I would enable Less Secure Apps, per this documentation:
If that does not work, please try port 587 instead of 465 for TLS, and failing that, I would recommend placing your username in the Optional section under the SMTP settings.
I hope this helps!
I set up Gmail on my instance and these are my current settings using Gmail SMTP that does seem to work when I send a test email:
This is as I've edited mine to work, so maybe it will help you too?
I WOULD DEFINITELY still make sure you have use less secure apps set on from the Google post I sent you, however, since this is what they recommend to do to fix the problem.
...PermissionsStartOnly=true User=www-data Group=www-data ExecStart=/opt/jira/bin/startup.sh ExecStop=/opt/jira/bin/shutdown.sh TimeoutStartSec=120 TimeoutStopSec=600 PrivateTmp=true [Install] WantedBy...
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