@mgsporer Not that I've found yet. And as kind as support is, they haven't been very helpful with this one. I gave up.

@PavelV I appreciate the effort. I have no idea what the problem is. I've run out of combinations to try. I've tried the following: Server: smtp.gmail.com Port: 465 SSL: Yes Authentication: Yes...

@JP77 Hi there. Yes, it has been enabled from the start.

I turned off 2FA on the gmail account. Turned on allow less secure apps. Changed the password back to the regular (non-app). Used your settings. Still failed. Have the same gmail address as the...

@PavelV Thanks very much. Unfortunately, same error. Literally the exact settings you posted. Tested with both the app password and the regular password. Something very strange going on here.

@JP77 Yes, I have. I tried my personal gmail account, my yahoo account, and my brother's gmail account. All are generating the failed message. :(