Error upgrading to Ruby 2.2.4

Question

I ran rvm install ruby-2.2.4 and got the following error:

$ rvm reinstall ruby-2.2.4
ruby-2.2.4 - #removing src/ruby-2.2.4..
ruby-2.2.4 - #removing rubies/ruby-2.2.4..
Searching for binary rubies, this might take some time.
No binary rubies available for: osx/10.9/x86_64/ruby-2.2.4.
Continuing with compilation. Please read 'rvm help mount' to get more information on binary rubies.
Checking requirements for osx.
Certificates in '/usr/local/etc/openssl/cert.pem' are already up to date.
Requirements installation successful.
Installing Ruby from source to: /Users/JAckerman/.rvm/rubies/ruby-2.2.4, this may take a while depending on your cpu(s)...
ruby-2.2.4 - #downloading ruby-2.2.4, this may take a while depending on your connection...
ruby-2.2.4 - #extracting ruby-2.2.4 to /Users/JAckerman/.rvm/src/ruby-2.2.4....
ruby-2.2.4 - #applying patch /Users/JAckerman/.rvm/patches/ruby/2.2.4/fix_installing_bundled_gems.patch.
ruby-2.2.4 - #configuring..........................................................
ruby-2.2.4 - #post-configuration.
ruby-2.2.4 - #compiling.............................................................
ruby-2.2.4 - #installing............
Error running '__rvm_make install',
showing last 15 lines of /Users/JAckerman/.rvm/log/1454705088_ruby-2.2.4/install.log
    from /Users/JAckerman/.rvm/src/ruby-2.2.4/lib/rubygems/core_ext/kernel_require.rb:54:in `require'
    from /Users/JAckerman/.rvm/src/ruby-2.2.4/lib/rubygems/core_ext/kernel_require.rb:54:in `require'
    from /Users/JAckerman/.rvm/src/ruby-2.2.4/lib/rubygems/dependency_installer.rb:3:in `<top (required)>'
    from /Users/JAckerman/.rvm/src/ruby-2.2.4/lib/rubygems/core_ext/kernel_require.rb:54:in `require'
    from /Users/JAckerman/.rvm/src/ruby-2.2.4/lib/rubygems/core_ext/kernel_require.rb:54:in `require'
    from /Users/JAckerman/.rvm/src/ruby-2.2.4/lib/rubygems.rb:556:in `install'
    from ./tool/rbinstall.rb:722:in `block (2 levels) in <main>'
    from ./tool/rbinstall.rb:721:in `each'
    from ./tool/rbinstall.rb:721:in `block in <main>'
    from ./tool/rbinstall.rb:757:in `call'
    from ./tool/rbinstall.rb:757:in `block in <main>'
    from ./tool/rbinstall.rb:754:in `each'
    from ./tool/rbinstall.rb:754:in `<main>'
make: *** [do-install-nodoc] Error 1
++ return 2
There has been an error while running make install. Halting the installation.

I tried these steps, running rvm reinstall ruby-2.2.4 after each step, to no avail:

• rvm get head
• rvm get master

• Then all of this:

  $ rvm gem list error
  
  Please note that `rvm gem ...` was removed, try `gem list error` or `rvm all do gem list error` instead. ( see: 'rvm usage' )
  
  JAckerman@Jasons-MacBook-Pro parkme3.1 (staging) $ gem list error
  /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/yaml.rb:4:in `<top (required)>':
  
  It seems your ruby installation is missing psych (for YAML output).
  
  To eliminate this warning, please install libyaml and reinstall your ruby.
  
  /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/rubygems/core_ext/kernel_require.rb:54:in `require': dlopen(/Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/x86_64-darwin13/psych.bundle, 9): Library not loaded: /usr/local/lib/libyaml-0.2.dylib (LoadError)
    Referenced from: /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/x86_64-darwin13/psych.bundle
    Reason: image not found - /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/x86_64-darwin13/psych.bundle
    from /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/rubygems/core_ext/kernel_require.rb:54:in `require'
    from /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/psych.rb:1:in `<top (required)>'
    from /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/rubygems/core_ext/kernel_require.rb:54:in `require'
    from /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/rubygems/core_ext/kernel_require.rb:54:in `require'
    from /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/yaml.rb:5:in `<top (required)>'
    from /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/rubygems/core_ext/kernel_require.rb:54:in `require'
    from /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/rubygems/core_ext/kernel_require.rb:54:in `require'
    from /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/rubygems.rb:624:in `load_yaml'
    from /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/rubygems/config_file.rb:328:in `load_file'
    from /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/rubygems/config_file.rb:197:in `initialize'
    from /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/rubygems/gem_runner.rb:74:in `new'
    from /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/rubygems/gem_runner.rb:74:in `do_configuration'
    from /Users/JAckerman/.rvm/rubies/ruby-2.2.4/lib/ruby/2.2.0/rubygems/gem_runner.rb:39:in `run'
    from /Users/JAckerman/.rvm/rubies/ruby-2.2.4/bin/gem:21:in `<main>'
  
  JAckerman@Jasons-MacBook-Pro parkme3.1 (staging) $ brew install libyaml
  
  Warning: libyaml-0.1.6 already installed
  
  JAckerman@Jasons-MacBook-Pro parkme3.1 (staging) $ brew reinstall libyaml
  
  ==> Reinstalling libyaml
  
  Warning: libyaml-0.1.6 already installed
  
  JAckerman@Jasons-MacBook-Pro parkme3.1 (staging) $ brew unlink libyaml
  
  Unlinking /usr/local/Cellar/libyaml/0.1.6... 1 symlinks removed
  
  JAckerman@Jasons-MacBook-Pro parkme3.1 (staging) $ brew reinstall libyaml
  
  ==> Reinstalling libyaml
  
  Warning: libyaml-0.1.6 already installed, it's just not linked
  
  JAckerman@Jasons-MacBook-Pro parkme3.1 (staging) $ brew link libyaml
  
  Linking /usr/local/Cellar/libyaml/0.1.6... 5 symlinks created
  

• Then I re-tried rvm get head and rvm get master, reinstalling after each.

Answer 1

Install / update autoconf brew install autoconf

Answer 2

The issue was that, while most of the above was right, none of it was working because my homebrew was not up to date, which I figured out by running brew doctor. Updating home brew (brew update) and then reinstalling the necessary libraries got it working.