KevinTheJedi ok, so I may have found a bug. Did you know that if you do not type in a message in the Diagnostics field and just select the FROM and TO with a Subject line, the screen flashes and you have no idea what happened? After reviewing the SMTP logs and checking both the php.ini file and the SMTP settings under the email and still not seeing anything causing the issue I just so happened to hit tab type in a few characters and hit Send Message and I then received the Successful message.
So it looks like you MUST put a message before clicking send or it will not send a test e-mail nor provide an error message saying that field is blank.