Unable to require openssl, install OpenSSL and rebuild ruby (preferred) or use non-HTTPS sources

Newer versions of OSX deprecated openSSL, leaving many dependencies broken. You need to reinstall ruby, but specify exactly where your openSSL libraries are. If you’re using rvm then that looks like:

rvm reinstall 2.3.0 --with-openssl-dir=/usr/local/opt/openssl

If you’re using homebrew, then a quick shortcut to where your libraries are is:

brew install openssl
rvm reinstall 2.3.0 --with-openssl-dir=`brew --prefix openssl`