Bug report
when using smtplib.SMTP.login, library is using different authentication schemes if available: cram-md5, plain, login
when cram-md5 fails with bad password (smtp error code 535), there is no point in trying plain and login.
Also when server is behind a proxy doing ssl termination, plain and login may fail with a different failure mode:
unprotected password needs ssl mode
leading to confusion on what the real problem is.
Your environment
- CPython versions tested on: conda python 3.9 (concerned code is identical on trunk)
- Operating system and architecture: Ubuntu 22.04
Linked PRs
Bug report
when using smtplib.SMTP.login, library is using different authentication schemes if available: cram-md5, plain, login
when cram-md5 fails with bad password (smtp error code 535), there is no point in trying plain and login.
Also when server is behind a proxy doing ssl termination, plain and login may fail with a different failure mode:
unprotected password needs ssl mode
leading to confusion on what the real problem is.
Your environment
Linked PRs