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There was a huge discussion "PIX problems with DKIM header fields" on the postfix-users@postfix.org mailinglist recently. One of the symptoms observed was that sites behind a CISCO PIX with "esmtp protocol fixup" wouldn't accept DKIM-signed emails. The connection would simply been dropped during the DATA stage.
Jim Fenton of CISCO solved the riddle for us and wrote this:
There are three bugs (all resolved) relating to Content-Type issues:
These bug fixes are all incorporated in version 7.2(2.19) and 8.0(2.7).
7.2(2.19) is available to registered users on cisco.com by clicking the "interim releases" link on the software download page. I'm still unsure of the availability of 8.0(2.7).
According to one of the bug descriptions, the message
SMTP: Multiple Content-Type headers!will be logged if ESMTP debugging is enabled and this is the cause.
Heise.de published an article about this as well: Cisco PIX behindert authentifizierten Mail-Versand
And another Cisco PIX and ASA problem with inspection of a SMTP protocol (actually, parsing of a mail header section):Problem description:
SMTP session is disconnected during DATA phase of a SMTP transaction for mail messages with a DKIM signature, where the start of a string "content-type" or "content-transfer-encoding" in a tag's value of an "h" tag of a DKIM signature happens to fall on a packet boundary at a start of a packet. The session is dropped with the next packet containing a Content-Type or Content-Transfer-Encoding header field.
Platform:
ASA5580-40
Cisco Adaptive Security Appliance Software Version 8.1(2)
To be fixed in releases 8.1.2(22) and 8.1.3
This file was last modified 27. Apr 2009 by root