Document:

<PAGE>

                                                                    EXHIBIT 4.46

THIS WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN REGISTERED UNDER
THE SECURITIES ACT OF 1933, AS AMENDED (THE "ACT"), OR THE SECURITIES LAWS OF
ANY STATE AND, EXCEPT AND PURSUANT TO THE PROVISIONS OF ARTICLE 5 BELOW, MAY NOT
BE OFFERED, SOLD OR OTHERWISE TRANSFERRED, PLEDGED OR HYPOTHECATED UNLESS AND
UNTIL REGISTERED UNDER SAID ACT AND APPLICABLE STATE SECURITIES LAW OR, IN THE
OPINION OF LEGAL COUNSEL IN FORM AND SUBSTANCE SATISFACTORY TO THE ISSUER OF
THESE SECURITIES, SUCH OFFER, SALE OR TRANSFER, PLEDGE OR HYPOTHECATION IS
EXEMPT FROM REGISTRATION.

                            WARRANT TO PURCHASE STOCK

Company: Critical Path, Inc., a California corporation
Number of Shares: 100,000
Class of Stock: Common Stock
Warrant Price: $2.07 per Share
Issue Date: March 12, 2004
Expiration Date: March 12, 2011

THIS WARRANT CERTIFIES THAT, for the agreed upon value of $1.00 and for other
good and valuable consideration, SILICON VALLEY BANK ("Holder") is entitled to
purchase the number of fully paid and nonassessable shares of the class of
securities (the "Shares") of the company (the "Company") at the Warrant Price
all as set forth above and as adjusted pursuant to Article 2 of this Warrant,
subject to the provisions and upon the terms and conditions set forth in this
Warrant.

ARTICLE 1.        EXERCISE.

                  1.1.     Method of Exercise. Holder may exercise this Warrant
by delivering a duly executed Notice of Exercise, in substantially the form
attached hereto as Appendix 1, to the principal office of the Company. Unless
Holder is exercising the conversion right set forth in Article 1.2, Holder shall
also deliver to the Company a check, wire transfer (to an account designated by
the Company), or other from of payment acceptable to the Company, for the
aggregate Warrant Price for the Shares being purchased.

                  1.2.     Conversion Right. In lieu of exercising this Warrant
as specified in Article 1.1, Holder may from time to time convert this Warrant,
in whole or in part, into a number of Shares determined by dividing (i) the
aggregate fair market value of the Shares or other securities otherwise issuable
upon exercise of this Warrant minus the aggregate Warrant Price of such Shares
by (ii) the fair market value of one Share. The fair market value of the Shares
shall be determined pursuant to Article 1.3.

                  1.3.     Fair Market Value. If the Company's common stock is
traded in a public market and the shares are common stock, the fair market value
of each Share shall be the closing price of a Share reported for the business
day immediately before Holder delivers its Notice of Exercise to the Company (or
in the instance where the Warrant is exercised immediately prior to the
effectiveness of the Company's initial public offering, the "price to public"
per share price specified in the final prospectus relating to such offering). If
the Company's common stock is traded in a public market and the Shares are
preferred stock, the fair market value of a Share shall be the closing price of
a share of the Company's common stock reported for the business day immediately
before Holder delivers its Notice of Exercise to the Company (or, in the
instance where the Warrant is exercised immediately prior to the effectiveness
of the Company's initial public offering, the initial "price to public" per
share price specified in the final prospectus relating to such offering), in
both cases, multiplied by the number of shares of the Company's common stock
into which a Share is convertible. If the Company's common stock is not traded
in a public market, the Board of Directors of the Company shall determine fair
market value in its reasonable good faith judgment.

<PAGE>

                  1.4.     Delivery of Certificate and New Warrant. Promptly
after Holder exercises or converts this Warrant and, if applicable, the Company
receives payment of the aggregate Warrant Price, the Company shall deliver to
Holder certificates for the Shares acquired and, if this Warrant has not been
fully exercised or converted and has not expired, a new Warrant representing the
Shares not so acquired.

                  1.5.     Replacement of Warrants. On receipt of evidence
reasonably satisfactory to the Company of the loss, theft, destruction or
mutilation of this Warrant and, in the case of loss, theft or destruction, on
delivery of an indemnity agreement reasonably satisfactory in form and amount to
the Company or, in the case of mutilation, surrender and cancellation of this
Warrant, the Company shall execute and deliver to Holder, in lieu of this
Warrant, a new warrant of like tenor.

                  1.6.     Treatment of Warrant Upon Acquisition of Company.

                           1.6.1    "Acquisition". For the purpose of this
Warrant, "Acquisition" means any sale, license, or other disposition of all or
substantially all of the assets of the Company, or any reorganization,
consolidation, or merger of the Company where the holders of the Company's
securities before the transaction beneficially own less than 50% of the
outstanding voting securities of the surviving entity after the transaction.

                           1.6.2    Treatment of Warrant at Acquisition.

                           (a)      Upon the written request of the Company,
Holder agrees that, in the event of an Acquisition that is not an asset sale and
in which the sole consideration is cash and the per-share value of the Company's
common stock at the time of such sale is at least ten times the Warrant Price,
either (i) Holder shall exercise its conversion or purchase right under this
Warrant and such exercise will be deemed effective immediately prior to the
consummation of such Acquisition or (ii) if Holder elects not to exercise the
Warrant, this Warrant will expire upon the consummation of such Acquisition. The
Company shall provide Holder with written notice of its request relating to the
foregoing (together with such reasonable information as Holder may request in
connection with such contemplated Acquisition giving rise to such notice), which
is to be delivered to Holder not less than thirty (30) days prior to the closing
of the proposed Acquisition.

