail accurately and fairly reflect in all material respects the transactions and dispositions
of the assets of the Company and its subsidiaries, (ii) provide assurance that transactions are recorded as necessary to permit preparation of financial statements in accordance with GAAP, and that receipts and expenditures of the Company and
its subsidiaries are being made only in accordance with appropriate authorizations of management and the Board of Directors of the Company and (iii) provide assurance regarding prevention or timely detection of unauthorized acquisition, use or
disposition of the material assets of the Company and its subsidiaries. Neither the Company nor any of its subsidiaries (including any employee thereof) nor, to the Company’s knowledge, the Company’s independent auditors, has identified or
been made aware of (i) any significant deficiency or material weakness in the system of internal accounting controls utilized by the Company and its subsidiaries, (ii) any fraud, whether or not material, that involves the Company’s
management or other employees who have a role in the preparation of financial statements or the internal accounting controls utilized by the Company and its subsidiaries or (iii) any claim or allegation regarding any of the foregoing.

 (i) Changes. Since the date of the Company’s most recent quarterly report on Form 10-Q filed with the SEC,
(i) there has not been any Company development that has not otherwise been publicly disclosed that would have or could reasonably be expected to have a material adverse effect on the business, properties, financial condition or operating
results of the Company, as such business is presently conducted, (ii) the Company and its subsidiaries have not incurred any debts or liabilities except for debts or liabilities incurred in the ordinary course of business and except in
connection with obligations under contracts and commitments incurred in the ordinary course of business, (iii) the Company and its subsidiaries have not entered into or terminated or contemplated entering into or terminating any Material
Contract and (iv) there has not been any change in the assets, liabilities, financial condition or operating results of the Company and its subsidiaries from that reflected in the consolidated financial statements included with the most recent
quarterly report on Form 10-Q, except changes in the ordinary course of business that have not been, in the aggregate, materially adverse. 
 (j) Registration Rights. Except as set forth in the Investors’ Rights Agreement, the Company has not granted or agreed to grant any registration rights, including piggy-back rights, to any person or
entity. 
  

 5 

 (k) Capitalization. 
 (i) As of June 20, 2006, the authorized capital stock of the Company consisted of 10,000,000 shares of Preferred Stock, none of which
were issued and outstanding, and 200,000,000 shares of Common Stock, 14,563,522 shares of which were issued and outstanding (the “Preferred Stock” and the “Common Stock” are collectively referred to herein as the
“Capital Stock”). All of the issued and outstanding shares of Capital Stock have been duly authorized, validly issued and are fully paid and nonassessable. The Company has options granted and shares available under the 1999 Stock
Incentive Plan, 1999 Director Option Plan, Employee Stock Purchase Plan and 2000 Supplemental Stock Option Plan. In addition, the Company has options outstanding under the 1996 Stock Option Plan and under the option plans that it assumed in
connection with its acquisitions of Entera, Inc, Springbank Networks, Inc., Cerberian, Inc., and Permeo Technologies, Inc. (together with the 1996 Stock Option Plan, 1999 Stock Incentive Plan, 1999 Director Option Plan, Employee Stock Purchase Plan
and 2000 Supplemental Stock Option Plan, the “Plans”). As of the date hereof, options to purchase 3,337,382 shares of Common Stock were outstanding under the Plans and, in addition to the aforementioned options, the Company has
reserved an additional 734,424 shares of its Common Stock for purchase upon exercise of options to be granted in the future under the Plans. The Company has reserved: (i) the Series A Preferred Shares for issuance pursuant to this Agreement and
2,400,000 shares of Common Stock (as may be adjusted in accordance with the provisions of the Certificate of Designation) for issuance upon conversion of the Series A Preferred Shares. Except as otherwise set forth in this Agreement and except for
(A) the conversion privileges of the Series A Preferred Shares, (B) options granted (or remaining available for grant) pursuant to the Plans, (C) warrants to purchase 626 shares of Common Stock of the Company, and (D) as provided
in the Schedule of Exceptions, there are no outstanding options, warrants, rights (including conversion or preemptive rights), agreements, arrangements or commitments of any character, whether or not contingent, relating to the issued or unissued
Capital Stock of the Company or obligating the Company to issue or sell any share of Capital Stock of, or other equity interest in, the Company. 
 (ii) The Series A Preferred Shares that are being purchased by the Investors hereunder, when issued, sold or delivered in accordance with the terms hereof, for the consideration expressed herein, will be duly and
validly issued, fully paid and nonassessable. The Conversion Shares have been duly and validly reserved and, when issued in compliance with the provisions of this Agreement, the Certificate of Designation and applicable law, will be validly issued,
fully paid and nonassessable. The Series A Preferred Shares and the Conversion Shares will be free of any liens and encumbrances created by the Company and, subject to the accuracy of the representations of each Investor in this Agreement, will be
issued in compliance with (and the offer, sale and issuance of the Series A Preferred Shares and the Conversion Shares are exempt from the registration requirements of) all applicable federal and state securities laws. 
 (l) Registration of Common Stock. The Company’s Common Stock is registered pursuant to Section 12(g) of the Exchange Act
and is listed on the Nasdaq Stock Market, and the Company has taken no action with the intention of, or likely to have the effect 

