Document:

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                                                                  EXHIBIT 10.30

                     SETTLEMENT AGREEMENT AND MUTUAL RELEASE

         This Settlement Agreement and Mutual Release ("Agreement") is made by
and between Critical Path, Inc. (the "Company"), and Mark J. Rubash
("Employee").

         WHEREAS, Employee was employed by the Company;

         WHEREAS, the Company and Employee have entered into a Proprietary
Information and Inventions Agreement (the "Confidentiality Agreement");

         WHEREAS, the Company and Employee have mutually agreed to terminate the
employment relationship and to release each other from any claims arising from
or related to the employment relationship;

         NOW THEREFORE, in consideration of the mutual promises made herein, the
Company and Employee (collectively referred to as "the Parties") hereby agree as
follows:

         1. Resignation. Employee resigned from his position as the Company's
Executive Vice President and Chief Financial Officer effective December 7, 2000.

         2. Consideration. The Company agrees to pay Employee a single, lump-sum
bonus payment of Two-Hundred and Fifty Thousand Dollars ($250,000.00) in cash,
less the principal and interest amount due from Employee to the Company under an
outstanding Note; such principal and interest totals One Hundred Five Thousand
Two-Hundred Thirty-Five Dollars and Seven Cents ($105,235.07). Therefore, the
net cash bonus payable to Employee is One Hundred Forty-Four Thousand Seven
Hundred and Sixty-Four Dollars and Ninety-Three Cents ($144,764.93), as shown on
in the attached exhibit less applicable federal and state withholding.

         The net cash bonus payable, less applicable federal and state
withholding, will be remitted to and received by Employee no later than January
5, 2001. The Company has the option to either remit the applicable amount
through a direct deposit to Employee's bank account or by manual payment advice
delivered by Federal Express to Employee's home address.

         3. Vesting of Stock. The Parties agree that for purposes of determining
the number of shares of the Company's common stock which Employee is entitled to
purchase from the Company, Employee will be entitled to continue vesting of
stock until December 7, 2000. The exercise of any stock options shall continue
to be subject to the terms and conditions of the Company's Stock Option Plan and
the applicable Stock Option Agreement between Employee and the Company.

         4. Benefits. Employee shall be covered by the Company's health
insurance until December 31, 2000. After that date Employee shall have the right
to convert his health and any other insurance benefits to individual coverage
pursuant to COBRA. Should Employee so elect, the Company shall reimburse
Employee for 1 months health care coverage.

         5. Confidential Information. Employee shall continue to maintain the
confidentiality of all confidential and proprietary information of the Company
and shall continue to comply with the

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terms and conditions of the Confidentiality Agreement between Employee and the
Company. Employee shall return all the Company property and confidential and
proprietary information in his possession to the Company on or before the
Effective Date of this Agreement.

         6. Payment of Salary. Employee acknowledges and represents that the
Company has paid all salary, wages, accrued vacation, commissions and any and
all other benefits due to Employee.

         7. Reimbursement of Expenses. The Company acknowledges and represents
that the Employee is due $1,470.26 for valid business expenses incurred on the
Company's behalf during the course of employment through December 7, 2000.
Company acknowledges and represents that reimbursement for such expenses will be
made to Employee on or before December 31, 2000.

         8. Release of Claims. Employee agrees that the foregoing consideration
represents settlement in full of all outstanding obligations owed to Employee by
the Company. Employee and the Company, on behalf of themselves, and their
respective heirs, family members, executors, officers, directors, employees,
investors, shareholders, administrators, affiliates, divisions, subsidiaries,
predecessor and successor corporations, and assigns, hereby fully and forever
release each other and their respective heirs, family members, executors,
officers, directors, employees, investors, shareholders, administrators,
affiliates, divisions, subsidiaries, predecessor and successor corporations, and
assigns, from, and agree 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 any of them may possess arising from any
omissions, acts or facts that have occurred up until and including the Effective
Date of this Agreement including, without limitation,

            (a) any and all claims relating to or arising from Employee's
employment relationship with the Company and the termination of that
relationship;

            (b) 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 fraud, misrepresentation, breach
of fiduciary duty, breach of duty under applicable state corporate law, and
securities fraud under any state or federal law;

            (c) any and all claims for wrongful discharge of employment; 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; assault; battery; invasion of privacy;
false imprisonment; and conversion;

            (d) 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.;

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            (e) any and all claims arising out of any other laws and regulations
relating to employment or employment discrimination; and

            (f) any and all claims for attorneys' fees and costs.

