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”).

 

1

--------------------------------------------------------------------------------

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.

 

2

--------------------------------------------------------------------------------

(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.

 

3

--------------------------------------------------------------------------------

(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.

 

4

--------------------------------------------------------------------------------

(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’)

 

5

--------------------------------------------------------------------------------

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.

 

6

--------------------------------------------------------------------------------

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

 

7

--------------------------------------------------------------------------------

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.

 

8

--------------------------------------------------------------------------------

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.

 

9

--------------------------------------------------------------------------------

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

 

10

--------------------------------------------------------------------------------

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.

 

11

--------------------------------------------------------------------------------

(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-2