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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?

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I don't want to change my gmail security settings. Is there any way to make an OpenSSL session meet google's security requirements?

In theory you could probably do all the necessary communication with openssl. In practice this will probably too hard to do everything by hand. What you would need to do is to use oauth for the authentication, see https://developers.google.com/gmail/oauth_overview.

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