However, I'm still convinced many would appreciate adding this ./configure option:

https://github.com/pyenv/pyenv/issues/1184#issuecomment-403149437
https://joshspicer.com/python37-ssl-issue
https://superuser.com/questions/1428109/install-python-3-7-3-from-source-with-ssl-failed
https://raspberrypi.stackexchange.com/questions/88150/how-to-install-python-3-7-with-ssl
https://stackoverflow.com/questions/53543477/building-python-3-7-1-ssl-module-failed
https://help.dreamhost.com/hc/en-us/articles/115000702772-Installing-a-custom-version-of-Python-3#3.7.1
https://stackoverflow.com/questions/55928393/compile-python-3-6-statically-with-openssl
https://readthisblog.net/2018/08/13/til-how-to-build-python-3-7-with-statically-linked-libssl-and-libcrypto/
https://gist.github.com/eddy-geek/9604982

If you look at the associated PR you will see it should work fine, and be useful, on other POSIX systems as well. I can test on *BSD if necessary.

Only extra depedency of --with-openssl-static compared to --with-openssl is an assumption of existing files libssl.a libcrypto.a and OpenSSL has provided these files (when compiled static) since the very beginning despite somewhat frequent ABI changes. Option --with-openssl-static works with current libressl as well.