Document:

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                                                                    EXHIBIT 4.20

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                              AMENDED AND RESTATED
                             STOCKHOLDERS AGREEMENT

                                      among

                              CRITICAL PATH, INC.,

                       GENERAL ATLANTIC PARTNERS 74, L.P.,

                       GAP COINVESTMENT PARTNERS II, L.P.,

                                  GAPSTAR, LLC,

                                   GAP-W, LLC,

                              GAPCO GMBH & CO. KG,

                          CAMPINA ENTERPRISES LIMITED,

                                CENWELL LIMITED,

                             GREAT AFFLUENT LIMITED,

                              DRAGONFIELD LIMITED,

                               LION COSMOS LIMITED

                                       and

                             VECTIS CP HOLDINGS, LLC

                            Dated: November 26, 2003

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                                TABLE OF CONTENTS

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1.       Definitions....................................................................................     2

2.       Future Issuance of Shares; Preemptive Rights...................................................     6
         2.1      Offering Notice.......................................................................     6
         2.2      Preemptive Rights; Exercise...........................................................     7
         2.3      Closing...............................................................................     8
         2.4      Sale to Subject Purchaser.............................................................     8

3.       Corporate Governance...........................................................................     8
         3.1      Board of Directors; Number and Composition............................................     8
         3.2      Reimbursement of Expenses; D&O Insurance..............................................     9
         3.3      Meetings of the Board of Directors....................................................     9
         3.4      Annual Budget.........................................................................     9

4.       Standstill; Nasdaq Matters.....................................................................     9
         4.1      Standstill............................................................................     9
         4.2      Nasdaq Matters........................................................................    11

5.       Miscellaneous..................................................................................    11
         5.1      Notices...............................................................................    11
         5.2      Successors and Assigns; Third Party Beneficiary.......................................    13
         5.3      Amendment and Waiver..................................................................    13
         5.4      Counterparts..........................................................................    13
         5.5      Specific Performance..................................................................    13
         5.6      Headings..............................................................................    13
         5.7      Governing Law.........................................................................    13
         5.8      Severability..........................................................................    13
         5.9      Rules of Construction.................................................................    14
         5.10     Entire Agreement......................................................................    14
         5.11     Term of Agreement.....................................................................    14
         5.12     Further Assurances....................................................................    14
</TABLE>

Schedule          Coinvestors

EXHIBITS

A                 Articles of Incorporation
B                 By-laws

                                       i

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                                    Schedule

                                   Coinvestors

Vectis CP Holdings, LLC

Campina Enterprises Limited

Cenwell Limited

Great Affluent Limited

Dragonfield Limited

Lion Cosmos Limited

                                       i

<PAGE>

                              AMENDED AND RESTATED

                             STOCKHOLDERS AGREEMENT

         AMENDED AND RESTATED STOCKHOLDERS AGREEMENT (this "Agreement"), dated
November __, 2003, among Critical Path, Inc., a California corporation (the
"Company"), General Atlantic Partners 74, L.P., a Delaware limited partnership
("GAP LP"), GAP Coinvestment Partners II, L.P., a Delaware limited partnership
("GAP Coinvestment"), GapStar, LLC, a Delaware limited liability company
("GapStar"), GAP-W, LLC, a Delaware limited liability company ("GAP-W"), GAPCO
GmbH & Co. KG, a German limited partnership ("GmbH Coinvestment"), and the
Persons listed on the Schedule hereto (the "Coinvestors").

         WHEREAS, pursuant to the Stock and Warrant Purchase and Exchange
Agreement, dated November 8, 2001, as amended from time to time (the "Stock
Purchase Agreement"), among the Company, GAP LP, GAP Coinvestment, GapStar and
the Coinvestors, the Company has (i) issued and sold to GAP LP, GAP
Coinvestment, GapStar and the Coinvestors an aggregate of 708,037 shares of
Series D Cumulative Redeemable Convertible Participating Preferred Stock, par
value $0.001 per share, of the Company, as amended from time to time (the
"Series D Preferred Stock"), (ii) issued and delivered to GAP LP, GAP
Coinvestment and GapStar an aggregate of 1,837,418 shares of Series D Preferred
Stock in exchange for a certain amount of convertible subordinated notes of the
Company and (iii) issued and sold to GAP LP, GAP Coinvestment and GapStar
warrants (the "Warrants") to purchase shares of Common Stock; and

         WHEREAS, pursuant to the Convertible Note Purchase and Exchange
Agreement, dated November 18, 2003 (the "Convertible Note Purchase and Exchange
Agreement"), among the Company, GAP LP, GAP Coinvestment, GapStar, GAP-W, GAPCO
GmbH Coinvestment, Campina Enterprises Limited ("Campina Enterprises Limited"),
Cenwell Limited ("Cenwell Limited"), Great Affluent Limited ("Great Affluent
Limited"), Dragonfield Limited ("Dragonfield Limited") and Lion Cosmos Limited
("Lion Cosmos Limited"), (i) the Company has issued and sold to GAP LP, GAP
Coinvestment, GapStar, GAP-W and GAPCO GmbH Coinvestment convertible promissory
notes in the principal amount of $10,000,000 (the "Notes"), which are
convertible into shares, par value $0.001 per share, of Series E Convertible
Preferred Stock of the Company (the "Series E Preferred Stock") and (ii) Campina
Enterprises Limited, Cenwell Limited, Great Affluent Limited, Dragonfield
Limited and Lion Cosmos Limited agreed upon the satisfaction of certain
conditions to exchange their CK Sub Notes (as hereinafter defined) for shares of
Series E Preferred Stock; and

         WHEREAS, the parties hereto wish to provide for, among other things,
preemptive rights, corporate governance rights and standstill obligations and
certain other rights under certain conditions.

         NOW, THEREFORE, in consideration of the mutual covenants and agreements
set forth herein and for good and valuable consideration, the receipt and
adequacy of which are hereby acknowledged, the parties hereto agree as follows:

<PAGE>

         1.       Definitions. As used in this Agreement, and unless the context
requires a different meaning, the following terms have the meanings indicated:

                  "Affiliate" shall mean any Person who is an "affiliate" as
defined in Rule 12b-2 of the General Rules and Regulations under the Exchange
Act.

                  "Agreement" means this Agreement as the same may be amended,
supplemented or modified in accordance with the terms hereof.

                  "Board of Directors" means the Board of Directors of the
Company.

                  "Business Day" means any day other than a Saturday, Sunday or
other day on which commercial banks in the State of New York or the State of
California are authorized or required by law or executive order to close.

                  "Campina Enterprises Limited" has the meaning set forth in the
recitals of this Agreement.

                  "Cenwell Limited" has the meaning set forth in the recitals of
this Agreement.

                  "Charter Documents" means the Articles of Incorporation and
the By-laws of the Company as in effect on the date hereof after giving effect
to the filing of the Amended and Restated Certificate of Determination with
respect to the Series D Preferred Stock and the Certificate of Determination
with respect to the Series E Preferred Stock with the Secretary of State of the
State of California, copies of which are attached hereto as Exhibit A and
Exhibit B, respectively.

                  "CK Sub Notes" means the 5 3/4% Convertible Subordinated
Notes, due April 1, 2005, issued by the Company in the principal face amount of
$32,795,000 pursuant to the Company's Indenture, dated March 31, 2000, and
standing in the name of Campina Enterprises Limited, Cenwell Limited, Great
Affluent Limited, Dragonfield Limited or Lion Cosmos Limited on the books of the
Company.

                  "Coinvestor Stockholders" means the Coinvestors and any
Affiliate of a Coinvestor that, after the date hereof, acquires Shares, and the
term "Coinvestor Stockholder" shall mean any such person.

                  "Coinvestors" has the meaning set forth in the preamble to
this Agreement.

                  "Coinvestors Sub-group" has the meaning set forth in Section
4.1(c) of this Agreement.

                  "Commission" means the Securities and Exchange Commission or
any similar agency then having jurisdiction to enforce the Securities Act.

                  "Common Stock" means the Common Stock, par value $.001 per
share, of the Company and any other capital stock of the Company into which such
stock is reclassified or reconstituted and any other common stock of the
Company.

                                       2
<PAGE>

                  "Common Stock Equivalents" means any security or obligation
which is by its terms convertible, exchangeable or exercisable into or for
shares of Common Stock, including, without limitation the Series D Preferred
Stock, Series E Preferred Stock and any option, warrant or other subscription or
purchase right with respect to Common Stock or any Common Stock Equivalent.

                  "Company" has the meaning set forth in the preamble to this
Agreement.

                  "Contingent Obligation" means, as applied to any Person, any
direct or indirect liability of that Person with respect to any Indebtedness,
lease, dividend, guaranty, letter of credit or other obligation, contractual or
otherwise (the "primary obligation") of another Person (the "primary obligor"),
whether or not contingent, (a) to purchase, repurchase or otherwise acquire such
primary obligations or any property constituting direct or indirect security
therefor, (b) to advance or provide funds (i) for the payment or discharge or
any such primary obligor or otherwise to maintain the net worth or solvency or
any balance sheet item, level of income or financial condition of the primary
obligor, (c) to purchase property, securities or services primarily for the
purpose of assuring the owner of any such primary obligation of the ability of
the primary obligor to make payment of such primary obligation, or (d) otherwise
to assure or hold harmless the owner of any such primary obligation against loss
or failure or inability to perform in respect thereof. The amount of any
Contingent Obligation shall be deemed to be an amount equal to the stated or
determinable amount of the primary obligation in respect of which such
Contingent Obligation is made or, if not stated or determinable, the maximum
reasonably anticipated liability in respect thereof.

                  "Convertible Note Purchase and Exchange Agreement" has the
meaning set forth in the recitals to this Agreement.

                  "Dragonfield Limited" has the meaning set forth in the
recitals of this Agreement.

                  "Escrow Agreement" has the meaning set forth in the recitals
to this Agreement.

                  "Excess New Securities" has the meaning set forth in Section
2.2(a) of this Agreement.

                  "Exchange" has the meaning set forth in the Convertible Note
Purchase and Exchange Agreement.

                  "Exchange Act" means the Securities Exchange Act of 1934, as
amended, and the rules and regulations of the Commission thereunder.

                  "Exempt Issuances" has the meaning set forth in Section 2.1 of
this Agreement.

                  "GAP Coinvestment" has the meaning set forth in the preamble
to this Agreement.

                                       3
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                  "GAP LLC" means General Atlantic Partners, LLC, a Delaware
limited liability company and the general partner of GAP LP and the managing
member of GapStar, and any successor to such entity.

