Mail SMTP port problems.

This is driving me nuts.
Send an email, it fails and Mail pops up a question on which SMTP server to use. I choose "Edit SMTP Server List".
Select "Advanced". My port is already using "Use Custom Port" set to 25. Yes, I know that is offered in the default, but it won't work. I select the default and close. Try to send the mail and it fails as before. I then set it back to custom port 25 and it works. ARRRGHH!!!!
I've deleted and reinstalled the SMTP server multiple times and I get a month or so of peace before this BS starts all over.
This all started when my ISP (Mountain Cable) got bought out by Shaw. That may be a coincidence or the problem.
Any ideas?
A solution to this will earn my eternal grattitude and reams of good kharma.

I wish it was just a matter of the right settings in the mail client. However, I was working with another NOC engineer and one of our IP admins for hours, testing every possible setting in Mac Mail, Entourage and Thunderbird. Using SSL, Password authentication, SPA off, port 537, it works on Outlook Express and Thunderbird for Windows. Using the exact same settings, no mail client works on the Mac. That's why we reached the point of creating a custom configuration file on a modem, packet sniffing at each point in the connection and monitoring the SMTP logs... to make sure there wasn't something on our network that was interfering with Mac's that would not affect Windows.
It's not just a matter of getting the mail client settings correct, otherwise the exact same settings that work for OE would work in Entourage, and the exact same settings that work for Thunderbird for Windows would work in Thunderbird for Mac.
Thunderbird for Mac was the most helpful in trying to track this down, because it said that the server did not accept the authentication request. However, the SMTP server shows that no attempt for authentication from a Mac even reached the server, and as far as we can tell, the attempt at password authentication on port 537 never even left the Mac and reached the router or modem, for any mail client used.

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Message was edited by: Bruce245

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