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Without going into the whys, I've got an ISA 2004 server behind a Cisco ASA.

Since the installation of the ASA, I can no longer send email to one particular domain. I get a "500 Non RFC-compliant response received" bounce.

Using a telnet session from a server in the DMZ, I verified that I can get a mail session to go through to this domain when only the ASA is in the chain. The ASA is supposedly not configured to filter email, but I do see that it's munging the initial response from the remote mail server (e.g. replacing the greeting with a bunch of asterisks, which from a cursory search seems to be a common Cisco thing).

When I directly replace the ASA with a different router of a different make, I have no trouble with email to the domain in question.

Thus, the problem is somehow the combination of whatever the Cisco is doing to the mail session, and whatever the ISA server is doing to the mail session.

Here's the catch: I have no control over the ASA, only the ISA Server. What's the quickest way out of this mess so that I can get email flowing to this domain as soon as possible?

Boden
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Any chance you can have the application filter on the Cisco turned off? There are various issues with Cisco's implementations of their application-level filters.

We had a situation where the Cisco filters would cause a SIP video session to consistently disconnect after a hour into the session. The situation was finally corrected by disabling the Cisco filters.

user48838
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  • As I said, I don't have access to the ASA directly. However, the guy in charge was able to fix the problem. He said it was due to mail header size restrictions. Thank you for your help! – Boden Oct 22 '10 at 17:41