My brew OpenSSL version is 1.0.2l and my Python OpenSSL version is 9.8. I've been trying to solve this issue for hours now. I've tried changing the path in the .bash profile, I've tried uninstalling and then reinstalling
python --with-brewed-openssl
I've updated/upgraded/pruned/doctored brew, I've tried linking openssl with the following command
brew link openssl --force
but that results in this error for both 1.0.2l and 1.0.1f,
Linking keg-only openssl means you may end up linking against the
insecure,
deprecated system OpenSSL while using the headers from Homebrew's
openssl.
Instead, pass the full include/library paths to your compiler e.g.:
-I/usr/local/opt/openssl/include -L/usr/local/opt/openssl/lib
I've tried creating symlinks for certain files (although I'm not sure what this was really doing) ... I don't know what else to try. My python version is 2.7.13_1.