         The Company and Employee agree 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. This release does not extend to any
obligations incurred under this Agreement.

         9. Acknowledgment of Waiver of Claims under ADEA. Employee 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 of this Agreement. 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. Employee further
acknowledges that he has been advised by this writing that (a) he should consult
with an attorney prior to executing this Agreement; (b) he has at least
twenty-one (21) days within which to consider this Agreement; (c) he has at
least seven (7) days following the execution of this Agreement by the parties to
revoke the Agreement; and (d) this Agreement shall not be effective until the
revocation period has expired.

         10. Civil Code Section 1542. The Parties represent that they are not
aware of any claim by either of them other than the claims that are released by
this Agreement. Employee and the Company acknowledge that they have been advised
by legal counsel and/or are familiar with the provisions of California Civil
Code Section 1542, which 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.

         Employee and the Company, being aware of said code section, agree to
expressly waive any rights they may have thereunder, as well as under any other
statute or common law principles of similar effect.

         11. No Pending or Future Lawsuits. Employee represents that he has no
lawsuits, claims, or actions pending in his name, or on behalf of any other
person or entity, against the Company or any other person or entity referred to
herein. Employee also represents that he does not intend to bring any claims on
his own behalf or on behalf of any other person or entity against the Company or
any other person or entity referred to herein.

         12. Application for Employment. Employee understands and agrees that,
as a condition of this Agreement, he shall not be entitled to any employment
with the Company, its subsidiaries, or any successor, and he hereby waives any
right, or alleged right, of employment or re-employment with the Company.

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         13. Confidentiality. 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. 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.

         14. No Cooperation. Employee agrees he will not act in any manner that
might damage the business of the Company. Employee agrees that he will not
counsel or assist any attorneys or their clients in the presentation or
prosecution of any disputes, differences, grievances, claims, charges, or
complaints by any third party against the Company and/or any officer, director,
employee, agent, representative, shareholder or attorney of the Company, unless
under a subpoena or other court order to do so.

         15. 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.

         16. Indemnification. The Company will provide Employee indemnification
pursuant to the indemnification agreement between the Company and Employee.

         17. Tax Consequences. The Company makes no representations or
warranties with respect to the tax consequences of the payment of any sums to
Employee under the terms of this Agreement. Employee agrees and understands that
he is responsible for payment, if any, of local, state and/or federal taxes on
the sums paid hereunder by the Company and any penalties or assessments thereon.
Employee further agrees to indemnify and hold the Company harmless from any
claims, demands, deficiencies, penalties, assessments, executions, judgments, or
recoveries by any government agency against the Company for any amounts claimed
due on account of Employee's failure to pay federal or state taxes or damages
sustained by the Company by reason of any such claims, including reasonable
attorneys' fees.

         18. No Admission of Liability. The Parties understand and acknowledge
that this Agreement constitutes a compromise and settlement of any current or
potential claims. No action taken by the Parties hereto, or either of them,
either previously or in connection with this Agreement shall be deemed or
construed to be (a) an admission of the truth or falsity of any current or
potential claims heretofore made or (b) an acknowledgement or admission by
either party of any fault or liability whatsoever to the other party or to any
third party.

         19. Costs. The Parties shall each bear their own costs, expert fees,
attorneys' fees and other fees incurred in connection with this Agreement.

         20. Arbitration. The Parties agree that any and all disputes arising
out of the terms of this Agreement, their interpretation, and any of the matters
herein released, shall be subject to binding arbitration in San Francisco County
before the American Arbitration Association under its California

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Employment Dispute Resolution Rules, or by a judge to be mutually agreed upon.
The Parties agree that the prevailing party in any arbitration shall be entitled
to injunctive relief in any court of competent jurisdiction to enforce the
arbitration award. The Parties agree that the prevailing party in any
arbitration shall be awarded its reasonable attorney's fees and costs.

