<PAGE>

                                                                     EXHIBIT 4.2

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                              AMENDED AND RESTATED
                          REGISTRATION RIGHTS AGREEMENT

                                      among

                               CRITICAL PATH, INC.

                       GENERAL ATLANTIC PARTNERS 74, L.P.,

                       GAP COINVESTMENT PARTNERS II, L.P.,

                                  GAPSTAR, LLC,

                                   GAP-W, LLC,

                               GAPCO GMBH & CO. KG

                                       and

                         THE OTHER PARTIES LISTED HEREIN

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                            Dated: November __, 2003

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<PAGE>

                                TABLE OF CONTENTS

<TABLE>
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1.       Definitions....................................................................................           2

2.       General; Securities Subject to this Agreement..................................................           5
         (a)      Grant of Rights.......................................................................           5
         (b)      Registrable Securities................................................................           5
         (c)      Holders of Registrable Securities.....................................................           5

3.       Demand Registration............................................................................           5
         (a)      Request for Demand Registration.......................................................           5
         (b)      Incidental or "Piggy-Back" Rights with Respect to a Demand Registration...............           6
         (c)      Effective Demand Registration.........................................................           7
         (d)      Expenses..............................................................................           7
         (e)      Underwriting Procedures...............................................................           7
         (f)      Selection of Underwriters.............................................................           8

4.       Incidental or "Piggy-Back" Registration........................................................           8
         (a)      Request for Incidental Registration...................................................           8
         (b)      Expenses..............................................................................           9

5.       Holdback Agreements............................................................................           9
         (a)      Restrictions on Public Sale by Designated Holders.....................................           9
         (b)      Restrictions on Public Sale by the Company............................................           9

6.       Registration Procedures........................................................................           9
         (a)      Obligations of the Company............................................................           9
         (b)      Seller Information....................................................................          12
         (c)      Notice to Discontinue.................................................................          12
         (d)      Registration Expenses.................................................................          13

7.       Indemnification; Contribution..................................................................          13
         (a)      Indemnification by the Company........................................................          13
         (b)      Indemnification by Designated Holders.................................................          14
         (c)      Conduct of Indemnification Proceedings................................................          14
         (d)      Contribution..........................................................................          15

8.       Rule 144.......................................................................................          15

9.       Miscellaneous..................................................................................          16
         (a)      Recapitalizations, Exchanges, etc.....................................................          16
         (b)      No Inconsistent Agreements............................................................          16
         (c)      Remedies..............................................................................          16
         (d)      Amendments and Waivers................................................................          16
         (e)      Notices...............................................................................          16
         (f)      Successors and Assigns; Third Party Beneficiaries.....................................          18
</TABLE>

                                       i

<PAGE>

<TABLE>
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(g)      Counterparts...................................................................................          19
(h)      Headings.......................................................................................          19
(i)      Governing Law..................................................................................          19
(j)      Severability...................................................................................          19
(k)      Rules of Construction..........................................................................          19
(l)      Entire Agreement...............................................................................          19
(m)      Further Assurances.............................................................................          19
(n)      Other Agreements...............................................................................          19
(o)      Effective Date and Termination.................................................................          20
</TABLE>

                                       ii

<PAGE>

                              AMENDED AND RESTATED

                          REGISTRATION RIGHTS AGREEMENT

         AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT, dated November __,
2003 (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"), GAP-W, LLC, a Delaware limited liability company ("GAP-W"),
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") and Vectis CP Holdings, LLC, a Delaware limited
liability company ("Vectis").

         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, Campina,
Cenwell, Great Affluent, Dragonfield and Lion Cosmos, (i) the Company has issued
and sold to GAP LP, GAP Coinvestment, GapStar, GAP-W and GmbH Coinvestment
convertible promissory notes (the "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; and

         WHEREAS, in order to induce (i) each of GAP LP, GAP Coinvestment,
GapStar, GAP-W and GmbH Coinvestment 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:

<PAGE>

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

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

                  "Agreement" mean 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, GAP-W, GmbH Coinvestment and the
Persons listed therein as "Coinvestors."

