Cameron
It sounds like that Email Server has been updated and is now using Extended
Simple Mail Transfer Protocol (ESMTP). Even with Mailguard off I had
problems getting a 515E to pass those packets. Google the terms esmtp pix
and you will find several possible fixes. IF you have a Cisco Tac login here
is a link discussing the problem.

http://www.ciscotaccc.com/security/s...case=K11355672

-----Original Message-----
From: firewall-wizards-admin@honor.icsalabs.com
[mailto:firewall-wizards-admin@honor.icsalabs.com] On Behalf Of Cameron
Matheson
Sent: Wednesday, April 05, 2006 10:41 AM
To: firewall-wizards@honor.icsalabs.com
Subject: [fw-wiz] PIX 501 outgoing SMTP problem - (reset-o)

Hi

Starting about three weeks ago, some outbound emails stopped flowing
properly (large emails to some domains with ip addresses very close to ours
were not being delivered). Inbound email is fine. The PIX (version 6.3(3))
syslog messages looked like this:

3/31/2006 19:38 built outbound tcp connection 268422 for
outside:/25 (/25) to
inside:/9112 (/34960)
3/31/2006 19:39 teardown tcp connection 268422 for
outside:/25 to inside:/9112
duration 0:01:04 bytes 36129 tcp reset-o
3/31/2006 19:39 inbound tcp connection denied from
/25 to /34960 flags rst on interface
outside
3/31/2006 19:39 deny tcp (no connection) from
/9112 to /25 flags ack on
interface inside

Further examination of the Exchange Server smtp logs shows that the smtp
conversation was not completing ...

199.246.2.14 - OutboundConnectionResponse [31/Mar/2006:19:38:45 -0500] "-
-?220+mailgate1.kos.net SMTP" 0 21
199.246.2.14 - OutboundConnectionCommand [31/Mar/2006:19:38:45 -0500] "HELO
-?exchange.OURDOMAIN SMTP" 0 4
199.246.2.14 - OutboundConnectionResponse [31/Mar/2006:19:38:45 -0500] "-
-?250+mailgate1.kos.net SMTP" 0 21
199.246.2.14 - OutboundConnectionCommand [31/Mar/2006:19:38:45 -0500] "MAIL
-?FROM: SMTP" 0 4
199.246.2.14 - OutboundConnectionResponse [31/Mar/2006:19:38:45 -0500] "-
-?250+Ok SMTP" 0 6
199.246.2.14 - OutboundConnectionCommand [31/Mar/2006:19:38:45 -0500] "RCPT
-?TO: SMTP" 0 4
199.246.2.14 - OutboundConnectionResponse [31/Mar/2006:19:38:45 -0500] "-
-?250+Ok SMTP" 0 6
199.246.2.14 - OutboundConnectionCommand [31/Mar/2006:19:38:45 -0500] "DATA
- SMTP" 0 4
199.246.2.14 - OutboundConnectionResponse [31/Mar/2006:19:38:45 -0500] "-
-?354+End+data+with+. SMTP" 0 35

There should be more lines after this one to show that the email was sent
successfully. They should look like this:

199.246.2.14 - OutboundConnectionResponse [03/Apr/2006:10:15:41 -0500] "-
-?250+Ok:+queued+as+5071BD01049B SMTP" 0 30
199.246.2.14 - OutboundConnectionCommand [03/Apr/2006:10:15:41 -0500] "QUIT
- SMTP" 0 4
199.246.2.14 - OutboundConnectionResponse [03/Apr/2006:10:15:41 -0500] "-
-?221+Bye SMTP" 0 7

Does this mean anything to you? Is the reset-o significant? Or is it the
inbound tcp connection denied that is the problem?

On Saturday I upgraded the firmware on our PIX 501 firewall to 6.3(5) and
checked the configuration to be certain that the "Mailguard" feature was
disabled. (no fixup protocol smtp 25) Still no improvement, so I replaced
the PIX firewall by a Linksys router as a test, and email flowed perfectly!
Then, I put the PIX back in place and went home. On Monday morning, mail was
flowing perfectly through the PIX and is still fine today (Tuesday). So I'm
not sure if the firmware upgrade solved the problem or if it was something
else. Our ISP claims that they did not change anything over the weekend, but
now the SMTP conversation completes properly and the firewall reports:

4/3/2006 10:15 built outbound tcp connection 2309 for
outside:/25 (/25) to
inside:/26715 (/2133)
4/3/2006 10:15 teardown tcp connection 2309 for
outside:/25 to inside:/26715
duration 0:00:10 bytes 5212799 tcp fins

I would love to know for sure if the problem is really fixed, or will it
come back? Is there something wrong with my PIX configuration? Do you have
any ideas?

Thanks again for all your help.

cmatheson@loyalist-township.on.ca
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