Yugster

Sorry for the long wait ?? but the issue persists.. ??

Had the same problem, and it turned out to be an ipv6 issue. If I telnet into gmail (telnet smtp.gmail.com 25), it tries connecting to the ipv6 address, which does not work for some reason I haven’t figured out yet (i’m on Linux, CentOS 6, 64 bit). If I put the ip4 address in the settings, everything works just fine.

Any ideas? Just to be clear, I have the SSL port setting in your plugin set to 2010 and the WordPress address and Site address (in the wordpress settings) set to the non-ssl port 2000.
It seems the :2000 doesn’t get replaced by :2010 after a redirect by your plugin to https. Could that be the case? Thanks!

Yes, the port is set. WordPress address and Site address are set to https://www.example.com:2000.