                  "GAP LP" has the meaning set forth in the preamble to this
Agreement.

                  "GAP-W" has the meaning set forth in the preamble to this
Agreement.

                  "GapStar" has the meaning set forth in the preamble to this
Agreement.

                  "General Atlantic Director" has the meaning set forth in
Section 3.2(a) of this Agreement.

                  "General Atlantic Stockholders" means GAP LP, GAP
Coinvestment, GapStar, GAP-W, GmbH Coinvestment and any Affiliate of GAP LLC
that, after the date hereof, acquires Shares, and the term "General Atlantic
Stockholder" shall mean any such Person.

                  "GmbH Coinvestment" has the meaning set forth in the preamble
to this Agreement.

                  "Governmental Authority" means the government of any nation,
state, city, locality or other political subdivision thereof, any entity
exercising executive, legislative, judicial, regulatory or administrative
functions of or pertaining to government, and any corporation or other entity
owned or controlled, through stock or capital ownership or otherwise, by any of
the foregoing.

                  "Great Affluent Limited" has the meaning set forth in the
recitals of this Agreement.

                  "Indebtedness" means, as to any Person, (a) all obligations of
such Person for borrowed money (including, without limitation, reimbursement and
all other obligations with respect to surety bonds, letters of credit and
bankers' acceptances, whether or not matured), (b) all obligations of such
Person to pay the deferred purchase price of property or services, except trade
accounts payable and accrued commercial or trade liabilities arising in the
ordinary course of business, (c) all interest rate and currency swaps, caps,
collars and similar agreements or hedging devices under which payments are
obligated to be made by such Person, whether periodically or upon the happening
of a contingency, (d) all indebtedness created or arising under any conditional
sale or other title retention agreement with respect to property acquired by
such Person (even though the rights and remedies of the seller or lender under
such agreement in the event of default are limited to repossession or sale of
such property), (e) all obligations of such Person under leases which have been
or should be, in accordance with United States generally accepted accounting
principles in effect from time to time, recorded as capital leases, (f) all
indebtedness secured by any Lien (other than Liens in favor of lessors under
leases other than leases included in clause (e)) on any property or asset owned
or held by that Person regardless of whether the indebtedness secured thereby
shall have been assumed by that Person or is non-recourse to the credit of that
Person and (g) any Contingent Obligation of such Person.

                                       4
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                  "Lien" means any mortgage, deed of trust, pledge,
hypothecation, assignment, encumbrance, lien (statutory or other) or preference,
priority, right or other security interest or preferential arrangement of any
kind or nature whatsoever (excluding preferred stock and equity related
preferences).

                  "Lion Cosmos Limited" has the meaning set forth in the
recitals of this Agreement.

                  "Nasdaq" means The Nasdaq Stock Market, Inc.

                  "New Issuance Notice" has the meaning set forth in Section 2.1
of this Agreement.

                  "New Securities" has the meaning set forth in Section 2.1 of
this Agreement.

                  "Notes" has the meaning set forth in the recitals to this
Agreement.

                  "Person" means any individual, firm, corporation, partnership,
trust, incorporated or unincorporated association, joint venture, joint stock
company, limited liability company, Governmental Authority or other entity of
any kind, and shall include any successor (by merger or otherwise) of such
entity.

                  "Preemptive Rightholder(s)" has the meaning set forth in
Section 2.1 of this Agreement.

                  "Proportionate Percentage" has the meaning set forth in
Section 2.2(a) of this Agreement.

                  "Proposed Price" has the meaning set forth in Section 2.1 of
this Agreement.

                  "Requirement of Law" means, as to any Person, any law,
statute, treaty, rule, regulation, right, privilege, qualification, license or
franchise or determination of an arbitrator or a court or other governmental
authority or stock exchange, in each case applicable or binding upon such Person
or any of its property or to which such Person or any of its property is subject
or pertaining to any or all of the transactions contemplated or referred to
herein.

                  "Securities Act" means the Securities Act of 1933, as amended,
and the rules and regulations of the Commission promulgated thereunder.

                  "Series D Preferred Stock" has the meaning set forth in the
recitals to this Agreement.

                  "Series E Preferred Stock" has the meaning set forth in the
recitals to this Agreement.

                  "Shares" means, with respect to each Stockholder, all shares,
whether now owned or hereafter acquired, of Common Stock, Series D Preferred
Stock and Series E Preferred Stock, and any other Common Stock Equivalents owned
thereby; provided, however, for the purposes

                                       5
<PAGE>

of any computation of the number of Shares pursuant to Sections 2.2 and 5.3, all
outstanding Common Stock Equivalents shall be deemed converted, exercised or
exchanged as applicable and the shares of Common Stock issuable upon such
conversion, exercise or exchange shall be deemed outstanding, whether or not
such conversion, exercise or exchange has actually been effected.

                  "Standstill Ceiling" has the meaning set forth in Section
4.1(a) of this Agreement.

                  "Standstill Expiration Date" means November 8, 2008.

                  "Stock Option Plans" means the Company's stock option plans
and employee purchase plans pursuant to which shares of restricted stock and
options to purchase shares of Common Stock are reserved and available for grant
to officers, directors, employees and consultants of the Company.

                  "Stock Purchase Agreement" has the meaning set forth in the
recitals to this Agreement.

                  "Stockholder Approval" has the meaning set forth in the
Convertible Note Purchase and Exchange Agreement.

                  "Stockholders" means the General Atlantic Stockholders and the
Coinvestor Stockholders.

                  "Stockholders Meeting" has the meaning set forth in Section
4.2 of this Agreement.

                  "Subject Purchaser" has the meaning set forth in Section 2.1
of this Agreement.

                  "Vectis Stockholders" has the meaning set forth in Section
4.1(c) of this Agreement.

                  "Warrants" has the meaning set forth in the recitals to this
Agreement.

                  "Written Consent" has the meaning set forth in Section 4.2 of
this Agreement.

         2.       Future Issuance of Shares; Preemptive Rights.

                  2.1      Offering Notice. Except for (a) options to purchase
Series E Preferred Stock or Common Stock or restricted stock which may be issued
pursuant to the Stock Option Plans, (b) a subdivision of the outstanding shares
of Common Stock into a larger number of shares of Common Stock, (c) capital
stock issued upon exercise, conversion or exchange of any Common Stock
Equivalent either (x) previously issued or (y) issued in accordance with the
terms of this Agreement or the Convertible Note Purchase and Exchange Agreement,
(d) capital stock of the Company issued in consideration of an acquisition,
approved by the Board of Directors, by the Company of another Person, (e) shares
of Common Stock issued as a dividend on the Series D Preferred Stock or Series E
Preferred Stock, (f) shares of Common Stock or Common Stock Equivalents issued
in strategic transactions (which may not be private equity or venture

                                       6
<PAGE>

capital financing transactions) approved by the Board of Directors to Persons
that are not principally engaged in financial investing and (g) up to 10,000,000
shares of Series E Preferred Stock which may be issued pursuant to Section 2.7
of the Convertible Note Purchase and Exchange Agreement ((a)-(g) being referred
to collectively as "Exempt Issuances"), if the Company wishes to issue any
capital stock or any other securities convertible into or exchangeable for
capital stock of the Company pursuant to a private placement exempt from
registration under the Securities Act, other than any such private placement
that is made solely to Qualified Institutional Buyers (as defined in the
Securities Act) in reliance on Rule 144A promulgated under the Securities Act
(collectively, "New Securities") to any Person (the "Subject Purchaser"), then
the Company shall offer such New Securities first to each of the General
Atlantic Stockholders and the Coinvestor Stockholders (each, a "Preemptive
Rightholder" and collectively, the "Preemptive Rightholders") by sending written
notice (the "New Issuance Notice") to the Preemptive Rightholders, which New
Issuance Notice shall state (x) the number of New Securities proposed to be
issued and (y) the proposed purchase price per security of the New Securities
(the "Proposed Price"). Upon delivery of the New Issuance Notice, such offer
shall be irrevocable unless and until the rights provided for in Section 2.2
shall have been waived or shall have expired.

                  2.2      Preemptive Rights; Exercise.

                           (a)      For a period of twenty (20) days after the
giving of the New Issuance Notice pursuant to Section 2.1, each of the
Preemptive Rightholders shall have the right to purchase its Proportionate
Percentage (as hereinafter defined) of the New Securities at a purchase price
equal to the Proposed Price and upon the same terms and conditions set forth in
the New Issuance Notice. Each Preemptive Rightholder shall have the right to
purchase that percentage of the New Securities determined by dividing (x) the
total number of Shares then owned by such Preemptive Rightholder by (y) the
total number of Shares owned by all of the Preemptive Rightholders (the
"Proportionate Percentage"). If any Preemptive Rightholder does not fully
subscribe for the number or amount of New Securities that it or he is entitled
to purchase pursuant to the preceding sentence, then each Preemptive Rightholder
which elected to purchase New Securities shall have the right for a five (5) day
period to purchase that percentage of the remaining New Securities not so
subscribed for (for the purposes of this Section 2.2(a), the "Excess New
Securities") determined by dividing (x) the total number of Shares then owned by
such fully participating Preemptive Rightholder by (y) the total number of
Shares then owned by all fully participating Preemptive Rightholders who elected
to purchase Excess New Securities. Each of the Stockholders may transfer all or
any portion of its rights to purchase New Securities under this Section 2 to any
of its Affiliates.

                           (b)      The right of each Preemptive Rightholder to
purchase the New Securities or Excess New Securities, as the case may be, under
subsection (a) above shall be exercisable by delivering written notice of the
exercise thereof, prior to the expiration of the 20-day period referred to in
subsection (a) above with respect to New Securities or prior to the expiration
of the 5-day period referred to in subsection (a) above with respect to Excess
New Securities, to the Company, which notice shall state the amount of New
Securities that such Preemptive Rightholder elects to purchase pursuant to
Section 2.2(a). The failure of a Preemptive Rightholder to respond within such
20-day or 5-day period shall be deemed to be a

                                       7
<PAGE>

waiver of such Preemptive Rightholder's rights under Section 2.2(a), provided
that each Preemptive Rightholder may waive its rights under Section 2.2(a) prior
to the expiration of such 20-day or 5-day period by giving written notice to the
Company.