  

 6 

 
of, terminating the registration of the Common Stock under the Exchange Act or delisting the Common Stock from the Nasdaq Stock Market. The Company has not
been notified by the Nasdaq Stock Market of any action or potential action by Nasdaq or of any violation of any Nasdaq Rules that could result in the delisting of the Company’s Common Stock from the Nasdaq Stock Market. 
 (m) Manipulation of Price. The Company has not taken and will not take any action outside the ordinary course of business designed
to or that might reasonably be expected to cause or result in unlawful manipulation of the price of the Common Stock to facilitate the sale or resale of the Series A Preferred Shares or the Conversion Shares. 
 (n) Intellectual Property. To its knowledge (with respect to patents, trademarks, service marks and trade names only), the Company
has sufficient title and ownership of all patents, trademarks, service marks, trade names, domain names, copyrights, trade secrets, information, proprietary rights and processes (“IP Rights”) necessary for its business as presently
conducted without any violation or infringement of the rights of others, except for any such violation or infringement the occurrence of which would not have a material adverse effect on the business, properties, financial condition or operating
results of the Company, as such business is presently conducted. The Company and its subsidiaries have not received written notice from a third party that the Company’s or the subsidiary’s products infringe on such third party’s IP
Rights. 
 (o) Authority. The Company has the requisite corporate power and authority to enter into and to perform its
obligations under this Agreement and the Investors’ Rights Agreement. Prior to the date of this Agreement, the Board of Directors has (a) determined that this Agreement is fair to, advisable and in the best interests of the Company and the
stockholders of the Company and (b) approved the transactions contemplated by this Agreement. The foregoing action taken by the Board of Directors constitutes approval, for purposes of Section 203 of the Delaware General Corporation Law
(“DGCL”), of the Private Placement and any other transactions that would make any Investor or the Investors an “interested stockholder” as defined in Section 203(c)(5) of the DGCL (an “Interested Stockholder
Transaction”), such that Section 203 of the DGCL does not apply to this Agreement, the transactions effected hereunder, any transaction consummated subsequent to the date of the Interested Stockholder Transaction that would constitute
a “business combination” (as defined in Section 203(c)(3) of the DGCL) (a “Business Combination”), and such approval has not been amended, rescinded or modified. 
 Section 6. Representations and Warranties of the Investors. 
 Each Investor hereby represents and warrants to the Company on the date hereof, and agrees with the Company, as follows: 
 (a) No Endorsement. Each Investor understands that no United States federal or state agency has passed on, reviewed or made any recommendation or endorsement of the Series A Preferred Shares or the Conversion
Shares. 
  