                           (b)      Upon the written request of the Company,
Holder agrees that, in the event of an Acquisition that is an "arms length" sale
of all or substantially all of the Company's assets (and only its assets) to a
third party that is not an Affiliate (as defined below) of the Company (a "True
Asset Sale"), either (i) Holder may exercise its conversion or purchase right
under this Warrant and such exercise will be deemed effective immediately prior
to the consummation of such Acquisition or (ii) if Holder elects not to exercise
the Warrant, this Warrant will continue until the Expiration Date if the Company
continues as a going concern following the closing of any such True Asset Sale.
The Company shall provide Holder with written notice of its request relating to
the foregoing (together with such reasonable information as Holder may request
in connection with such contemplated Acquisition giving rise to such notice),
which is to be delivered to Holder not less than thirty (30) days prior to the
closing of the proposed Acquisition.

                           (c)      Upon the closing of any Acquisition other
than those particularly described in subsections (a) and (b) above, the
successor entity shall assume the obligations of this Warrant, and this Warrant
shall be exercisable for the same securities, cash, and property as would be
payable for the Shares issuable upon exercise of the unexercised portion of this
Warrant as if such Shares were outstanding on the record date for the
Acquisition and subsequent closing. The Warrant Price and/or number of Shares
shall be adjusted accordingly.

As used herein "Affiliate" shall mean any person or entity that owns or controls
directly or indirectly ten (10) percent or more of the stock of Company, any
person or entity that controls or is controlled by or is under common control
with such persons or entities, and each of such person's or entity's officers,
directors, joint venturers or partners, as applicable.

                                       2
<PAGE>

ARTICLE 2.        ADJUSTMENTS TO THE SHARES.

                  2.1.     Stock Dividends, Splits, Etc. If the Company declares
or pays a dividend on the Shares payable in its common stock or other
securities, then upon exercise of this Warrant, for each Share acquired, Holder
shall receive, without cost to Holder, the total number and kind of securities
to which Holder would have been entitled had Holder owned the Shares of record
as of the date on which the dividend occurred. If the Company subdivides the
Shares by reclassification or otherwise into a greater number of shares or takes
any other action which increase the amount of stock into which the Shares are
convertible, the number of shares purchasable hereunder shall be proportionately
increased and the Warrant Price shall be proportionately decreased. If the
outstanding shares are combined or consolidated, by reclassification or
otherwise, into a lesser number of shares, the Warrant Price shall be
proportionately increased and the number of Shares shall be proportionately
decreased.

                  2.2.     Reclassification, Exchange, Combinations or
Substitution. Upon any reclassification, exchange, combination, substitution or
other event that results in a change of the number and/or class of the
securities issuable upon exercise or conversion of this Warrant, Holder shall be
entitled to receive, upon exercise or conversion of this Warrant, the number and
kind of securities and property that Holder would have received for the Shares
if this Warrant had been exercised immediately before such reclassification,
exchange, combination, substitution or other event. Such an event shall include
any automatic conversion of the outstanding or issuable securities of the
Company of the same class or series as the Shares to common stock pursuant to
the terms of the Company's Articles of Incorporation upon the closing of a
registered public offering of the Company's common stock. The Company or its
successor shall promptly issue to Holder an amendment to this Warrant setting
forth the number and kind of such new securities or other property issuable upon
exercise or conversion of this Warrant as a result of such reclassification,
exchange, combination, substitution or other event that results in a change of
the number and/or class of securities issuable upon exercise or conversion of
this Warrant. The amendment to this Warrant shall provide for adjustments which
shall be as nearly equivalent as may be practicable to the adjustments provided
for in this Article 2 including, without limitation, adjustments to the Warrant
Price and to the number of securities or property issuable upon exercise of the
new Warrant. The provisions of this Article 2.2 shall similarly apply to
successive reclassifications, exchanges, substitutions, or other events.

                  2.3.     Adjustments for Diluting Issuances. The Warrant Price
and the number of Shares issuable upon exercise of this Warrant or, if the
Shares are Preferred Stock, the number of shares of common stock issuable upon
conversion of the Shares, shall be subject to adjustment, from time to time in
the manner set forth in the Company's Articles or Certificate of Incorporation
as if the Shares were issued and outstanding on and as of the date of any such
required adjustment. The provisions set forth for the Shares in the Company's
Articles of Incorporation relating to the above in effect as of the Issue Date
may not be amended, modified or waived without the prior written consent of
Holder unless such amendment, modification or waiver affects the rights
associated with the Shares in the same manner as such amendment, modification or
waiver affects the rights associated with all other shares of the same series
and class as the Shares granted to the Holder.

                  2.4.     No Impairment. The Company shall not, by amendment of
its Articles of Incorporation or through a reorganization, transfer of assets,
consolidation, merger, dissolution, issue or sale of securities, or any other
voluntary action, avoid or seek to avoid the observance or performance of any of
the terms to be observed or performed under this Warrant by the Company, but
shall at all times in good faith assist in carrying out of all the provisions of
this Article 2 and in taking all such action as may be necessary or appropriate
to protect Holder's rights under this Article against impairment.

