Hi Darrin,
You didn't have HAL or Google setup correctly. After I set the port to 465 and adjusted your google account to allow access it worked fine. You should have gotten an email today with the following contents of which has a typo LOL.
Testing 123 Sending an Emial from HA...
11/15/2016 16:40:03 - Execute Action
See this early post in this thread for the instructions you should have followed...
http://www.automatedliving.com/forum...ad.php?p=31581
Attached is a screen shot of the setting change I made in your google account.
Please change your gmail password now for security purposes...
Cheers,
Tim