Document:

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                                                                     EXHIBIT 4.1

                                  FORM OF 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

$                                                     San Francisco, California
 ---------------------                                March 9, 2004

               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 _____________________________,
or its registered assigns ("Holder"), the sum of _______________________________
dollars ($_________), 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)
March 9, 2008, (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").

               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:

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

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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, GAP-W, 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 "Common Conversion Date" shall have the meaning set
forth in Section 3.1(b) hereof.

                      1.6 "Common Stock" means the common stock, par value
$0.001 per share, of the Company.

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

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

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

                      1.10 "GA Notes" shall mean the Convertible Subordinated
Promissory Notes, each dated November 26, 2003, issued by the Company to the GAP
Entities pursuant to the Purchase and Exchange Agreement.

                      1.11 "GAP Entities" shall mean General Atlantic Partners
74, L.P., GAP Coinvestment Partners II, L.P., GapStar, LLC and GAPCO GmhH & Co.
KG.

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

                      1.13 "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 Note Purchase
Agreement.

                      1.14 "Intercreditor Agreement" shall mean the
Intercreditor Agreement, dated the date hereof, among the GAP Entities, the
January Lenders, Guggenheim Portfolio Company XIII, Crosslink Crossover Fund IV,
L.P., Sagamore Hill Hub Fund, Ltd., Criterion Capital Partners, Ltd., Criterion
Capital Partners, Institutional, Criterion Capital Partners, L.P. and Capital
Ventures International.

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

                      1.16 "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), and (iii)
any other capital contribution to or investment in any Person, including,
without limitation, any guaranty obligation incurred for the benefit of any
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.

                      1.17 "January Lenders" shall mean Permal U.S.
Opportunities Limited, Zaxis Equity Neutral, L.P., Zaxis Institutional Partners,
L.P., Zaxis Offshore Limited, Zaxis Partners, L.P. and Passport Master Fund,
L.P.

                      1.18 "January Note Agreement" shall mean the Convertible
Note Purchase Agreement, dated January 16, 2004, among the January Lenders and
the Company.

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                      1.19 "January 2004 Notes" shall mean the Convertible
Subordinated Promissory Notes, each dated January 16, 2003, issued by the
Company to the January Lenders pursuant to the January Note Agreement.

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

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

                      1.22 "Note Purchase Agreement" means that certain
Convertible Note Purchase Agreement, dated March 9, 2004, among the Company, the
Holder and the other parties thereto from time to time, and all amendments,
modifications and extensions thereto.

                      1.23 "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 Note 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
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 Note 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.

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

                      1.25 "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.

                      1.26 "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.

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                      1.27 "Purchase and Exchange Agreement" shall mean the
Convertible Note Purchase and Exchange Agreement, dated November 18, 2003, among
the Company, the GAP Entities, GAP-W, LLC and the other parties thereto, as
amended.

                      1.28 "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.

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

                      1.30 "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.

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

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

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

                      1.34 "Subsequent Closing Date" shall have the meaning set
forth in Section 2.4(e) of the Note Purchase Agreement.

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

                      1.36 "Ten Percent Holder" means, with respect to a class
of equity securities of the Company, a Person (together with such Person's
Affiliates) who, directly or indirectly, beneficially owns 9.9% or more of such
class of equity securities of

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the Company, as defined by Section 13(d) of the Securities Exchange Act of 1934,
as amended, and the rules and regulations promulgated thereunder.

                      1.37 "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.

                             (a) On the Conversion Date, the principal amount of
this Note plus the accrued and unpaid interest thereon (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.

                             (b) In the event that the Conversion Date has not
occurred on or prior to August 15, 2004 (the "Common Conversion Date"), then,
following the Common Conversion Date, the principal amount of this Note plus the
Interest Amount shall be convertible, at the option of Holder and from time to
time, only into Common Stock at a conversion price per share equal to $2.18, as
adjusted for any stock dividends, stock splits or similar consolidations or
subdivisions, following the date hereof; provided, however, that Holder shall
not be permitted to convert any portion of the principal of this Note or the
Interest Amount into Common Stock pursuant to this Section 3.1(b) if, at the
time of such conversion, the conversion would cause Holder to be a Ten Percent
Holder.

                      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 Preferred Stock or Common Stock, as the case may be, are to
be issued. The Person or Persons entitled to receive the shares of Series E
Preferred Stock or Common Stock, as the case may be, issuable upon such
conversion shall be treated for all purposes as the record holder or holders (a)
of such shares of Series E Preferred Stock as of the

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Conversion Date and (b) of such shares of Common Stock as of the date of any
conversion pursuant to Section 3.1(b).

                      3.3 Delivery of Stock Certificates. Upon conversion of
this Note as provided in Section 3.1, 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 or Common Stock, as the case may be, issuable upon such
conversion.

                      3.4 Mechanics and Effect of Conversion. No fractional
shares of Series E Preferred Stock or Common Stock, as the case may be, 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
or Common 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.

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In all events, appropriate adjustment (as determined in good faith by the
Company's 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 or Common Stock into a different number of securities of the same class,
the Price Per Share or conversion price, as the case may be, 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.

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                      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 date on which all amounts
outstanding under the Notes have converted pursuant to Section 3.1(a) or Section
3.1(b):

                      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 Note
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
Note 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, as
set forth on Schedule 3.22 to the Note 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

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

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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;

                             (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 lessor 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 Note 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

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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 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 Note 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 Note 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

                                       12
<PAGE>
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 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.

                                       13
<PAGE>
                      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 Note Purchase Agreement, and
incorporated by reference in this Note in Section 5.2.

                      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
Note 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

                                       14
<PAGE>
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 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.

                             (a) Except as set forth in the Subordination
Agreement, the Notes will rank senior in right of payment to all other
indebtedness of the Company, other than the GA Notes and the January 2004 Notes,
with respect to which the Notes will be pari passu in right of payment in
accordance with the Intercreditor Agreement.

                             (b) Notwithstanding anything to the contrary
contained in the Notes, this Note and the other Notes, and the terms and the
conditions hereof and thereof, are subject to the Intercreditor Agreement.

               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

                                       15
<PAGE>
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 Note 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 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. This Note is
registered as to both principal and stated interest with the Company (or its
agent) within the meaning of section 1.871-14(c)(1)(i) of the Income Tax
Regulations. Accordingly, notwithstanding anything to the contrary in this
paragraph, this Note, together with any interest thereon, may be transferred
only (i) upon surrender of the Note by the transferor to the Company (or its
agent) and the reissuance of the Note (or the issuance of a new Note) to the
transferee, or (ii) by transfer of the right to principal and interest through a
book-entry system meeting the requirements of section 1.871-14(c)(1)(i)(B) of
the Income Tax Regulations that is maintained by the Company (or its agent). In
the case of a Holder that is not a "United States person" within the meaning of
section 7701(a)(30) of the Internal Revenue Code of 1986, as amended (the
"Code"), so long as an exception under section 871(h) or section 881(c) of the
Code does not apply, the Company (or its agent) shall not withhold any U.S.
federal income tax with respect to such Holder provided that the Holder timely
provides the Company (or its agent) with a statement that meets the requirements
of section 871(h)(5) of the Code.

               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

                                       16
<PAGE>
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 Note 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.

               19. WAIVER OF JURY TRIAL. EACH OF 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

                                       17
<PAGE>
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]

                                       18
<PAGE>

               IN WITNESS WHEREOF, the Company has caused this Note to be issued
this 9th day of March, 2004.

