Apple Mail and SMTP Offline issues

Client called me this morning, I found out that the apple mail email settings has gone awry. For some weird reasons, my SmarterMail Server settings is shown 'offline' all the time.

I tweaked, re-created account and nothing short of banging the mac on the table... and I realized that Apple Mail on the Mac OS-X (mountain-lion and above) doesn't like non-SSL based SMTP.

Gmail SMTP, or SMTP server that does not uses password authentication works well, but when SMTP authentication is enabled, it seems like a requirement for SSL to be enabled.

As such, since my server utilizes SSL (TLS Authentication) on a separate name for it's server, I had to use our own registered server name - cloudmail.b**.co*.s* and VIOLA! it worked almost immediately.

While it's a nice gesture to make the application smarter and think-ahead for it's users, I do feel that Apple should incorporate some form of warning or alerts into the Apple Mail configuration instead of simply blocking access for unsecured connectivity.

Oh well, time and efforts are already spent... glad that it is all resolved within the hour.