CRITICAL PATH, INC. AMENDED AND RESTATED 1998 STOCK OPTION PLAN RESTRICTED STOCK AGREEMENT

/s/ MARK FERRER

/s/ MICHAEL J. ZUKERMAN

The text of the Plan and your Employment Agreement are incorporated in this Agreement by this reference. You and the Company agree to execute such further instruments and to take such further action as may reasonably be necessary to carry out the intent of this Agreement. Unless otherwise defined in this Agreement, certain capitalized terms used in this Agreement are defined in the Plan or your Employment Agreement.

This Agreement, the Employment Agreement, the attached Exhibits and the Plan constitute the entire understanding between you and the Company regarding this Award of Restricted Stock. Any prior agreements, commitments or negotiations are superseded. The terms of your Employment Agreement shall be controlling over any conflicting term of this Agreement or the Plan.

Vesting Date

29-Mar

29-Jun

29-Sep

29-Dec

Yearly Total:

For purposes of this Agreement, the terms “vesting,” “vested shares” or words of similar import or effect shall mean that the Restricted Stock is no longer subject to forfeiture and is freely transferable without restriction.

Notwithstanding the foregoing, you will receive accelerated vesting of your Restricted Stock if there is a Qualifying Termination (as defined in your Employment Agreement) and if you timely satisfy the conditions specified

in your Employment Agreement (including but not limited to your execution and non-revocation of a
separation agreement and release of claims) (the “Acceleration”). If a Qualifying Termination occurs
within twelve months after a Change in Control (as defined in your Employment Agreement) or if a
Qualifying Termination occurs within three (3) months before a Change in Control that you can
demonstrate would not have occurred absent such Change in Control, then the Acceleration shall be the
greater of seventy-five percent of your then unvested restricted shares or twelve months of accelerated
vesting of your unvested restricted shares. For a Qualifying Termination occurring under other
circumstances, the Acceleration shall be twelve months of accelerated vesting of your unvested restricted
shares.

Upon cessation of your Service, you will immediately forfeit to the Company without consideration all of
the then unvested Restricted Stock subject to this Award, after application, as applicable, of the
Acceleration provision described above.

Your vesting will cease in the event that your Service terminates for any reason. A leave of absence,
regardless of the reason, shall be deemed to constitute the cessation of your employment unless such
leave is authorized by the Company and you return to active employee status within the time specified in
such authorization. Subject to applicable law, during such leave your vesting shall be suspended until you
return to active Service and, upon such return, your vesting will commence again at the vested percentage
as of when the leave began so that the vesting schedule will be extended by the amount of time during
which you were on leave.

All vesting hereunder shall be effected in whole numbers of shares rounded down to the nearest whole
number.

The certificates for the Restricted Stock shall be deposited in escrow with the Secretary of the Company to be held in accordance with the provisions of this section. Each deposited certificate shall be accompanied by a duly executed Assignment Separate from Certificate in the form attached hereto as Exhibit A. The deposited certificates, shall remain in escrow until such time as the certificates are to be released or otherwise surrendered for cancellation. Upon delivery of the certificates to the Company, you shall be issued an instrument of deposit acknowledging the number of shares of Restricted Stock delivered in escrow to the Secretary of the Company.

All regular cash dividends on the Restricted Stock (if any) shall be paid directly to you and shall not be held in escrow.

The Restricted Stock held in escrow hereunder shall be subject to the following terms and conditions relating to their release from escrow or their

surrender to the Company:

•      When your interest in the Restricted Stock vests as described above, the certificates for such vested shares shall be released from escrow and delivered to you, at your request, in accordance with the following schedule:

•      The initial release of any vested Restricted Stock from escrow shall be effected on the date that is six (6) months after the Date of Award. Subsequent releases of vested shares from escrow shall occur on each date that such shares become vested.

•      Upon termination of your Service, all unvested Restricted Stock, after application, as applicable, of the Acceleration provision described above shall be surrendered to the Company without consideration.

