Apple OSX Yosemite Outbound SMTP Mail Issues

If you recently did the Yosemite update on your Mac / Macbook, you might have experienced some issues with outbound / SMTP email. Here is a great starting point in Apple forums to help resolve your issue.

Unfortunately, I’m still experiencing outbound email issues and will update this post and additional links once everything is finally resolved. It also appears that the recent Yosemite update to Apple OSX is generating numerous issues for Mac users.