                  2.5.     Fractional Shares. No fractional Shares shall be
issuable upon exercise or conversion of the Warrant, and the number of Shares to
be issued shall be rounded down to the nearest whole Share. If a fractional
share interest arises upon any exercise or conversion of the Warrant, the
Company shall eliminate such fractional share interest by paying Holder the
amount computed by multiplying the fractional interest by the fair market value
of a full Share.

                                       3
<PAGE>

                  2.6.     Certificate as to Adjustments. Upon each adjustment
of the Warrant Price, the Company shall promptly notify Holder in writing and,
at the Company's expense, promptly compute such adjustment and furnish Holder
with a certificate of its Chief Financial Officer setting forth such adjustment
and the facts upon which such adjustment is based. The Company shall, upon
written request, furnish Holder with a certificate setting forth the Warrant
Price in effect upon the date thereof and the series of adjustments leading to
such Warrant Price.

ARTICLE 3.        REPRESENTATIONS AND COVENANTS OF THE COMPANY.

                  3.1.     Representations and Warranties. The Company
represents and warrants to the Holder as follows:

                           (a)      The initial Warrant Price referenced on the
first page of this Warrant is not greater than (i) the price per share at which
the Shares were last issued in an arms-length transaction in which the Shares
were sold and (ii) the fair market value of the Shares as of the date of this
Warrant.

                           (b)      All Shares which may be issued upon the
exercise of the purchase right represented by this Warrant, and all securities,
if any, issuable upon conversion of the Shares, shall upon issuance be duly
authorized, validly issued, fully paid and nonassessable, and free of any liens
and encumbrances except for restrictions on transfer provided for herein or
under applicable federal and state securities laws.

                           (c)      The Capitalization Table previously provided
to Holder remains true and complete as of the Issue Date.

                  3.2.     Notice of Certain Events. If the Company proposes at
any time (i) to declare any dividend or distribution upon any of its stock,
whether in cash, property, stock or other securities and whether or not a
regular cash dividend, (ii) to offer for sale additional shares of any class or
series of the Company's stock, (iii) to effect any reclassification or
recapitalization of any of its stock, (iv) to merge or consolidate with or into
any other corporation, or sell, lease, license or convey all or substantially
all of its assets, or liquidate, dissolve or wind up, or (v) to offer holders of
registration rights the opportunity to participate in an underwritten public
offering of the company's securities for cash, then, in connection with each
such event, the Company shall give Holder: (1) at least 30 days prior written
notice of the date on which a record will be taken for such dividend,
distribution or subscription rights (and specifying the date on which the
holders of common stock will be entitled thereto) or for determining rights to
vote (if any) in respect of the matters referred to in (i) and (ii) above; (2)
in the case of the matters referred to in (iii) and (iv) above at least 30 days
prior written notice of the date when the same will take place (and specifying
the date on which the holders of common stock will be entitled to exchange their
common stock for securities or other property deliverable upon the occurrence of
such event); and (3) in the case of the matter referred to in (v) above, the
same notice as is given to the holders of such registration rights.

                  3.3.     Registration Under Securities Act of 1933, as amended
(the "Act"). The Company agrees that the Shares (or, if the Shares are
convertible into common stock of the Company, such common stock) shall have
certain incidental, or "Piggyback," and Form S-3 registration rights pursuant to
and as set forth in the Company's Investor Rights Agreement or similar
agreement. The provisions set forth in the Company's Investors' Right Agreement
or similar agreement relating to the above in effect as of the Issue Date may
not be amended, modified or waived without the prior written consent of Holder
unless such amendment, modification or waiver affects the rights associated with
the Shares in the same manner as such amendment, modification or waiver affects
the rights associated with all other shares of the same series and class as the
Shares granted to the Holder.

                  3.4.     No Shareholder Rights. Except as provided in this
Warrant, the Holder will not have any rights as a shareholder of the Company
until the exercise of this Warrant.

                                       4
<PAGE>

ARTICLE 4.        REPRESENTATIONS, WARRANTIES OF THE HOLDER. THE HOLDER
REPRESENTS AND WARRANTS TO THE COMPANY AS FOLLOWS:

                  4.1.     Purchase for Own Account. This Warrant and the
securities to be acquired upon exercise of this Warrant by the Holder will be
acquired for investment for the Holder's account, not as a nominee or agent, and
not with a view to the public resale or distribution within the meaning of the
Act. Holder also represents that the Holder has not been formed for the specific
purpose of acquiring this Warrant or the Shares.

                  4.2.     Disclosure of Information. The Holder has received or
has had full access to all the information it considers necessary or appropriate
to make an informed investment decision with respect to the acquisition of this
Warrant and its underlying securities. The Holder further has had an opportunity
to ask questions and receive answers from the Company regarding the terms and
conditions of the offering of this Warrant and its underlying securities and to
obtain additional information (to the extent the Company possessed such
information or could acquire it without unreasonable effort or expense)
necessary to verify any information furnished to the Holder or to which the
Holder has access.

                  4.3.     Investment Experience. The Holder understands that
the purchase of this Warrant and its underlying securities involves substantial
risk. The Holder has experience as an investor in securities of companies in the
development stage and acknowledges that the Holder can bear the economic risk of
such Holder's investment in this Warrant and its underlying securities and has
such knowledge and experience in financial or business matters that the Holder
is capable of evaluating the merits and risks of its investment in this Warrant
and its underlying securities and/or has a preexisting personal or business
relationship with the Company and certain of its officers, directors or
controlling persons of a nature and duration that enables the Holder to be aware
of the character, business acumen and financial circumstances of such persons.

