Gem Install Fails with Openssl Failure

gem install fails with openssl failure

This is fixed by avoiding https and using the insecure http instead. Running this worked for me.

gem source -a http://rubygems.org/

Update

Now that I've karma wh..err mined enough from this answer everyone should know that this should have been fixed.

re: via Ownatik again bundle install fails with SSL certificate verification error

gem update --system

My answer is still correct and left below for reference if that ends up not working for you.

Honestly the best temporary solution is to

[...] use the non-ssl version of rubygems in your gemfile as a temporary workaround.

via user Ownatik

what they mean is at the top of the Gemfile in your rails application directory change

source 'https://rubygems.org'

source 'http://rubygems.org'

note that the second version is http instead of https

It looks like it's an issue with El Capitan not providing openSSL headers.

https://github.com/eventmachine/eventmachine/issues/643

The solution is to install openssl using Homebrew or MacPorts brew install openssl

I had to do brew link openssl --force as openSSL was already installed