                                    COMPANY:

                                    CRITICAL PATH, INC.,
                                    a California corporation

                                    By:
                                       -----------------------------------------
                                       Name:  William E. McGlashan, Jr.
                                       Title:  Chairman, Chief Executive Officer

                                       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:
               --------------------------------
Address:
         --------------------------------------

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

Telephone:
          -------------------------------------
Facsimile:
          -------------------------------------<PAGE>

                                                                     EXHIBIT 4.2

                           THIRD AMENDED AND RESTATED

                          REGISTRATION RIGHTS AGREEMENT

        THIRD AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT, dated March 9,
2004 (this "Agreement"), 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"), GAPCO GmbH & Co. KG, a German limited partnership ("GmbH
Coinvestment"), Cenwell Limited ("Cenwell"), Campina Enterprises Limited
("Campina"), Great Affluent Limited ("Great Affluent"), Dragonfield Limited
("Dragonfield"), Lion Cosmos Limited ("Lion Cosmos"), Vectis CP Holdings, LLC, a
Delaware limited liability company ("Vectis"), Permal U.S. Opportunities Limited
("Permal"), Zaxis Equity Neutral, L.P. ("Zaxis Equity"), Zaxis Institutional
Partners, L.P. ("Zaxis Institutional"), Zaxis Offshore Limited ("Zaxis
Offshore"), Zaxis Partners, L.P. ("Zaxis Partners"), Guggenheim Portfolio
Company XIII ("Guggenheim" and collectively with Permal, Zaxis Equity, Zaxis
Institutional, Zaxis Offshore and Zaxis Partners, "Apex Capital"), Passport
Master Fund, L.P. ("Passport Capital"), Crosslink Crossover Fund IV, L.P.
("Crosslink"), Sagamore Hill Hub Fund, Ltd. ("Sagamore"), Criterion Capital
Partners, Ltd. ("Criterion Limited"), Criterion Capital Partners, Institutional
("Criterion Institutional"), Criterion Capital Partners, L.P. ("Criterion LP"
and together with Criterion Limited and Criterion Institutional, "Criterion")
and Capital Ventures International ("Heights Capital");

        WHEREAS, pursuant to the Stock and Warrant Purchase Agreement, dated
November 8, 2001, as amended from time to time (the "Stock Purchase Agreement"),
among the Company, GAP LP, GAP Coinvestment, GapStar, Cenwell, Campina and
Vectis, the Company has (i) issued and sold to GAP LP, GAP Coinvestment,
GapStar, Cenwell, Campina and Vectis, an aggregate of 2,162,582 shares of Series
D Cumulative Redeemable Convertible Participating Series D 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 to purchase shares of Common Stock (as hereinafter defined) (the
"Warrants");

        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, LLC, a
Delaware limited liability company, GmbH Coinvestment, Campina, Cenwell, Great
Affluent, Dragonfield and Lion Cosmos, as amended, (i) the Company has issued
and sold to GAP LP, GAP Coinvestment, GapStar and GmbH Coinvestment convertible
promissory notes (the "GA Notes") which are convertible into shares, par value
$0.001 per share, of Series E Redeemable Convertible Preferred Stock of the
Company (the "Series E Preferred Stock") and (ii) Campina, Cenwell, Great
Affluent, Dragonfield and Lion Cosmos agreed upon the satisfaction of certain
conditions to exchange their CK Sub Notes (as hereinafter defined) for shares of
Series E Preferred Stock;

<PAGE>

        WHEREAS, pursuant to the Convertible Note Purchase Agreement, dated
January 16, 2004, among the Company, Permal, Zaxis Equity, Zaxis Institutional,
Zaxis Offshore, Zaxis Partners and Passport Capital (the "January Convertible
Note Agreement"), the Company has issued and sold to Permal, Zaxis Equity, Zaxis
Institutional, Zaxis Offshore, Zaxis Partners and Passport Capital convertible
promissory notes (the "January 2004 Notes") which are convertible into shares of
Series E Preferred Stock;

        WHEREAS, pursuant to the Convertible Note Purchase Agreement, dated
March 9, 2004, among the Company, Apex Capital, Crosslink, Sagamore, Criterion
and Heights Capital (the "March Convertible Note Agreement" and, together with
the January Convertible Note Agreement, the "Convertible Note Agreements"), the
Company has issued and sold to Apex Capital, Crosslink, Sagamore, Criterion and
Heights Capital convertible promissory notes in the principal amount of up to
$18,500,000 (the "March 2004 Notes" and, collectively with the GA Notes and the
January 2004 Notes, the "Notes") which are convertible into shares of Series E
Preferred Stock; and

        WHEREAS, in order to induce (i) each of GAP LP, GAP Coinvestment,
GapStar, GmbH Coinvestment, Apex Capital, Passport Capital, Crosslink, Sagamore,
Criterion and Heights Capital to purchase the Notes and (ii) Campina, Cenwell,
Great Affluent, Dragonfield and Lion Cosmos to exchange the CK Sub Notes for
shares of Series E Preferred Stock, the Company has agreed to grant registration
rights with respect to the Registrable Securities (as hereinafter defined) as
set forth in this Agreement:

        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:

        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.

               "Amended and Restated Stockholders Agreement" shall mean the
Amended and Restated Stockholders Agreement, dated the date hereof, among the
Company, GAP LP, GAP Coinvestment, GapStar, GmbH Coinvestment and the Persons
listed therein as "Coinvestors."

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

               "Apex Stockholders" means Apex Capital, Passport Capital,
Crosslink, Sagamore, Criterion and Heights Capital and any Affiliate thereof
that, after the date hereof, acquires Registrable Securities.

                                       2
<PAGE>

               "Approved Underwriter" has the meaning set forth in Section 3(f)
of this Agreement.

               "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 are authorized or
required by law or executive order to close.

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

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

               "Coinvestor Stockholders" means Cenwell, Campina, Great Affluent,
Dragonfield, Lion Cosmos and any Affiliate thereof that, after the date hereof,
acquires Registrable Securities.

               "CK Sub Notes" means the 53/4% Convertible Subordinated Notes due
April 1, 2005 issued by the Company in the principal face amount of thirty-two
million seven hundred ninety-five thousand dollars ($32,795,000), pursuant to
the Company's Indenture, dated March 31, 2000.

               "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 $0.001 per
share, of the Company or any other capital stock of the Company into which such
stock is reclassified or reconstituted and any other common stock of the
Company.

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

               "Company Underwriter" has the meaning set forth in Section 4(a)
of this Agreement.

               "Conversion" has the meaning set forth in the Convertible Note
Agreements.

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

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

               "Convertible Note Agreements" has the meaning set forth in the
recitals to this Agreement.

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

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

                                       3
<PAGE>

               "Daily Trade Amount" means, (a) as to each of the General
Atlantic Stockholders, the Coinvestor Stockholders, the Vectis Stockholders and
the Apex Stockholders (other than Passport Capital, Crosslink, Sagamore,
Criterion and Heights Capital), the greater of (i) with respect to any date a
proposed sale pursuant to a Registration Statement is to be executed, 20% of the
daily trading volume of the Common Stock on the Nasdaq National Market System on
the date a proposed trade is to take place and (ii) 20% of the average daily
trading volume of the Common Stock on the Nasdaq National Market for the five
trading days immediately preceding such date, (b) as to Passport Capital, the
greater of (i) 6.7% of the daily trading volume of the Common Stock on the
Nasdaq National Market System on the date a proposed trade is to take place and
(ii) 6.7% of the average daily trading volume of the Common Stock on the Nasdaq
National Market for the five trading days immediately preceding such date, (c)
as to Crosslink, the greater of (i) 8.9% of the daily trading volume of the
Common Stock on the Nasdaq National Market System on the date a proposed trade
is to take place and (ii) 8.9% of the average daily trading volume of the Common
Stock on the Nasdaq National Market for the five trading days immediately
preceding such date, (d) as to Sagamore, the greater of (i) 5.3% of the daily
trading volume of the Common Stock on the Nasdaq National Market System on the
date a proposed trade is to take place and (ii) 5.3% of the average daily
trading volume of the Common Stock on the Nasdaq National Market for the five
trading days immediately preceding such date, (e) as to Criterion, the greater
of (i) 6.2% of the daily trading volume of the Common Stock on the Nasdaq
National Market System on the date a proposed trade is to take place and (ii)
6.2% of the average daily trading volume of the Common Stock on the Nasdaq
National Market for the five trading days immediately preceding such date and
(f) as to Heights Capital, the greater of (i) 3.6% of the daily trading volume
of the Common Stock on the Nasdaq National Market System on the date a proposed
trade is to take place and (ii) 3.6% of the average daily trading volume of the
Common Stock on the Nasdaq National Market for the five trading days immediately
preceding such date; provided, however, that for the purpose of calculating the
Daily Trade Amount, a block trade effected by a party outside the Nasdaq
National Market System shall be disregarded for purposes of calculating the
amount disposed of by the party and the daily trading volume. The Daily Trade
Amount shall apply to each such stockholder severally and not jointly, shall not
be aggregated among or between such stockholders, and such stockholders shall
not be required hereby to coordinate their sales or dispositions of Common
Stock.

               "Demand Registration" has the meaning set forth in Section 3(a)
of this Agreement.

               "Designated Holder" means each of the General Atlantic
Stockholders, the Coinvestor Stockholders, the Vectis Stockholders and the Apex
Stockholders and any transferee of any of them to whom Registrable Securities
have been transferred in accordance with Section 9(f) of this Agreement, other
than a transferee to whom Registrable Securities have been transferred pursuant
to a Registration Statement under the Securities Act or Rule 144 (or any
successor rule thereto).

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

                                       4
<PAGE>

               "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.

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

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

               "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.

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

               "General Atlantic Stockholders" means GAP LP, GAP Coinvestment,
GapStar, GmbH Coinvestment and any Affiliate of GAP LLC that, after the date
hereof, acquires Registrable Securities.

               "GmbH Coinvestment" means GAPCO GmbH & Co. KG, a German limited
partnership.