                  4.4.     Accredited Investor Status. The Holder is an
"accredited investor" within the meaning of Regulation D promulgated under the
Act.

                  4.5.     No Registration. The Holder understands that this
Warrant and the Shares issuable upon exercise or conversion hereof have not been
registered under the Act in reliance upon a specific exemption therefrom, which
exemption depends upon, among other things, the bona fide nature of the Holder's
investment intent as expressed herein. The Holder understands that this Warrant
and the Shares issued upon any exercise or conversion hereof must be held
indefinitely unless subsequently registered under the Act and qualified under
applicable state securities laws, or unless exemption from such registration and
qualification are otherwise available.

ARTICLE 5.        MISCELLANEOUS.

                  5.1.     Term. This Warrant is exercisable in whole or in part
at any time and from time to time on or before the Expiration Date (except as
otherwise expressly provided in Sections 1.6 and 1.7 hereof).

                  5.2.     Legends. This Warrant and the Shares (and the
securities issuable, directly or indirectly, upon conversion of the Shares, if
any) shall be imprinted with a legend in substantially the following form:

                  THIS WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE
                  NOT BEEN REGISTERED UNDER THE ACT, OR THE SECURITIES
                  LAWS OF ANY STATE AND, EXCEPT AND PURSUANT TO THE
                  PROVISIONS OF ARTICLE 5 BELOW, MAY NOT BE OFFERED,
                  SOLD OR OTHERWISE TRANSFERRED, PLEDGED OR
                  HYPOTHECATED UNLESS AND UNTIL REGISTERED UNDER SAID
                  ACT AND APPLICABLE STATE SECURITIES LAW OR, IN THE
                  OPINION OF

                                  5
<PAGE>

                  LEGAL COUNSEL IN FORM AND SUBSTANCE SATISFACTORY TO
                  THE ISSUER OF THESE SECURITIES, SUCH OFFER, SALE OR
                  TRANSFER, PLEDGE OR HYPOTHECATION IS EXEMPT FROM
                  REGISTRATION.

                  5.3.     Compliance with Securities Laws on Transfer. This
Warrant and the Shares issuable upon exercise of this Warrant (and the
securities issuable, directly or indirectly, upon conversion of the
Shares, if any) may not be transferred or assigned in whole or in part
without compliance with applicable federal and state securities laws
by the transferor and the transferee (including, without limitation,
the delivery of investment representation letters and legal opinions
reasonably satisfactory to the Company, as reasonably requested by the
Company). The Company shall not require Holder to provide an opinion
of counsel if the transfer is to Silicon Valley Bancshares (Holder's
parent company) or any other affiliate of Holder. Additionally, the
Company shall also not require an opinion of counsel if there is no
material question as to the availability of current information as
referenced in Rule 144(c), Holder represents that it has complied with
Rule 144(d) and (e) in reasonable detail, the selling broker
represents that it has complied with Rule 144(f), and the Company is
provided with a copy of Holder's notice of proposed sale.

                  5.4.     Transfer Procedure. Upon receipt by Holder of the
executed Warrant, Holder will transfer all of this Warrant to Silicon
Valley Bancshares, Holder's parent company, by execution of an
Assignment substantially in the form of Appendix 2. Subject to the
provisions of Article 5.3 and upon providing Company with written
notice, Silicon Valley Bancshares and any subsequent Holder may
transfer all or part of this Warrant or the Shares issuable upon
exercise of this Warrant (or the Shares issuable directly or
indirectly, upon conversion of the Shares, if any) to any transferee,
provided, however, in connection with any such transfer, Silicon
Valley Bancshares or any subsequent Holder will give the Company
notice of the portion of the Warrant being transferred with the name,
address and taxpayer identification number of the transferee and
Holder will surrender this Warrant to the Company for reissuance to
the transferee(s) (and Holder if applicable). The Company may refuse
to transfer this Warrant or the Shares to any person who directly
competes with the Company, unless, in either case, the stock of the
Company is publicly traded.

                  5.5.     Notices. All notices and other communications from
the Company to the Holder, or vice versa, shall be deemed delivered
and effective when given personally or mailed by first-class
registered or certified mail, postage prepaid, at such address as may
have been furnished to the Company or the Holder, as the case may (or
on the first business day after transmission by facsimile) be, in
writing by the Company or such holder from time to time. Effective
upon receipt of the fully executed Warrant and the initial transfer
described in Article 5.4 above, all notices to the Holder shall be
addressed as follows until the Company receives notice of a change of
address in connection with a transfer or otherwise:

                           Silicon Valley Bancshares
                           Attn: Treasury Department
                           3003 Tasman Drive, HA 200
                           Santa Clara, CA 95054
                           Telephone: 408-654-7400
                           Facsimile: 408-496-2405

         Notice to the Company shall be addressed as follows until the Holder
receives notice of a change in address:

                           _________________________
                           Attn:____________________
                           _________________________
                           _________________________
                           Telephone:  (___) _______________
                           Facsimile:  (___) _______________

                                  6
<PAGE>

                  5.6.     Waiver. This Warrant and any term hereof
may be changed, waived, discharged or terminated only by an instrument
in writing signed by the party against which enforcement of such
change, waiver, discharge or termination is sought.