                  "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 5 3/4 % 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.

                                       2

<PAGE>

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

                  "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 and the Vectis 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.

                  "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.

                  "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.

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

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

                  "General Atlantic Stockholders" means GAP LP, GAP
Coinvestment, GapStar, GAP-W, 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.

                  "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.

                                       3

<PAGE>

                  "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.

                  "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.

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

                  "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, Series E Preferred Stock or exercise of the Warrants,
(b) 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 (c) 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.

                  "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.

                                       4

<PAGE>

                  "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 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
commencing one year after the date hereof, either the General Atlantic
Stockholders or the Coinvestor Stockholders

                                       5

<PAGE>

(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) and
more than one such Demand Registration for the Coinvestor Stockholders (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 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

                                       6

<PAGE>

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 after such filing. A
registration shall not constitute a Demand Registration until it has become
effective and remains continuously effective for the lesser of (i) the period
during which all Registrable Securities registered in the Demand Registration
are sold and (ii) one hundred twenty (120) days; 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 effective.

                  (e)      Underwriting Procedures.

                           (i)      If the Company or the Initiating Holders
holding a majority of the Registrable Securities held by all of the Initiating
Holders so elect, the Company shall use all commercially reasonable efforts to
cause such Demand Registration to be in the form of 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.

                                       7

<PAGE>

                           (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.

         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

                                       8

<PAGE>

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 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.

                  (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

                                       9

<PAGE>

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;

                           (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;

                                       10

<PAGE>

                           (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
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" letters dated the effective date of the
Registration Statement and the date of the closing

                                       11

<PAGE>

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
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, 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 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

                                       12

<PAGE>

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 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.

                                       13

<PAGE>

                  (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 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

                                       14

<PAGE>

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 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.

                                       15

<PAGE>

         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.

                  (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 and Vectis 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 and Vectis Stockholders; provided, however, that to the extent any
amendment or waiver shall adversely affect any of the 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:

                                       16

<PAGE>

                                (i) if to the Company:

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

                                    with a copy to:

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

                               (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

                                       17

<PAGE>

                               (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

                                    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 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 or
the Coinvestor 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 or a Coinvestor 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

                                       18

<PAGE>

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.

                  (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), 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 or the Amended and Restated Stockholders
Agreement.

                                       19

<PAGE>

                  (o)      Effective Date and Termination. Notwithstanding
anything in this Agreement to the contrary, this Agreement shall become
effective immediately following the Subsequent Closing. If the Subsequent
Closing does not occur and the obligation to consummate the Conversion and the
Exchange (each as defined in the Convertible Note Purchase Agreement) has been
terminated pursuant to Article IX of the Convertible Note Purchase and Exchange
Agreement, this Agreement shall immediately terminate and be of no further force
or effect.

              [the remainder of this page intentionally left blank]

                                       20

<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:

                                    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:

      SIGNATURE PAGE TO AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT

<PAGE>

                                    GAP-W, LLC

                                    By: GENERAL ATLANTIC PARTNERS, LLC,
                                        its Manager

                                    By: _________________________________
                                        Name:
                                        Title:

                                    CAPCO GMBH & CO. KG

                                    By: GAPCO MANAGEMENT GMBH,
                                        its General Partner

                                    By: _________________________________
                                        Name:
                                        Title:

                                    VECTIS CP HOLDINGS, LLC,
                                    a Delaware limited liability company

                                    By: VECTIS GROUP, LLC
                                        its Managing Member

                                    By: _____________________________________
                                        Name:
                                        Title:

      SIGNATURE PAGE TO AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT

<PAGE>

                                    CENWELL LIMITED

                                    By: _____________________________________
                                        Name:
                                        Title:

                                    CAMPINA ENTERPRISES LIMITED

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                                        Name:
                                        Title:

                                    GREAT AFFLUENT LIMITED

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                                        Name:
                                        Title:

                                    DRAGONFIELD LIMITED

                                    By: _____________________________________
                                        Name:
                                        Title:

                                    LION COSMOS LIMITED

                                    By: _____________________________________
                                        Name:
                                        Title:

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