                  2.3      Closing. The closing of the purchase of New
Securities or Excess New Securities subscribed for by the Preemptive
Rightholders under Section 2.2 shall be held at the executive office of the
Company at 11:00 a.m., local time, on (a) the 30th day after the giving of the
New Issuance Notice pursuant to Section 2.1, if the Preemptive Rightholders
elect to purchase all of the New Securities under Section 2.2, (b) the date of
the closing of the sale to the Subject Purchaser made pursuant to Section 2.4 if
the Preemptive Rightholders elect to purchase some, but not all, of the New
Securities under Section 2.2 or (c) at such other time and place as the parties
to the transaction may agree. At such closing, the Company shall deliver
certificates representing the New Securities, and such New Securities shall be
issued free and clear of all Liens (other than those attributable to actions by
the purchasers thereof) and the Company shall so represent and warrant, and
further represent and warrant (in addition to other customary representations
and warranties) that such New Securities shall be, upon issuance thereof to the
Preemptive Rightholders and after payment therefor, duly authorized, validly
issued, fully paid and non-assessable. Each Preemptive Rightholder purchasing
the New Securities shall deliver at the closing payment in full in immediately
available funds for the New Securities purchased by him or it. At such closing
all of the parties to the transaction shall execute such additional documents as
are customary for transactions of this type.

                  2.4      Sale to Subject Purchaser. The Company may sell to
the Subject Purchaser all of the New Securities not purchased by the Preemptive
Rightholders pursuant to Section 2.2 on terms and conditions that are no more
favorable to the Subject Purchaser than those set forth in the New Issuance
Notice; provided, however, that such sale is bona fide and made pursuant to a
contract entered into within ninety (90) days following the earlier to occur of
(i) the waiver by the Preemptive Rightholders of their option to purchase New
Securities or Excess New Securities pursuant to Section 2.2, or (ii) the
expiration of the 20-day or 5-day period referred to in Section 2.2. If such
sale is not consummated within such 90-day period for any reason, then the
restrictions provided for herein shall again become effective, and no issuance
and sale of New Securities may be made thereafter by the Company without again
offering the same in accordance with this Section 2. The closing of any issuance
and sale pursuant to this Section 2.4 shall be held at a time and place as the
parties to the transaction may agree within such 90-day period.

         3.       Corporate Governance.

                  3.1      Board of Directors; Number and Composition.

                           (a)      The Company shall take all actions
reasonably necessary to cause the nomination to the Board of Directors of one
(1) individual designated by the General Atlantic Stockholders but only if the
General Atlantic Stockholders are not entitled to elect one director of the
Company by virtue of their rights as the holders of a majority of the shares of
Series D Preferred Stock (the "General Atlantic Director").

                                       8
<PAGE>

                           (b)      If so requested by the Coinvestor Sub-group,
the Company shall cause the nomination to the Board of Directors of one (1)
individual designated by the Coinvestor Sub-group but only if the Coinvestor
Sub-group is not entitled to elect one director of the Company by virtue of
their rights as the holders of a majority of the shares of Series E Preferred
Stock (the "Sub-group Director").

                  3.2      Reimbursement of Expenses; D&O Insurance. The Company
shall reimburse the General Atlantic Director for all reasonable travel and
accommodation expenses incurred by him in connection with the performance of his
duties as director of the Company upon presentation of appropriate documentation
therefor. The Company shall use reasonable commercial efforts to maintain a
directors' liability insurance policy that is reasonably acceptable to the Board
of Directors.

                  3.3      Meetings of the Board of Directors. The Company
agrees to take such actions as are necessary to cause the Board of Directors to
meet in person or telephonically not less frequently than once during each
calendar month.

                  3.4      Annual Budget. Not less than thirty (30) days prior
to the end of each fiscal year, the Company shall prepare and submit to the
Board of Directors for its approval an annual operating budget of the Company
for the next succeeding fiscal year in reasonable detail.

                  3.5      Coinvestor Sub-group Rights. Notwithstanding anything
to the contrary set forth in the Charter Documents, so long as the Coinvestor
Sub-group owns at least 7,000,000 shares of Series E Preferred Stock (subject to
anti-dilution adjustment for stock splits of, combinations of and capital
reorganizations with respect to the Series E Preferred Stock) the consent and
approval of the Coinvestor Sub-group, voting separately as a class, shall be a
prerequisite to:

                           (a)      any action that would result in a deemed
dividend to the shares of Series E Preferred Stock under Section 305 of the
Internal Revenue Code of 1986, as amended; or

                           (b)      the issuance, incurrence, assumption or
guarantee by the Corporation or any Subsidiary of the Corporation of any funded
Indebtedness (excluding capital leases incurred in the ordinary course of
business but including the incurrence of any debt in connection with any
borrowing arrangements with Silicon Valley Bank, provided that, with respect to
the incurrence of any debt in connection with any borrowing arrangements with
Silicon Valley Bank, if the members of the Coinvestor Sub-group do not respond
to a written request for consent by the Company within two Business Days of
receiving such request, such members shall be deemed to have consented).

         4.       Standstill; Nasdaq Matters.

                  4.1      Standstill. Without the approval or written consent
of the Board of Directors, none of the General Atlantic Stockholders or any of
their Affiliates, and none of the Coinvestor Stockholders or any of their
respective Affiliates shall, severally and not jointly, at any time prior to the
Standstill Expiration Date:

                                       9
<PAGE>

                           (a)      purchase or otherwise acquire, or propose or
offer to purchase or acquire, any shares of the Company's capital stock, whether
by tender offer, market purchase, privately negotiated purchase, merger or
otherwise, any shares of the Company's capital stock or any Common Stock
Equivalents in excess of the number of shares of the Company's capital stock and
Common Stock Equivalents purchased pursuant to the Stock Purchase Agreement
(subject to adjustments and issuances of additional Common Stock Equivalents
pursuant to the Amended and Restated Certificate of Determination with respect
to the Series D Preferred Stock) and the Convertible Note Purchase and Exchange
Agreement (subject to adjustments and issuances of additional Common Stock
Equivalents pursuant to the Certificate of Determination with respect to the
Series E Stock) with respect to each such Stockholder and its Affiliates
considered severally and not jointly with any other Stockholder and its
Affiliates (the "Standstill Ceiling"); provided, however, that in no event shall
any such Stockholder acquire any Shares in a transaction in such an amount that
when aggregated with the shares of the Company's capital stock already owned by
such Stockholder, the acquisition of such shares of the Company's capital stock
would require stockholder approval under applicable Nasdaq rules and policies;
and provided, further, that the dividends that accrue on the shares of Series D
Preferred Stock and Series E Preferred Stock pursuant to the terms thereof shall
be excluded for purposes of calculating whether or not a Stockholder and its
Affiliates have exceeded the Standstill Ceiling;

                           (b)      except as specified in this Agreement, make,
or in any way participate, directly or indirectly, in any "solicitation" of
"proxy" (as such terms are defined or used in Regulation 14A of the Exchange
Act) to vote, or seek to advise or influence any Person with respect to the
voting of, any shares of the Company's capital stock, or become a "participant"
in any "election contest" (as such terms are used or defined in Regulation 14A
of the Exchange Act) relating to the election of directors of the Company;
provided, however, that none of the General Atlantic Stockholders, the
Coinvestor Stockholders or any of their respective Affiliates shall be deemed to
have engaged in a "solicitation" or to have become a "participant" by reason of
the membership of designees of the General Atlantic Stockholders, the Coinvestor
Stockholders or any of their respective Affiliates on the Board of Directors;

                           (c)      form, join or in any way participate in a
"group" (within the meaning of Section 13(d)(3) of the Exchange Act) or
otherwise act in concert with any Person for the purpose of acquiring, holding,
voting or disposing of any shares of the Company's capital stock; provided,
however, that (i) the General Atlantic Stockholders may act as a group for the
purpose of acquiring, holding, voting or disposing of any shares of the
Company's capital stock, (ii) Vectis CP Holdings, LLC and any Affiliate thereof
that acquires shares of the Company's capital stock (the "Vectis Stockholders")
may act as a group for the purpose of acquiring, holding, voting or disposing of
any shares of the Company's capital stock, (iii) Cenwell Limited, Campina
Enterprises Limited, Great Affluent Limited, Dragonfield Limited, or Lion Cosmos
Limited or any Affiliate thereof that acquires shares of the Company's capital
stock (the "Coinvestor Sub-group") may act as a group for the purpose of
acquiring, holding, voting or disposing of any shares of the Company's capital
stock; and provided further, that, for the avoidance of doubt, the General
Atlantic Stockholders, the Vectis Stockholders and the Coinvestor Sub-group may
not together act as a group for the purpose of acquiring, holding, voting or
disposing of any shares of the Company's capital stock; or

                                       10
<PAGE>

                           (d)      request the Company (or its directors,
officers, employees or agents), to take any action which would reasonably be
expected to require pursuant to law the Company to make a public announcement or
proposal or offer with respect to (i) any form of business combination or
transaction involving the Company including, without limitation, a merger,
consolidation, tender or exchange offer, sale or purchase of assets, or
dissolution or liquidation of the Company or (ii) instigate, encourage or assist
any Person to do any of the foregoing.

                  4.2      Nasdaq Matters. The Company shall use all
commercially reasonable efforts to maintain the quotation and listing on Nasdaq
of all of the shares of Common Stock issuable upon conversion of the Series D
Preferred Stock and Series E Preferred Stock and all of the shares of Common
Stock issuable upon exercise of the Warrants.

         5.       Miscellaneous.

                  5.1      Notices. All notices, demands or other communications
provided for or permitted hereunder shall be made in writing and shall be by
registered or certified first class mail, return receipt requested, telecopier,
courier service or personal delivery:

                           (a)      if to the Company:

                                    Critical Path, Inc.
                                    532 Folsom Street
                                    San Francisco, CA  94105
                                    Telecopy: (415) 808-8898
                                    Attention: Chief Financial Officer

                                    with a copy to, which shall not constitute
                                    notice:

                                    Pillsbury Winthrop LLP
                                    50 Fremont Street
                                    San Francisco, CA 94105
                                    Telecopy: (415) 983-1200
                                    Attention: Gregg F. Vignos, Esq.

                           (b)      if to any of the General Atlantic
                                    Stockholders:

                                    c/o General Atlantic Service Corporation
                                    3 Pickwick Plaza
                                    Greenwich, CT  06830
                                    Telecopy: (203) 622-8818
                                    Attention: Matthew Nimetz
                                               Thomas J. Murphy

                                    with a copy to, which shall not constitute
                                    notice:

                                    Paul, Weiss, Rifkind, Wharton & Garrison LLP
                                    1285 Avenue of the Americas

                                       11
<PAGE>

                                    New York, NY  10019-6064
                                    Telecopy: (212) 757-3990
                                    Attention: Douglas A. Cifu, Esq.