                  5.7.     Attorneys' Fees. In the event of any
dispute between the parties concerning the terms and provisions of
this Warrant, the party prevailing in such dispute shall be entitled
to collect from the other party all costs incurred in such dispute,
including reasonable attorneys' fees.

                  5.8.     Automatic Conversion upon Expiration. In
the event that upon the Expiration Date the fair market value of one
Share (or other security issuable upon the exercise hereof) as
determined in accordance with Section 1.3 above is greater than the
Exercise Price in effect on such date, then this Warrant shall
automatically be deemed on and as of such date to be converted
pursuant to Section 1.2 above as to all Shares (or such other
securities) for which it shall not previously have been exercised or
converted, and the Company shall promptly deliver a certificate
representing the Shares (or such other securities) issued upon such
conversion to the Holder.

                  5.9.     Counterparts. This Warrant may be executed
in counterparts, all of which together shall constitute one and the
same agreement.

                                  7
<PAGE>

                  5.10.    Governing Law. This Warrant shall be
governed by and construed in accordance with the laws of the State of
California, without giving effect to its principles regarding
conflicts of law.

                                    "HOLDER"

                                    Silicon Valley Bank

                                    By: /s/ Brian Harrison
                                       -------------------------------------
                                    Name:  Brian Harrison
                                           ----------------------------------
                                           (Print)
                                    Title: Vice President

                                    "COMPANY"
                                    Critical Path, Inc.
                                    a California corporation

                                    By: /s/ William E. McGlashan, Jr.
                                       -------------------------------------

                                    Name: /s/ William E. McGlashan, Jr.
                                         -----------------------------------
                                           (Print)
                                    Title: Chairman of the Board,
                                           President or Vice President

                                    By: /s/ James A. Clark
                                       -------------------------------------

                                    Name:  James A. Clark
                                           ----------------------------------
                                           (Print)
                                    Title: Chief Financial Officer,
                                           Secretary, Assistant Treasurer
                                           or Assistant Secretary

                                  8
<PAGE>

                                   APPENDIX 1

                               NOTICE OF EXERCISE

         1.       Holder elects to purchase ___________ shares of the
Common/Series ______ Preferred [strike one] Stock of _________________
pursuant to the terms of the attached Warrant, and tenders payment of
the purchase price of the shares in full.

                  [or]

         1.       Holder elects to convert the attached Warrant into
Shares/cash [strike one] in the manner specified in the Warrant. This
conversion is exercised for _____________________ of the Shares
covered by the Warrant.

         [Strike paragraph that does not apply.]

         2.       Please issue a certificate or certificates
representing the shares in the name specified below:

                           ___________________________________________
                                    Holders Name

                           ___________________________________________

                           ___________________________________________
                                    (Address)

         3.       By its execution below and for the benefit of the
Company, Holder hereby restates each of the representations and
warranties in Article 4 of the Warrant as the date hereof.

                                    HOLDER:

                                    By:_____________________________________

                                    Name:___________________________________

                                    Title:__________________________________

                                    (Date):_________________________________

                                  9
<PAGE>

                              APPENDIX 2

                              ASSIGNMENT

For value received, Silicon Valley Bank hereby sells, assigns and
transfers unto

                           Name:      Silicon Valley Bancshares
                           Address:   3003 Tasman Drive (HA-200)
                                      Santa Clara, CA 95054

                           Tax ID:    91-1962278

that certain Warrant to Purchase Stock issued by Critical Path, Inc.
(the "Company"), on March 11, 2004 (the "Warrant") together with all
rights, title and interest therein.

                                    SILICON VALLEY BANK

                                    By:_____________________________________

                                    Name:___________________________________

                                    Title:__________________________________

Date: [insert Issue Date] ________________

By its execution below, and for the benefit of the Company, Silicon
Valley Bancshares makes each of the representations and warranties set
forth in Article 4 of the Warrant as of the date hereof.

                                    SILICON VALLEY BANCSHARES

                                    By:_____________________________________

                                    Name:___________________________________

                                    Title:__________________________________

                                  10<PAGE>

                                                                   EXHIBIT 10.42

                        AMENDMENT TO EMPLOYMENT AGREEMENT
                              AND RELEASE OF CLAIMS

         This Amendment to Employment Agreement and Release of Claims
("Agreement") is made by and between CRITICAL PATH, INC. (the "Company"), and
Bernard Harguindeguy ("Employee") (collectively referred to herein as the
"Parties") and dated as of May 16, 2003.

         WHEREAS, Employee has been employed by the Company pursuant to an
Employment Agreement by and between the Parties dated as of January 14, 2002
("Employment Agreement");

         WHEREAS, Employee and Company hereby agree to terminate certain terms
and conditions of such Employment Agreement, and amend and replace in its
entirety that certain Employment Agreement; and

         WHEREAS, Employee and Company hereby agree to the terms and conditions
of a modified employment relationship going forward;

         NOW THEREFORE, in consideration of the mutual promises made herein, the
Company and Employee hereby agree as follows:

1.       Modification of Employment. Employee's full-time employment as
Executive Vice President and Chief Marketing Officer, including all payment of
regular base salary and eligibility for bonuses, will terminate as of May 16,
2003 ("Effective Date"), and the Employment Agreement shall thereafter be null
and void and have no further force and effect, except as specifically
contemplated and described herein. As of the Effective Date, Employee's services
to the Company shall continue as General Manager, Identity Management, reporting
to Bill McGlashan. As of the Effective Date, Employee shall provide services in
this capacity and shall be compensated in accordance with a new Compensation
Plan ("Plan"), as mutually identified, agreed and determined by the Parties, no
later than June 20, 2003. Such Plan shall be appended to this Agreement in the
form of EXHIBIT A hereto, as soon as such Plan is finalized and shall thereafter
be incorporated by reference and form a part of this Agreement. The failure for
any reason to finalize the plan shall not affect any provision of this Agreement
or the validity of any release given hereunder.. Employee shall continue to be
covered by all employee health and welfare benefit plans pursuant to the terms
and conditions of the Employment Agreement other than Paid Time Off which ceased
accruing as of January 2003. Employee's right to continued indemnification under
the Employment Agreement shall terminate as of the Effective Date.