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

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

               "Holders' Counsel" has the meaning set forth in Section 6(a)(i)
of this Agreement.

               "Incidental Registration" has the meaning set forth in Section
4(a) of this Agreement.

               "Indemnified Party" has the meaning set forth in Section 7(c) of
this Agreement.

               "Indemnifying Party" has the meaning set forth in Section 7(c) of
this Agreement.

               "Initiating Holders" has the meaning set forth in Section 3(a) of
this Agreement.

               "Inspector" has the meaning set forth in Section 6(a)(vii) of
this Agreement.

               "January Convertible Note Agreement" has the meaning set forth in
the recitals to this Agreement.

               "January 2004 Notes" has the meaning set forth in the recitals to
this Agreement.

                                       5
<PAGE>

               "Liability" has the meaning set forth in Section 7(a) of this
Agreement.

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

               "March Convertible Note Agreement" has the meaning set forth in
the recitals to this Agreement.

               "March 2004 Notes" has the meaning set forth in the recitals to
this Agreement.

               "NASD" means the National Association of Securities Dealers, Inc.

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

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

               "Public Offering" means any public offering of the shares of
Common Stock of the Company pursuant to an effective Registration Statement
filed under the Securities Act.

               "Records" has the meaning set forth in Section 6(a)(vii) of this
Agreement.

               "Registrable Securities" means each of the following: (a) any and
all shares of Common Stock issued or issuable upon conversion of shares of
Series D Preferred Stock or exercise of the Warrants, and, subject to
Stockholder Approval, any and all shares of Common Stock issued or issuable upon
conversion of shares of Series E Preferred Stock, (b) if the Subsequent Closing
does not occur by August 15, 2004, the shares of Common Stock issued upon
conversion of the January 2004 Notes and the March 2004 Notes, (c) any other
shares of Common Stock acquired or owned by any of the Designated Holders after
the date hereof if such Designated Holder is an Affiliate of the Company and (d)
any shares of Common Stock issued or issuable to any of the Designated Holders
with respect to the Registrable Securities by way of stock dividend or stock
split or in connection with a combination of shares, recapitalization, merger,
consolidation or other reorganization or otherwise and any shares of Common
Stock or voting common stock issuable upon conversion, exercise or exchange
thereof.

               "Registration Expenses" has the meaning set forth in Section 6(d)
of this Agreement.

               "Registration Statement" means a Registration Statement filed
pursuant to the Securities Act.

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

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

                                       6
<PAGE>

               "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.

               "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.

               "Valid Business Reason" has the meaning set forth in Section 3(a)
of this Agreement.

               "Vectis" has the meaning set forth in the preamble of this
Agreement.

               "Vectis Stockholders" means Vectis and any Affiliate thereof
that, after the date hereof, acquires Registrable Securities.

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

        2. General; Securities Subject to this Agreement.

               (a) Grant of Rights. The Company hereby grants registration
rights to the Designated Holders upon the terms and conditions set forth in this
Agreement.

               (b) Registrable Securities. For the purposes of this Agreement,
Registrable Securities will cease to be Registrable Securities, when (i) a
Registration Statement covering such Registrable Securities has been declared
effective under the Securities Act by the Commission and such Registrable
Securities have been disposed of pursuant to such effective Registration
Statement, (ii) (x) the entire amount of the Registrable Securities owned by a
Designated Holder may be sold in a single sale, in the opinion of counsel
satisfactory to the Company and such Designated Holder, each in their reasonable
judgment, without any limitation as to volume pursuant to Rule 144 (or any
successor provision then in effect) under the Securities Act and (y) such
Designated Holder owning such Registrable Securities owns less than one percent
(1%) of the outstanding shares of Common Stock on a fully diluted basis, or
(iii) the Registrable Securities are proposed to be sold or distributed by a
Person not entitled to the registration rights granted by this Agreement.

               (c) Holders of Registrable Securities. A Person is deemed to be a
holder of Registrable Securities whenever such Person owns of record Registrable
Securities, or holds an option to purchase, or a security convertible into or
exercisable or exchangeable for, Registrable Securities whether or not such
acquisition or conversion has actually been effected. If the Company receives
conflicting instructions, notices or elections from two or more Persons with

                                       7
<PAGE>

respect to the same Registrable Securities, the Company may act upon the basis
of the instructions, notice or election received from the registered owner of
such Registrable Securities. Registrable Securities issuable upon exercise of an
option or upon conversion of another security shall be deemed outstanding for
the purposes of this Agreement.

        3. Demand Registration.

               (a) Request for Demand Registration. At any time after the
earliest of (i) the expiration or consummation of the exercise of the right of
the General Atlantic Stockholders and the Coinvestor Stockholders (or their
respective permitted transferees) to purchase those shares of Series E Preferred
Stock offered in the Rights Offering but not acquired by holders of shares of
the Company's Common Stock, (ii) the termination of the Rights Offering and the
occurrence of the special meeting to seek Stockholder Approval and (iii) August
15, 2004, if the Conversion and Exchange and the Conversion have not occurred on
or prior to such date, each of (A) the General Atlantic Stockholders, (B) the
Coinvestor Stockholders, (C) Apex Capital, (D) Passport Capital, (E) Crosslink,
(F) Sagamore, (G) Criterion and (H) Heights Capital (the "Initiating Holders"),
may each make a written request to the Company to register, and the Company
shall register, under the Securities Act and on an appropriate registration
statement form as reasonably determined by the Company and approved by the
Initiating Holders (a "Demand Registration"), the number of Registrable
Securities stated in such request; provided, however, that the Company shall not
be obligated to effect more than one such Demand Registration for the General
Atlantic Stockholders (subject to Section 3(e)(ii) below), more than one such
Demand Registration for the Coinvestor Stockholders (subject to Section 3(e)(ii)
below), more than one such Demand Registration for Apex Capital (subject to
Section 3(e)(ii) below), more than one such Demand Registration for Passport
Capital (subject to Section 3(e)(ii) below), more than one such Demand
Registration for Crosslink (subject to Section 3(e)(ii) below), more than one
such Demand Registration for Sagamore (subject to Section 3(e)(ii) below), more
than one such Demand Registration for Criterion (subject to Section 3(e)(ii)
below) and more than one such Demand Registration for Heights Capital (subject
to Section 3(e)(ii) below). If following receipt of a written request for a
Demand Registration the Board of Directors, in its good faith judgment,
determines that any registration of Registrable Securities should not be made or
continued because it would materially interfere with any material financing,
acquisition, corporate reorganization or merger or other material transaction
involving the Company (a "Valid Business Reason"), the Company may (x) postpone
filing a Registration Statement relating to a Demand Registration until such
Valid Business Reason no longer exists, but in no event for more than ninety
(90) days, and (y) in case a Registration Statement has been filed relating to a
Demand Registration, if the Valid Business Reason has not resulted from actions
taken by the Company, the Company, upon the approval of a majority of the Board
of Directors, such majority to include at least one Director appointed by the
General Atlantic Stockholders, may cause such Registration Statement to be
withdrawn and its effectiveness terminated or may postpone amending or
supplementing such Registration Statement. The Company shall give written notice
of its determination to postpone or withdraw a Registration Statement and of the
fact that the Valid Business Reason for such postponement or withdrawal no
longer exists, in each case, promptly after the occurrence thereof.
Notwithstanding anything to the contrary contained herein, the Company may not
postpone or withdraw a filing under this Section 3(a) more than once in any
twelve (12) month period. Each request for a Demand Registration by the
Initiating

                                       8
<PAGE>

Holders shall state the amount of the Registrable Securities proposed to be sold
and the intended method of disposition thereof.

               (b) Incidental or "Piggy-Back" Rights with Respect to a Demand
Registration. Each of the Designated Holders (other than Initiating Holders
which have requested a registration under Section 3(a)) may offer its or his
Registrable Securities under any Demand Registration pursuant to this Section
3(b). Within five (5) days after the receipt of a request for a Demand
Registration from an Initiating Holder, the Company shall (i) give written
notice thereof to all of the Designated Holders (other than Initiating Holders
which have requested a registration under Section 3(a)) and (ii) subject to
Section 3(e), include in such registration all of the Registrable Securities
held by such Designated Holders from whom the Company has received a written
request for inclusion therein within ten (10) days of the receipt by such
Designated Holders of such written notice referred to in clause (i) above. Each
such request by such Designated Holders shall specify the number of Registrable
Securities proposed to be registered. The failure of any Designated Holder to
respond within such 10 day period referred to in clause (ii) above shall be
deemed to be a waiver of such Designated Holder's rights under this Section 3
with respect to such Demand Registration. Any Designated Holder may waive its
rights under this Section 3 prior to the expiration of such 10-day period by
giving written notice to the Company, with a copy to the Initiating Holders. If
a Designated Holder sends the Company a written request for inclusion of part or
all of such Designated Holder's Registrable Securities in a registration, such
Designated Holder shall not be entitled to withdraw or revoke such request
without the prior written consent of the Company in its sole discretion unless,
as a result of facts or circumstances arising after the date on which such
request was made relating to the Company or to market conditions, such
Designated Holder reasonably determines that participation in such registration
would have a material adverse effect on such Designated Holder.