                                    (c)     if to the Coinvestor Stockholders:

                                    (i)     if to Vectis CP Holdings, LLC:

                                    c/o Vectis Group, LLC
                                    117 Greenwich Street
                                    San Francisco, CA  94111
                                    Telecopy:  (415) 352-5310
                                    Attention:  Matthew Hobart

                                    with a copy to, which shall not constitute
                                    notice:

                                    Kirkland & Ellis
                                    153 East 53rd Street
                                    New York, NY  10022-4675
                                    Telecopy:  (212) 446-4900
                                    Attention:  Michael Movsovich, Esq.

                                    (ii)    if to Campina Enterprises Limited,
                                            Great Affluent Limited, Dragonfield
                                            Limited or Lion Cosmos Limited:

                                            c/o 7th Floor
                                            Cheung Kong Center
                                            2 Queen's Road Central
                                            Hong Kong
                                            Telecopy: (852) 2845-2057
                                            Attention: Mr. Edmond Ip

                                    (iii)   if to Cenwell Limited:

                                            c/o 22nd Floor
                                            Hutchison House
                                            10 Harcourt Road
                                            Hong Kong
                                            Telecopy: (852) 2128-1778
                                            Attention: Company Secretary

         All such notices, demands and other communications shall be deemed to
have been duly given when delivered by hand, if personally delivered; when
delivered by courier, if delivered by commercial courier service; five (5)
Business Days after being deposited in the mail, postage prepaid, if mailed; and
when receipt is mechanically acknowledged, if telecopied. Any party may by
notice given in accordance with this Section 5.1 designate another address or
Person for receipt of notices hereunder.

                                       12
<PAGE>

                  5.2      Successors and Assigns; Third Party Beneficiary. This
Agreement shall inure to the benefit of and be binding upon successors and
permitted assigns of the parties hereto. No person other than the parties hereto
and their successors and permitted assigns is intended to be a beneficiary of
this Agreement.

                  5.3      Amendment and Waiver.

                           (a)      No failure or delay on the part of any party
hereto in exercising any right, power or remedy hereunder shall operate as a
waiver thereof, nor shall any single or partial exercise of any such right,
power or remedy preclude any other or further exercise thereof or the exercise
of any other right, power or remedy. The remedies provided for herein are
cumulative and are not exclusive of any remedies that may be available to the
parties hereto at law, in equity or otherwise.

                           (b)      Any amendment, supplement or modification of
or to any provision of this Agreement, any waiver of any provision of this
Agreement, and any consent to any departure by any party from the terms of any
provision of this Agreement, shall be effective only if it is made or given in
writing and signed by (i) the Company, (ii) the General Atlantic Stockholders
and (iii) the Coinvestor Stockholders holding a majority of the voting power of
the Shares held by the Coinvestor Stockholders; provided, however, that to the
extent that any such amendment or waiver adversely affects any of the
Stockholders, such amendment or waiver shall require the prior written consent
of each Stockholder so adversely affected; provided further, that any
Stockholder may waive in writing any right that inures to such Stockholder. Any
such amendment, supplement, modification, waiver or consent shall be binding
upon the Company and all of the Stockholders.

                  5.4      Counterparts. This Agreement may be executed in any
number of counterparts and by the parties hereto in separate counterparts, each
of which when so executed shall be deemed to be an original and all of which
taken together shall constitute one and the same agreement.

                  5.5      Specific Performance. The parties hereto intend that
each of the parties have the right to seek damages or specific performance in
the event that any other party hereto fails to perform such party's obligations
hereunder. Therefore, if any party shall institute any action or proceeding to
enforce the provisions hereof, any party against whom such action or proceeding
is brought hereby waives any claim or defense therein that the plaintiff party
has an adequate remedy at law.

                  5.6      Headings. The headings in this Agreement are for
convenience of reference only and shall not limit or otherwise affect the
meaning hereof.

                  5.7      GOVERNING LAW. THIS AGREEMENT SHALL BE GOVERNED BY
AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK, WITHOUT
REGARD TO THE PRINCIPLES OF CONFLICTS OF LAW THEREOF.

                  5.8      Severability. If any one or more of the provisions
contained herein, or the application thereof in any circumstance, is held
invalid, illegal or unenforceable in any respect

                                       13
<PAGE>

for any reason, the validity, legality and enforceability of any such provision
in every other respect and of the remaining provisions hereof shall not be in
any way impaired, unless the provisions held invalid, illegal or unenforceable
shall substantially impair the benefits of the remaining provisions hereof.

                  5.9      Rules of Construction. Unless the context otherwise
requires, references to sections or subsections refer to sections or subsections
of this Agreement.

                  5.10     Entire Agreement. This Agreement, together with the
exhibits hereto, is intended by the parties as a final expression of their
agreement and intended to be a complete and exclusive statement of the agreement
and understanding of the parties hereto in respect of the subject matter
contained herein and therein. There are no restrictions, promises,
representations, warranties or undertakings, other than those set forth herein
or therein or set forth in the Stock Purchase Agreement or the Convertible Note
Purchase and Exchange Agreement. Subject to Section 5.11, upon the Subsequent
Closing (as defined in the Convertible Note Purchase and Exchange Agreement),
this Agreement, together with the exhibits hereto, shall supersede all prior
agreements and understandings among the parties with respect to such subject
matter.

                  5.11     Term of Agreement. Notwithstanding anything in this
Agreement to the contrary, this Agreement shall become effective immediately
following the Subsequent Closing. If the Subsequent Closing does not occur and
the obligation to consummate the Conversion and the Exchange (each as defined in
the Convertible Note Purchase and Exchange Agreement) is terminated pursuant to
Article IX of the Convertible Note Purchase and Exchange Agreement, this
Agreement shall immediately terminate and be of no further force or effect. If
the Subsequent Closing does occur, this Agreement shall terminate upon the
earlier of (a) with respect to a particular Stockholder, on the date that such
Stockholder and its Affiliates beneficially own less than 5% of the actual
outstanding shares of Common Stock (assuming conversion of the shares of Series
D Preferred Stock and Series E Preferred Stock) or (b) the twentieth anniversary
of the date hereof.

                  5.12     Further Assurances. Each of the parties shall, and
 shall cause their respective Affiliates to, execute such documents and perform
such further acts as may be reasonably required or desirable to carry out or to
perform the provisions of this Agreement.

              [the remainder of this page intentionally left blank]

<PAGE>

         IN WITNESS WHEREOF, the undersigned have executed, or have caused to be
executed, this Amended and Restated Stockholders Agreement on the date first
written above.

                                    CRITICAL PATH, INC.

                                    By: /s/ Michael J. Zukerman
                                        ___________________________
                                        Name: Michael J. Zukerman
                                        Title: Senior Vice President
                                               and General Counsel

          SIGNATURE PAGE TO AMENDED AND RESTATED STOCKHOLDERS AGREEMENT

<PAGE>

                                    GENERAL ATLANTIC PARTNERS 74, L.P.

                                    By: GENERAL ATLANTIC PARTNERS, LLC,
                                        its General Partner

                                    By: /s/ Matthew Nimetz
                                        ___________________________
                                        Name: Matthew Nimetz
                                        Title: A Managing Member

                                    GAP COINVESTMENT PARTNERS II, L.P.

                                    By: /s/ Matthew Nimetz
                                        ___________________________
                                        Name: Matthew Nimetz
                                        Title: A General Partner

                                    GAPSTAR, LLC

                                    By: GENERAL ATLANTIC PARTNERS, LLC,
                                        its Managing Member

                                    By: /s/ Matthew Nimetz
                                        ___________________________
                                        Name: Matthew Nimetz
                                        Title: A Managing Member

                                    GAP-W, LLC

                                    By: GENERAL ATLANTIC PARTNERS, LLC,
                                        its Manager

                                    By: /s/ Matthew Nimetz
                                        ___________________________
                                        Name: Matthew Nimetz
                                        Title: A Managing Member

                                    GAPCO GMBH & CO. KG

                                    By: GAPCO MANAGEMENT GMBH,
                                        its General Partner

                                    By: /s/ Matthew Nimetz
                                        ___________________________
                                        Name: Matthew Nimetz
                                        Title: A Managing Director

          SIGNATURE PAGE TO AMENDED AND RESTATED STOCKHOLDERS AGREEMENT

<PAGE>

                                    VECTIS CP HOLDINGS, LLC,
                                    a Delaware limited liability company

                                    By: VECTIS GROUP, LLC,
                                        its Managing Member

                                    By: /s/ Matthew T. Hobart
                                        ___________________________
                                        Name: Matthew T. Hobart
                                        Title: Managing Director

          SIGNATURE PAGE TO AMENDED AND RESTATED STOCKHOLDERS AGREEMENT

<PAGE>

                                    CENWELL LIMITED

                                    By: /s/ Ip Tak Chuen, Edmond
                                        ___________________________
                                        Name: Ip Tak Chuen, Edmond
                                        Title: Authorised Person

                                    CAMPINA ENTERPRISES LIMITED

                                    By: /s/ Ip Tak Chuen, Edmond
                                        ___________________________
                                        Name: Ip Tak Chuen, Edmond
                                        Title: Director

                                    GREAT AFFLUENT LIMITED

                                    By: /s/ Ip Tak Chuen, Edmond
                                        ___________________________
                                        Name: Ip Tak Chuen, Edmond
                                        Title: Director

                                    DRAGONFIELD LIMITED

                                    By: /s/ Pau Yee Wan, Ezra
                                        ___________________________
                                        Name: Pau Yee Wan, Ezra
                                        Title: Authorized Person

                                    LION COSMOS LIMITED

                                    By: /s/ Pau Yee Wan, Ezra
                                        ___________________________
                                        Name: Pau Yee Wan, Ezra
                                        Title: Director

          SIGNATURE PAGE TO AMENDED AND RESTATED STOCKHOLDERS AGREEMENT<PAGE>
                                                                    EXHIBIT 4.21

                                      NOTE

     THIS NOTE HAS BEEN ACQUIRED FOR INVESTMENT AND NOT WITH A VIEW TO, OR FOR
     SALE IN CONNECTION WITH, THE DISTRIBUTION THEREOF. THIS NOTE HAS NOT BEEN
     REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR ANY STATE
     SECURITIES LAWS, AND MAY NOT BE PLEDGED, SOLD, OFFERED FOR SALE,
     TRANSFERRED, OR OTHERWISE DISPOSED OF IN THE ABSENCE OF REGISTRATION UNDER
     OR EXEMPTION FROM SUCH ACT AND ALL APPLICABLE STATE SECURITIES LAWS.