Notwithstanding anything to the contrary, upon the Company’s issuance to you of a notice indicating the Company’s intention to terminate your Service for Cause, no vested shares shall be released from escrow unless and until you timely cure to the Company’s satisfaction the act or acts which precipitated the notice of termination.

For purposes of this option, your employment does not terminate when you go on a bona fide leave of absence, that was approved by the Company in writing, if the terms of the leave provide for continued service crediting, or when continued service crediting is required by applicable law. Your Service terminates in any event when the approved leave ends if you fail or refuse to return to active Service.

The Company determines which leaves count for this purpose, and when your Service terminates for all purposes under the Plan.

By signing this Agreement, you agree not to sell or otherwise dispose of any Restricted Stock prior to its vesting or sell any Shares acquired under this Award at a time when applicable laws, regulations or Company or underwriter trading policies prohibit sale.

In the event that the sale of Shares under the Plan is not registered under the Securities Act of 1933 but an exemption is available which requires an investment representation or other representation, you shall represent and agree at the time of sale of Shares to make such representations as are deemed necessary or appropriate by the Company and its counsel.

Prior to any Change in Control of the Company, the shares acquired under this Award can be sold or transferred only pursuant to an SEC Rule 10b5-1 trading plan that is pre-approved by the Company’s Board of Directors’ Compensation Committee provided, however, that

i)       this provision shall not apply to your transfer of any or all of the shares acquired under this Award, either (a) during your lifetime where the transfer is without consideration and is to one or more members of your immediate family, to a trust for the exclusive benefit of you or your

immediate family members, to any other entity owned exclusively by you or your immediate family members, or to any combination of the foregoing, or (b) on or subsequent to your death where the transfer is by will or the laws of descent and distribution,; and

ii)     this provision shall cease to apply subsequent to the termination of your employment for any reason.

For purposes of this Agreement, “Immediate family member” shall include your spouse or former spouse, children, grandchildren, parents or siblings, nieces and nephews including in each case in-laws and adoptive or step relations.

If, at any time during your Service or within one year after termination of such Service, you engage in any of the following, then all unvested shares remaining in escrow will be forfeited to the Company without consideration effective as of the date on which you first engaged in such activity, unless terminated or forfeited sooner by operation of another term or condition of this Award, the Plan or your Employment Agreement.

•      You are convicted of a felony (other than a traffic violation) or are otherwise conclusively determined by the Board to have committed an act constituting common law fraud against the Company which has or is likely to have a material adverse effect on the Company,

•      You intentionally and without justification breach your obligation to the Company with respect to the Company’s confidential information, which breach has a material adverse effect on the Company or its affiliates or shareholders,

•      You intentionally act or intentionally omit to act where such action or omission violates the explicit obligations imposed on chief executive officers under the Sarbanes-Oxley Act of 2002 (“S-Ox”), as determined by a court of competent jurisdiction or the Securities and Exchange Commission.

•      You materially breach a material provision of either this Agreement, your Employment Agreement or any separation of employment agreement that you enter into with the Company.

All certificates representing the Restricted Stock issued under this Award shall, where applicable, have endorsed thereon the following legend and any other applicable legends:

“THE SHARES REPRESENTED BY THIS CERTIFICATE ARE SUBJECT TO CERTAIN RESTRICTIONS ON TRANSFER SET FORTH IN AN AGREEMENT BETWEEN THE COMPANY AND THE REGISTERED HOLDER, OR HIS OR HER PREDECESSOR IN INTEREST. A COPY OF SUCH AGREEMENT IS ON FILE AT THE PRINCIPAL OFFICE OF THE COMPANY AND WILL BE FURNISHED UPON WRITTEN REQUEST TO THE SECRETARY OF THE COMPANY BY THE HOLDER OF RECORD OF THE SHARES REPRESENTED BY THIS CERTIFICATE.”

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