         21. 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 has the capacity to act on his own
behalf and on behalf of all who might claim through him 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.

         22. No Representations. Each party represents that it has had the
opportunity to consult with an attorney, and has carefully read and understands
the scope and effect of the provisions of this Agreement. Neither party has
relied upon any representations or statements made by the other party hereto
which are not specifically set forth in this Agreement.

         23. 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.

         24. Entire Agreement. This Agreement represents the entire agreement
and understanding between the Company and Employee concerning Employee's
separation from the Company, and supersedes and replaces any and all prior
agreements and understandings concerning Employee's relationship with the
Company and his compensation by the Company.

         25. No Oral Modification. This Agreement may only be amended in writing
signed by Employee and the President of the Company.

         26. Governing Law. This Agreement shall be governed by the laws of the
State of California.

         27. Effective Date. This Agreement is effective seven days after it has
been signed by both Parties.

         28. 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.

         29. 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. The Parties
acknowledge that:

            (a) They have read this Agreement;

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            (b) They have been represented in the preparation, negotiation, and
execution of this Agreement by legal counsel of their own choice or that they
have voluntarily declined to seek such counsel;

            (c) They understand the terms and consequences of this Agreement and
of the releases it contains;

            (d) They are fully aware of the legal and
binding effect of this Agreement.

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         IN WITNESS WHEREOF, the Parties have executed this Settlement Agreement
and Mutual Release on the respective dates set forth below.

                                      Critical Path, Inc.

Dated:          , 2000               By: /s/ David A. Thatcher
       ---------                         ---------------------------------------
                                             David A. Thatcher
                                             President

                                     MARK J. RUBASH, an individual

Dated: December 19, 2000               By: /s/ Mark J. Rubash
       ------------                      ---------------------------------------
                                             Mark J. Rubash

APPROVED AS TO FORM:

                                     WILSON SONSINI GOODRICH & ROSATI, P.C.

Dated:           , 2000              By: /s/ MARK L. REINSTRA
      ----------                         ---------------------------------------
                                             Mark L. Reinstra, Esq.
                                             Attorneys for the Company<PAGE>   1
                                                                  EXHIBIT 10.31

         Agreement and Release made effective as of February 9, 2001 by and
between Critical Path, Inc., a California corporation (the "Company") and
Douglas Hickey ("Executive").

                                   WITNESSETH:

         WHEREAS, Executive is Chief Executive Officer of the Company;

         WHEREAS, Executive and the Company entered into an employment agreement
dated October 1, 1998 (the "Employment Agreement") and an indemnification
agreement in 1999 (the "Indemnification Agreement");

         WHEREAS, certain issues have arisen as to the reporting of the
Company's earnings and revenues for 2000 (the "Issues");

         WHEREAS, since the Issues arose while Executive was Chief Executive
Officer, it is desirable that Executive step down from his position;

         NOW, THEREFORE, the parties agree as follows:

         1. Effective February 9, 2001, Executive hereby resigns from all
directorships and officer positions with the Company and its affiliates and as a
fiduciary of any benefit plan of the Company or its affiliates. The Executive
shall execute such additional documents with regard thereto as reasonably
requested by the Company.

         2. The Executive shall cooperate with and assist the Company with
regard to transition of his responsibilities and transition of matters that he
has been involved in while an officer of the Company. The parties shall
cooperate with each other with regard to any matters related to the Issues,
including any investigation, action or other proceedings, unless Executive acted

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unlawfully. In addition, the Executive shall assist the Company with regard to
providing information, to the extent he has knowledge, on any other matters that
relates to his period of service with the Company. The Company shall reimburse
any reasonable expenses incurred by Executive and which have been preapproved in
writing by the Company in connection with the foregoing assistance.

         3. Payments made to Executive by the Company as set forth in Section 5,
below, shall be offset by the Company in the amount of $23,297.04 for personal
charges made to Executive's Company credit card, less any amounts that Executive
is able to prove to Company's reasonable satisfaction to be Company
expenditures.

