Sending emails via gmail?

Anyone got any tips using gmail to send ?
I’m getting an error #64 that I cant seem to find any info on
Will a macOS app require special permissions or plist entries ? (which since the allow unsafe loads has been ignored since 10.12)

A bit stumped as this code supposedly works

you made a per-app password for gmail?
Also use TLS 1.2?

Maybe try MBS classes?

this is existing code thats supposed to work and I’m flailing around trying to figure out why it wont work
its supposed to but I’ll be damned

it fails trying to update an oauth token and isnt actually getting to calling the send mail api

Happy debugging!

I’m able to send gmail using SMTPSecureSocket normally (can post code if you want), but the problem for me is that with every mail sent I get 27 security alerts from google that an unknown user is trying to send from my account, which renders the whole thing useless.

FWIW this is in a Web app
And I finally figured out WHY this was having issues
Using 2019r1.1 on 10.15.7 and trying to access the oauth2 apis to reauthorize a token is what fails
Literally a simple URLConnection.SendSync just fails
Use the exact same code on 10.13 works. 10.14 works. 10.15 fails
So … off to figure out how to fix this

It was my mistake in thinking it was SMTPSecureSocket at all