                               CRITICAL PATH, INC.

                    CONVERTIBLE SUBORDINATED PROMISSORY NOTE

$8,277,526.00                                          San Francisco, California
                                                       November 26, 2003

          Critical Path, Inc., a California corporation (the "Company"), the
principal office of which is located in San Francisco, California, for value
received hereby promises to pay to the order of General Atlantic Partners 74,
L.P., or its registered assigns ("Holder"), the sum of eight million two hundred
seventy-seven thousand five hundred twenty-six and 0/100 dollars
($8,277,526.00), or such lesser amount as shall then equal the outstanding
principal amount hereof on the terms and conditions set forth hereinafter. The
outstanding principal amount hereof and all accrued and unpaid interest hereon,
as set forth below, shall be due and payable on the earlier to occur of (i)
November 26, 2007, (ii) when declared due and payable by Holder upon the
occurrence of an Event of Default (as defined below), (iii) consummation of a
Qualified Asset Sale, (iv) a Change of Control, or (v) any sale of capital stock
or Stock Equivalents by the Company, any cash capital contribution from any
third person or any other debt or equity financing consummated by the Company
after the date of issuance of this Note which, in the case of (v), individually
or in the aggregate raises proceeds of at least forty million dollars
($40,000,000) in cash or cash equivalents (the earliest of the events set forth
in items (i)-(v) immediately above, the "Maturity Date"); provided, however,
that in the event that the Maturity Date is on or before November 26, 2004, the
Company shall also make an additional payment to Holder equal to the amount of
interest which would have otherwise accrued on the outstanding principal amount
of the Note on the Maturity Date between the Maturity Date and November 26,
2004.

          The following is a statement of the rights of the Holder of this Note
and the conditions to which this Note is subject, and to which the Holder
hereof, by the acceptance of this Note, agrees:
<PAGE>
                                                                               2

          1. Definitions. Except as otherwise defined herein, each capitalized
term used herein shall have the meaning assigned to it in the Purchase
Agreement, as in effect on the date hereof, and without regard to any subsequent
termination of the Purchase Agreement. All other references to the Purchase
Agreement in this Note refer to the Purchase Agreement as in effect on the date
hereof, and without regard to any subsequent termination of the Purchase
Agreement. As used in this Note, the following terms, unless the context
otherwise requires, have the following meanings:

               1.1 "Affiliate" means any Person who is an "affiliate" as defined
in Rule 12b-2 of the General Rules and Regulations of the Securities Exchange
Act of 1934, as amended.

               1.2 "Capitalized Lease Obligations" means, with respect to any
Person, all rental obligations of such Person which, under GAAP, are or will be
required to be capitalized on the books of such Person, in each case taken at
the amount thereof accounted for as indebtedness in accordance with such
principles.

               1.3 "Change of Control" shall mean (i) any merger, consolidation
or other business combination transaction (or series of related transactions) in
which the stockholders owning a majority of the voting securities of the Company
prior to such transaction do not own a majority of the voting securities of the
surviving entity, (ii) any tender offer, exchange offer or other transaction
whereby any Person or "group" (as defined in Rule 13d-3 of the General Rules and
Regulations of the Securities Exchange Act of 1934, as amended) (other than
General Atlantic Partners 74, L.P., GAP Coinvestment Partners II, L.P., GapStar,
LLC, GAPCO GmbH & Co. KG, Campina Enterprises Limited, Cenwell Limited, Great
Affluent Limited, Dragonfield Limited and Lion Cosmos Limited and the Affiliates
of the foregoing, provided that Affiliates shall be deemed not to include any
portfolio companies of any of the foregoing) obtains a majority of the
outstanding shares of capital stock entitled to vote in the election of
directors, (iii) any proxy contest in which a majority of the Board of Directors
of the Company (or persons appointed by such Board of Directors) prior to such
contest do not constitute a majority of the Company's Board of Directors after
such contest or (iv) any other transaction described in any stockholder rights
agreement or "poison pill," if any, to which the Company is party, which may
permit the holders of any rights or similar certificates to exercise the rights
evidenced thereby.

               1.4 "Company" shall have the meaning set forth in the recitals
hereto, and includes any corporation that shall succeed to or assume the
obligations of the Company under this Note.

               1.5 "Conversion Date" shall mean the Subsequent Closing Date.

               1.6 "Designated Preferred Stock" shall mean the Series D
Preferred Stock, par value $0.001, of the Company and the Series E Preferred
Stock.
<PAGE>
                                                                               3

               1.7 "Domestic Subsidiary" shall have the meaning set forth in
Section 5.10 hereof.

               1.8 "Event of Default" shall have the meaning set forth in
Section 6 hereof.

               1.9 "Guaranteed Interest" shall mean the total amount of interest
that would accrue on this Note, at the Interest Rate specified in Section 2,
from the date of this Note until the one year anniversary of the date of this
Note.

               1.10 "Guarantor" shall have the meaning set forth in the Security
Agreement.

               1.11 "Holder" shall mean the registered holder of this Note from
time to time, and in the plural, shall mean all registered holders of Notes from
time to time issued by the Company pursuant to the Purchase Agreement.

               1.12 "Interest Amount" shall have the meaning set forth in
Section 3.1 hereof.

               1.13 "Investment" means (i) the acquisition (whether for cash,
property, services, assumption of Indebtedness, securities or otherwise) of
assets (other than equipment, inventory, supplies or other assets acquired in
the ordinary course of business of the Company), capital stock, bonds, notes,
debentures, partnership, joint venture or other ownership interests or other
securities of any Person, (ii) any deposit with, or advance, loan or other
extension of credit to, or on behalf of, any Person (other than deposits made in
connection with the purchase of equipment, inventory, services, leases, supplies
or other assets in the ordinary course of business of the Company), (iii) any
other capital contribution to or investment in such Person, including, without
limitation, any guaranty obligation incurred for the benefit of such Person. For
the sake of clarity, Investments shall include any transfer of property or
assets by the Company to any of its Subsidiaries or by any Subsidiary of the
Company to any other Subsidiary.

               1.14 "Loan Documents" shall have the meaning set forth in the
Security Agreement.

               1.15 "Note" shall mean this note, and in the plural, shall mean
all notes issued to the Lenders pursuant to the terms of the Purchase Agreement,
including this Note, and all amendments, modifications and extensions thereto.

               1.16 "Permitted Investments" means (i) Investments in cash or
cash equivalents, (ii) accounts receivable created, acquired or made in the
ordinary course of business and payable or dischargeable in accordance with
customary trade terms; (iii) Investments existing on the closing date, and
listed on Schedule 3.27 to the Purchase Agreement, (iv) guaranty obligations
permitted by Section 5.3 of this Agreement, (v) loans to employees, directors or
officers of the Company in connection with the award of convertible bonds or
capital stock under a stock incentive plan, stock option plan or other
equity-based compensation plan or arrangement, (vi) other advances or loans to
<PAGE>
                                                                               4

employees, directors, officers or agents of the Company in the ordinary course
of business not to exceed $500,000 in the aggregate at any time outstanding;
(vii) loans, advances and investments in foreign Subsidiaries (that are not
incorporated or otherwise organized under the laws of the United States of
America or any state thereof) in an amount not to exceed $1,000,000 in the
aggregate at any time outstanding; (viii) any acquisition for which the prior
written consent of the Holders of a majority of the outstanding principal amount
of all of the Notes issued by the Company pursuant to the Purchase Agreement has
been obtained, (ix) other loans, advances and investments of a nature not
contemplated by the foregoing sections in an amount not to exceed $500,000 in
the aggregate at any time outstanding or (x) Investments by the Company in the
Guarantor.

               1.17 "Permitted Liens" shall have the meaning set forth in
Section 5.4.

               1.18 "Person" means any individual, firm, corporation,
partnership, trust, joint venture, joint stock company, limited liability
company, Governmental Authority or other entity of any kind, and shall include
any successor (by merger or otherwise) of such entity.

               1.19 "Price Per Share" shall have the meaning attributed to such
term in the Series E Certificate of Determination, as filed with the Secretary
of State of the State of California.

               1.20 "Purchase Agreement" means that certain Convertible Note
Purchase and Exchange Agreement, dated November 18, 2003, among the Company, the
Holder and the other parties thereto from time to time, and all amendments,
modifications and extensions thereto.

               1.21 "Qualified Asset Sale" means the sale, transfer or other
disposition of any of the assets of the Company or any of its Subsidiaries,
other than (a) sales of assets in the ordinary course of business, (b) sales of
assets where the proceeds are used to repay Indebtedness owing to SVB, (c) the
sale, transfer or other disposition of assets of the Company where the proceeds
are applied to the purchase price or traded in for credit against the purchase
price of other assets, provided that any such purchase is made, or credit
issued, within 90 days of the sale, transfer or other disposition, and (d) one
or more sales of the Company's assets (other than sales otherwise included in
clauses (a), (b), and (c) immediately above) which collectively yield up to an
aggregate of one million dollars ($1,000,000) in gross proceeds to the Company
while this Note is outstanding.

               1.22 "Restricted Payment" means (a) any dividend or other
distribution (whether in cash, securities or other property) with respect to any
shares of any class of capital stock of the Company or any of its Subsidiaries
or (b) any payment (whether in cash, securities or other property), including
any sinking fund or similar deposit, on account of the purchase, redemption,
retirement, acquisition, cancellation or termination of any shares of any class
of capital stock of the Company or any Subsidiary
<PAGE>
                                                                               5

or any option, warrant or other right to acquire any such shares of capital
stock of the Company or any Subsidiary.

               1.23 "Security Agreement" means that certain Guaranty and
Security Agreement, of even date herewith between the Company, Compass Holding
Corp., the Lenders and the other parties thereto from time to time, and all
amendments, modifications and extensions thereto.

               1.24 "Series E Conversion Price" shall have the meaning set forth
in the Series E Certificate of Determination.

               1.25 "Series E Preferred Stock" means the Series E Preferred
Stock, par value $0.001, of the Company.

               1.26 "Subordination Agreement" shall have the meaning set forth
in Section 5.3.

               1.27 "SVB" means Silicon Valley Bank, a California chartered
bank, or any Affiliates thereof.

               1.28 "UCC" shall have the meaning set forth in Section 5.4.