               (c) Effective Demand Registration. The Company shall use all
commercially reasonable efforts to cause any such Demand Registration to be
filed not later than thirty (30) days after it receives a request under Section
3(a) hereof and to become and remain effective as soon as practicable thereafter
but, in any event, not later than ninety (90) days (or, if the Company is
eligible to effect such registration on Form S-3, sixty (60) days) after such
filing. A registration shall not constitute a Demand Registration unless it has
become effective and remains continuously effective until the earlier of the
date (i) on which all Registrable Securities registered in the Demand
Registration are sold and (ii) that is the second anniversary of the
effectiveness of the Registration Statement relating to such Demand
Registration; provided, however, that a registration shall not constitute a
Demand Registration if (x) after such Demand Registration has become effective,
such registration or the related offer, sale or distribution of Registrable
Securities thereunder is interfered with by any stop order, injunction or other
order or requirement of the Commission or other governmental agency or court for
any reason not attributable to the Initiating Holders and such interference is
not thereafter eliminated or (y) the conditions specified in the underwriting
agreement, if any, entered into in connection with such Demand Registration are
not satisfied or waived, other than by reason of a failure by the Initiating
Holder.

               (d) Expenses. The Company shall pay all Registration Expenses in
connection with a Demand Registration, whether or not such Demand Registration
becomes

                                       9
<PAGE>

effective, except for an underwritten Demand Registration pursuant to Section
3(e)(i)(y) below, as to which each participating Designated Holder shall bear
its pro rata portion of expenses based on the number of shares of Common Stock
registered pursuant thereto.

               (e) Underwriting Procedures.

                        (i) If (x) any of the Initiating Holders so elects for
itself or (y) with respect to any given trading day, a Designated Holder
proposes to sell or dispose of more than the Daily Trade Amount and the
Company's board of directors determines in good faith that it is necessary for
an orderly distribution to be made pursuant to a firm commitment underwritten
offering, then the Company shall use all commercially reasonable efforts to
cause such Demand Registration to be in the form of, and such Designated Holder
or Designated Holders shall be obligated to sell or dispose of its or their
Registrable Securities pursuant to, a firm commitment underwritten offering and
the managing underwriter or underwriters selected for such offering shall be the
Approved Underwriter selected in accordance with Section 3(f). In connection
with any Demand Registration under this Section 3 involving an underwritten
offering, none of the Registrable Securities held by any Designated Holder
making a request for inclusion of such Registrable Securities pursuant to
Section 3(b) hereof shall be included in such underwritten offering unless such
Designated Holder accepts the terms of the offering as agreed upon by the
Company, the Initiating Holders and the Approved Underwriter, and then only in
such quantity as will not, in the opinion of the Approved Underwriter,
jeopardize the success of such offering by the Initiating Holders. If the
Approved Underwriter advises the Company in its reasonable opinion that the
aggregate amount of such Registrable Securities requested to be included in such
offering is sufficiently large to have a material adverse effect on the success
of such offering, then the Company shall include in such registration only the
aggregate amount of Registrable Securities that the Approved Underwriter
believes may be sold without any such material adverse effect and shall reduce
the amount of Registrable Securities to be included in such registration by
removing from such registration securities owned, first by the Company and
second by the Designated Holders (including the Initiating Holders) pro rata
based on the number of Registrable Securities owned by each such Designated
Holder.

                        (ii) If an Initiating Holder makes a request for a
Demand Registration and, pursuant to Section 3(e)(i) above, the Approved
Underwriter advises the Company to reduce the aggregate amount of Registrable
Securities requested to be included in such offering such that less than
seventy-five percent (75%) of the Registrable Securities requested to be
included by any Initiating Holder are ultimately included in and sold pursuant
to such Demand Registration, the Initiating Holder shall have the right to
require the Company to effect an additional Demand Registration; provided,
however, that in no event shall the aggregate number of Demand Registrations to
be effected by the Company for any one Initiating Holder exceed two (2).

               (f) Selection of Underwriters. If any Demand Registration of
Registrable Securities is in the form of an underwritten offering, the Company
shall select and obtain an investment banking firm of national reputation to act
as the managing underwriter of the offering (the "Approved Underwriter");
provided, however, that the Approved Underwriter shall, in any case, also be
approved by the Initiating Holders.

                                       10
<PAGE>

        4. Incidental or "Piggy-Back" Registration.

               (a) Request for Incidental Registration. If at any time the
Company proposes to file a Registration Statement under the Securities Act with
respect to an offering by the Company for its own account (other than a
Registration Statement on Form S-4 or S-8 or any successor thereto) or for the
account of any stockholder of the Company other than the Designated Holders,
then the Company shall give written notice of such proposed filing to each of
the Designated Holders at least twenty (20) days before the anticipated filing
date, and such notice shall describe the proposed registration and distribution
and offer such Designated Holders the opportunity to register the number of
Registrable Securities as each such Designated Holder may request (an
"Incidental Registration"). The Company shall use all commercially reasonable
efforts (within twenty (20) days of the notice provided for in the preceding
sentence) to cause the managing underwriter or underwriters in the case of a
proposed underwritten offering (the "Company Underwriter") to permit each of the
Designated Holders who have requested in writing to participate in the
Incidental Registration to include its or his Registrable Securities in such
offering on the same terms and conditions as the securities of the Company or
the account of such other stockholder, as the case may be, included therein. In
connection with any Incidental Registration under this Section 4(a) involving an
underwritten offering, the Company shall not be required to include any
Registrable Securities in such underwritten offering unless the Designated
Holders thereof accept the terms of the underwritten offering as agreed upon
between the Company, such other stockholders, if any, and the Company
Underwriter, and then only in such quantity as the Company Underwriter believes
will not jeopardize the success of the offering by the Company. If the Company
Underwriter determines that the registration of all or part of the Registrable
Securities which the Designated Holders have requested to be included would
materially adversely affect the success of such offering, then the Company shall
be required to include in such Incidental Registration, to the extent of the
amount that the Company Underwriter believes may be sold without causing such
adverse effect, first, all of the securities to be offered for the account of
the Company or on the account of the selling stockholder that caused the
registration statement that has triggered the Incidental Registration to be
filed, as the case may be; second, the Registrable Securities to be offered for
the account of the Designated Holders pursuant to this Section 4, pro rata based
on the number of Registrable Securities owned by each such Designated Holder;
and third, any other securities requested to be included in such offering.

               (b) Expenses. The Company shall bear all Registration Expenses in
connection with any Incidental Registration pursuant to this Section 4, whether
or not such Incidental Registration becomes effective.

        5. Holdback Agreements.

               (a) Restrictions on Public Sale by Designated Holders. To the
extent (i) requested (A) by the Company or the Initiating Holders, as the case
may be, in the case of a non-underwritten public offering and (B) by the
Approved Underwriter or the Company Underwriter, as the case may be, in the case
of an underwritten public offering and (ii) all of the Company's officers,
directors and holders in excess of one percent (1%) of its outstanding capital
stock execute agreements identical to those referred to in this Section 5(a),
each Designated Holder agrees (x) not to effect any public sale or distribution
of any Registrable

                                       11
<PAGE>

Securities or of any securities convertible into or exchangeable or exercisable
for such Registrable Securities, including a sale pursuant to Rule 144 under the
Securities Act, or offer to sell, contract to sell (including without limitation
any short sale), grant any option to purchase or enter into any hedging or
similar transaction with the same economic effect as a public sale any
Registrable Securities and (y) not to make any request for a Demand Registration
under this Agreement, during the ninety (90) day period or such shorter period,
if any, mutually agreed upon by such Designated Holder and the requesting party
beginning on the effective date of the Registration Statement (except as part of
such registration) for such public offering. No Designated Holder of Registrable
Securities subject to this Section 5(a) shall be released from any obligation
under any agreement, arrangement or understanding entered into pursuant to this
Section 5(a) unless all other Designated Holders of Registrable Securities
subject to the same obligation are also released. All Designated Holders of
Registrable Securities shall be automatically released from any obligations
under any agreement, arrangement or understanding entered into pursuant to this
Section 5(a) immediately upon the expiration of the 90 day period, and in any
case, on the date that is two years from the date of this Agreement.