 7 

 (b) Authorization. Each Investor has full power and authority to enter into this
Agreement and the Investors’ Rights Agreement, and such agreements constitute valid and legally binding obligations, enforceable in accordance with their respective terms, except (i) as limited by applicable bankruptcy, insolvency,
reorganization, moratorium, and other laws of general application affecting enforcement of creditors’ rights generally and (ii) as limited by laws relating to the availability of specific performance, injunctive relief, or other equitable
remedies. 
 (c) Investment Intent. This Agreement is made with each Investor in reliance upon such Investor’s
representation to the Company, which by such Investor’s execution of this Agreement such Investor hereby confirms, that the Series A Preferred Shares and the Conversion Shares to be received by such Investor (together, the
“Securities”) will be acquired for investment for such Investor’s own account, not as a nominee or agent, and not with a view to the resale or distribution of any part thereof, and that such Investor has no present intention of
selling, granting any participation in, or otherwise distributing the same. Notwithstanding the foregoing, Francisco Partners II, L.P. and Francisco Partners Parallel Fund II, L.P. may transfer shares of Series A Preferred Stock to one another over
the sixty (60) day period following the date of this Agreement. 
 (d) Investment Experience. Each Investor is an
investor in securities of companies in the development stage and acknowledges that it can bear the economic risk of its investment, and has such knowledge and experience in financial or business matters that it is capable of evaluating the merits
and risks of the investment in the Securities. Each Investor also represents it has not been organized for the purpose of acquiring the Securities. 
 (e) Accredited Investor. Each Investor is an “accredited investor” within the meaning of SEC Rule 501(a) of Regulation D, as presently in effect. 
 (f) Exemption from Registration. Each Investor understands that the Securities are being offered and sold in reliance on a
transactional exemption from the registration requirements of Federal and state securities laws and that the Company is relying upon the truth and accuracy of the representations, warranties, agreements, acknowledgments and understandings of each
Investor set forth herein in order to determine the applicability of such exemptions and the suitability of each Investor to acquire the Securities. 
 (g) Rule 144. Each Investor understands that the Securities it is purchasing are characterized as “restricted securities” under the federal securities laws inasmuch as they are being acquired from the
Company in a transaction not involving a public offering and that under such laws and applicable regulations such securities may be resold without registration under the Securities Act, only in certain limited circumstances. In this connection, each
Investor represents that it is familiar with SEC Rule 144, as presently in effect, and understands the resale limitations imposed thereby and by the Securities Act. 
  

 8 

 (h) Restrictions on Transfer. Without in any way limiting the representations set
forth above, each Investor further agrees not to make any disposition of all or any portion of the Securities unless and until the transferee has agreed in writing for the benefit of the Company to be bound by the provisions of this
Section 5(h) provided and to the extent such provisions are then applicable, and: 
 (i) There is then in effect a
Registration Statement under the Securities Act covering such proposed disposition and such disposition is made in accordance with such Registration Statement; or 
 (ii) (i) Such Investor shall have notified the Company of the proposed disposition and shall have furnished the Company with a statement
in reasonable detail of the circumstances surrounding the proposed disposition, and (ii) if reasonably requested by the Company, such Investor shall have furnished the Company with an opinion of counsel, reasonably satisfactory to the Company,
that such disposition will not require registration of such shares under the Securities Act. It is agreed that the Company will not require opinions of counsel for transactions made pursuant to Rule 144. 
 (i) It is understood that the certificates evidencing the Securities will bear the following legends: 
 “These securities have not been registered under the Securities Act of 1933, as amended. They may not be sold, offered for sale, pledged or
hypothecated in the absence of a registration statement in effect with respect to the securities under such Act, pursuant to Rule 144 of such Act or an exemption from the registration requirements of the Act, in which case an opinion of counsel
satisfactory to the Company that such registration is not required may be required.” 
 (j) No Advice. Each
Investor understands that nothing in this Agreement or the Investors’ Rights Agreement or any other materials presented to such Investor in connection with the purchase and sale of the Securities constitutes legal, tax or investment advice.
Each Investor has consulted such legal, tax and investment advisors as it, in its sole discretion, has deemed necessary or appropriate in connection with its purchase of the Securities. 
 (k) Disclosure of Information. Each Investor believes it has received all the information it considers necessary or appropriate for
deciding whether to purchase the Series A Preferred Shares. Such Investor further represents that it has had an opportunity to ask questions and receive answers from the Company regarding terms and conditions of the offering of the Series A
Preferred Shares and the business, properties, prospects and financial condition of the Company. The foregoing, however, does not limit or modify the representations and warranties of the Company in Section 4 of this Agreement or the right of
the Investors to rely thereon. 
 Section 7. Covenants 
 (a) Registration of Common Stock. The Company covenants and agrees with each Investor that for so long as any of the Series A
Preferred Shares or the Conversion Shares are outstanding, the Company (i) will use its commercially reasonable efforts to cause its Common Stock to continue to be registered under Sections 12(b) or 12(g) of the Exchange Act, (ii) will
comply on and after April 30, 2007 in all respects with its reporting and filing obligations under said act, and (iii) will not take any action or file any document (whether or not permitted by the Act or the Exchange Act or the rules
thereunder) to terminate or suspend on and 

