Homebrew, rbenv, ruby-build, openssl…

How to upgrade OpenSSL on Mac OS. Homebrew issues led me down a lovely garden path… and this guide helped.

Explicitly specifying the OpenSSL can work when installing a new version of Ruby with rbenv.

RUBY_CONFIGURE_OPTS=--with-openssl-dir=/usr/local/Cellar/openssl/1.0.2k rbenv install 2.3.1

---