Tumbleweed Positioned in Leaders Quadrant of 2008 Magic Quadrant for Managed File Transfer

Tumbleweed® Communications Corp. (NASDAQ:TMWD), an industry leader in managed file transfer and email security, today announced that it has been positioned in the Leaders Quadrant of the newly released "Gartner Magic Quadrant for Managed File Transfer,” (L. Frank Kenney, James Lennard, 23 June 2008). According to the analyst firm, "leaders (in the Gartner Magic Quadrant for Managed File Transfer (MFT)) are most likely to have high revenue and commitment to the market, high market share and installed bases, and products that are of interest to a large audience. Additionally, leaders have presented domain expertise and compelling messages that have penetrated the market." "We are delighted to be positioned in the leaders quadrant – from our perspective, this event reinforces our continued market leadership in the managed file transfer space,” said Jim Scullion, CEO of Tumbleweed Communications. "This segment represents a tremendous market opportunity, and with our vision and discipline, Tumbleweed is poised to deliver leading-edge solutions to our partners and customers.” According to the report, "Gartner estimates that the market for MFT suites and services is approximately $450 million and is growing at a rate of 21% to 26% year over year." About the Magic Quadrant The Magic Quadrant is copyrighted June 23, 2008 by Gartner, Inc. and is reused with permission. The Magic Quadrant is a graphical representation of a marketplace at and for a specific time period. It depicts Gartner's analysis of how certain vendors measure against criteria for that marketplace, as defined by Gartner. Gartner does not endorse any vendor, product or service depicted in the Magic Quadrant, and does not advise technology users to select only those vendors placed in the "Leaders" quadrant. The Magic Quadrant is intended solely as a research tool, and is not meant to be a specific guide to action. Gartner disclaims all warranties, express or implied, with respect to this research, including any warranties of merchantability or fitness for a particular purpose. SAFE HARBOR STATEMENT Tumbleweed cautions that forward-looking statements contained in this press release are based on plans and expectations as of the date of the 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 Tumbleweed’s market position, as well as the features and capabilities of Tumbleweed’s managed file transfer solutions. 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 17, 2008 and Tumbleweed’s Form 10-Q filed May 12, 2008. 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 Tumbleweed Tumbleweed Communications Corp. (NASDAQ:TMWD), an industry leader in managed file transfer, email security and identity validation, provides enterprise-class solutions to organizations of all sizes. Tumbleweed’s innovative products enable organizations to effectively manage and protect business-critical Internet communications, with capabilities that span secure file transfer, encryption, data loss prevention, and email security. Tumbleweed has more than 3,300 customers worldwide, including blue-chip companies across an array of industries such as Technology, Retail, Finance, Healthcare, Manufacturing, Consumer Packaged Goods, Telecom, Energy, and the U.S. Government. The world’s most security conscious organizations rely upon Tumbleweed technology including Bank of America Securities, JP Morgan Chase & Co., the U.S. Food and Drug Administration, and the U.S. Department of Defense. Our award-winning products build on 15 years of R&D and 29 security patents in the U.S. alone – many of which are licensed by other security vendors. More information can be found at www.tumbleweed.com. Tumbleweed is a registered trademark of Tumbleweed Communications Corp. in the United States and/or other countries. All other trademarks are the property of their respective owners.