With openssl 1.1.1 the python test suite now fails. To replicate, install python3-tests in an image and run: $ python3 -m test test_ssl poky-contrib:ross/py has some hacks attempting to cherry-pick bits of the SSL work from the upstream 3.6 branch but obviously not enough.
I cherry picked some patches and updated python 3.5 to 3.5.6: https://git.yoctoproject.org/clean/cgit.cgi/poky-contrib/commit/?h=anujm/ssl&id=56f716a142a725afa6e69ecd592896d8f66b4751 All the tests pass for me.
Merged: https://git.yoctoproject.org/cgit/cgit.cgi/poky/commit/?id=3c32b1525ad5ce3ec82542846369547efc62f25a