         4. Executive acknowledges that during his employment, he may have
obtained confidential, proprietary and trade secret information, including
information relating to the Company's products, plans, designs and other
valuable confidential information. Executive agrees not to disclose any such
confidential information unless required by subpoena or court order, and that
Executive will first give the Company written notice of such subpoena or court
order with reasonable advance notice to the extent possible (except as
prohibited by law) to permit the Company to oppose such subpoena or court order
if it chooses to do so. Further, Executive acknowledges that he does not have in
his possession and has returned all Company property (including all laptop
computers, hardware and software), proprietary, trade secret and confidential
information, as well as all copies and duplicates thereof.

         5. Provided that the Executive executes and does not revoke the Release
annexed hereto as Exhibit A within the time specified therein, Executive shall
receive or has been provided:

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         (a) Within ten (10) business days after the date of execution of
Exhibit A, a lump sum payment equal to nine (9) months of base salary plus
automobile allowance, less deductions required by law;

         (b) Promptly any accrued but unpaid amounts, including but not limited
to unpaid salary, accrued but unused paid time off ("PTO") and, unreimbursed
business expenses (which Executive shall promptly submit accompanied by
documentation in accordance with Company policy);

         (c) Any option or Restricted Stock that would vest on or prior to
August 9, 2001 shall be deemed to be immediately vested. Otherwise, all vesting
shall cease effective as of February 9, 2001. The Company acknowledges that
Executive (including vested shares previously gifted by him) will have 1,274,687
shares of Restricted Stock fully vested, 29,000 unrestricted shares fully vested
and 449,006 options for shares of stock fully vested (of which 299,946 will be
incentive stock options). The Company further acknowledges that the Executive
has ninety (90) days from February 9, 2001 to exercise any vested options;

         (d) The Company will pay the cost for Executive's and his eligible
dependent's group health benefit coverage continuation under the Consolidated
Omnibus Budget Reconciliation Act of 1985 ("COBRA"), to the same extent
previously provided to Executive, through February 9, 2002, or until Executive
becomes eligible for group health insurance benefits from another employer,
whichever occurs first. Executive understands and agrees that he has obligation
to inform immediately the Company if he becomes eligible for such insurance from
another employer and that Executive may not increase the number of his
designated dependants, if any, during this time unless Executive does so at his
own expense. In addition, the Company shall

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pay up to $5,000 for Executive's annual physical scheduled for February 2001 at
Mayo Clinic and up to $5000 in travel and other expenses associated therewith.
Such amounts shall be paid or, if paid by Executive, reimbursed within ten days
of Executive's providing the Company with documentation with regard thereto;

         (e) The Company shall continue to provide at its expense (or reimburse
Executive for) continuation of Executive's existing financial planning services
through AYCO company for one (1) year at a fee of $18,500;

         (f) The repayment date of the nonrecourse Promissory Note for Five
Hundred Thousand Dollars ($500,000) dated 1998 (a copy of which is annexed
hereto as Exhibit C) shall be extended until March 9, 2002 and shall remain
nonrecourse;

         (g) The repayment date of the recourse Promissory Note for One Million
Sixty Five Thousand Six Hundred Thirty Eight Dollars and Ninety-Four Cents
($1,065,638.94) dated November 1998 (a copy of which is annexed hereto as
Exhibit D) shall be extended to May 9, 2002;

         (h) The Promissory Notes referred to in paragraph (f) and (g) above are
incorporated herein and shall remain secured by Common Stock as currently
provided. In the event Executive desires to sell any such Common Stock, the
Company shall release such stock from the security interest provided Executive
promptly upon sale pays to the Company against the loans (the (g) loan first)
the after tax net proceeds received by Executive upon such sale;

         (i) Executive's Common Stock and Options shall continue to be
registered under an S-8; and

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         (j) Executive shall be entitled to use the Company apartment for ninety
(90) days from February 9, 2001, so as to be available to assist the Company
under Section 2 with regard to transition during this period.

Executive understands and agrees that he shall be responsible for all tax
obligations, if any, associated with any of the benefits set forth in Section 5.

