Finally found a perfect alternative instead of spending more money on SSL certificates. For anyone using a similar config, keep the outgoing setup with stevie.heliohost.org on port 465 (in case you want to reply mails from your custom email) and forward every mail that get to your custom email to Gmail by simply going to "User Level Filtering" in the cPanel and add a rule of your email as it is: Select in the fields “To” and “contains” (as I’ve read it is much more forgiving than “equals”). For the "Actions", set the first to “Redirect to email” and paste in your Gmail address. That's all, you can flag this thread as solved, mods.