2.       Consideration. Upon the Effective Date, the Company agrees to pay
Employee three-hundred thousand dollars and zero cents ($300,000.00), which
equals twelve (12) month's salary at the Employee's then current base salary and
will be paid less all the

<PAGE>

applicable withholdings, in accordance with the Company's standard payroll
practices (the "Employment Agreement Amount").

3.       Vesting of Stock Options. As of the Effective Date, you shall continue
to vest in all previously granted options to purchase shares of Company common
stock in accordance with the applicable vesting schedules found in each Stock
Option Agreement and as provided in the Employment Agreement. Nothing in this
Agreement is intended to otherwise supersede or modify the terms and conditions
of the Company's Stock Option Plans or any agreements issued in connection with
those plans including any provision contained in any agreement (including the
Employment Agreement) for accelerated vesting and/or any change of control
arrangement.

4.       Benefits. Employee shall continue to receive all applicable health and
welfare benefit plans as previously provided. Nothing in this Agreement is
intended to supercede or modify the terms and conditions of the Company's health
benefits plans. The other benefits provided for under the Employment Agreement
which shall continue under this Agreement shall include reimbursement for
amounts used for the lease of an automobile, parking and commute fuel expenses.

5.       Payment of Salary. On the Effective Date, Company shall pay Employee
for final earned but unpaid salary through the Effective Date. Company will
continue to reimburse Employee for approved business related expenses incurred
in accordance with the current Company travel and expense policies applicable to
Employee and properly submitted. In addition, Company shall pay Employee any
salary, variable compensation or other amounts as agreed in the Plan. However,
if the Plan is not agreed upon, Employee shall have no claim for salary, wages
or any other amounts due other than as expressly set forth in this Agreement.

6.       Release of Claims.

         a.       Civil Code Section 1542. In connection with all releases given
under this Agreement ("Release"), Employee expressly waives any rights or
benefits under Section 1542 of the California Civil Code, or any other
equivalent statute. California Civil Code Section 1542 (or similar state
statutes), provides as follows:

                  A GENERAL RELEASE DOES NOT EXTEND TO
                  CLAIMS WHICH THE CREDITOR DOES NOT KNOW OR
                  SUSPECT TO EXIST IN HIS FAVOR AT THE TIME
                  OF EXECUTING THE RELEASE, WHICH IF KNOWN
                  BY HIM MUST HAVE MATERIALLY AFFECTED HIS
                  SETTLEMENT WITH THE DEBTOR.

Without limiting the generality of the foregoing, Employee fully understands
that if any fact, with respect to any matter, covered by this Release is found
hereafter to be other

<PAGE>

than or different from the facts now believed by him to be true, he expressly
agrees that this Release shall be and remain effective, notwithstanding such
difference in the facts.

         b.       Release. Employee agrees that the Employment Agreement Amount
represents adequate consideration for the purpose of this Release and such
Employment Agreement Amount constitutes settlement in full of all outstanding
obligations owed to Employee by the Company under the Employment Agreement.
Except for the promises or obligations made or undertaken in this Agreement and
in exchange for the payments and other consideration provided hereunder,
Employee, on behalf of himself, and his respective heirs, family members,
executors, and assigns, hereby fully and forever releases, acquits, and
discharges the Company and its respective officers, directors, employees,
investors, shareholders, administrators, affiliates, divisions, subsidiaries,
predecessor and successor corporations, and assigns, from, and agrees not to sue
concerning, any claim, duty, obligation or cause of action relating to any
matters of any kind, whether presently known or unknown, suspected or
unsuspected, that he or she may possess arising from any omissions, acts or
facts that have occurred up until the Effective Date, including, without
limitation, any and all claims relating to or arising from Employee's employment
relationship with the Company and the termination or modification of that
relationship; any and all claims relating to, or arising from, Employee's right
to purchase, or actual purchase of shares of stock of the Company, including,
without limitation, any claims for rights of rescission, personal tax
liabilities, fraud, misrepresentation, breach of fiduciary duty, breach of duty
under applicable state corporate law, and securities fraud under any state or
federal law; any and all claims for wrongful discharge of employment, wages or
other compensation, including but not limited to bonuses and commissions; breach
of contract, both express and implied; breach of a covenant of good faith and
fair dealing, both express and implied; negligent or intentional infliction of
emotional distress; negligent or intentional misrepresentation; negligent or
intentional interference with contract or prospective economic advantage;
defamation; negligence; personal injury; discrimination, disability
discrimination; violation of public policy; retaliation; harassment; any tort
claims, including wrongful discharge, assault; battery; harassment; invasion of
privacy; false imprisonment; and conversion; any and all claims for violation of
any federal, state or municipal statute, including, but not limited to, Title
VII of the Civil Rights Act of 1964, the Civil Rights Act of 1991, the Age
Discrimination in Employment Act of 1967, the Americans with Disabilities Act of
1990, the Fair Labor Standards Act, the California Fair Employment and Housing
Act, and Labor Code section 201, et seq., and all as may be amended from time to
time; any and all claims arising out of any other laws and regulations relating
to employment or employment discrimination; and any and all claims for
attorneys' fees and costs. This release extends to any and all administrative or
criminal charges whether before the Division of Labor Standards, Equal
Employment Opportunity Commission or the Department of Fair Employment and
Housing or any other court or agency to which Employee currently is or shall
later become a party. Should Employee ever become a party to any such
proceeding, he shall immediately ask any such administrative agency or court to
withdraw any such charge as to him.

