I am still not able to get it to work. I'm running OS X 10.12.1, and Mac Mail 10.1. I have two gmail accounts, one at gmail.com, the other through my university.edu. In both cases, my Mac Mail program is showing the IMAP connection to be fine, but the SMTP to be offline. I tried deleted both through System Preferences > Internet Accounts, and reading them. I made sure "Access for Less Secure Apps" was turned ON for both accounts. Still no connection. Then I went to Mail > Preferences > Accounts > Server Settings > Outgoing Mail Account > Edit SMTP List, and this is where it got a little weird. Though in Outgoing Mail Account I could select from three different possible servers (for each of my three emails), when I went to Edit SMTP List the list was totally blank. Nothing on it at all. I tried to add a new one using these settings (https://support.google.com/a/answer/176600?hl=en) but it isn't selecting, is weirdly disappearing from the list, and regardless isn't connecting at all. I am not sure what to do. Any suggestions?