Greg Earle wrote:
Entourage 2004, on the other hand, sits there like a bump on a log. So of course "couriertls" times out eventually, because Entourage never talks to it. Apparently if you override port 25 in Entourage with a "Use SSL" and "use authentication" setting in your outgoing SMTP server setup, it loses its marbles and doesn't know what to do.
Chalking this up to Entourage brain-damage. Sorry for the noise.
Entourage probably expects "Use SSL" to mean that the server supports TLS. Few servers offer SMTP over SSL on an alternate port; most do STARTTLS instead.
Sometimes it's OK to trust software to work right. If you'd set "Use SSL" and left the port setting alone, the client probably would have done The Right Thing.
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