Document:

<PAGE>
                                                                   EXHIBIT 10.20

ADDENDUM TO CONSULTING AGREEMENT BETWEEN LAUREEN DEBUONO AND CRITICAL PATH, INC.
DATED AUGUST 16, 2001

This Addendum ("Addendum") is made as of October 31, 2001 by and between Laureen
DeBuono, an individual, located at __________ ("Consultant") and Critical Path,
Inc., a company located at 532 Folsom Street, San Francisco, CA 94105
("Critical Path"), to the original Consulting Agreement dated August 21, 2001
("Consulting Agreement"), between the parties to this Addendum.

The following are changes to the Consulting Agreement; all other terms in the
Consulting Agreement remain the same, apply to the new Term, defined below, and
are in full force and effect:

Section 2 "Term". The Term of the consulting agreement shall be extended through
September 30, 2002, unless terminated under the provisions of Section 9 of the
Consulting Agreement, or extended upon mutual agreement of the parties.

Section 4 "Fees and Expenses". Consultant shall continue to be paid $52,000 per
month payable on the first of each month through September 2002. In addition,
Consultant shall be granted, on October 31, 2001, at the market price on that
date, a fully vested option to purchase 233,333 shares of Critical Path stock.
In addition, as stated in the Consulting Agreement, in the event other executive
officers receive stock options as a result of a financing, stock split, annual
option grant program or other similar event, then the Consultant will receive
additional stock options on a "proportional basis". During the Term of the
Agreement, Consultant will be subject to all the restrictions imposed on
executive officers with regard to trading in Critical Path stock. After the Term
of the Agreement, there will be no such restrictions imposed on Consultant.

Section 9 "Termination". The provisions of this section extend to the Term
through September 30, 2002.

Lastly, the parties agree that Consultant shall have a flexible work schedule
that permits Consultant to work from home on an occasional basis.

BY: /s/ LAUREEN DEBUONO
    ---------------------------------
Laureen DeBuono
"Consultant"

BY: /s/ BILL MCGLASHAN
    ---------------------------------
Bill McGlashan
CEO
Critical Path, Inc.<PAGE>
                                                                   EXHIBIT 10.21

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NOTICE OF GRANT OF STOCK OPTIONS                CRITICAL PATH, INC.
AND OPTION AGREEMENT                            ID: 91-1788-300
                                                532 Folsom Street
                                                San Francisco, CA 94105

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LAUREEN DEBUONO                                 OPTION NUMBER:  003374
                                                PLAN:           1998
                                                ID:

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Effective 11/1/2001, you have been granted a(n) Non-Qualified Stock Option to
buy 233,333 shares of Critical Path, Inc. (the Company) stock at $0.9100 per
share.

The total option price of the shares granted is $212,333.03.

Shares in each period will become fully vested on the date shown.

                Shares       Vest Type       Full Vest       Expiration
                ------       ---------       ---------       ----------
               233,333     On Vest Date      11/1/2001        11/1/2011

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By your signature and the Company's signature below, you and the Company agree
that these options are granted under and governed by the terms and conditions of
the Company's Stock Option Plan as amended and the Option Agreement, all of
which are attached and made a part of this document.

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-----------------------------------             --------------------------------
Critical Path, Inc.                             Date

-----------------------------------             --------------------------------
Laureen DeBuono                                 Date<PAGE>
                                                                   EXHIBIT 10.22

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NOTICE OF GRANT OF STOCK OPTIONS                CRITICAL PATH, INC.
AND OPTION AGREEMENT                            ID: 91-1788-300
                                                532 Folsom Street
                                                San Francisco, CA 94105

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LAUREEN DEBUONO                                 OPTION NUMBER:  003432
                                                PLAN:           1998
                                                ID:

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Effective 11/9/2001, you have been granted a(n) Non-Qualified Stock Option to
buy 234,686 shares of Critical Path, Inc. (the Company) stock at $1.1300 per
share.

The total option price of the shares granted is $265,195.18.

Shares in each period will become fully vested on the date shown.

                Shares       Vest Type       Full Vest       Expiration
                ------       ---------       ---------       ----------
               234,686      On Vest Date     11/9/2001        11/9/2011

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By your signature and the Company's signature below, you and the Company agree
that these options are granted under and governed by the terms and conditions of
the Company's Stock Option Plan as amended and the Option Agreement, all of
which are attached and made a part of this document.