          2. Interest. Simple interest shall accrue at the rate of ten percent
(10%) per annum (or such lesser amount as shall equal the highest rate of
interest allowable under applicable law) (the "Interest Rate"), on the
outstanding principal of this Note from the date of this Note until the Maturity
Date or the date this Note is otherwise repaid. The Company shall not be
obligated to make any payments of interest which shall have accrued under this
Note prior to the Maturity Date. Interest shall be calculated on the basis of a
360-day year for the actual number of days elapsed. In the event that the
principal amount of this Note, any interest, or any amount payable hereunder is
not paid in full when such amount becomes due and payable, or upon the
occurrence of an Event of Default, interest shall accrue at the lesser of (a)
the initial Interest Rate plus five percent (5%) per annum or (b) the highest
rate of interest allowable under applicable law, on the balance of all amounts
outstanding until such overdue amounts are paid or the Event of Default is
cured, and such interest shall be payable on demand.

          3. Conversion.

               3.1 Conversion. On the Conversion Date, the principal amount of
this Note plus the greater of (i) the accrued and unpaid interest thereon and
(ii) the Guaranteed Interest (the greater of clause (i) and (ii), the "Interest
Amount"), shall be automatically converted into the number of fully paid and
nonassessable shares of Series E Preferred Stock equal to the quotient obtained
by dividing (a) the entire principal amount of this Note plus the Interest
Amount by (b) the Price Per Share.

               3.2 Notice of Conversion. Upon conversion of this Note as
provided in Section 3.1, Holder shall surrender this Note to the Company and
shall state the name or names in which the certificate or certificates for such
shares of Series E
<PAGE>
                                                                               6

Preferred Stock are to be issued. The Person or Persons entitled to receive the
shares of Series E Preferred Stock issuable upon such conversion shall be
treated for all purposes as the record holder or holders of such shares of
Series E Preferred Stock as of the Conversion Date.

               3.3 Delivery of Stock Certificates. On the Conversion Date, the
Company at its expense will issue and deliver to Holder of this Note a
certificate or certificates (bearing such legends as are required by applicable
state and federal securities laws in the opinion of counsel to the Company) for
the number of full shares of Series E Preferred Stock issuable upon such
conversion.

               3.4 Mechanics and Effect of Conversion. No fractional shares of
Series E Preferred Stock shall be issued upon conversion of this Note. In lieu
of the Company issuing any fractional shares to Holder upon the conversion of
this Note, the Company shall pay to Holder the amount of outstanding principal
and interest that is not so converted. Upon conversion of all amounts due under
this Note, the Company shall be released from all of its obligations under this
Note.

          4. Adjustments. The number of shares of Series E Preferred Stock
convertible hereunder are subject to adjustment from time to time as follows:

               4.1 Merger, Sale of Assets, Etc. Subject to Section 4.2, if at
any time while this Note remains outstanding and unexpired there shall be (a) a
reorganization (other than a combination, reclassification, exchange or
subdivision of shares otherwise provided for herein), (b) a merger or
consolidation of the Company with or into another corporation in which the
Company is not the surviving entity, or a merger in which the Company is the
surviving entity but the shares of the Company's capital stock outstanding
immediately prior to the merger are converted by virtue of the merger into other
property, whether in the form of securities, cash or otherwise or (c) a sale or
transfer of the Company's stock, properties or assets as, or substantially as,
an entirety to any other Person, then, as a part of such reorganization, merger,
consolidation, sale or transfer, lawful provision shall be made so that Holder
shall thereafter be entitled to receive by converting this Note the number of
shares of stock or other securities or property of the successor corporation
resulting from such reorganization, merger, consolidation, sale or transfer that
a holder of the shares deliverable upon conversion of this Note would have been
entitled to receive in such reorganization, consolidation, merger, sale or
transfer if this Note had been converted immediately before such reorganization,
merger, consolidation, sale or transfer (notwithstanding that the Stockholder
Approval may not yet have been obtained), all subject to further adjustment as
provided in this Section 4. The foregoing provisions of this Section 4.1 shall
similarly apply to successive reorganizations, consolidations, mergers, sales
and transfers and to the stock or securities of any other corporation. If the
per share consideration payable to Holder hereof for shares in connection with
any such transaction is in a form other than cash or marketable securities, then
the value of such consideration shall be determined in good faith by the
Company's Board of Directors based on the amount the Holder would have otherwise
been entitled to receive had the transaction or transactions not occurred. In
all events, appropriate adjustment (as determined in good faith by the Company's
<PAGE>
                                                                               7

Board of Directors) shall be made in the application of the provisions of this
Note with respect to the rights and interests of Holder after the transaction,
to the end that the provisions of this Note shall be applicable after that
event, as near as reasonably may be, in relation to any shares or other property
deliverable after that event upon conversion of this Note. The Company shall be
obligated to retain and set aside, or otherwise make fair provision for exercise
of the right of the Holder to receive, the shares of stock and/or other
securities, cash or other property provided for in this Section 4.1.

               4.2 Election of Holder upon Merger or Sale of Assets.
Notwithstanding anything to the contrary contained herein, if an event shall
occur as provided in Section 4.1 hereof that would otherwise result in the
occurrence of the Maturity Date pursuant to clause (iii) or (iv) of the first
paragraph of this Note, then the Holder may, in its sole discretion, by written
notice to the Company elect to convert the principal amount of this Note plus
the Interest Amount into the number of shares of stock or other securities or
property described in Section 4.1, in lieu of receiving payment in full of all
amounts outstanding under this Note. The number of shares of stock or other
securities or property to be issued upon such conversion shall be determined in
accordance with Section 4.1 hereof, taking into account the occurrence of such
event.

               4.3 Reclassification, Etc. If the Company shall, at any time
while this Note, or any portion thereof, remains outstanding and unexpired, by
reclassification of securities or otherwise, change any of the securities as to
which conversion rights under this Note exist into the same or a different
number of securities of any other class or classes, this Note shall thereafter
represent the right to acquire such number and kind of securities as would have
been issuable with respect to the securities that were subject to the conversion
rights under this Note immediately prior to such reclassification or other
change, and the Price Per Share shall be appropriately adjusted, all subject to
further adjustment as provided in this Section 4.

               4.4 Split, Subdivision or Combination of Shares. If the Company
at any time while this Note, or any portion thereof, remains outstanding and
unexpired shall split, subdivide or combine the shares of Series E Preferred
Stock into a different number of securities of the same class, the Price Per
Share shall be proportionately adjusted.

               4.5 Series E Adjustments. The initial Series E Conversion Price
of the shares of Series E Preferred Stock issued upon conversion of this Note
pursuant to Section 3.1 shall equal the Series E Conversion Price in effect on
the Conversion Date, subject to the adjustment of such Series E Conversion Price
from time to time thereafter as provided in the Series E Certificate of
Determination.

               4.6 Certificate as to Adjustments. Upon the occurrence of each
adjustment or readjustment pursuant to this Section 4, the Company at its
expense shall promptly compute such adjustment or readjustment in accordance
with the terms hereof and furnish to Holder a certificate setting forth such
adjustment or readjustment and showing in detail the facts upon which such
adjustment or readjustment is based.
<PAGE>
                                                                               8

               4.7 No Impairment. The Company will not, by any voluntary action,
avoid or seek to avoid the observance or performance of any of the terms to be
observed or performed hereunder by the Company, but will at all times in good
faith assist in the carrying out of all the provisions of this Section 4 and in
the taking of all such action as may be necessary or appropriate in order to
protect the rights of Holder against impairment.

          5. Covenants. The Company covenants and agrees that until the earlier
of (i) the date on which all Obligations (as defined in the Security Agreement)
have been paid in full or (ii) the Conversion Date:

               5.1 Financial Statements and Other Information. The Company shall
deliver to the Holder of this Note the financial statements and other
information required to be delivered under Section 8.1 of the Purchase
Agreement.

               5.2 Financial Covenants. The Company shall at all times comply
with the financial and other covenants set forth in Schedule 8.5 to the Purchase
Agreement as if such covenants were set forth herein.

               5.3 Indebtedness. The Company shall not, and shall not permit any
Subsidiary to, issue, incur, assume, create or have outstanding any
Indebtedness, provided, however, that the foregoing shall not restrict nor
operate to prevent:

                    (a) Indebtedness in favor of the Holders under the Loan
Documents;

                    (b) Indebtedness existing on the date hereof, and as set
forth on Schedule 3.22 to the Purchase Agreement;

                    (c) Indebtedness for accounts payable incurred in the
ordinary course of business by the Company;

                    (d) Indebtedness incurred solely for the purpose of
financing the acquisition of any equipment, machinery, software, improvements or
any other similar property, or extensions, renewals or replacements of any of
the foregoing for the same or a lesser amount; provided, that the aggregate
outstanding principal amount of all Indebtedness permitted pursuant to this
clause (d) outstanding for more than sixty (60) days after the incurrence of
such Indebtedness shall not at any time exceed $500,000;

                    (e) Indebtedness of the Company evidenced by Capitalized
Lease Obligations, provided, that in no event shall the aggregate principal
amount of Capitalized Lease Obligations permitted by this clause (e) exceed
$500,000 at any time outstanding; and

                    (f) Any extension renewal, refinancing, refunding, or
replacement (each, a "refinancing") of Indebtedness permitted by clauses (b) and
(e)
<PAGE>
                                                                               9

above, on such terms and conditions as are, on the whole, not materially
more onerous to the Company than the terms and conditions of such original
Indebtedness on the date of such refinancing (including that the principal
amount of such refinancing Indebtedness does not exceed the principal amount of,
plus the amount of accrued and unpaid interest on, the Indebtedness so
refinanced (plus the amount of reasonable premium and fees and expenses incurred
in connection therewith)), provided that, in the case of a refinancing of
Indebtedness owed by the Company or any Subsidiary to SVB, this clause (f) shall
only apply to the extent consistent with the Subordination Agreement, dated as
of the date hereof, by and among SVB, the Holders and the Company (the
"Subordination Agreement").