<PAGE>

         The parties acknowledge and agree that all potential or actual disputes
between them with respect to the Employment Agreement have been fully and
finally settled to their complete satisfaction, leaving no disputes,
controversies, claims or grievances of any kind between them. The parties
therefore covenant and agree that, except as may be compelled by legal process,
they will not raise or in any way pursue any claims which are being released and
discharged in this Agreement in any forum of any kind, including, without
limitation, the federal, state or local courts, or federal, state or local
agencies or offices of any kind, be they administrative, regulatory, judicial,
quasi-judicial, or otherwise. The parties further agree that, except as
compelled by legal process, they will not aid, assist, abet or in any way
encourage any third party to in any way pursue any claims which are being
released and discharged in this Agreement. Except pursuant to formal process
with appropriate prior notice to Company's counsel, the parties further agree
that they will not provide documents, information or testimony to any
prospective or actual claimant against one another. The Parties represent and
warrant that they have not, to date, discussed with any third party the
possibility of that third party pursuing claims against the other party; that
they have not encouraged any such pursuit of claims. If either Party at any time
commences or in any manner seeks relief against any of the other Party through
any suit or other legal proceeding, then that Party shall pay in addition to any
other damages caused thereby, all attorneys' fees and costs incurred by the
other Party in defending or otherwise responding to said suit or proceeding.

         Employee agrees that the release set forth in this section shall be and
remain in effect in all respects as a complete general release as to the matters
released. Employee understands and agrees that this Release extinguishes all
claims by the Employee as of the Effective Date whether known or unknown and
foreseen or unforeseen.

         c.       Acknowledgment of Waiver of Claims under ADEA. To the extent
applicable, Employee further acknowledges that he is waiving and releasing any
rights he may have under the Age Discrimination in Employment Act of 1967
("ADEA") and that this waiver and release is knowing and voluntary. Employee and
the Company agree that this waiver and release does not apply to any rights or
claims that may arise under ADEA after the Effective Date. Employee acknowledges
that the consideration given for this waiver and release Agreement is in
addition to anything of value to which Employee was already entitled. To the
extent the ADEA is applicable to Employee, Employee further acknowledges that he
or she has been advised by this writing, as required by the ADEA, that (a) he or
she has the right to and should consult with an attorney prior to executing this
Agreement (although he or she may execute this Agreement voluntarily earlier);
(b) he or she has at least forty-five (45) days within which to consider this
Agreement; (c) Employee has been advised that a roster of all individuals
affected by the current reduction in force plan of the Company is immediately
available to Employee upon request from the Human Resources department; (d) he
or she has seven (7) days following the execution of this Agreement to revoke
the Agreement by sending a written notice to the Company to the attention of
General Counsel, Critical Path, Inc., 350 The Embarcadero, 6th Floor, San
Francisco, California 94105-1204; and (e) this Agreement shall not be effective
until the revocation period has expired, which shall be the eighth day after it
is signed by Employee and Company.

<PAGE>

7.       Confidentiality. Employee understands and agrees that because of his
former senior executive level position with the Company, comments by him
concerning the Company, its plans, prospects, its personnel or any other aspect
of the Company's past or future performance could be understood as being based
on substantial information not available to the public. Accordingly, Employee
agrees to continue to remain in compliance with all terms and conditions of all
Confidentiality Agreements (as defined in Section 8) executed by Employee and
not to otherwise comment on such aspects of the Company after the Effective
Date. In addition, the terms of this Agreement are highly confidential and the
Parties hereto each agree to use their best efforts to maintain in confidence
the existence of this Agreement, the contents and terms of this Agreement, and
the consideration for this Agreement (hereinafter collectively referred to as
"Settlement Information"). Each Party hereto agrees to take every reasonable
precaution to prevent disclosure of any Settlement Information to third parties,
and each agrees that there will be no publicity, directly or indirectly,
concerning any Settlement Information, except where such disclosure is required
by law and as required the by the regulations promulgated under the Securities
and Exchange Act of 1934, as amended. The Parties hereto agree to take every
precaution to disclose Settlement Information only to those employees, officers,
directors, attorneys, accountants, governmental entities, and family members who
have a reasonable need to know of such Settlement Information.

8.       Proprietary Information and Inventions Agreement and/or Non-Disclosure
Agreement. Employee acknowledges and is reminded of, and affirms his agreement
to abide by, the terms and conditions of a previously executed Proprietary
Information and Inventions Agreement and/or a Non-Disclosure Agreement (together
the "Confidentiality Agreement") between the Parties. Employee further agrees
and understands that he may not disclose to any person or entity any
confidential information in violation of the Confidentiality Agreement, whether
directly or indirectly, or use or misuse such information in any way. A copy of
this Confidentiality Agreement shall be made available to Employee upon request.