         6. (a) The Company acknowledges and agrees that, subject to the terms
and conditions of the Indemnification Agreement, Executive is entitled to
indemnification under the terms and conditions of the Indemnification Agreement
and under the Company's Articles and Bylaws with regard to any Proceedings (as
defined in the Indemnification Agreement) with regard to the Issues and
represents that such indemnification has been approved by the directors in
accordance with Section 5.2 of the Indemnification Agreement. Furthermore,
Executive shall be reimbursed for Expenses (as defined in the Indemnification
Agreement) pursuant to Section 4.1 of the Indemnification Agreement.

         (b) The Company agrees that Executive shall be entitled to separate
counsel of his choice with regard to Proceedings and that the Expenses in
connection therewith will be covered under the Indemnification provisions set
forth in Section 6(a) above. Notwithstanding the foregoing, with regard to any
Proceedings that is a civil litigation (other than administrative or criminal
matters) where both the Company and the Executive are defendants, the Company
may appoint its counsel of record as counsel of record for Executive in the
matter (subject to, and until, the exceptions in Section 11(b)(i) - (iii) of the
Indemnification Agreement become effective) but Executive may have "shadow"
counsel of his choice for any Proceeding that is civil litigation as referenced
above, the Expenses of whom shall be paid by the Company notwithstanding the

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appointment of different counsel of record by the Company. If Executive
determines in good faith that shadow counsel should become counsel of record for
Executive in any such Proceeding so as to best protect his interests, the
Company agrees to honor such request on the same basis as under the first
sentence of this paragraph. Executive agrees to make such decision only after
consultation with counsel for the Company. The Company further agrees that any
internal investigation by the Company is a Proceeding.

         (c) Executive acknowledges and agrees that under Section 4.1 of the
Indemnification Agreement the Company is entitled to repayment by Executive for
all payments advanced to Executive pursuant to the Indemnification Agreement if
it shall ultimately be determined that Executive is not entitled to be
indemnified pursuant to the terms of the Indemnification Agreement.

         7. The parties shall not willfully and intentionally defame each other
in any public forum, provided the foregoing shall not in any way obstruct
justice, limit any claims made in any litigation, or prevent a party from
"correcting the record."

         8. The provisions set forth in the Executive's Proprietary Information
and Inventions Agreement (a copy of which is annexed hereto as Exhibit E) shall
continue to apply, provided Executive shall be entitled to retain copies of any
documents in his possession with regard to the Issues.

         9. The Company shall pay Executive's reasonable legal fees (based on
standard hourly rates of Executive's counsel) in negotiating this Agreement, up
to a maximum of $15,000.00.

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         10. Executive shall execute the release set forth in Exhibit A hereto
and the Company shall execute the release set forth in Exhibit B hereto.

         11. This Agreement and Releases (Exhibits A & B) is the entire
agreement between the parties and supersedes the Employment Agreement and any
other prior agreements or understandings, whether written or oral, between them
regarding the subject matter herein unless such agreements are incorporated
herein, provided, however, neither the Promissory Notes (Exhibits C & D), the
Proprietary Information Agreement (Exhibit E), the Indemnification Agreement,
nor any other rights of indemnification, contribution, to be held harmless or
for director and officer liability insurance coverage shall be superseded. It
may not be terminated or modified orally, but only by a writing executed by the
party to be charged. The Agreement and Release shall be interpreted under the
laws of the State of California without regard to principles of conflict of
laws.

         12. The Agreement and Releases are binding on and for the benefit of
Executive, the Releasees and their respective heirs, executors, administrators,
successors and assigns, whenever the context requires. If any term or condition
is determined to be overbroad or invalid, the remainder of the provisions shall
remain in full force and effect.

         13. The execution and delivery of the Agreement and Releases or any
performance of any acts in connection therewith shall not be deemed at any time
or place to be an admission by Releasees or Executive that either Releasees or
Executive performed or failed to perform any act in violation the other parties'
rights. It is the sole purpose of this Agreement and Releases to avoid the
expense and vexation of possible litigation between them.