  

 9 

 
after April 30, 2007 its reporting and filing obligations under said acts, except as permitted herein or pursuant to the Investors’ Rights
Agreement. For so long as any of the Series A Preferred Shares or the Conversion Shares are outstanding, the Company will use its commercially reasonable efforts to continue the listing or trading of its Common Stock on and after April 30, 2007
on the Nasdaq Stock Market or on a national securities exchange (as defined in the Exchange Act) and will comply on and after April 30, 2007 in all respects with the Company’s reporting, filing and other obligations under the Nasdaq Rules.
Notwithstanding the foregoing, the provisions of this subsection shall not in any way restrict the Company’s ability to negotiate and consummate the consolidation, reorganization or merger of the Company with or into any other corporation or
corporations or the sale, conveyance, or other disposition of all or substantially all of the Company’s property or business. 
 (b) Section 203 Restrictions. No Investor, individually or as part of a “group” (as defined in Rule 13d-5(b)(1) under the Exchange Act), shall engage in any transaction with the Company that would constitute a Business
Combination prior to the third anniversary of the Closing Date without the approval of a majority of the Company’s Board of Directors, excluding any directors elected solely by the holders of Series A Preferred Shares in accordance with
Section 7(d) of the Certificate of Designation (a “Series A Director”) or nominated by the Investors pursuant to Section 2 of the Investors’ Rights Agreement; provided, however, that a Series A Director
may be counted in determining the presence of a quorum at a meeting of the Company’s Board of Directors approving a Business Combination. 
 (c) Restrictions on Transfer. Each Investor covenants and agrees with the Company that neither such Investor nor any of such Investor’s affiliates nor any person acting on its or their behalf will at any
time offer or sell any of the Securities other than pursuant to registration under the Securities Act or pursuant to an available exemption therefrom. 
 (d) Company SEC Reports. The Company shall, prior to filing a Form 8-K with the SEC describing the private placement contemplated by this Agreement, furnish to the Investors for review a copy of such Form 8-K.

 Section 8. Conditions Precedent to Investor’s Obligations. 
 The obligations of each Investor under Section 2 of this Agreement are subject to the fulfillment on or before the Closing of each of the following
conditions, unless such condition or conditions are expressly waived in writing by the Majority Investors: 
 (a) The
representations and warranties of the Company contained in Section 5 shall be true in all material respects on and as of the Closing as though such representations and warranties had been made on and as of the Closing Date, except for
representations and warranties made as of a particular date, which shall be true and correct as of such date. 
 (b) The
Company shall have performed and complied in all material respects with all agreements, obligations and conditions contained in this Agreement that are required to be performed or complied with by it on or before the Closing. 
  

 10 

 (c) The Chief Executive Officer of the Company shall deliver to each Investor at the
Closing a certificate stating that the conditions specified in Sections 8(a) and 8(b) have been fulfilled. 
 (d) No statute,
rule, regulation, executive order, decree, ruling or injunction shall have been enacted, entered, promulgated or endorsed by any court or governmental authority of competent jurisdiction which prohibits the consummation of any of the transactions
contemplated by this Agreement. 
 (e) Each Investor shall have received from Gunderson Dettmer Stough Villeneuve
Franklin & Hachigian, LLP, counsel for the Company (“Gunderson”), an opinion, dated as of the Closing Date, in substantially the form attached hereto as Exhibit B. 
 (f) The Company and the Investors shall have entered into that certain Investors’ Rights Agreement in substantially the form attached
hereto as Exhibit C (the “Investors’ Rights Agreement”). 
 (g) The Company shall have filed a
listing application with the Nasdaq Stock Market for the Conversion Shares, and either (a) fifteen (15) days shall have lapsed from the filing of such listing application without objection from the Nasdaq Stock Market or (b) the
Nasdaq Stock Market shall have accepted or indicated that it will not object to such listing application prior to the expiration of such fifteen (15) day period. The Company shall continue to have its shares of Common Stock listed for trading
on the Nasdaq Stock Market. 
 (h) (i) Keith Geeslin shall have been appointed to the Board of Directors of the Company,
(ii) Mr. Geeslin shall be named as an additional insured under the Company’s directors and officers liability insurance in an amount not less than $10,000,000 and (iii) the Company shall have entered into an Indemnification
Agreement with Mr. Geeslin in substantially the form attached hereto as Exhibit D. 
 Section 9. Conditions Precedent to the
Company’s Obligations. 
 The obligations of the Company to each Investor under this Agreement are subject to the fulfillment on or
before the Closing of each of the following conditions by the Investors, unless such condition or conditions are expressly waived in writing by the Company: 
 (a) The representations and warranties of each of the Investors contained in Section 6 shall be true on and as of the Closing in all
material respects as though such representations and warranties had been made on and as of the Closing Date, except for representations and warranties made as of a particular date, which shall be true and correct as of such date. 
 (b) Each Investor shall have performed and complied in all material respects with all agreements, obligations and conditions contained in
this Agreement that are required to be performed or complied with by it on or before the Closing. 
 (c) No statute, rule,
regulation, executive order, decree, ruling or injunction shall have been enacted, entered, promulgated or endorsed by any court or governmental 