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/s/ David Hayden
-----------------------------------             --------------------------------
Critical Path, Inc.                             Date

/s/ Laureen DeBuono
-----------------------------------             --------------------------------
Laureen DeBuono                                 Date<PAGE>
                                                                   EXHIBIT 10.23

January 14, 2002

Mr. Bernard Harguindeguy

Dear Bernard:

        On behalf of Critical Path, Inc. (the "Company"), I am pleased to offer
you the position of Executive Vice President, Chief Marketing Officer. The terms
of your new position with the Company are as set forth below:

        1.      POSITION.

                a.      You will be Executive Vice President, Chief Marketing
                        Officer, reporting to William E. McGlashan, Jr., Vice
                        Chairman and Chief Executive Officer. Mr. McGlashan will
                        be responsible for your annual review and compensation.
                        You will have a matrix reporting relationship with
                        Pierre Van Beneden, President, relative to certain
                        Marketing initiatives that will require your expertise.
                        You will be working out of the Company's offices in San
                        Francisco, CA.

                b.      You agree to the best of your ability and experience
                        that you will at all times loyally and conscientiously
                        perform all of the duties and obligations required of
                        and from you pursuant to the express and implicit terms
                        hereof, and to the reasonable satisfaction of the
                        Company. During the term of your employment, you further
                        agree that you will devote all of your business time and
                        attention to the business of the Company.

        2. START DATE. Subject to fulfillment of any conditions imposed by this
letter agreement, you will commence this new position with the Company on
Tuesday, January 22, 2002. On your first day, your orientation will take place
at 9:15 am at 532 Folsom Street in San Francisco. Please bring your employment
eligibility documents with you.

        3. PROOF OF RIGHT TO WORK. For purposes of federal immigration law, you
will be required to provide to the Company documentary evidence of your identity
and eligibility for employment in the United States. A list of acceptable
documents is available for your reference.

        4. COMPENSATION.

                a.      BASE SALARY. You will be paid a monthly salary of
                        $25,000.00, which is equivalent to $300,000.00 on an
                        annualized basis. Your salary will be payable in two
                        equal payments per month pursuant to the Company's
                        regular payroll.

                b.      ADDITIONAL COMPENSATION. You will be eligible to
                        participate in the Company's Executive Incentive
                        Compensation Program. Your incentive earnings will be
                        based 50% on EBITDA attainment and 50% on MBO's to be
                        mutually agreed upon between yourself and Mr. McGlashan.
                        The amount of incentive earnings is $300,000.00
                        annually.

                c.      SIGNING BONUS. Upon signing your employment agreement,
                        the Company will provide you with a signing bonus in the
                        amount of $100,000.00.

<PAGE>

PRIVATE & CONFIDENTIAL                            CRITICAL PATH, INC.

                d.      SEVERANCE PERIOD. In the event your employment is
                        terminated without cause, you will receive one year
                        compensation in the amount of $300,000.00 as severance
                        pay.

                e.      COMMUTING EXPENSE REIMBURSEMENT. The Company will
                        reimburse you for car lease expenses, mileage and
                        parking expenses associated with your commute to/from
                        your home and the San Francisco office.

                f.      REVIEW. Your base salary generally will be reviewed
                        annually every January as part of the Company's salary
                        review process. However, nothing in this provision
                        changes the at-will nature of the employment
                        relationship.

                g.      PAID TIME OFF. You will receive 18 paid days off per
                        year for the first five years of service. This Paid Time
                        Off will accrue at the rate of 12 hours per month.

        5. STOCK OPTIONS. In connection with the commencement of your
employment, the Company will recommend that the Board of Directors grant you an
option to purchase 1,250,000 shares of the Company's Common Stock ("Shares")
with an exercise price equal to the fair market value on the date of the grant.
These option shares will vest over four years, with 25% vesting on your one year
anniversary with Critical Path. Vesting will, of course, depend on your
continued employment with the Company. The option will be subject to the terms
of the applicable Company Stock Option Plan and the Stock Option Agreement
between you and the Company. Your stock option agreement will provide for
acceleration of your options upon the following circumstance: If you are
terminated without cause or by constructive discharge following a change of
control, 100% of your then unvested shares will automatically vest. If you
resign or are terminated for any reason before your one year anniversary, the
Company will accelerate vesting on 25% of the above mentioned options.
Additionally, the Company will recommend that the Board of Directors grant you
an option to purchase 250,000 options if you meet specific first year objectives
which will be mutually agreed upon between Mr. McGlashan and you.

        6. BENEFITS. The Company will provide you and your eligible dependents
with generous Medical, Dental, and Vision benefits. You will also receive
Short-term Disability, Long-term Disability, and Life Insurance. In addition,
the Company offers employees the opportunity to participate in its Flexible
Spending Account, Employee Assistance Program, 401(k), and Employee Stock
Purchase Plans. A complete overview of benefits will be presented to you on your
start date.

        7. PROPRIETARY INFORMATION AND INVENTIONS AGREEMENT. Your acceptance of
this offer and commencement of employment with the Company is contingent upon
the execution and submission of the Company's Proprietary Information and
Inventions Agreement ("Proprietary Agreement"), a copy of which has been
provided to you with this offer letter.

        8. AT-WILL EMPLOYMENT. Notwithstanding the Company's obligation
described herein, your employment with the Company will be on an "at-will"
basis, meaning that either you or the Company may terminate your employment at
any time for any reason or no reason, without further obligation or liability.