               5.4 Liens. The Company shall not, and shall not permit any of its
Subsidiaries to, create, incur, assume or suffer to exist any Lien upon or with
respect to any property or assets (real or personal, tangible or intangible) of
the Company or any of its Subsidiaries, whether now owned or hereafter acquired,
or sell any such property or assets subject to an understanding or agreement,
contingent or otherwise, to repurchase such property or assets (including sales
of accounts receivable), or assign any right to receive income or permit the
filing of any financing statement under the Uniform Commercial Code, as from
time to time in effect in the relevant jurisdiction (the "UCC"), or any other
similar notice of Lien under any similar recording or notice statute; provided,
that the provisions of this Section 5.4 shall not prevent the creation,
incurrence, assumption or existence of the following:

                    (a) Liens arising in the ordinary course of business by
statute in connection with worker's compensation, unemployment insurance, old
age benefits, social security obligations, statutory obligations or other
similar charges (other then Liens arising under ERISA), good faith cash deposits
in connection with tenders, contracts or leases to which the Company or any
Subsidiary is a party or other cash deposits required to be made in the ordinary
course of business, provided, that such Liens do not have a material adverse
effect on the ability of the Company to repay amounts due under the Notes;

                    (b) inchoate Liens for taxes, assessments or governmental
charges or levies not yet due or Liens for taxes, assessments or governmental
charges or levies being contested in good faith and by appropriate proceedings
for which adequate reserves have been established in accordance with GAAP;

                    (c) Liens in respect of property or assets of the Company or
its Subsidiaries imposed by law, which were incurred in the ordinary course of
business and do not secure Indebtedness for borrowed money, such as carriers',
warehousemen's, materialmen's and mechanics' liens and other similar Liens
arising in the ordinary course of business, and (i) which do not in the
aggregate materially detract from the value of the Company's and its
Subsidiaries' property or assets taken as a whole or result in a material
adverse effect on the Condition of the Company or (ii) which are being contested
in good faith by appropriate proceedings, which proceedings have the effect of
preventing the forfeiture or sale of the property or assets subject to any such
Lien;
<PAGE>
                                                                              10

                    (d) the pledge of assets for the purpose of securing an
appeal, stay or discharge in the course of any legal proceeding, provided that
the aggregate amount of liabilities of the Company and its Subsidiaries secured
by a pledge of assets permitted under this subsection, including interest and
penalties thereon, if any, shall not be in excess of $500,000 at any one time
outstanding;

                    (e) any interest or title of a lesser under any operating
lease;

                    (f) easements, rights-of-way, restrictions and other similar
encumbrances against real property incurred in the ordinary course of business;

                    (g) the Liens existing on the date hereof identified on
Schedule 3.22 to the Purchase Agreement;

                    (h) Liens on cash deposited with account debtors to secure
performance by the Company or any Subsidiary in the ordinary course of business
subject to customary and reasonable terms;

                    (i) Liens upon assets of the Company or its Subsidiaries
subject to Capitalized Lease Obligations, provided, that (A) such Liens only
serve to secure the payment of Indebtedness permitted by Section 5.3(e) arising
under such Capitalized Lease Obligation and (B) the Lien encumbering the asset
giving rise to the Capitalized Lease Obligation does not encumber any other
asset of the Company or its Subsidiaries;

                    (j) Liens placed upon equipment, machinery, software,
improvements or any other similar property, used in the ordinary course of
business of the Company or any of its Subsidiaries at the time of the
acquisition thereof by the Company or any of its Subsidiaries or within ninety
(90) days thereafter to secure Indebtedness permitted by Section 5.3(d) above;
provided, that the Liens encumbering the equipment, machinery software,
improvements or any other similar property so acquired do not encumber any other
asset of the Company or its Subsidiaries;

                    (k) set-off rights of depository institutions; and

                    (l) Liens created by the Security Agreement (collectively
with clauses (a) through (k) hereof, the "Permitted Liens").

               5.5 Fundamental Changes. The Company will not, and will not
permit any Subsidiary to, merge into or consolidate with any other Person, or
permit any other Person to merge into or consolidate with it, or sell, transfer,
lease or otherwise dispose of (in one transaction or a series of transactions)
all or substantially all of its assets, or all or substantially all of the stock
of any of its Subsidiaries (in each case, whether now owned or hereafter
acquired), or liquidate or dissolve, except that, if at the time and immediately
after giving effect thereto no Event of Default shall have occurred and be
continuing (i) the Company or any of its Subsidiaries may, with the prior
written consent of the Holders, merge with or into any other Person; (ii) any
wholly-owned
<PAGE>
                                                                              11

Subsidiary of the Company (other than the Guarantor) may merge with or into the
Company or any other wholly-owned Subsidiary of the Company; (iii) any
Subsidiary (other than the Guarantor, and except as otherwise prohibited by this
Note) may sell, transfer, lease or otherwise dispose of its assets to the
Company or to another wholly-owned Subsidiary of the Company; and (iv) any
Subsidiary may liquidate or dissolve if the board of directors of the Company
determine in good faith that such liquidation or dissolution is in its best
interests and is not disadvantageous to the Holders.

               5.6 Restricted Payments. The Company will not, and the Company
will not permit any Subsidiary to, declare or make, or agree to pay or make,
directly or indirectly, any Restricted Payment, except that (i) any Subsidiary
may make a Restricted Payment to the Company or any of its wholly-owned
Subsidiaries, and (ii) the Company or any of its Subsidiaries may make any
Restricted Payment required by the terms of the Purchase Agreement and the other
documents executed in connection therewith.

               5.7 Transactions with Affiliates. The Company will not, and the
Company will not permit any Subsidiary to, sell, lease or otherwise transfer any
property or assets to, or purchase lease or otherwise acquire any property or
assets from, or otherwise engage in any other transactions with, any of its
Affiliates, except (a) transactions that are at prices and on terms and
conditions not less favorable to the Company or such Subsidiary than could be
obtained on an arm's length basis from unrelated third parties, (b) transactions
exclusively between the Company and the Guarantor and (c) transactions under the
agreements listed on Schedule 3.17 to the Purchase Agreement.

               5.8 Investments. The Company will not, and the Company will not
permit any Domestic Subsidiary (as hereinafter defined) to, make an Investment
in any Person, except for Permitted Investments.

               5.9 Nature of Business. The Company will not, and the Company
will not permit any Subsidiary to, engage in any business other than that
conducted on the date hereof and any businesses reasonably related thereto.

               5.10 Property of Existing Domestic Subsidiaries. The Company will
not permit, or suffer to allow, any Subsidiary that is incorporated or otherwise
organized under the laws of the United States of America or any state thereof (a
"Domestic Subsidiary"), excluding the Guarantor, to (i) own, hold, lease,
license, purchase or otherwise acquire any personal or real property (excluding
any material intellectual property) in excess of $50,000 for all property held
by such Subsidiary, or $250,000 in the aggregate for all property held by all
Domestic Subsidiaries (ii) maintain any deposit account in its name, (iii) own
or otherwise hold any rights to any material intellectual property or (iv)
otherwise conduct any business or maintain operations.

               5.11 Formation of Subsidiaries. The Company will not, and will
not cause or permit any of its Subsidiaries to, form, acquire or permit the
existence of any new domestic Subsidiary, without causing such domestic
Subsidiary to execute and
<PAGE>
                                                                              12

deliver to the Holders a secured guaranty of the Notes and related security
document, in form and substance satisfactory to the Holders.

               5.12 Books and Records. The Company shall keep proper books of
record and account, in which full and correct entries shall be made of all
financial transactions and the assets and business of the Company and its
Subsidiaries in accordance with GAAP consistently applied.

               5.13 Inspection. The Company shall, and shall cause each of its
Subsidiaries to, permit representatives of the Holders to visit and inspect any
of its properties, to examine its corporate, financial and operating records and
make copies thereof or abstracts therefrom, and to discuss its affairs, finances
and accounts with their respective directors, officers and independent public
accountants, all at such reasonable times during normal business hours and as
often as may be reasonably requested upon notice to the Company.

               5.14 Maintenance of Business. The Company shall, and shall cause
each Subsidiary to, preserve and maintain its existence. The Company shall, and
shall cause each Subsidiary to, preserve and keep in force and effect all
licenses, permits, franchises, approvals, patents, trademarks, trade names,
trade styles, copyrights, and other property rights necessary to the proper
conduct of its business, except where the failure to do so could not reasonably
be expected to have a material adverse effect on the Condition of the Company or
on the prospects of repayment of the Notes.

               5.15 Maintenance of Properties. The Company shall, and shall
cause each Subsidiary to, maintain, preserve and keep its property and equipment
in good repair, working order and condition (ordinary wear and tear excepted)
and shall from time to time make all needful and proper repairs, renewals,
replacements, additions and betterments thereto so that at all times the
efficiency thereof shall by fully preserved and maintained, except in each case
to the extent that, in the reasonable business judgment of such Person, any such
property or equipment is no longer necessary for the proper conduct of the
business of such Person.

          6. The occurrence of any one or more of the following events shall
constitute an "Event of Default":

               6.1 Failure To Pay. (i) The failure of the Company to pay any
principal due under any of the Notes when due and payable (whether by
acceleration, declaration, extension or otherwise), or (ii) the failure of the
Company to pay any other amounts due under any of the Notes when due and payable
if such failure is not cured within five (5) days of Company's receipt of notice
thereof from any of the Holders.

               6.2 Financial Covenants. The failure of Company or any of its
Subsidiaries to perform, observe or comply with any of the Financial Covenants
set forth on Schedule 8.5 to the Purchase Agreement, and incorporated by
reference in this Note in Section 5.2.
<PAGE>
                                                                              13

               6.3 Other Covenants and Agreements. The failure of Company or any
of its Subsidiaries to perform, observe or comply with any of the covenants of
this Note, the Security Agreement or any of the other Loan Documents (other than
the Financial Covenants set forth on Schedule 8.5 to the Purchase Agreement, and
incorporated by reference in this Note in Section 5.2), if such failure is not
cured within sixty (60) days.

               6.4 Representations and Warranties. If any representation or
warranty made by the Company or any of its Subsidiaries in the Loan Documents is
not true and correct in all material respects on the Initial Closing Date.

               6.5 Default on Other Obligations. The occurrence of any condition
or default under any other indebtedness for borrowed money of the Company or any
of its Subsidiaries with a principal amount of at least five hundred thousand
dollars ($500,000) that results in the acceleration of such indebtedness which
is not cured within sixty (60) days.

               6.6 Involuntary Bankruptcy. There shall be filed against the
Company or any of its Subsidiaries an involuntary petition or other pleading
seeking the entry of a decree or order for relief under the United States
Bankruptcy Code or any similar federal or state insolvency or similar laws
ordering: (a) the liquidation of the Company or any of its Subsidiaries or (b) a
reorganization of the Company or any of its Subsidiaries or the business and
affairs of the Company or any of its Subsidiaries or (c) the appointment of a
receiver, liquidator, assignee, custodian, trustee or similar official for the
Company or any of its Subsidiaries of the property of the Company or any of its
Subsidiaries.