  

 11 

 
authority of competent jurisdiction which prohibits the consummation of any of the transactions contemplated by this Agreement. 
 (d) Each Investor shall have delivered the Purchase Price for the Series A Preferred Shares. 
 Section 10. Fees and Expenses. 
 Irrespective of whether the Closing is effected, the Company shall pay all costs and expenses that it incurs with respect to the Private Placement and the Acquisition, including the negotiation, execution, delivery and performance of this
Agreement, the Investors’ Rights Agreement and the Asset Purchase Documents. If the Closing is effected, the Company shall reimburse the Investors for their reasonable fees and out-of-pocket expenses of O’Melveny & Myers LLP
(“OMM”) and Deloitte & Touche LLP (“D&T”) that relate to either the Private Placement or the Acquisition. If the Acquisition closes within 150 days of the date of this Agreement, the Company shall pay
AFK Inc. (“AFK”) an amount determined by Francisco Partners Management, LLC not to exceed $500,000. If the Acquisition does not close within 150 days of the date of this Agreement, the Investors shall promptly repay to the
Company all fees and expenses paid to OMM, D&T and AFK (or to the Investors on behalf of OMM, D&T or AFK) pursuant to this paragraph (which includes all fees and expenses related to both the Private Placement and the Acquisition). The
repayment obligations described in the preceding sentence will be allocated among the Investors pro rata based on the number of shares of Series A Preferred Stock purchased by each such Investor pursuant to this Agreement. 
 Section 11. Survival of the Representations, Warranties, etc. 
 The respective representations, warranties, and agreements made herein by or on behalf of the parties hereto shall remain in full force and effect for a period of one (1) year from the Closing Date, regardless of
any investigation made by or on behalf of any party to this Agreement or any officer, director or employee of, or person controlling or under common control with, such party and will survive delivery of and payment for the Series A Preferred Shares;
provided, however, that Sections 7(a) and 7(b) shall survive until the Series A Preferred Shares or the Conversion Shares are no longer held by any Investor. 
 Section 12. 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 
 Attn: General Counsel 
 Phone: (408) 220-2200 
 Telecopy: (408) 220-2250 
  

 12 

 (b) with a copy mailed to: 
 Gunderson Dettmer Stough Villeneuve Franklin & Hachigian, LLP 
 155 Constitution Drive 
 Menlo Park, California 94025 
 Attn: Daniel E. O’Connor, Esq. 
 Phone: (650) 321-2400 
 Telecopy: (650) 321-2800 
 (c) if to the Investors, at the addresses set forth on
Schedule A hereto, or at such other address or addresses as may be furnished to the Company in writing. 
 Section 13.
Miscellaneous. 
 (a) This Agreement may be executed in two or more counterparts and it is not necessary that signatures
of all parties appear on the same counterpart, but such counterparts together shall constitute one and the same agreement. 
 (b) Any provision of this Agreement may be amended, waived or modified only upon the written consent of the Company and the Majority Investors. Any amendment or waiver affected in accordance with this Section 13(b) shall be binding
upon each Investor and the Company. 
 (c) This Agreement shall inure to the benefit of and be binding upon the parties hereto
and their respective successors and assigns. 
 (d) This Agreement shall be governed by, and construed in accordance with, the
internal laws of the State of California without regard to principles of conflict of laws. 
 (e) The provisions of this
Agreement are severable, and if any clause or provision hereof shall be held invalid, illegal or unenforceable in whole or in part, such invalidity or unenforceability shall not in any manner affect any other clause or provision of this Agreement.