               (b) Restrictions on Public Sale by the Company. The Company
agrees not to effect any public sale or distribution of any of its securities,
or any securities convertible into or exchangeable or exercisable for such
securities (except pursuant to registrations on Form S-4 or S-8 or any successor
thereto), during the period beginning on the effective date of any Registration
Statement in which the Designated Holders of Registrable Securities are
participating and ending on the earlier of (i) the date on which all Registrable
Securities registered on such Registration Statement are sold and (ii) 120 days
after the effective date of such Registration Statement (except as part of such
registration).

        6. Registration Procedures.

               (a) Obligations of the Company. Whenever registration of
Registrable Securities has been requested pursuant to Section 3 or Section 4 of
this Agreement, the Company shall use all commercially reasonable efforts to
effect the registration and sale of such Registrable Securities in accordance
with the intended method of distribution thereof as quickly as practicable, and
in connection with any such request, the Company shall, as expeditiously as
possible:

                        (i) prepare and file with the Commission a Registration
Statement on any form for which the Company then qualifies or which counsel for
the Company shall deem appropriate and which form shall be available for the
sale of such Registrable Securities in accordance with the intended method of
distribution thereof, and cause such Registration Statement to become effective;
provided, however, that (x) before filing a Registration Statement or prospectus
or any amendments or supplements thereto, the Company shall provide counsel
selected by the Designated Holders holding a majority of the Registrable
Securities being registered in such registration ("Holders' Counsel") with an
adequate opportunity to review and comment on such Registration Statement and
each prospectus included therein (and each amendment or supplement thereto) to
be filed with the Commission, subject to such documents being under the
Company's control, and (y) the Company shall notify the Holders' Counsel and
each seller of Registrable Securities of any stop order issued or threatened by
the Commission and take all action required to prevent the entry of such stop
order or to remove it if entered;

                                       12
<PAGE>

                        (ii) prepare and file with the Commission such
amendments and supplements to such Registration Statement and the prospectus
used in connection therewith as may be necessary to keep such Registration
Statement effective for the lesser of (x) 120 days and (y) such shorter period
which will terminate when all Registrable Securities covered by such
Registration Statement have been sold, and comply with the provisions of the
Securities Act with respect to the disposition of all securities covered by such
Registration Statement during such period in accordance with the intended
methods of disposition by the sellers thereof set forth in such Registration
Statement;

                        (iii) furnish to each seller of Registrable Securities,
prior to filing a Registration Statement, at least one copy of such Registration
Statement as is proposed to be filed, and thereafter such number of copies of
such Registration Statement, each amendment and supplement thereto (in each case
including all exhibits thereto), and the prospectus included in such
Registration Statement (including each preliminary prospectus) and any
prospectus filed under Rule 424 under the Securities Act as each such seller may
reasonably request in order to facilitate the disposition of the Registrable
Securities owned by such seller;

                        (iv) register or qualify such Registrable Securities
under such other securities or "blue sky" laws of such jurisdictions as any
seller of Registrable Securities may request, and to continue such qualification
in effect in such jurisdiction for as long as permissible pursuant to the laws
of such jurisdiction, or for as long as any such seller requests or until all of
such Registrable Securities are sold, whichever is shortest, and do any and all
other acts and things which may be reasonably necessary or advisable to enable
any such seller to consummate the disposition in such jurisdictions of the
Registrable Securities owned by such seller; provided, however, that the Company
shall not be required to (x) qualify generally to do business in any
jurisdiction where it would not otherwise be required to qualify but for this
Section 6(a)(iv), (y) subject itself to taxation in any such jurisdiction or (z)
consent to general service of process in any such jurisdiction;

                        (v) notify each seller of Registrable Securities at any
time when a prospectus relating thereto is required to be delivered under the
Securities Act, upon discovery that, or upon the happening of any event as a
result of which, the prospectus included in such Registration Statement contains
an untrue statement of a material fact or omits to state any material fact
required to be stated therein or necessary to make the statements therein, in
light of the circumstances under which they were made, not misleading and the
Company shall promptly prepare a supplement or amendment to such prospectus and
furnish to each seller of Registrable Securities a reasonable number of copies
of such supplement to or an amendment of such prospectus as may be necessary so
that, after delivery to the purchasers of such Registrable Securities, such
prospectus shall not contain an untrue statement of a material fact or omit to
state any material fact required to be stated therein or necessary to make the
statements therein, in light of the circumstances under which they were made,
not misleading;

                        (vi) enter into and perform customary agreements
(including an underwriting agreement containing representations, warranties,
covenants and indemnities for securities law matters and otherwise in customary
form with the Approved Underwriter or Company Underwriter, if any, selected as
provided in Section 3 or Section 4, as the case may be) and take such other
actions as are prudent and reasonably required in order to expedite or

                                       13
<PAGE>

facilitate the disposition of such Registrable Securities, including causing its
officers to participate in "road shows" and other information meetings organized
by the Approved Underwriter or Company Underwriter;

                        (vii) make available at reasonable times for inspection
by any seller of Registrable Securities, any managing underwriter participating
in any disposition of such Registrable Securities pursuant to a Registration
Statement, Holders' Counsel and any attorney, accountant or other agent retained
by any such seller or any managing underwriter (each, an "Inspector" and
collectively, the "Inspectors"), all financial and other records, pertinent
corporate documents and properties of the Company and its subsidiaries
(collectively, the "Records") as shall be reasonably necessary to enable them to
exercise their due diligence responsibility, and cause the Company's and its
subsidiaries' officers, directors and employees, and the independent public
accountants of the Company, to supply all information reasonably requested by
any such Inspector in connection with such Registration Statement. Records that
the Company determines, in good faith, to be confidential and which it notifies
the Inspectors are confidential shall not be disclosed by the Inspectors (and
the Inspectors shall confirm their agreement in writing in advance to the
Company if the Company shall so request) unless (x) the disclosure of such
Records is necessary, in the Company's judgment, to avoid or correct a
misstatement or omission in the Registration Statement, (y) the release of such
Records is ordered pursuant to a subpoena or other order from a court of
competent jurisdiction after exhaustion of all appeals therefrom or (z) the
information in such Records was known to the Inspectors on a non-confidential
basis prior to its disclosure by the Company or has been made generally
available to the public. Each seller of Registrable Securities agrees that it
shall, upon learning that disclosure of such Records is sought in a court of
competent jurisdiction, give notice to the Company and allow the Company, at the
Company's expense, to undertake appropriate action to prevent disclosure of the
Records deemed confidential;

                        (viii) if such sale is pursuant to an underwritten
offering, obtain a "cold comfort" letter dated the effective date of the
Registration Statement and the date of the closing under the underwriting
agreement from the Company's independent public accountants in customary form
and covering such matters of the type customarily covered by "cold comfort"
letters as the managing underwriter reasonably requests;

                        (ix) furnish, at the request of any seller of
Registrable Securities on the date such securities are delivered to the
underwriters for sale pursuant to such registration or, if such securities are
not being sold through underwriters, on the date the Registration Statement with
respect to such securities becomes effective, an opinion, if reasonably
available, dated such date, of counsel representing the Company for the purposes
of such registration, addressed to the underwriters, if any, and to the seller
making such request, covering such legal matters with respect to the
registration in respect of which such opinion is being given as the
underwriters, if any, and such seller may reasonably request and are customarily
included in such opinions;

                        (x) comply with all applicable rules and regulations of
the Commission, and make available to its security holders, as soon as
reasonably practicable but no later than fifteen (15) months after the effective
date of the Registration Statement, an earnings statement covering a period of
twelve (12) months beginning after the effective date of the

                                       14
<PAGE>

Registration Statement, in a manner which satisfies the provisions of Section
11(a) of the Securities Act and Rule 158 thereunder;

                        (xi) cause all such Registrable Securities to be listed
on each securities exchange on which similar securities issued by the Company
are then listed, provided that the applicable listing requirements are
satisfied;

                        (xii) cooperate with each seller of Registrable
Securities and each underwriter participating in the disposition of such
Registrable Securities and their respective counsel in connection with any
filings required to be made with the NASD; and

                        (xiii) take all other steps reasonably necessary to
effect the registration of the Registrable Securities contemplated hereby.

               (b) Seller Information. The Company may require each seller of
Registrable Securities as to which any registration is being effected to
furnish, and such seller shall furnish, to the Company such information
regarding the distribution of such securities as the Company may from time to
time reasonably request in writing.

