Casey <caseylfa...@gmail.com> added the comment:

Update: After digging further (and enabling the "Less secure app access" 
setting on the test Google account) it looks like Python 2.7 caps TLS at 1.2 
rather than using 1.3 when OpenSSL is upgraded. This prevents breakage, and it 
looks like the SSLSocket class silences the handshake complaints.

If this were an active branch, this could be worth revisiting - but since 2.7 
is soon to be EOL and we can't reproduce the breakage, not sure it's worth it.

----------
stage:  -> resolved
status: open -> closed
type: crash -> behavior

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Python tracker <rep...@bugs.python.org>
<https://bugs.python.org/issue37777>
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