 (f) The headings of the sections of this document have been inserted for convenience of reference only and shall not be
deemed to be a part of this Agreement. 
 (g) This Agreement and the Investors’ Rights Agreement constitute the entire
agreement and supersede all prior agreements and understandings, both written and oral, between the parties hereto with respect to the subject matter of this Agreement and is not intended to confer upon any person other than the parties hereto any
rights or remedies hereunder. 
  

 13 

 (h) Notwithstanding any provision of this Agreement to the contrary, any confidential
disclosure agreement previously executed by the Company and any Investor in connection with the transactions contemplated by this Agreement shall remain in full force and effect in accordance with its terms following the execution of this Agreement
and the consummation of the transactions contemplated hereby. 
 (i) Notwithstanding any provision of this Agreement to the
contrary, any party to this Agreement (and any of such party’s respective employees, representatives, or other agents) may disclose to any and all persons, without limitation of any kind, the tax treatment and tax structure of the transactions
contemplated by this Agreement and all materials of any kind (including opinions or other tax analyses) that are provided to it relating to such tax treatment and tax structure; provided, however, that for this purpose, (a) the
“tax treatment” of a transaction means the purported or claimed federal income tax treatment of the transaction and (b) the “tax structure” of a transaction means any fact that may be relevant to understanding the purported
or claimed federal income tax treatment of the transaction. 
 (j) The Company will provide the Investors and their counsel
with a copy of any proposed announcement of, or Form 8-K regarding, this transaction and a reasonable opportunity to review and comment on any such materials. 
  

 14 

 IN WITNESS WHEREOF, each of the parties hereto has executed this Series A Preferred Stock Purchase
Agreement as of the date first written above 
  

			
	BLUE COAT SYSTEMS, INC.
		
	By:	 	  
		 	 Name: Brian NeSmith

		 	 Title: President and Chief Executive Officer

 SIGNATURE PAGE TO THE BLUE COAT SYSTEMS, INC. 
 SERIES A PREFERRED STOCK PURCHASE 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	 	  
		 	Name:
		 	Title:
	
	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	 	  
		 	Name:
		 	Title:

 SIGNATURE PAGE TO THE BLUE COAT SYSTEMS, INC. 
 SERIES A PREFERRED STOCK PURCHASE AGREEMENT 

			
	INVESTORS
	
	SEQUOIA CAPITAL GROWTH FUND III
		
	By:	 	 SCGF III Management, LLC
 A Delaware Limited Liability
Company
 General Partner

		
	By:	 	  
		 	Name:
		 	Title: Managing Member
	
	SEQUOIA CAPITAL GROWTH PARTNERS III
		
	By:	 	 SCGF III Management, LLC
 A Delaware Limited Liability
Company
 General Partner

		
	By:	 	  
		 	Name:
		 	Title: Managing Member
	
	 SEQUOIA CAPITAL GROWTH III
 PRINCIPALS FUND

		
	By:	 	 SCGF III Management, LLC
 A Delaware Limited Liability
Company
 General Partner

		
	By:	 	  
		 	Name:
		 	Title: Managing Member

 SIGNATURE PAGE TO THE BLUE COAT SYSTEMS, INC. 
 SERIES A PREFERRED STOCK PURCHASE AGREEMENT 

 SCHEDULE A 
  

								
	 Investor
	  	 Shares
	  	Purchase Price
	 Francisco Partners II, L.P.
	  	Series A Preferred:	  	24,891	  	$	24,891,000
	 Francisco Partners Parallel Fund II, L.P.
	  	Series A Preferred:	  	345	  	$	345,000
	 Sequoia Capital Growth Fund III
	  	Series A Preferred:	  	15,872	  	$	15,872,000
	 Sequoia Capital Growth Partners III
	  	Series A Preferred:	  	175	  	$	175,000
	 Sequoia Capital Growth III Principals Fund
	  	Series A Preferred:	  	777	  	$	777,000
		  		  	 	  	 	 
		  		  	42,060	  	$	42,060,000

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