STINNER Victor <vstin...@redhat.com> added the comment:

I wrote a fix for bpo-36037 "test_ssl fails on RHEL8 strict OpenSSL 
configuration" which should fix test_ssl on Debian as well, but my change 
doesn't apply to Python 2.7 nor 3.6 since these Python versions lack 
SSLContext.minimum_version attribute (introduced in Python 3.7).

https://docs.python.org/dev/library/ssl.html#ssl.SSLContext.minimum_version

For Python 2.7 and 3.6, "export OPENSSL_CONF=/non-existing-file" is a 
workaround.

Benjamin:
> I agree that we need to be more resistant to system configuration, but it 
> doesn't seem worth holding 2.7 up for.

My fix requires SSLContext.minimum_version, but I'm not sure that it's ok to 
backport the attribute to Python 2.7 since Python 3.6 doesn't have it. IMHO 
"export OPENSSL_CONF=/non-existing-file" workaround is acceptable.

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<https://bugs.python.org/issue35925>
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