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EXHIBIT 10.55 AMENDMENT NO. 2 TO CONVERTIBLE NOTE PURCHASE AND EXCHANGE AGREEMENT AMENDMENT NO. 2, dated March 9, 2004 (this Amendment), among Critical
Path, Inc., a California corporation (the Company), General Atlantic Partners
74, L.P., a Delaware limited partnership, GAP Coinvestment Partners II, L.P., a
Delaware limited partnership, GapStar, LLC, a Delaware limited liability
company, GAPCO GmbH & Co. KG, a German limited partnership, Campina Enterprises
Limited, Cenwell Limited, Great Affluent Limited, Dragonfield Limited and Lion
Cosmos Limited (collectively with the Company, the Parties), WITNESSETH: WHEREAS, the Parties are each a party to that certain Convertible Note
Purchase and Exchange Agreement, dated November 18, 2003, as amended on January
16, 2004 (the November 2003 Note Exchange Agreement); and WHEREAS, the Company entered into a Convertible Note Purchase Agreement,
dated January 16, 2004, pursuant to which the Company issued and sold to Permal
U.S. Opportunities Limited, Zaxis Equity Neutral, L.P., Zaxis Institutional
Partners, L.P., Zaxis Offshore Limited, Zaxis Partners, L.P. and Passport
Master Fund, L.P. convertible notes having an aggregate principal amount of $15
million, which notes are convertible, subject to Stockholder Approval, into
shares of Series E Redeemable Convertible Preferred Stock of the Company, par
value $0.001 per share (the January 2004 Note Purchase Agreement); and WHEREAS, in connection with the execution of the January 2004 Note
Purchase Agreement, the Parties entered into an amendment to the November 2003
Note Exchange Agreement; and WHEREAS, the Company desires to enter into a Convertible Note Purchase
Agreement, pursuant to which the Company proposes to issue and sell to Permal
U.S. Opportunities Limited, Zaxis Equity Neutral, L.P., Zaxis Institutional
Partners, L.P., Zaxis Offshore Limited, Zaxis Partners, L.P., Guggenheim
Portfolio Company XIII, Crosslink Crossover Fund IV, L.P., Sagamore Hill Hub
Fund, Ltd., Criterion Capital Partners, Ltd., Criterion Capital Partners,
Institutional, Criterion Capital Partners, L.P. and Capital Ventures
International convertible notes having an aggregate principal amount of $18.5
million which notes will be convertible, subject to Stockholder Approval, into
shares of Series E Redeemable Convertible Preferred Stock of the Company, par
value $0.001 per share (the March 2004 Note Purchase Agreement); and WHEREAS, in connection with the execution of the March 2004 Note Purchase
Agreement, the Parties desire to amend the November 2003 Note Exchange
Agreement as set forth herein; and WHEREAS, capitalized terms used in this Amendment and not defined herein
shall have the meanings ascribed to such terms in the November 2003 Note
Exchange Agreement:




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NOW, THEREFORE, in consideration of the mutual covenants and agreements
herein contained, for the covenants and agreements set forth in the November
2003 Note Exchange Agreement, and for other good and valuable consideration,
the receipt and sufficiency of which is hereby acknowledged, and intending to
be legally bound hereby, the Parties hereby agree as follows: 1.1 Amendments to the November 2003 Note Exchange Agreement. The November
2003 Note Exchange Agreement shall be amended as set forth below: (a) Section 1.1 of the November 2003 Note Exchange Agreement shall be
amended to add the following: March 2004 Note Purchase Agreement means that certain
Convertible Note Purchase Agreement, dated March 9, 2004, among
Permal U.S. Opportunities Limited, Zaxis Equity Neutral, L.P.,
Zaxis Institutional Partners, L.P., Zaxis Offshore Limited, Zaxis
Partners, L.P., Guggenheim Portfolio Company XIII, Crosslink
Crossover Fund IV, L.P., Sagamore Hill Hub Fund, Ltd., Criterion
Capital Partners, Ltd., Criterion Capital Partners, Institutional,
Criterion Capital Partners, L.P., Capital Ventures International
and Critical Path, Inc., a California corporation (the Company),
pursuant to which the Company shall issue and sell convertible
notes in an aggregate principal amount of up to $18.5 million,
which notes shall be convertible into Series E Preferred Stock,
subject to Stockholder Approval and concurrently with the
Conversion and Exchange, or into Common Stock, in each case in
accordance with such agreement. (b) The definition of Note Purchase Agreement in Section 1.1 of the
November 2003 Note Exchange Agreement shall be deleted and replaced with the
following: Note Purchase Agreement means that certain Convertible
Note Purchase Agreement, dated January 16, 2004, among Permal U.S.
Opportunities Limited, Zaxis Equity Neutral, L.P., Zaxis
Institutional Partners, L.P., Zaxis Offshore Limited, Zaxis
Partners, L.P., Passport Master Fund, L.P. and Critical Path,
Inc., a California corporation (the Company), pursuant to which
the Company shall issue and sell convertible notes in an aggregate
principal amount of up to $15 million, which notes shall be
convertible into Series E Preferred Stock, subject to Stockholder
Approval and concurrently with the Conversion and Exchange, or
into Common Stock, in each case in accordance with such
agreement. (c) The definition of Subsequent Lenders in Section 1.1 of the November
2003 Note Exchange Agreement shall be deleted and replaced with the following: Subsequent Lenders shall include the Lenders, as defined in the Note
Purchase Agreement, and the Lenders, as defined in the March 2004 Note Purchase
Agreement. 2




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(d) Section 2.6(f) of the November 2003 Note Exchange Agreement is hereby
deleted and amended and restated in its entirety to read as follows: (f) Subsequent Closing. The consummation of the Exchange
and Conversion (the Subsequent Closing) shall take place
concurrently with the Subsequent Closing under the Note Purchase
Agreement and the Subsequent Closing under the March 2004 Note
Purchase Agreement, as soon as practicable following the
satisfaction of the closing conditions set forth in Article VI of
this Agreement, Article VI of the Note Purchase Agreement and
Article VI of the March 2004 Note Purchase Agreement (the
Subsequent Closing Date), at the offices of Pillsbury Winthrop
LLP, 50 Fremont Street, San Francisco, California, or at such
other time and place as the Company, the Lenders, the CK
Purchasers and the Subsequent Lenders may mutually agree. At the
Subsequent Closing, signature pages transmitted by facsimile will
be acceptable, with originals to follow as soon as practicable
thereafter. (e) Article VIII of the November 2003 Note Exchange Agreement shall be
amended to add a new Section 8.8 which shall read as follows: 8.8 Proxy Matters. Notwithstanding anything herein to the
contrary, but subject to the provisions of Section 9.1 of this
Agreement, if the Registration Statement has not been declared
effective by the Commission on or prior to May 15, 2004, the
Company will promptly take all such actions as may be necessary to
withdraw the Registration Statement, and the Company shall
continue to have an obligation under Section 8.4 of this Agreement
to seek Stockholder Approval. If the Company withdraws the
Registration Statement pursuant to this Section 8.8 and receives
Stockholder Approval, the Company may, subject to approval by the
Board of Directors, file a subsequent registration statement with
the Commission and provide the Companys shareholders the
opportunity to participate in a subsequent rights offering. (f) In the first sentence of Section 9.1 of the November 2003 Note
Exchange Agreement, the words April 30 shall be deleted and replaced with the
words August 15. 1.2 Amendments to Schedules to the November 2003 Note Exchange Agreement.
Schedule 8.5 of the November 2003 Note Exchange Agreement is hereby deleted and
amended and restated to read in its entirety in the form set forth as Annex 1
attached hereto. 1.3 Counterparts. This Amendment may be executed in any number of
counterparts and by the Parties 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. Signature pages transmitted by
facsimile will be acceptable, with originals to immediately follow. 1.4 Continuing Agreement. Except as specifically amended hereby, all of
the terms of the November 2003 Note Exchange Agreement shall remain and
continue in full force and effect and are hereby confirmed in all respects. 3




