Tumbleweed SecureTransport Wins “Best Intellectual Property Protection” At SC Magazine European Awards Show

Recognition Reinforces Global Industry Leadership and Product Innovation

Redwood City, CA – May 10, 2006 – Tumbleweed® Communications Corp. (NASDAQ:TMWD), a leading provider of email security, managed file transfer, and identity validation appliance and software products, announced that Tumbleweed’s SecureTransport™ was named the Best Intellectual Property Protection Solution by SC Magazine - the largest information security magazine today. The award was presented at the SC Magazine European Awards ceremony, which took place at The Grosvenor House, Park Lane, on April 25 th in London, England. Tumbleweed’s MailGate® Email Firewall™ was recently named the Best Email Content Filtering Solution by SC Magazine at the U.S. awards show earlier this year.

With over 1,300 product and service nominations from over 330 competing companies globally, the SC Awards are the world's leading awards program for the information security industry. Recognizing achievement and technical excellence across 32 different product and service categories, the SC Awards is a global program with participation from developers and users around the world.

“We are honored to receive SC Magazine’s European award for Best Intellectual Property Protection Solution,” said John Thielens, CTO for Tumbleweed Communications. “Tumbleweed management and employees are incredibly excited to have received our second SC Magazine award this year. This award recognizes our continuing effort to providing the most effective and comprehensive approach to securing online communications for all of our customers around the globe.”

The SC Global Awards program spans the U.S., Asia, and the U.K. The SC Awards are composed of both the Reader Trust Technology Awards—voted on by SC readers in each region and the SC Awards Council, a group of carefully selected senior CSOs—and the Professional Awards that are judged by a panel of the industry's top talents.

About Tumbleweed SecureTransport
Tumbleweed' SecureTransport is the industry’s leading enterprise managed file transfer solution. It enables the exchange of valuable and sensitive data over the Internet in a secure and reliable manner. SecureTransport is a centrally managed, client-server solution supporting a broad set of secure, open standard file transfer protocols, including FTP, FTPS, HTTP, HTTPS, SSH (SFTP and SCP), and AS2. SecureTransport is available as an appliance or software.

SAFE HARBOR STATEMENT
Tumbleweed cautions that forward-looking statements contained in this press release are based on current plans and expectations as of the date of this press release, and that a number of factors could cause the actual results to differ materially from the guidance given at this time. These factors are described in the Safe Harbor statement below.

Except for the historical information contained herein, the matters discussed in this press release may constitute forward-looking statements that involve risks and uncertainties that could cause actual results to differ materially from those projected, particularly with respect to the performance and functionality of Tumbleweed’s products. In some cases, forward-looking statements can be identified by terminology such as “may,” “will,” “should,” “potential,” “continue,” “expects,” “anticipates,” “intends,” “plans,” “believes,” “estimates,” and similar expressions. For further cautions about the risks of investing in Tumbleweed, we refer you to the documents Tumbleweed files from time to time with the Securities and Exchange Commission, particularly Tumbleweed's Form 10-K filed March 16, 2006.

Tumbleweed assumes no obligation to update information contained in this press release. Although this release may remain available on Tumbleweed’s website or elsewhere, its continued availability does not indicate that Tumbleweed is reaffirming or confirming any of the information contained herein.

About SC Magazine Awards 2006
Recognizing technical excellence and professional achievement across a variety of different categories, the SC Awards is a truly unique program developed to bring attention to the industry's top products and highlight the professionals that have both created them and use them within their companies.

About Tumbleweed Communications Corp.
Tumbleweed provides security solutions for email protection, file transfers, and identity validation that allow organizations to safely conduct business over the Internet. Tumbleweed offers these solutions in three comprehensive product suites: MailGate, SecureTransport, and Validation Authority™. MailGate provides protection against spam, viruses, and attacks, and enables policy-based message filtering, encryption, and routing. SecureTransport enables business to safely exchange large files and transactions without proprietary software. Validation Authority is the world-leading solution for determining the validity of digital certificates. Tumbleweed’s enterprise and government customers include ABN Amro, Bank of America Securities, Catholic Healthcare West, JP Morgan Chase & Co., The Regence Group (Blue Cross/Blue Shield), St. Luke’s Episcopal Healthcare System, the U.S. Food and Drug Administration, the U.S. Department of Defense, and all four branches of the U.S. Armed Forces. Tumbleweed was founded in 1993 and is headquartered in Redwood City, Calif. For additional information about Tumbleweed go to www.tumbleweed.com or call 650-216-2000.

Tumbleweed, the Arrows logo, MailGate, MailGate Email Firewall, SecureTransport and Validation Authority are either registered trademarks or trademarks of Tumbleweed Communications Corp. in the United States and/or other countries. All other trademarks are the property of their respective owners.

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