               (c) Notice to Discontinue. Each Designated Holder agrees that,
not more than two times in any 12-month period, upon receipt of any notice from
the Company of the happening of any event of the kind described in Section
6(a)(v), such Designated Holder shall, for a total period not longer than 90
days during each such 12-month period (inclusive of any delay pursuant to a
Valid Business Reason under Section 3(a) or period during which the Designated
Holder is unable to dispose of Registrable Securities under the Registration
Statement pursuant to a notice by the Company under Section 6(a)(v) hereof),
forthwith discontinue disposition of Registrable Securities pursuant to the
Registration Statement covering such Registrable Securities until such
Designated Holder's receipt of the copies of the supplemented or amended
prospectus contemplated by Section 6(a)(v) and, if so directed by the Company,
such Designated Holder shall deliver to the Company (at the Company's expense)
all copies, other than permanent file copies then in such Designated Holder's
possession, of the prospectus covering such Registrable Securities which is
current at the time of receipt of such notice. If the Company shall give any
such notice, the Company shall extend the period during which such Registration
Statement shall be maintained effective pursuant to this Agreement (including,
without limitation, the period referred to in Section 6(a)(ii)) by the number of
days during the period from and including the date of the giving of such notice
pursuant to Section 6(a)(v) to and including the date when sellers of such
Registrable Securities under such Registration Statement shall have received the
copies of the supplemented or amended prospectus contemplated by and meeting the
requirements of Section 6(a)(v).

               (d) Registration Expenses. The Company shall pay all expenses
arising from or incident to its performance of, or compliance with, this
Agreement, including, without limitation, (i) Commission, stock exchange and
NASD registration and filing fees, (ii) all fees and expenses incurred in
complying with securities or "blue sky" laws (including reasonable fees, charges
and disbursements of counsel to any underwriter incurred in connection with
"blue sky" qualifications of the Registrable Securities as may be set forth in
any underwriting agreement), (iii) all printing, messenger and delivery expenses
and (iv) the fees, charges and

                                       15
<PAGE>

expenses of counsel to the Company and of its independent public accountants and
any other accounting fees, charges and expenses incurred by the Company
(including, without limitation, any expenses arising from any "cold comfort"
letters or any special audits incident to or required by any registration or
qualification) and any reasonable legal fees, charges and expenses incurred by
one counsel for the General Atlantic Stockholders. All of the expenses described
in the preceding sentence of this Section 6(d) are referred to herein as
"Registration Expenses." The Designated Holders of Registrable Securities sold
pursuant to a Registration Statement shall bear the expense of any underwriter's
discount or commission relating to registration and sale of such Designated
Holders' Registrable Securities.

        7. Indemnification; Contribution.

               (a) Indemnification by the Company. The Company agrees to
indemnify and hold harmless each Designated Holder, its partners, directors,
officers, affiliates and each Person who controls (within the meaning of Section
15 of the Securities Act) such Designated Holder from and against any and all
losses, claims, damages, liabilities and expenses (including reasonable costs of
investigation) (each, a "Liability" and collectively, "Liabilities"), arising
out of or based upon any untrue, or allegedly untrue, statement of a material
fact contained in any Registration Statement, prospectus or preliminary
prospectus (as amended or supplemented if the Company shall have furnished any
amendments or supplements thereto) or arising out of or based upon any omission
or alleged omission to state therein a material fact required to be stated
therein or necessary to make the statements therein not misleading in the light
of the circumstances under which such statements were made, except insofar as
such Liability arises out of or is based upon any untrue statement or alleged
untrue statement or omission or alleged omission contained in such Registration
Statement, preliminary prospectus or final prospectus in reliance and in
conformity with information concerning such Designated Holder furnished in
writing to the Company by such Designated Holder expressly for use therein,
including, without limitation, the information furnished to the Company pursuant
to Section 7(b). The Company shall also provide customary indemnities to any
underwriters of the Registrable Securities, their officers, directors and
employees and each Person who controls such underwriters (within the meaning of
Section 15 of the Securities Act) to the same extent as provided above with
respect to the indemnification of the Designated Holders of Registrable
Securities.

               (b) Indemnification by Designated Holders. In connection with any
Registration Statement in which a Designated Holder is participating pursuant to
Section 3 or Section 4 hereof, each such Designated Holder shall promptly
furnish to the Company in writing such information with respect to such
Designated Holder as the Company may reasonably request or as may be required by
law for use in connection with any such Registration Statement or prospectus and
all information required to be disclosed in order to make the information
previously furnished to the Company by such Designated Holder not materially
misleading or necessary to cause such Registration Statement not to omit a
material fact with respect to such Designated Holder necessary in order to make
the statements therein not misleading. Each Designated Holder agrees to
indemnify and hold harmless the Company, each of its directors, each of its
officers who has signed the Registration Statement, any underwriter retained by
the Company and each Person who controls the Company or such underwriter (within
the meaning of Section 15 of the Securities Act) to the same extent as the
foregoing indemnity from the Company to the Designated Holders, but only if such
statement or alleged statement or omission

                                       16
<PAGE>

or alleged omission was made in reliance upon and in conformity with information
with respect to such Designated Holder furnished in writing to the Company by
such Designated Holder expressly for use in such Registration Statement or
prospectus, including, without limitation, the information furnished to the
Company pursuant to this Section 7(b); provided, however, that the total amount
to be indemnified by such Designated Holder pursuant to this Section 7(b) shall
be limited to the net proceeds (after deducting the underwriters' discounts and
commissions) received by such Designated Holder in the offering to which the
Registration Statement or prospectus relates.

               (c) Conduct of Indemnification Proceedings. Any Person entitled
to indemnification hereunder (the "Indemnified Party") agrees to give prompt
written notice to the indemnifying party (the "Indemnifying Party") after the
receipt by the Indemnified Party of any written notice of the commencement of
any action, suit, proceeding or investigation or threat thereof made in writing
for which the Indemnified Party intends to claim indemnification or contribution
pursuant to this Agreement; provided, however, that the failure so to notify the
Indemnifying Party shall not relieve the Indemnifying Party of any Liability
that it may have to the Indemnified Party hereunder (except to the extent that
the Indemnifying Party is materially prejudiced or otherwise forfeits
substantive rights or defenses by reason of such failure). If notice of
commencement of any such action is given to the Indemnifying Party as above
provided, the Indemnifying Party shall be entitled to participate in and, to the
extent it may wish, jointly with any other Indemnifying Party similarly
notified, to assume the defense of such action at its own expense, with counsel
chosen by it and reasonably satisfactory to such Indemnified Party. The
Indemnified Party shall have the right to employ separate counsel in any such
action and participate in the defense thereof, but the fees and expenses of such
counsel shall be paid by the Indemnified Party unless (i) the Indemnifying Party
agrees to pay the same, (ii) the Indemnifying Party fails to assume the defense
of such action with counsel reasonably satisfactory to the Indemnified Party or
(iii) the named parties to any such action (including any impleaded parties)
include both the Indemnifying Party and the Indemnified Party and such parties
have been advised by such counsel that either (x) representation of such
Indemnified Party and the Indemnifying Party by the same counsel would be
inappropriate under applicable standards of professional conduct or (y) there
may be one or more legal defenses available to the Indemnified Party which are
different from or additional to those available to the Indemnifying Party. In
any of such cases, the Indemnifying Party shall not have the right to assume the
defense of such action on behalf of such Indemnified Party, it being understood,
however, that the Indemnifying Party shall not be liable for the fees and
expenses of more than one separate firm of attorneys (in addition to any local
counsel) for all Indemnified Parties. No Indemnifying Party shall be liable for
any settlement entered into without its written consent, which consent shall not
be unreasonably withheld. No Indemnifying Party shall, without the consent of
such Indemnified Party, effect any settlement of any pending or threatened
proceeding in respect of which such Indemnified Party is a party and indemnity
has been sought hereunder by such Indemnified Party, unless such settlement
includes an unconditional release of such Indemnified Party from all liability
for claims that are the subject matter of such proceeding.

               (d) Contribution. If the indemnification provided for in this
Section 7 from the Indemnifying Party is unavailable to an Indemnified Party
hereunder in respect of any Liabilities referred to herein, then the
Indemnifying Party, in lieu of indemnifying such Indemnified Party, shall
contribute to the amount paid or payable by such Indemnified Party as a

                                       17
<PAGE>

result of such Liabilities in such proportion as is appropriate to reflect the
relative fault of the Indemnifying Party and Indemnified Party in connection
with the actions which resulted in such Liabilities, as well as any other
relevant equitable considerations. The relative faults of such Indemnifying
Party and Indemnified Party shall be determined by reference to, among other
things, whether any action in question, including any untrue or alleged untrue
statement of a material fact or omission or alleged omission to state a material
fact, has been made by, or relates to information supplied by, such Indemnifying
Party or Indemnified Party, and the parties' relative intent, knowledge, access
to information and opportunity to correct or prevent such action. The amount
paid or payable by a party as a result of the Liabilities referred to above
shall be deemed to include, subject to the limitations set forth in Sections
7(a), 7(b) and 7(c), any legal or other fees, charges or expenses reasonably
incurred by such party in connection with any investigation or proceeding;
provided that the total amount to be contributed by such Designated Holder shall
be limited to the net proceeds (after deducting the underwriters' discounts and
commissions) received by such Designated Holder in the offering.