9.       Insider Trading. Employee acknowledges that Employee may continue to be
considered an "Affiliate" of the Company as such meaning is defined under the
U.S. Securities and Exchange Act of 1934, as amended, for a certain period after
the Effective Date and that such Employee's trading activities and conduct will
continue to be governed by the terms of the Company Insider Trading Policy.

10.      Intentionally Deleted.

11.      Arbitration. The Parties agree that any and all future disputes or
claims arising out of the terms of this Agreement, their interpretation, its
breach, and any of the matters herein released, shall be subject to binding
arbitration in San Francisco County, California, before the American Arbitration
Association under its Employment Dispute Resolution Rules. In addition to
arbitration, the Company is entitled to enforce the terms of this Agreement by
seeking injunctive relief in any court of competent jurisdiction. The Parties
agree that the prevailing party in any arbitration shall be entitled to
injunctive

<PAGE>
relief in any court of competent jurisdiction to enforce the arbitration award.
The Company shall bear the costs of the arbitration except that Employee may be
required to pay costs to the same extent as in a civil action filed in the State
of California, unless the arbitrator orders otherwise. Parties agree that the
prevailing party in any claim for injunctive relief shall pay each of their own
attorney's fees and costs.

12.      Non-Disparagement. Each party agrees to refrain from any defamation,
libel or slander of the other, or tortious interference with the contracts and
relationships of the other. Employee agrees that he or she will refrain from
disparaging the Company's business and any and all of its past or present
officers, director or other employees.

13.      Authority. The Company represents and warrants that the undersigned has
the authority to act on behalf of the Company and to bind the Company and all
who may claim through it to the terms and conditions of this Agreement. Employee
represents and warrants that he or she has the capacity to act on his or her own
behalf and on behalf of all who might claim through him or her to bind them to
the terms and conditions of this Agreement. Each Party warrants and represents
that there are no liens, or claims of lien, or assignments in law or equity or
otherwise of or against any of the claims or causes of action released herein.

14.      No Representations. Neither party has relied upon any representations
or statements made by the other party hereto which are not specifically set
forth in this Agreement.

15.      Severability. In the event that any provision hereof becomes or is
declared by a court of competent jurisdiction to be illegal, unenforceable or
void, this Agreement shall continue in full force and effect without said
provision. Such provision shall be modified by the court so as to be rendered
enforceable insofar as possible consistent with the intent of the Parties to all
remaining portions of the Agreement.

16.      Entire Agreement. This Agreement represents the entire agreement and
understanding between the Company and Employee concerning Employee's employment
with and separation from the Company, and supersedes and replaces any and all
prior agreements and understandings, whether oral or written, concerning
Employee's relationship with the Company and his or her compensation by the
Company, except for (i) the Confidentiality Agreement (as defined herein), (ii)
any prior agreement or understanding to indemnify Employee as against third
party claims which may arise in connection with Employee's service as an
executive officer, including but not limited to employee's Indemnification
Agreement and (iii) employee's stock option agreements and the provisions of any
other agreement related to such stock option agreements. Parole evidence shall
be inadmissible to show agreement by and between the Parties as to any term or
condition contrary to or in addition to the terms and conditions hereof,
including without limitation any intermediate drafts of this Agreement. Any and
all such prior agreements and understandings with respect to the subject matter
herein, including agreements for compensation, including bonuses and
commissions, are also hereby terminated and of no further force and effect, and
Employee hereby expressly disclaims

<PAGE>

any and all rights in connection with any previous agreements, if any, whether
oral or written.

17.      No Oral Modification. This Agreement may only be amended in writing
signed by Employee and the Chief Executive Officer or Chief Financial Officer of
the Company.

18.      Governing Law. This Agreement shall be governed by the laws of the
State of California. Both Parties submit to jurisdiction in California and
further agree that any cause of action arising under this Agreement shall be
brought before an arbitrator in a court in San Francisco County, California.

19.      Counterparts. This Agreement may be executed in counterparts, and each
counterpart shall have the same force and effect as an original and shall
constitute an effective, binding agreement on the part of each of the
undersigned.

20.      Voluntary Execution of Agreement. This Agreement is executed
voluntarily and without any duress or undue influence on the part or behalf of
the Parties hereto, with the full intent of releasing all claims. Employee
acknowledges that: (a) he or she has read this Agreement; (b) has been
represented in the preparation, negotiation, and execution of this Agreement by
legal counsel of his or her own choice or that he or she has voluntarily
declined to seek such counsel; (c) understands the terms and consequences of
this Agreement and of the releases it contains; (d) is fully aware of the legal
and binding effect of this Agreement.

         IN WITNESS WHEREOF, the Parties have executed this Agreement as of the
date set forth on the first page of this Agreement.

Dated: As of May 16, 2003           By /s/ Paul H. Bartlett
                                      ------------------------------------
                                      Name:  Paul H. Bartlett
                                      Title: Chief Financial Officer & EVP of
                                             Corporate Development

Dated: As of May 16, 2003           By /s/ Bernard Harguindeguy
                                      ------------------------------------
                                           Bernard Harguindeguy

Source: [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00062-of-00352.parquet"}, [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00062-of-00352.parquet"}]]