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         14. With the exception of the Indemnification Agreement, which shall be
controlled by its terms, if any suit is brought relating to the enforcement or
breach of this Agreement and Release (with the exception of a claim by Executive
challenging the validity of this Release under the ADEA, as amended by the
OWBPA), the Court shall have the discretion to award the prevailing party in
such suit shall be entitled to all remedies and reimbursement for reasonable
costs, expenses and attorney's fees incurred by it.

         15. The parties shall keep the terms of this Agreement confidential
except to the extent such terms become public (other then by virtue of an
improper act of the party), provided that (a) a party may comply with required
governmental filing and disclosure requirements, (b) a party may comply with
legal process provided that (to the extent legally permitted to do so), the
party gives the other party prompt written notice thereof so that the other
party if it desires may oppose such legal process, (c) the Company may disclose
it on a need to know basis to its officers, board members, employees , attorneys
and auditors and the Executive may disclose it to his attorneys, financial
advisors, accountants, family and current girlfriend and, on a need to know
basis as to any limitations on Executive's activities, to any potential
employer, provided that any such entities or persons shall be informed to the
confidentiality obligations with regard to the information and that any
violation by such person or entity shall be deemed a violation by the party
disclosing it to such person or entity, and (d)as necessary to enforce or defend
his or its rights hereunder.

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         16. The parties hereby agree that this Agreement may be executed in
counterparts.

         In witness whereof, the parties have executed this Agreement this _____
day of February, 2001.

                                           CRITICAL PATH, INC.

                                           By: /s/ DOUGLAS HICKEY
                                               --------------------------------
                                                   Douglas Hickey

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                                    EXHIBIT A

         1. In consideration of the provisions set forth in the Agreement
attached hereto, Douglas Hickey ("Executive"), on behalf of himself and his
heirs, executors, administrators, successors and assigns, hereby unconditionally
releases and discharges Critical Path, Inc. (the "Company"), and its past and
present subsidiaries, successors, affiliate companies and assigns, and their
respective past and present directors, officers, representatives, agents,
investigators, attorneys and employees, in such capacities as well as any
benefit plan and its fiduciaries (collectively "Releasees" and individually
"Releasee") from all known and unknown claims (including claims for attorneys'
fees and costs), charges, actions and causes of action, demands, damages, and
liabilities of any kind or character, in law or equity, suspected or
unsuspected, known or unknown, past or present, that he ever had, may now have,
or may later assert against any Releasee heretofore occurring on or before
February 9, 2001, other than Executive's rights under the Indemnification
Agreement (as defined in the Agreement), any other rights of indemnification,
contribution or to be held harmless and any rights to, or under any policy with
regard to, directors and officers liability insurance, if any, and matters
expressly excluded under the Agreement. To the fullest extent permitted by law,
this release includes but is not limited to: (a) claims arising under the Age
Discrimination in Employment Act of 1967 ("ADEA"), as amended by the Older
Workers Benefit Protection Act ("OWBPA") (except as it relates to the validity
of this Release under the ADEA/OWBPA), the Workers' Adjustment and Retraining
Notification Act, the ERISA, the Family and Medical Leave Act of 1993, the ADA,
the California Fair Employment and Housing Act, and any other federal, state, or
local law prohibiting age, race, color, gender, creed, religion, sexual
preference/orientation, marital status, national origin, mental or physical
disability, veteran status, or any other form of unlawful

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discrimination or claim with respect to or arising out of Executive's employment
with or termination from the Company; (b) claims (whether based on common law or
otherwise) arising out of or related to any contract (whether express or
implied); (c) claims under any federal, state or local constitutions, statutes,
rules or regulations; (d) claims (whether intentional or otherwise, common law
or tort) including but not limited to, wrongful termination, defamation,
violation or public policy; and (e) claims included in, related to, or which
could have been included in any presently pending federal, state or local
lawsuit filed by Executive or on his behalf against any Releasee. Executive
represents that he has no claims currently pending against any Releasee in any
forum and that if Executive does have any such claims, Executive agrees to
immediately dismiss with prejudice.

Section 1542 of the Civil Code of the State of California states:

         "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."

