Using openssl as below when I do
EHLO
auth login
and then enter my username and password I get the following error:
Please log in via your web browser and then try again.
Learn more at https://support.google.com/mail/answer/78754
To quote from that location, I seem to most likely be suffering from this symptom:
Your app might not support the latest security standards. Try changing a few settings to allow less secure apps access to your account.
I don't want to change my gmail security settings. Is there any way to make an OpenSSL session meet google's security requirements?