openssl version: 1.0.1i, rbenv version: 0.4.0, ruby-build as plugin in the ~/.rbenv/plugins directory.

The version of openssl on a Mavericks machine got out of sync with rbenv and ruby-build for some reason. For every attempt at installing a ruby version through rbenv attempted, we got the following message:

“The Ruby openssl extension was not compiled. Missing the OpenSSL lib?”

Tried every permutation of trying to fix one thing at a time, but ultimately ended up doing the following:

~/.rbenv/plugins/ruby-build directory
brew unlink openssl rbenv ruby-build
brew uninstall openssl rbenv ruby-build
brew update
brew install openssl
brew link openssl --force
brew install rbenv
eval "$(rbenv init -)"
brew install ruby-build

Then we were able to install whatever ruby version we wanted.

I’m sure some of the above process was overkill and unnecessary, but the steps in total did the job.