Hello...

I am trying to configure Outlook Express to use port 25 and SSL to send
mail through my smtp server(s), which are load balanced behind an F5
BigIP 6400 device. When I have the SSL certificate installed on the
BigIP, OE cannot send mail through port 25 with SSL. If I configure
both OE and the BigIP to use port 465, it works fine. Also, if I do
not terminate the SSL session on the BigIP and install the certificate
on the server itself, I can send mail via port 25.

To confuse matters even further, other mail clients work just fine when
the certificate is on the BigIP and I am using port 25 (the full
Outlook client configured as a POP client and Mozilla Thunderbird are 2
that work).

F5 does not believe this is an issue with their device, since other
mail clients work fine and they state that they do not even see the OE
client making an SSL request to the BigIP device when they look at
network traffic dumps.

Has anyone out there ever seen or heard of an issue similar to this? I
have been banging my head against the wall for a couple of weeks now,
and it is starting to hurt!

Note: I do have the OE client configured correctly for secure
smtp....and I have tried this from several different workstations....
Thanks!

Chris