Notwithstanding the provisions of Section 1542, and for the purpose of
implementing a full and complete release and discharge of all Releasees with
respect to claims in California as well as all other jurisdictions, Executive
expressly acknowledges that this Release is intended to include not only claims
that are known, anticipated or disclosed, but also claims that are unknown,
unanticipated and undisclosed.

         2. Except as to claims relating to the validity of this Release under
the ADEA as amended by the OWBPA, Executive agrees not to bring any action, suit
or administrative

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<PAGE>   12

proceeding contesting the validity of this Release or attempting to negate,
modify or reform it, nor to sue any Releasee for any reason with regard to any
released matter.

         3. Executive understands that, pursuant to the Older Workers Benefit
Protection Act, he has the right to (and should) consult with an attorney before
signing this Release and represents that he has done so. Executive understands
that he has up to twenty-one (21) days to consider the Release before signing it
and he may revoke the Release within seven (7) calendar days after signing it.
Revocation can be made by delivering a written notice of revocation to: Brett
Robertson, Esq., Critical Path, Inc., 320 First Street, San Francisco,
California 94105.

         BY SIGNING THIS RELEASE, EXECUTIVE STATES THAT:

         a) HE HAS READ IT AND HAS HAD SUFFICIENT TIME TO CONSIDER ITS TERMS;

         b) HE UNDERSTANDS IT AND KNOWS THAT HE IS GIVING UP IMPORTANT RIGHTS;

         c) HE ACCEPTS ITS TERMS;

         d) HE IS AWARE OF HIS RIGHT TO (AND THAT HE SHOULD) CONSULT AN ATTORNEY
            BEFORE SIGNING IT AND HAS DONE SO; AND

                                       12

<PAGE>   13

         e) HE HAS SIGNED IT KNOWINGLY AND VOLUNTARILY.

            /s/ DOUGLAS HICKEY
            ----------------------------
            Douglas Hickey

            Date:

                                       13

<PAGE>   14

                                    EXHIBIT B

         1. Critical Path, Inc. on behalf of itself and its subsidiaries (which
right to act on behalf of it represents and warrants it has) hereby
unconditionally releases and discharges Douglas Hickey ("Executive") and his
heirs, executors, administrators, successors and assigns (collectively
"Releasees" and individually "Releasee") from all known and unknown claims
(including claims for attorneys' fees and costs), charges, actions and causes of
action, demands, damages, and liabilities of any kind or character, in law or
equity, suspected or unsuspected, past or present, that it or they ever had, may
now have, or may later assert against any Releasee, other than with regard to
any acts or omissions related to the Issues, as defined in the Agreement and
Release effective February 9, 2001 between the Company and Executive (the
"Agreement") or as provided in the Agreement.

Section 1542 of the Civil Code of the State of California states:

       "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."

         Notwithstanding the provisions of Section 1542, and for the purpose of
implementing a full and complete release and discharge of all Releasees with
respect to claims in California as well as all other jurisdictions, the Company
expressly acknowledges that this Release is intended to include not only claims
that are known, anticipated or disclosed, but also claims that are unknown,
unanticipated and undisclosed.

         2. The Company agrees not to bring any action, suit or administrative
proceeding contesting the validity of this Release or attempting to negate,
modify or reform it, nor to sue any Releasee for any reason with regard to any
released matter.

                                       14

<PAGE>   15

         BY SIGNING THIS RELEASE, THE COMPANY STATES THAT;

         a) IT HAS READ IT AND HAS HAD SUFFICIENT TIME TO CONSIDER ITS TERMS;

         b) IT UNDERSTANDS IT AND KNOWS THAT IT IS GIVING UP IMPORTANT RIGHTS;

         c) IT ACCEPTS ITS TERMS;

         d) IT IS AWARE OF ITS RIGHT TO (AND THAT IT SHOULD) CONSULT AN ATTORNEY
            BEFORE SIGNING IT AND HAS DONE SO; AND e) IT HAS SIGNED IT KNOWINGLY
            AND VOLUNTARILY.

                               Critical Path, Inc.

         By:   /s/ BRETT ROBERTSON
             -------------------------------------------
               Brett Robertson, Esq.
               Vice President of Strategic Development,
               General Counsel

         Date:    February 28, 2001
               -----------------------------------------

                                       15

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