        9. DISPUTE RESOLUTION PROCEDURE. You and the Company ("the parties")
agree that any dispute arising out of or related to the employment relationship
between them, including the termination of that relationship and any allegations
of unfair or discriminatory treatment arising under state or federal law or
otherwise, that cannot be resolved through the Company's informal grievance
procedure, shall be resolved by final and binding arbitration, except where the
law specifically forbids the use of arbitration as a final and binding remedy.
The following dispute resolution shall apply:

                (a)     The complainant shall provide the other party with a
                        written statement of the claim identifying any
                        supporting witnesses or documents and the requested
                        relief.

                (b)     The respondent shall furnish a statement of the relief,
                        if any, that it is willing to provide, and identify
                        supporting witnesses or documents. If the matter is not
                        resolved, the parties shall submit the dispute to
                        nonbinding mediation, paid for by the Company, before a
                        mediator to be selected by the parties.

                (c)     If the matter is not resolved through mediation, the
                        parties agree that the dispute shall be resolved by
                        binding arbitration. If the parties are unable to
                        jointly select an arbitrator, they will obtain a list of
                        arbitrators from the Federal Mediation and Conciliation
                        Service and select an arbitrator by striking names from
                        that list.

                                                                               2

<PAGE>

PRIVATE & CONFIDENTIAL                            CRITICAL PATH, INC.

                (d)     The arbitrator shall have the authority to determine
                        whether the conduct complained of in section (a) of this
                        section violates the complainant's rights and, if so, to
                        grant any relief authorized by law; subject the
                        exclusions of section (g) below. The arbitrator shall
                        not have the authority to modify, change or refuse to
                        enforce the terms of any employment agreement between
                        the parties, or change any lawful policy or benefit
                        plan.

                (e)     Critical Path, Inc. shall bear the costs of the
                        arbitration if you prevail. If Critical Path, Inc.
                        prevails, you will pay half the cost of the arbitration
                        or $500, whichever is less. Each party shall pay its own
                        attorneys fees, unless the arbitrator orders otherwise
                        pursuant to applicable law.

                (f)     ARBITRATION SHALL BE THE EXCLUSIVE FINAL REMEDY FOR ANY
                        DISPUTE BETWEEN THE PARTIES, SUCH AS DISPUTES INVOLVING
                        CLAIMS FOR DISCRIMINATION OR HARASSMENT (SUCH AS CLAIMS
                        UNDER THE FAIR EMPLOYMENT AND HOUSING ACT, TITLE VII OF
                        THE CIVIL RIGHTS ACT OF 1964, THE AMERICANS WITH
                        DISABILITIES ACT, OR THE AGE DISCRIMINATION IN
                        EMPLOYMENT ACT), WRONGFUL TERMINATION, BREACH OF
                        CONTRACT, BREACH OF PUBLIC POLICY, PHYSICAL OR MENTAL
                        HARM OR DISTRESS OR ANY OTHER DISPUTES, AND THE PARTIES
                        AGREE THAT NO DISPUTE SHALL BE SUBMITTED TO ARBITRATION
                        WHERE THE COMPLAINANT HAS NOT COMPLIED WITH THE
                        PRELIMINARY STEPS PROVIDED FOR IN SECTIONS (a) AND (b)
                        ABOVE.

                (g)     The parties agree that the arbitration award shall be
                        enforceable in any court having jurisdiction to enforce
                        this Agreement, so long as the arbitrator's findings of
                        fact are supported by substantial evidence on the whole
                        and the arbitrator has not made errors of law; however,
                        either party may bring an action in a court of competent
                        jurisdiction regarding or related to inventions that you
                        may claim to have developed prior to joining the
                        company, pursuant to California Labor Code Section 2870
                        ("Disputes Related to Inventions"). The parties further
                        agree that for Disputes Related to Inventions which the
                        parties have elected to submit to arbitration, each
                        party retains the right to seek preliminary injunctive
                        relief in court in order to preserve the status quo or
                        prevent irreparable injury before the matter can be
                        heard in arbitration.

        10. OFFER CONDITIONS. This offer is null and void if not accepted or
declined by January 16, 2002. This offer is also contingent upon receiving the
successful results of our independent verification of your application.

        We are delighted to be able to extend you this offer and look forward to
working with you. To indicate your acceptance of the Company's offer, please
sign and date this letter in the space provided below and FAX IT TO HR AT (415)
808-8797, along with a signed and dated copy of the Proprietary Agreement. This
letter, together with the Proprietary Agreement constitutes the full, complete
and exclusive agreement between you and the company regarding the matters herein
and supersedes any prior representations or agreements, whether written or oral.
This letter may not be modified or amended except by a written agreement, signed
by the Company and by you.

ACCEPTED AND AGREED:                        CRITICAL PATH, INC.

Name:                                       By:     /s/ William McGlashan
     ---------------------------------         ---------------------------------
                                                 William E. McGlashan, Jr.
      /s/ Bernard Harguindeguy                   Vice Chairman and CEO
--------------------------------------
Signature                        Date

                                                                               3

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