Ok, that could be it.

The main culprit I am trying to figure out is Entourage (I just noticed a bunch of messages on that I should look through).

The log for it looks like this:

Dec 11 14:49:48 arnold postfix/smtpd[6341]: connect from c-24-63-203-109.hsd1.nh.comcast.net[24.63.203.109] Dec 11 14:49:48 arnold postfix/smtpd[6341]: lost connection after EHLO from c-24-63-203-109.hsd1.nh.comcast.net[24.63.203.109] Dec 11 14:49:48 arnold postfix/smtpd[6341]: disconnect from c-24-63-203-109.hsd1.nh.comcast.net[24.63.203.109] Dec 11 14:56:28 arnold postfix/smtpd[4671]: connect from c-24-63-203-109.hsd1.nh.comcast.net[24.63.203.109] Dec 11 14:56:28 arnold postfix/smtpd[4671]: setting up TLS connection from c-24-63-203-109.hsd1.nh.comcast.net[24.63.203.109] Dec 11 14:56:29 arnold postfix/smtpd[4671]: TLS connection established from c-24-63-203-109.hsd1.nh.comcast.net[24.63.203.109]: TLSv1 with cipher DES-CBC3-SHA (168/168 bits) Dec 11 14:56:29 arnold postfix/smtpd[4671]: lost connection after EHLO from c-24-63-203-109.hsd1.nh.comcast.net[24.63.203.109] Dec 11 14:56:29 arnold postfix/smtpd[4671]: disconnect from c-24-63-203-109.hsd1.nh.comcast.net[24.63.203.109]

The error I am getting now is that the server does not support any of the authentication methods. Before I was getting a greylist "try later" message. I think it is trying on port 25.

Wrapper mode is not on and if I try Thunderbird with SSL it does default to that port which is open in the firewall. But I get no attempted TLS connection. My syslog just tracks that the ip/mac address is hitting it.

I notice in my log that there is one other instance of 168 DES ciphers that appears to be failing while all other types appear to be working. Could that be the issue? If so how do I fix it?
Noel Jones wrote:
John Baker wrote:
We have a few people using programs (mostly MS crap) that insist on older versions of SSL rather than tls.

Internally this works okay but externally ssl gets bounced by my grey listing. This seems to indicate that it is not actually authenticating right but allowing it to pass internally because its on the network and the port is open.

"legacy" SSL makes me think of the long-deprecated "smtps" wrapper mode SSL on port 465 that some MS products (still) seem to prefer rather than using STARTTLS on a standard port.

Do you have the smtps port enabled in postfix and your firewall?

Do your logs show these clients using SSL/TLS and attempting authentication? Use "smtpd_tls_loglevel = 1" in main.cf.




--
John Baker
Network Systems Administrator
Marlboro College
Phone: 451-7551 off campus; 551 on campus

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