Actually I spoke a little too soon. Ok, I have the NAS sending mail to gmail fine, but I have a second NAS that I need to send mail to this other address which is not gmail, it's a unix box running sendmail. The sendmail box is known to work, it gets a ton of mail. This NAS was sending mail to the sendmail box fine with 1.05 firmware, but now with 1.06, it is broken.
The sendmail box requires an authentication. It doesn't require TLS but it will use it. From the packet trace, I see the NAS connect to the sendmail server and say EHLO localhost and the NAS just drops the connetion. The NAS is set to use a login method of account and a username and password are configure.
<<< 220 example.org ESMTP server
>>> EHLO localhost
<<< 250-example.org Hello adsl-1-2-3-4.example.net [1.2.3.4], pleased to meet you
<<< 250-ENHANCEDSTATUSCODES
<<< 250-PIPELINING
<<< 250-8BITMIME
<<< 250-SIZE
<<< 250-ETRN
<<< 250-AUTH PLAIN LOGIN
<<< 250-STARTTLS
<<< 250-DELIVERBY
<<< 250 HELP
>>> (the NAS closes the connection)
Does the NAS perhaps not like the proposed AUTH methods of PLAIN and LOGIN? I notice that the gmail server doesn't emit the AUTH line at all and the NAS goes right in and starts TLS.