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Tumbleweed Wins “Best Communications Security” Award From SC Magazine

Industry’s Largest Information Security Magazine Honors Tumbleweed’s
Secure File Transfer Software

Redwood City, CA – May 3rd, 2004 – Tumbleweed® Communications Corp. (NASDAQ:TMWD), a leading provider of secure Internet messaging software and hardware for enterprises and government agencies, announced today that its secure file transfer software product, Tumbleweed SecureTransport™, was awarded "Best Communications Security” solution by SC Magazine - the largest information security magazine today - at the publication's SC Awards 2004 ceremony held recently in London.

SC Magazine Global Awards is the leading awards program for the information security industry and this year’s awards were the most competitive with well over 900 product and service nominations from around the world and nearly 300 companies participating. The awards recognize achievement and technical excellence and are a truly global program with participation from developers and users around the world.

Recognizing achievement and technical excellence across 32 different product and service categories, the SC Awards is a truly global program with participation from developers and users around the world. Tumbleweed’s SecureTransport fought off competition from other finalists in the Best Communications Security solution category, including Aladdin Knowledge Systems’ eToken and SSH Communications’ SSH Tectia Client/Server 4.0.

“We are excited that the industry has recognized Tumbleweed’s SecureTransport as the best communications security solution for the Internet,” said Dave Jevans, Chief Marketing Officer for Tumbleweed Communications. “Receiving this prestigious award is a testament to Tumbleweed’s leadership position in the secure Internet messaging marketplace.”

About Tumbleweed SecureTransport
According to industry analyst Gartner, secure file transfer with automation and back-office integration has become a critical piece of an enterprise’s B2B strategy and overall application integration initiatives. Tumbleweed SecureTransport is a family of enterprise-quality secure file transfer products for moving critical business files, very large documents, XML, EDI and B2B transactions over the Internet.

Tumbleweed Secure Transport Enterprise Edition is designed for customers with high-grade security requirements, large-scale deployments or more advanced integration needs. The Enterprise Edition builds on SecureTransport Standard Edition and includes these additional components and capabilities:

o An Application Proxy component for secure DMZ streaming deployment
o Transaction Manager for rule-based integration options using Active Agents or Java agents
o Signed audit records for tracking file transfer transactions and non-repudiation
o Access Manager for enhanced user management and permission capabilities

In addition to this prestigious SC Magazine award, industry analyst Meta Group recently rated Tumbleweed SecureTransport as a Market Leader in the enhanced file transfer market.

About SC Magazine Global Awards 2004
With over 900 nominations in the SC Magazine Global Awards 2004 and over 300 individual companies participating, this is the world's leading awards program for the information security industry. www.scmagazine.com. Recognizing achievement and technical excellence across 32 different product and service categories, the SC Awards is a truly global program with participation from developers and users around the world. Finalists were published globally on Friday, March 19th and the winners in all categories were announced at the SC Awards Gala dinner to be held at the Grosvenor Hotel, Park Lane, London on Tuesday, April 27th. For more information contact Chris Thomas, Global Publisher of SC Magazine at cthomas@westcoast.com.

About Tumbleweed Communications:
Tumbleweed is a leading provider of secure Internet messaging software and hardware for enterprises and government agencies. By making Internet communications secure, reliable and automated, Tumbleweed's anti-spam email firewall, secure file transfer, secure email, and identity validation solutions help customers significantly reduce the cost of doing business. Tumbleweed products are used to communicate with millions of end-users and tens of thousands of corporations. Tumbleweed has more than 600 enterprise customers, including 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 US Food and Drug Administration, and the US Navy and Marine Corps. Tumbleweed Communications was founded in 1993 and is headquartered in Redwood City, California. For additional information about Tumbleweed go to www.tumbleweed.com or call 650-216-2000.

SAFE HARBOR STATEMENT

Tumbleweed cautions that forward-looking statements contained in this press release are based on current plans and expectations, 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 Tumbleweed's leadership in the secure Internet messaging marketplace. 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 15, 2004.

Tumbleweed assumes no obligation to update information contained in this press release, including for example its guidance regarding its future performance, which represents the Company's expectations only as of the date of this release and should not be viewed as a statement about the Company's expectations after such date. Although this release may remain available on the Company's website or elsewhere, its continued availability does not indicate that the Company is reaffirming or confirming any of the information contained herein.

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