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1.5 Headings. The headings in this Amendment are for convenience of
reference only and shall not limit or otherwise affect the meaning hereof. 1.6 Governing Law. This Amendment shall be governed by and construed in
accordance with the laws of the State of California, without regard to the
principles of conflicts of law thereof. 1.7 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. 1.8 Entire Agreement. This Amendment, together with the November 2003
Note Exchange Agreement and the exhibits and schedules thereto, and the other
Transaction Documents, are intended by the parties as a final expression of
their agreement and intended to be a complete and exclusive statement of the
agreement and understanding of the parties hereto in respect of the subject
matter contained herein and therein. There are no restrictions, promises,
representations, warranties or undertakings, other than those set forth or
referred to herein or therein. This Amendment and the November 2003 Note
Exchange Agreement, together with the exhibits and schedules thereto, and the
other Transaction Documents, supersede all prior agreements and understandings
between the parties with respect to such subject matter. [the remainder of this page intentionally left blank] 4




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IN WITNESS WHEREOF, the undersigned have executed, or have caused to be
executed, this Amendment on the date first written above. CRITICAL PATH, INC.,
a California corporationBy:
    /s/ William E. McGlashan, Jr.Name:
    William E. McGlashan, Jr.Title:
    Chairman, Chief Executive Officer


SIGNATURE PAGE TO AMENDMENT
NO. 2 TO CONVERTIBLE NOTE PURCHASE AND EXCHANGE AGREEMENT



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GENERAL ATLANTIC PARTNERS 74, L.P.By:
    GENERAL ATLANTIC PARTNERS, LLC,its General PartnerBy:
    /s/   Thomas J. MurphyName:
    Thomas J. MurphyTitle:
    Attorney-in-factGAP COINVESTMENT PARTNERS II, L.P.By:
    /s/   Thomas J. MurphyName:
    Thomas J. MurphyTitle:
    Attorney-in-factGAPSTAR, LLCBy:
    GENERAL ATLANTIC PARTNERS, LLC,its Managing MemberBy:
    /s/   Thomas J. MurphyName:
    Thomas J. MurphyTitle:
    Attorney-in-factGAPCO GMBH & CO. KGBy:
    GAPCO MANAGEMENT GMBH,its General PartnerBy:
    /s/   Thomas J. MurphyName:
    Thomas J. MurphyTitle:
    Procuration Officer SIGNATURE PAGE TO AMENDMENT NO. 2  TO CONVERTIBLE NOTE PURCHASE AND EXCHANGE AGREEMENT




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CENWELL LIMITEDBy:
    /s/   Ip Tak Chuen, EdmondName:
    Ip Tak Chuen, EdmondTitle:
    Authorised Person CAMPINA ENTERPRISES LIMITEDBy:
    /s/   Ip Tak Chuen, EdmondName:
    Name:  Ip Tak Chuen, EdmondTitle:
    Director GREAT AFFLUENT LIMITEDBy:
    /s/   Ip Tak Chuen, EdmondName:
    Ip Tak Chuen, EdmondTitle:
    Director DRAGONFIELD LIMITEDBy:
    /s/   Pau Yee Wan, EzraName:
    Pau Yee Wan, EzraTitle:
    Authorised Person LION COSMOS LIMITEDBy:
    /s/   Pau Yee Wan, EzraName:
    Pau Yee Wan, EzraTitle:
    Director SIGNATURE PAGE TO AMENDMENT NO. 2 TO CONVERTIBLE NOTE PURCHASE AND EXCHANGE AGREEMENT