Hi guys,

I have an intermittent problem with users trying to send mails through the our C150. It happens from Vista and XP users using Outlook 2003 and 2007.

From the users point of view the error message is "Your outgoing SMTP server does not support SSL-secured connections".

TLS is enabled on the Ironport, outlook 2003 only has the SSL option, but 2007 and Thunderbird users see the error message sometimes even though TLS is selected.
The Ironport works for 99% of users all of the time, but every now and again this error will rear its head.

If anyone has any wisdom to impart it would be greatly appreciated.

This is what it looks like from the smtp_conversation

address 77.95.162.96 dns host unknown sbrs None
Fri Apr 24 17:23:23 2009 Info: ICID 517652 >> 220 smtps.tssg.org ESMTP
Fri Apr 24 17:23:23 2009 Info: ICID 517652 <<x80L>> 500 #5.5.1 command not recognized
Fri Apr 24 17:23:23 2009 Info: ICID 517652 close
Fri Apr 24 17:23:23 2009 Info: ICID 517653 address 77.95.162.96 dns host unknown sbrs None
Fri Apr 24 17:23:23 2009 Info: ICID 517653 >> 220 smtps.tssg.org ESMTP

Fri Apr 24 17:23:26 2009 Info: ICID 517653 - Error occured during incoming SMTP command: ('oserrors.pyx oserrors.map_exception|26', "<class>", '[Errno 54] Connection reset by peer', '[imh/smtp_server.py read_line_timeout|273] [read_stream.pyx read_stream.stream_reader.read_line|340] [read_stream.pyx read_stream.stream_reader.read_search|383] [imh/smtp_server.py read|248] [imh/smtp_server.py _with_appropriate_timeouts|222] [_coro.pyx coro._coro.sched.with_timeout|1052] [imh/injector.py read|830] [_coro.pyx coro._coro.sched.with_timeout|1052] [socket.pyx coro._coro.sock.recv|473] [socket.pyx coro._coro.sock._wait_for_read|870] [poller.pyx coro._coro.kqueue_poller._wait_for_read|304] [poller.pyx coro._coro.kqueue_poller._wait_for_with_eof|299] [pyrex_helpers.pyx coro._coro.raise_oserror_with_errno|15] [oserrors.pyx oserrors.map_exception|26]')