Exhibit 31.1



CERTIFICATION

of the Chief Executive Officer



Pursuant to
18 U.S.C. Section 1350,

as adopted pursuant to Section 302 of the Sarbanes-Oxley Act of 2002



I, Jeffrey C. Smith, Chairman and Chief Executive Officer of Tumbleweed Communications Corp.
(the Company), certify that:



1. I have reviewed this report on
Form 10-Q of Tumbleweed Communications Corp.;



2. Based on my knowledge, this
report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period
covered by this report;



3. Based on my knowledge, the financial statements,
and other financial information included in this quarterly report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;



4. The registrants other certifying officer and I are responsible for
establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) for the registrant and we have:



(a) Designed such disclosure controls and procedures, or caused such disclosure and procedures to be designed under our supervision, to ensure that material information
relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this quarterly report is being prepared;



(b) Evaluated the effectiveness of the registrants disclosure controls and procedures
and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and



(c) Disclosed in this report any change in the registrants internal control over
financial reporting that occurred during the registrants most recent fiscal quarter (the registrants fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the
registrants internal control over financial reporting; and



5. The
registrants other certifying officer and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrants auditors and the audit committee of the registrants board of directors
(or persons performing the equivalent functions):



(a) All significant
deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrants ability to record, process, summarize and report financial
information; and



(b) Any fraud, whether or not material, that involves
management or other employees who have a significant role in the registrants internal control over financial reporting.



Date: November 9, 2004



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|/s/ JEFFREY C. SMITH                                 
|Jeffrey C. Smith Chairman and Chief Executive Officer