openssl - Ruby Bundle Symbol not found: _SSLv2_client_method (LoadError)

Question

I was doing attempting to do some updates to openssl using homebrew and I somehow managed to break everything. I can't do anything now, this is what I get when I try to do bundle install:

$ bundle install
/Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/rubygems/core_ext/kernel_require.rb:55:in    `require': dlopen(/Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/x86_64-darwin13.0/openssl.bundle, 9): Symbol not found: _SSLv2_client_method (LoadError)
Referenced from: /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/x86_64-darwin13.0/openssl.bundle
Expected in: /usr/local/opt/openssl/lib/libssl.1.0.0.dylib
in /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/x86_64-darwin13.0/openssl.bundle - /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/x86_64-darwin13.0/openssl.bundle
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/rubygems/core_ext/kernel_require.rb:55:in `require'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/openssl.rb:17:in `<top (required)>'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/rubygems/core_ext/kernel_require.rb:55:in `require'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/rubygems/core_ext/kernel_require.rb:55:in `require'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/rubygems/security.rb:11:in `<top (required)>'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/rubygems/core_ext/kernel_require.rb:55:in `require'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/rubygems/core_ext/kernel_require.rb:55:in `require'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/rubygems/package.rb:43:in `<top (required)>'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/rubygems/core_ext/kernel_require.rb:55:in `require'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/rubygems/core_ext/kernel_require.rb:55:in `require'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/rubygems/dependency_installer.rb:3:in `<top (required)>'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/rubygems/core_ext/kernel_require.rb:55:in `require'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/2.1.0/rubygems/core_ext/kernel_require.rb:55:in `require'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/gems/2.1.0/gems/bundler-1.6.3/lib/bundler/installer.rb:2:in `<top (required)>'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/gems/2.1.0/gems/bundler-1.6.3/lib/bundler/cli/install.rb:78:in `run'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/gems/2.1.0/gems/bundler-1.6.3/lib/bundler/cli.rb:146:in `install'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/gems/2.1.0/gems/bundler-1.6.3/lib/bundler/vendor/thor/command.rb:27:in `run'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/gems/2.1.0/gems/bundler-1.6.3/lib/bundler/vendor/thor/invocation.rb:121:in `invoke_command'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/gems/2.1.0/gems/bundler-1.6.3/lib/bundler/vendor/thor.rb:363:in `dispatch'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/gems/2.1.0/gems/bundler-1.6.3/lib/bundler/vendor/thor/base.rb:440:in `start'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/gems/2.1.0/gems/bundler-1.6.3/lib/bundler/cli.rb:9:in `start'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/gems/2.1.0/gems/bundler-1.6.3/bin/bundle:20:in `block in <top (required)>'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/gems/2.1.0/gems/bundler-1.6.3/lib/bundler/friendly_errors.rb:5:in `with_friendly_errors'
    from /Users/asServer/.rbenv/versions/2.1.2/lib/ruby/gems/2.1.0/gems/bundler-1.6.3/bin/bundle:20:in `<top (required)>'
    from /Users/asServer/.rbenv/versions/2.1.2/bin/bundle:23:in `load'
    from /Users/asServer/.rbenv/versions/2.1.2/bin/bundle:23:in `<main>'

Answer 1

I just fixed a similar issue on my system. You need to rebuild your install of Ruby 2.1.2 and it will re-link against the newly-updated SSL.

$ rbenv install 2.1.2
rbenv: /Users/ryan/.rbenv/versions/2.1.2 already exists
continue with installation? (y/N) y
Downloading ruby-2.1.2.tar.gz...
-> http://dqw8nmjcqpjn7.cloudfront.net/f22a6447811a81f3c808d1c2a5ce3b5f5f0955c68c9a749182feb425589e6635
Installing ruby-2.1.2...
Installed ruby-2.1.2 to /Users/ryan/.rbenv/versions/2.1.2