               The parties hereto agree that it would not be just and equitable
if contribution pursuant to this Section 7(d) were determined by pro rata
allocation or by any other method of allocation which does not take account of
the equitable considerations referred to in the immediately preceding paragraph.
No Person guilty of fraudulent misrepresentation (within the meaning of Section
11(f) of the Securities Act) shall be entitled to contribution from any Person
who was not guilty of such fraudulent misrepresentation.

        8. Rule 144. The Company covenants that it shall (a) file any reports
required to be filed by it under the Exchange Act and (b) take such further
action as each Designated Holder may reasonably request (including providing any
information necessary to comply with Rule 144 under the Securities Act), all to
the extent required from time to time to enable such Designated Holder to sell
Registrable Securities without registration under the Securities Act within the
limitation of the exemptions provided by (i) Rule 144 under the Securities Act,
as such rule may be amended from time to time or (ii) any similar rules or
regulations hereafter adopted by the Commission. The Company shall, upon the
request of any Designated Holder, deliver to such Designated Holder a written
statement as to whether it has complied with such requirements.

        9. Miscellaneous.

               (a) Recapitalizations, Exchanges, etc. The provisions of this
Agreement shall apply to the full extent set forth herein with respect to (i)
the shares of Common Stock, (ii) any and all shares of voting common stock of
the Company into which the shares of Common Stock are converted, exchanged or
substituted in any recapitalization or other capital reorganization by the
Company and (iii) any and all equity securities of the Company or any successor
or assign of the Company (whether by merger, consolidation, sale of assets or
otherwise) which may be issued in respect of, in conversion of, in exchange for
or in substitution of, the shares of Common Stock and shall be appropriately
adjusted for any stock dividends, splits, reverse splits, combinations,
recapitalizations and the like occurring after the date hereof. The Company
shall use all commercially reasonable efforts to cause any successor or assign
(whether by merger, consolidation, sale of assets or otherwise) to enter into a
new registration rights agreement with the Designated Holders on terms
substantially the same as this Agreement as a condition of any such transaction.

                                       18
<PAGE>

               (b) No Inconsistent Agreements. The Company shall not enter into
any agreement with respect to its securities that is inconsistent with the
rights granted to the Designated Holders in this Agreement or grant any
additional registration rights to any Person or with respect to any securities
which are not Registrable Securities which are prior in right to or inconsistent
with the rights granted in this Agreement.

               (c) Remedies. The Designated Holders, in addition to being
entitled to exercise all rights granted by law, including recovery of damages,
shall be entitled to specific performance of their rights under this Agreement.
The Company agrees that monetary damages would not be adequate compensation for
any loss incurred by reason of a breach by it of the provisions of this
Agreement and hereby agrees to waive in any action for specific performance the
defense that a remedy at law would be adequate.

               (d) Amendments and Waivers. Except as otherwise provided herein,
the provisions of this Agreement may not be amended, modified or supplemented,
and waivers or consents to departures from the provisions hereof may not be
given unless consented to in writing by (i) the Company and (ii) the General
Atlantic Stockholders, Coinvestor Stockholders, Vectis Stockholders and Apex
Stockholders holding Registrable Securities representing (after giving effect to
any adjustments) at least a majority of the aggregate number of Registrable
Securities owned by all of the General Atlantic Stockholders, Coinvestor
Stockholders, Vectis Stockholders and Apex Stockholders; provided, however, that
to the extent any amendment or waiver shall adversely affect any of such
stockholders, such amendment or waiver shall require the prior written consent
of each stockholder so adversely affected. Any such written consent shall be
binding upon the Company and all of the Designated Holders.

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

                      (i)    if to the Company:

                             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 F. Vignos, Esq.

                                       19
<PAGE>

                      (ii)   if to the General Atlantic Stockholders:

                             c/o General Atlantic Service Company
                             3 Pickwick Plaza
                             Greenwich, CT  06830
                             Telecopy:  (203) 622-8818
                             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
                             Telecopy:  (212) 757-3990
                             Attention:  Douglas A. Cifu, Esq.

                      (iii)  if to Campina, Great Affluent, Dragonfield or Lion
                      Cosmos:

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

                      (iv)   if to Cenwell:

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

                      (v)    if to Vectis:

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

                                       20
<PAGE>

                             with a copy to:

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

                      (vi)   if to Apex Capital:

                             Apex Capital, LLC
                             25 Orinda Way, Suite 300
                             Orinda, CA 94563
                             Telecopy:  (925) 253-1809
                             Attention: Adam Fiore, General Counsel

                      (vii)  if to Passport Capital:

                             Passport Capital, LLC
                             One Sansome Street, 39th Floor
                             San Francisco, CA 94104
                             Telecopy:  (415) 399-7608
                             Attention: John Burbank, Managing Partner

                      (viii) if to Crosslink:

                             Crosslink Capital
                             Two Embarcadero Center, Suite 2200
                             San Francisco, CA 94111
                             Telecopy:  (415) 617-1801
                             Attention: Jason Sanders

                      (ix)   if to Sagamore:

                             Sagamore Hill Hub Fund, Ltd.
                             c/o Sagamore Hill Capital Management
                             10 Glenville Street, 3rd Floor
                             Greenwich, CT 06831
                             Telecopy:  (203) 422-7214
                             Attention: Legal Department

                      (x)    if to Criterion:

                             Criterion Capital Management
                             One Maritime Plaza, Suite 1460
                             San Francisco, CA 94111
                             Telecopy:___________________

                                       21
<PAGE>

                             Attention: R. Daniel Beckham

                      (xi)   if to Heights Capital:

                             Capital Ventures International
                             c/o Heights Capital Management, Inc.
                             425 California Street, Suite 1100
                             San Francisco, CA 94104
                             Telecopy:  (415) 403-6525
                             Attention: Martin Kobinger

                      (xii)  if to any other Designated Holder, at its address
                             as it appears on the record books of the Company.

        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 9(e) designate another address or
Person for receipt of notices hereunder.

               (f) Successors and Assigns; Third Party Beneficiaries. This
Agreement shall inure to the benefit of and be binding upon the successors and
permitted assigns of the parties hereto as hereinafter provided. The Demand
Registration rights and related rights of the General Atlantic Stockholders, the
Coinvestor Stockholders or the Apex Stockholders contained in Section 3 hereof
shall be (i) with respect to any Registrable Security that is transferred to an
Affiliate of a General Atlantic Stockholder, a Coinvestor Stockholder or an Apex
Stockholder, automatically transferred to such Affiliate and (ii) with respect
to any Registrable Security that is transferred in all cases to a non-Affiliate,
transferred only with the consent of the Company which consent shall not be
unreasonably withheld, conditioned or delayed. The incidental or "piggy-back"
registration rights of the Designated Holders contained in Sections 3(b) and 4
hereof and the other rights of each of the Designated Holders with respect
thereto shall be, with respect to any Registrable Security, automatically
transferred to any Person who is the transferee of such Registrable Security so
long as such transferee agrees to be bound by this Agreement. All of the
obligations of the Company hereunder shall survive any such transfer. Except as
provided in Section 7, no Person other than the parties hereto and their
successors and permitted assigns is intended to be a beneficiary of this
Agreement.

               (g) 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.

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

                                       22
<PAGE>

               (i) 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.

               (j) 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 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.

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

               (l) Entire Agreement. This Agreement 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
with respect to the subject matter contained herein. There are no restrictions,
promises, representations, warranties or undertakings with respect to the
subject matter contained herein, other than those set forth or referred to
herein. Subject to Section 9(o), upon the Subsequent Closing (as defined in the
Convertible Note Purchase and Exchange Agreement and the Convertible Note
Agreements), this Agreement shall supersede all prior agreements and
understandings among the parties with respect to such subject matter.

               (m) Further Assurances. Each of the parties shall 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.

               (n) Other Agreements. Nothing contained in this Agreement shall
be deemed to be a waiver of, or release from, any obligations any party hereto
may have under, or any restrictions on the transfer of Registrable Securities or
other securities of the Company imposed by, any other agreement including, but
not limited to, the Stock Purchase Agreement, the Convertible Note Purchase and
Exchange Agreement, the Convertible Note Agreements or the Amended and Restated
Stockholders Agreement.

               (o) Effective Date and Termination. Subject to the provisions of
this Section 9(o), 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 and the Conversion has
been terminated pursuant to Article IX of the Convertible Note Purchase and
Exchange Agreement or Article IX of the Convertible Note Agreements, then this
Agreement shall become effective as of the date of such termination; provided,
however, that Registrable Securities shall not include any shares of Common
Stock issued or issuable upon conversion of the Series E Preferred Stock.

