Exhibit 4.4 FACE SERIES E PREFERRED STOCK Critical Path, Inc. SERIES E PREFERRED STOCK - ------------------ --------------------------- INCORPORATED UNDER THE LAWS OF SEE REVERSE FOR STATEMENTS RELATING THE STATE OF CALIFORNIA TO RIGHTS, PREFERENCES, PRIVILEGES AND RESTRICTIONS, IF ANY CUSIP ______________ THIS CERTIFIES THAT is the record holder of FULLY PAID AND NONASSESSABLE SHARES OF THE SERIES E PREFERRED STOCK, $.001 PAR VALUE, OF - -------------------------------CRITICAL PATH, INC.------------------------------ transferable only on the books of the Corporation by the holder hereof in person or by duly authorized attorney upon surrender of this Certificate properly endorsed. This Certificate is not valid unless countersigned and registered by the Transfer Agent and Registrar. WITNESS the facsimile seal of the Corporation and the facsimile signatures of its duly authorized officers. Dated: Senior Vice President, Chief Executive Officer General Counsel and Secretary BACK CRITICAL PATH, INC. A STATEMENT OF THE RIGHTS, PREFERENCES, PRIVILEGES AND RESTRICTIONS GRANTED TO OR IMPOSED UPON THE RESPECTIVE CLASSES OR SERIES OF SHARES AND UPON THE HOLDERS THEREOF AS ESTABLISHED, FROM TIME TO TIME, BY THE ARTICLES OF INCORPORATION OF THE CORPORATION AND BY ANY CERTIFICATE OF DETERMINATION, AND THE NUMBER OF SHARES CONSTITUTING EACH CLASS AND SERIES OF SHARES AND THE DESIGNATIONS THEREOF, MAY BE OBTAINED BY THE HOLDER HEREOF UPON WRITTEN REQUEST AND WITHOUT CHARGES FROM THE SECRETARY OF THE CORPORATION AT ITS CORPORATE HEADQUARTERS. THE SHARES REPRESENTED BY THIS CERTIFICATE ARE REDEEMABLE BY THE CORPORATION AT ITS OPTION ON OR AFTER [____________] UPON THE HAPPENING OF CERTAIN CIRCUMSTANCES. FOR SO LONG AS THE SHARES REPRESENTED BY THIS CERTIFICATE ARE OUTSTANDING, THE SHARES ARE CONVERTIBLE INTO SHARES OF THE CORPORATION'S COMMON STOCK AT ANY TIME UPON THE OPTION OF THE HOLDER IN ACCORDANCE WITH THE PROVISIONS SET FORTH IN THE CERTIFICATE OF DETERMINATION OF PREFERENCES OF SERIES E REDEEMABLE CONVERTIBLE PREFERRED STOCK, A COPY OF WHICH MAY BE OBTAINED BY THE HOLDER HEREOF UPON WRITTEN REQUEST AND WITHOUT CHARGES FROM THE SECRETARY OF THE CORPORATION AT ITS CORPORATE HEADQUARTERS. The following abbreviations, when used in the inscription on the face of this certificate, shall be construed as though they were written out in full according to applicable laws or regulations: TEN COM - as tenants in common TEN ENT - as tenants by the entireties JT TEN - as joint tenants with right of survivorship and not as tenants in common UNIF GIFT MIN ACT___________Custodian______ (Cust) (Minor) under Uniform Gifts to Minors Act _____________________ (State) UNIF TRF MIN ACT ______Custodian (until age ___ (Cust) ______under Uniform Transfers (Minor) to Minors Act ______________ (State) Additional abbreviations may also be used though not in the above list. FOR VALUE RECEIVED, _______________________ hereby sell, assign and transfer unto PLEASE INSERT SOCIAL SECURITY OR OTHER IDENTIFYING NUMBER OF ASSIGNEE ________________________________________________________________________________ (PLEASE PRINT OR TYPEWRITE NAME AND ADDRESS, INCLUDING ZIP CODE OF ASSIGNEE) ________________________________________________________________________________ ________________________________________________________________________________ ________________________________________________________________________________ __________________________________________________________________________Shares of the capital stock represented by the within Certificate, and do hereby irrevocably constitute and appoint ________________________________________________________________________Attorney to transfer the said stock on the books of the within named Corporation with full power of substitution in the premises. Dated ____________________________________ X ___________________________________________ X ___________________________________________ NOTICE THE SIGNATURE(S) TO THIS ASSIGNMENT MUST CORRESPOND WITH THE NAME(S) AS WRITTEN UPON THE FACE OF THE CERTIFICATE IN EVERY PARTICULAR, WITHOUT ALTERATION OR ENLARGEMENT OR ANY CHANGE WHATSOEVER. Signature(s) Guaranteed By ______________________________________________________________ THE SIGNATURE(S) MUST BE GUARANTEED BY AN ELIGIBLE GUARANTOR INSTITUTION (BANKS, STOCKHOLDERS, SAVINGS AND LOAN ASSOCIATIONS AND CREDIT UNIONS WITH MEMBERSHIP IN AN APPROVED SIGNATURE GUARANTEE MEDALLION PROGRAM), PURSUANT TO S.E.C. Rule 17ad-15