               6.7 Voluntary Bankruptcy. The commencement by the Company or any
of its Subsidiaries of a voluntary case under the federal bankruptcy laws or any
federal or state insolvency or similar laws or the consent by the Company or any
of its Subsidiaries to the appointment of or taking possession by a receiver,
liquidator, assignee, trustee, custodian or similar official for the Company or
any of its Subsidiaries of any of the property of the Company or any of its
Subsidiaries or the making by the Company or any of its Subsidiaries of an
assignment for the benefit of creditors, or the failure by Company or any of its
Subsidiaries generally to pay its debts as the debts become due.

               6.8 Judgments, Awards. Any judgment or order for the payment of
money is rendered against the Company or any of its Subsidiaries in an amount in
excess of five hundred thousand dollars ($500,000) individually or in the
aggregate and either (i) enforcement proceedings are commenced by any creditor
upon such judgment or order and not stayed, or (ii) there is any period of sixty
(60) consecutive days during which such judgment has not been paid in full or a
stay of enforcement of such judgment or order, by reason of a pending appeal or
otherwise, is not in effect.

               6.9 Attachment by Lenders. Any assets of the Company or any of
its Subsidiaries shall be attached, levied upon, seized or repossessed, or come
into the
<PAGE>
                                                                              14

possession of a trustee, receiver or other custodian and a determination by any
Holder, in good faith but in its sole discretion, that the same could have a
material adverse effect on the prospect for the Holders to fully and punctually
realize the full benefits conferred on the Holders by the Loan Documents.

               6.10 Adverse Change in Financial Condition. Any event having a
material adverse effect on the business, operations, assets, properties or
condition of the Company and its Subsidiaries taken as a whole shall have
occurred and be continuing or a material adverse effect on the validity or
enforceability of this or any of the other Loan Documents or the rights or
remedies of the Holders hereunder or thereunder.

          7. Remedies. Upon and after the occurrence of an Event of Default, the
Holder shall be entitled to the exercise the rights and remedies set forth in
the Security Agreement, the other Loan Documents and under applicable law, all
such rights and remedies being cumulative and enforceable alternatively,
successively or concurrently.

          8. Prepayment. The Company may not prepay this Note prior to the
Maturity Date without the prior written consent of the Holders.

          9. Seniority. Except as set forth in the Subordination Agreement, the
Notes will rank senior in right of payment to all other indebtedness of the
Company.

          10. Assignment. Subject to the restrictions on transfer described in
Section 12 below, the rights and obligations of the Company and Holder shall be
binding upon and benefit the successors, assigns, heirs, administrators and
transferees of the parties. The Company shall not be permitted to assign this
Note without the prior written consent of the Holders.

          11. Waiver of Notice. The Company hereby waives notice, presentment,
demand, protest and notice of dishonor.

          12. Transfer of This Note. With respect to any offer, sale or other
disposition of this Note, Holder will give written notice to the Company prior
thereto, describing briefly the manner thereof, together with a written opinion
of such Holder's counsel, to the effect that such offer, sale or other
distribution may be effected without registration or qualification (under any
federal or state law then in effect); provided, that no opinion shall be
required for any transfer to an Affiliate or if the transfer is made in
compliance with the Securities Act, so long as the transferee can make the same
representations and warranties at the time of transfer as set forth in Sections
4.5, 4.6, 4.7, 4.8, 4.9, 4.10 and 4.11 of the Purchase Agreement. Promptly upon
delivering such written notice and opinion, if so required, Holder may sell or
otherwise dispose of this Note, all in accordance with the terms of the notice
delivered to the Company. Each Note thus transferred shall bear a legend as to
the applicable restrictions on transferability in order to ensure compliance
with the Securities Act, unless in the opinion of counsel for the Company such
legend is not required in order to ensure compliance with the Securities Act.
The Company may issue stop transfer instructions to its transfer agent in
<PAGE>
                                                                              15

connection with such restrictions. Notwithstanding the foregoing, the Holder
shall not be permitted to transfer this Note to any Person who is not an
Affiliate until the earlier of (i) the obtaining of Stockholder Approval, (ii)
the receipt of written notice from the Company that Stockholder Approval cannot
be obtained, or the occurrence of an actual vote of the Company's shareholders
entitled to vote (whether by written consent or at a meeting specially called
for such purpose), the result of which is a decision by a majority of the
Company's shareholders entitled to vote to decline to grant Stockholder
Approval, (iii) six (6) months from the date hereof and (iv) the occurrence of
an Event of Default.

          13. Treatment of Note. To the extent permitted by generally accepted
accounting principles, the Company will treat, account and report the Note as
debt and not equity for accounting purposes and with respect to any returns
filed with federal, state or local tax authorities.

          14. Notices. Any notice, request or other communication required or
permitted hereunder shall be in writing and shall be deemed to have been duly
given if personally delivered or if sent by nationally recognized courier
service or mailed by registered or certified mail, postage prepaid, to the
respective addresses of the parties as set forth on the signature pages hereto
or if sent by facsimile to the respective facsimile numbers of the parties set
forth on the signature pages hereto. Any party hereto may by notice so given
change its address for future notice hereunder. Notice shall conclusively be
deemed to have been given and received when personally delivered or three (3)
business days after deposited in the mail or one business day after sent by
courier or upon confirmation of facsimile delivery in the manner set forth
above.

          15. No Stockholder Rights. Nothing contained in this Note shall be
construed as conferring upon Holder or any other Person the right to vote or to
consent or to receive notice as a stockholder in respect of meetings of
stockholders for the election of directors of the Company or any other matters
or any rights whatsoever as a stockholder of the Company.

          16. Governing Law. This Note shall be governed by and construed in
accordance with the laws of the State of California, excluding that body of law
relating to conflict of laws.

          17. Amendments and Waivers. No amendments or waivers of any provision
of this Note, and no consent by the Holder to any departure by the Company,
shall in any event be effective unless the same shall be in writing, and signed
by the Holders of a majority of the outstanding principal amount of all of the
Notes issued by the Company pursuant to the Purchase Agreement, and then such
waiver or consent shall be effective only in the specific instance and for the
purpose for which given.

          18. Severability. Any provision of this Note that is prohibited or
unenforceable in a jurisdiction shall, as to such jurisdiction, be ineffective
to the extent of such prohibition or unenforceability without invalidating the
remaining provisions hereof, and any such prohibition or unenforceability in any
jurisdiction shall not invalidate or render unenforceable such provision in any
other jurisdiction.
<PAGE>
                                                                              16

          19. WAIVER OF JURY TRIAL. THE COMPANY AND THE HOLDER HEREBY (A)
COVENANTS AND AGREES NOT TO ELECT A TRIAL BY JURY OF ANY ISSUE TRIABLE OF RIGHT
BY A JURY, AND (B) WAIVES TRIAL BY JURY IN ANY ACTION OR PROCEEDING TO WHICH THE
COMPANY AND THE HOLDER MAY BE PARTIES, ARISING OUT OF, IN CONNECTION WITH OR IN
ANY WAY PERTAINING TO THIS NOTE, ANY OF THE LOAN DOCUMENTS AND/OR ANY
TRANSACTIONS, OCCURRENCES, COMMUNICATIONS, OR UNDERSTANDINGS (OR THE LACK OF ANY
OF THE FOREGOING) RELATING IN ANY WAY TO DEBTOR-CREDITOR RELATIONSHIP BETWEEN
THE PARTIES. IT IS UNDERSTOOD AND AGREED THAT THIS WAIVER CONSTITUTES A WAIVER
OF TRIAL BY JURY OF ALL CLAIMS AGAINST ALL PARTIES TO SUCH ACTIONS OR
PROCEEDINGS, INCLUDING CLAIMS AGAINST PARTIES WHO ARE NOT PARTIES TO THIS NOTE.
THIS WAIVER OF JURY TRIAL IS SEPARATELY GIVEN, KNOWINGLY, WILLINGLY AND
VOLUNTARILY MADE BY THE COMPANY AND THE HOLDER, AND THE COMPANY AND THE HOLDER
HEREBY AGREE THAT NO REPRESENTATIONS OF FACT OR OPINION HAVE BEEN MADE BY ANY
INDIVIDUAL TO INDUCE THIS WAIVER OF TRIAL BY JURY OR TO IN ANY WAY MODIFY OR
NULLIFY ITS EFFECT. THE COMPANY AND THE HOLDER ARE HEREBY AUTHORIZED TO SUBMIT
THIS NOTE TO ANY COURT HAVING JURISDICTION OVER THE SUBJECT MATTER AND THE
COMPANY AND THE HOLDER, SO AS TO SERVE AS CONCLUSIVE EVIDENCE OF SUCH WAIVER OF
RIGHT TO TRIAL BY JURY. EACH OF THE COMPANY AND THE HOLDER REPRESENTS AND
WARRANTS THAT IT HAS BEEN REPRESENTED IN THE SIGNING OF THIS NOTE AND IN THE
MAKING OF THIS WAIVER BY INDEPENDENT LEGAL COUNSEL, SELECTED OF ITS OWN FREE
WILL, AND/OR THAT IT HAS HAD THE OPPORTUNITY TO DISCUSS THIS WAIVER WITH
COUNSEL.

          20. Heading; References. All headings used herein are used for
convenience only and shall not be used to construe or interpret this Note.
Except as otherwise indicated, all references herein to Sections refer to
Sections hereof.

              [the remainder of this page intentionally left blank]
<PAGE>
                                                                              17

          IN WITNESS WHEREOF, the Company has caused this Note to be issued this
26th day of November, 2003.

                                         COMPANY:

                                         CRITICAL PATH, INC.,
                                         a California corporation

                                         By: /s/ Michael J. Zukerman
                                             -----------------------------------
                                             Name: Michael J. Zukerman.
                                             Title: Senior Vice President and
                                             General Counsel

                                             Critical Path, Inc.
                                             350 The Embarcadero
                                             San Francisco, CA 94105-1204
                                             Telecopy: (415) 541-2300
                                             Attention: Chief Financial Officer

                                             With a copy to:

                                             Pillsbury Winthrop LLP
                                             50 Fremont Street
                                             San Francisco, CA 94105
                                             Telecopy: (415) 983-1200
                                             Attention: Gregg Vignos, Esq.

Name of Holder: General Atlantic Partners 74, L.P.

Address:        c/o General Atlantic Service Corporation
                3 Pickwick Plaza
                Greenwich, CT 06830
                Telecopy: (203) 618-9207
                Attention: Matthew Nimetz
                           Thomas J. Murphy

With a copy to:

                Paul, Weiss, Rifkind, Wharton & Garrison LLP
                1285 Avenue of the Americas
                New York, NY 10019-6064
                Attention: Douglas A. Cifu, Esq.
                Telecopy: (212) 757-3990

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