              [the remainder of this page intentionally left blank]

                                       23
<PAGE>

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

                             CRITICAL PATH, INC.

                             By:
                                    --------------------------------------------
                                    Name:
                                    Title:

   SIGNATURE PAGE TO THIRD AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT

<PAGE>

                             GENERAL ATLANTIC PARTNERS 74, L.P.

                                    By:     GENERAL ATLANTIC PARTNERS, LLC,
                                            its General Partner

                                    By:
                                            ------------------------------------
                                            Name:
                                            Title:

                             GAP COINVESTMENT PARTNERS II, L.P.

                             By:
                                    --------------------------------------------
                                    Name:
                                    Title:

                             GAPSTAR, LLC

                                    By:     GENERAL ATLANTIC PARTNERS, LLC,
                                            its Managing Member

                                    By:
                                            ------------------------------------
                                            Name:
                                            Title:

                             GAPCO GMBH & CO. KG

                                    By:     GAPCO MANAGEMENT GMBH,
                                            its General Partner

                                    By:
                                            ------------------------------------
                                            Name:
                                            Title:

   SIGNATURE PAGE TO THIRD AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT

<PAGE>

                             VECTIS CP HOLDINGS, LLC,
                             a Delaware limited liability company

                             By:    VECTIS GROUP, LLC
                                    its Managing Member

                             By:
                                    --------------------------------------------
                                    Name:
                                    Title:

   SIGNATURE PAGE TO THIRD AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT

<PAGE>

                             CENWELL LIMITED

                             By:
                                    --------------------------------------------
                                    Name:
                                    Title:

                             CAMPINA ENTERPRISES LIMITED

                             By:
                                    --------------------------------------------
                                    Name:
                                    Title:

                             GREAT AFFLUENT LIMITED

                             By:
                                    --------------------------------------------
                                    Name:
                                    Title:

                             DRAGONFIELD LIMITED

                             By:
                                    --------------------------------------------
                                    Name:
                                    Title:

                             LION COSMOS LIMITED

                             By:
                                    --------------------------------------------
                                    Name:
                                    Title:

   SIGNATURE PAGE TO THIRD AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT

<PAGE>

                             PERMAL U.S. OPPORTUNITIES LIMITED

                             By:    Apex Capital, LLC, its Authorized Investment
                                    Advisor

                                    By:
                                       -----------------------------------------
                                    Name: Sanford J. Colen
                                    Title: Manager and Principal

                             ZAXIS PARTNERS, L.P.

                             By:    Apex Capital, LLC, its General Partner

                                    By:
                                       -----------------------------------------
                                       Name: Sanford J. Colen
                                       Title: Manager and Principal

                             ZAXIS EQUITY NEUTRAL, L.P.

                             By:    Apex Capital, LLC, its General Partner

                                    By:
                                       -----------------------------------------
                                       Name: Sanford J. Colen
                                       Title: Manager and Principal

                             ZAXIS OFFSHORE LIMITED

                             By:    Apex Capital, LLC, its Authorized Investment
                                    Advisor

                                    By:
                                       -----------------------------------------
                                       Name: Sanford J. Colen
                                       Title: Manager and Principal

   SIGNATURE PAGE TO THIRD AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT

<PAGE>

                             ZAXIS INSTITUTIONAL PARTNERS, L.P.

                             By:  Apex Capital, LLC, its General Partner

                                    By:
                                       -----------------------------------------
                                       Name: Sanford J. Colen
                                       Title: Manager and Principal

                             GUGGENHEIM PORTFOLIO COMPANY XIII

                             By:  Apex Capital, LLC, its Authorized Investment
                                  Advisor

                                    By:
                                       -----------------------------------------
                                       Name: Sanford J. Colen
                                       Title: Manager and Principal

   SIGNATURE PAGE TO THIRD AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT

<PAGE>

                             PASSPORT MASTER FUND, LP

                             By:
                                    --------------------------------------------
                                    Name: John Burbank
                                    Title: Managing Partner

   SIGNATURE PAGE TO THIRD AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT

<PAGE>

                             CROSSLINK CROSSOVER FUND IV, L.P.

                             By:    Crossover Fund IV Management, L.L.C.,
                                    its General Partner

                                    By:
                                       -----------------------------------------
                                       Name: Michael J. Stark
                                       Title: Managing Member

   SIGNATURE PAGE TO THIRD AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT

<PAGE>

                             SAGAMORE HILL HUB FUND, LTD.

                             By:    Sagamore Hill Capital Management L.P.,
                                    Investment Manager

                                    By:
                                       -----------------------------------------
                                       Name: Steven H. Bloom
                                       Title:  President

   SIGNATURE PAGE TO THIRD AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT

<PAGE>

                             CAPITAL VENTURES INTERNATIONAL

                             By:    Heights Capital Management, Inc., an
                                    authorized signatory

                                    By:
                                       -----------------------------------------
                                       Name: Martin Kobinger
                                       Title: Investment Manager

   SIGNATURE PAGE TO THIRD AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT

<PAGE>

                             CRITERION CAPITAL PARTNERS, LTD.

                             By:    Derivatives Portfolio Management, an
                                    authorized signatory

                                    By:
                                       -----------------------------------------
                                       Name: Guy J. Castranova
                                       Title:  Chief Operating Officer

                             CRITERION CAPITAL PARTNERS, INSTITUTIONAL

                             By:    Criterion Capital Partners, LLC, an
                                    authorized signatory

                                    By:
                                       -----------------------------------------
                                       Name: R. Daniel Beckham
                                       Title:  Chief Operating Officer

                             CRITERION CAPITAL PARTNERS, L.P.

                             By:    Criterion Capital Partners, LLC, an
                                    authorized signatory

                                    By:
                                       -----------------------------------------
                                       Name: R. Daniel Beckham
                                       Title:  Chief Operating Officer

   SIGNATURE PAGE TO THIRD AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT

<PAGE>

================================================================================

                           THIRD AMENDED AND RESTATED
                          REGISTRATION RIGHTS AGREEMENT

                                      among

                               CRITICAL PATH, INC.

                       GENERAL ATLANTIC PARTNERS 74, L.P.,

                       GAP COINVESTMENT PARTNERS II, L.P.,

                                  GAPSTAR, LLC,

                               GAPCO GMBH & CO. KG

                                       and

                         THE OTHER PARTIES LISTED HEREIN

                          ----------------------------
                              Dated: March 9, 2004
                          ----------------------------

================================================================================

<PAGE>

                                TABLE OF CONTENTS

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

2.      General; Securities Subject to this Agreement.................................7
        (a)    Grant of Rights........................................................7
        (b)    Registrable Securities.................................................7
        (c)    Holders of Registrable Securities......................................7

3.      Demand Registration...........................................................8
        (a)    Request for Demand Registration........................................8
        (b)    Incidental or "Piggy-Back" Rights with Respect to a Demand Registration9
        (c)    Effective Demand Registration..........................................9
        (d)    Expenses...............................................................9
        (e)    Underwriting Procedures...............................................10
        (f)    Selection of Underwriters.............................................10

4.      Incidental or "Piggy-Back" Registration......................................11
        (a)    Request for Incidental Registration...................................11
        (b)    Expenses..............................................................11

5.      Holdback Agreements..........................................................11
        (a)    Restrictions on Public Sale by Designated Holders.....................11
        (b)    Restrictions on Public Sale by the Company............................12

6.      Registration Procedures......................................................12
        (a)    Obligations of the Company............................................12
        (b)    Seller Information....................................................15
        (c)    Notice to Discontinue.................................................15
        (d)    Registration Expenses.................................................15

7.      Indemnification; Contribution................................................16
        (a)    Indemnification by the Company........................................16
        (b)    Indemnification by Designated Holders.................................16
        (c)    Conduct of Indemnification Proceedings................................17
        (d)    Contribution..........................................................17

8.      Rule 144.....................................................................18

9.      Miscellaneous................................................................18
        (a)    Recapitalizations, Exchanges, etc.....................................18
        (b)    No Inconsistent Agreements............................................19
        (c)    Remedies..............................................................19
        (d)    Amendments and Waivers................................................19
        (e)    Notices...............................................................19
        (f)    Successors and Assigns; Third Party Beneficiaries.....................22
</TABLE>

                                       i
<PAGE>

<TABLE>
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        (g)    Counterparts..........................................................22
        (h)    Headings..............................................................22
        (i)    Governing Law.........................................................23
        (j)    Severability..........................................................23
        (k)    Rules of Construction.................................................23
        (l)    Entire Agreement......................................................23
        (m)    Further Assurances....................................................23
        (n)    Other Agreements......................................................23
        (o)    Effective Date and Termination........................................23
</TABLE>

                                       ii

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