Question

I am having trouble compiling Phusion Passenger with my new OSX Mountain Lion Install. Do you have any advice?

Installing Phusion Passenger Standalone...
[*******************************              ] Compiling Phusion Passenger... 
*** ERROR: the following command failed:
mkdir -p 'ext/ruby/ruby-1.9.3-x86_64-macosx/'
cd 'ext/ruby/ruby-1.9.3-x86_64-macosx/' && /Users/boris/.rvm/wrappers/ruby-1.9.3-p194@apps2/ruby '/Users/boris/.passenger/standalone/3.0.13-x86_64-ruby1.9.3-macosx-10.8/support/ext/ruby/extconf.rb'
checking for alloca.h... *** /Users/boris/.passenger/standalone/3.0.13-x86_64-ruby1.9.3-macosx-10.8/support/ext/ruby/extconf.rb failed ***
Could not create Makefile due to some reason, probably lack of
necessary libraries and/or headers.  Check the mkmf.log file for more
details.  You may need configuration options.

Provided configuration options:
    --with-opt-dir
    --with-opt-include
    --without-opt-include=${opt-dir}/include
    --with-opt-lib
    --without-opt-lib=${opt-dir}/lib
    --with-make-prog
    --without-make-prog
    --srcdir=/Users/boris/.passenger/standalone/3.0.13-x86_64-ruby1.9.3-macosx-10.8/support/ext/ruby
    --curdir
    --ruby=/Users/boris/.rvm/rubies/ruby-1.9.3-p194/bin/ruby
/Users/boris/.rvm/rubies/ruby-1.9.3-p194/lib/ruby/1.9.1/mkmf.rb:381:in `try_do': The compiler failed to generate an executable file. (RuntimeError)
You have to install development tools first.
    from /Users/boris/.rvm/rubies/ruby-1.9.3-p194/lib/ruby/1.9.1/mkmf.rb:506:in `try_cpp'
    from /Users/boris/.rvm/rubies/ruby-1.9.3-p194/lib/ruby/1.9.1/mkmf.rb:931:in `block in have_header'
    from /Users/boris/.rvm/rubies/ruby-1.9.3-p194/lib/ruby/1.9.1/mkmf.rb:790:in `block in checking_for'
    from /Users/boris/.rvm/rubies/ruby-1.9.3-p194/lib/ruby/1.9.1/mkmf.rb:284:in `block (2 levels) in postpone'
    from /Users/boris/.rvm/rubies/ruby-1.9.3-p194/lib/ruby/1.9.1/mkmf.rb:254:in `open'
    from /Users/boris/.rvm/rubies/ruby-1.9.3-p194/lib/ruby/1.9.1/mkmf.rb:284:in `block in postpone'
    from /Users/boris/.rvm/rubies/ruby-1.9.3-p194/lib/ruby/1.9.1/mkmf.rb:254:in `open'
    from /Users/boris/.rvm/rubies/ruby-1.9.3-p194/lib/ruby/1.9.1/mkmf.rb:280:in `postpone'
    from /Users/boris/.rvm/rubies/ruby-1.9.3-p194/lib/ruby/1.9.1/mkmf.rb:789:in `checking_for'
    from /Users/boris/.rvm/rubies/ruby-1.9.3-p194/lib/ruby/1.9.1/mkmf.rb:930:in `have_header'
    from /Users/boris/.passenger/standalone/3.0.13-x86_64-ruby1.9.3-macosx-10.8/support/ext/ruby/extconf.rb:36:in `<main>'
rake aborted!
Command failed with status (1): [cd 'ext/ruby/ruby-1.9.3-x86_64-macosx/' &&...]
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/file_utils.rb:53:in `block in create_shell_runner'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/file_utils.rb:45:in `call'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/file_utils.rb:45:in `sh'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/file_utils_ext.rb:39:in `sh'
/Users/boris/.passenger/standalone/3.0.13-x86_64-ruby1.9.3-macosx-10.8/support/build/ruby_extension.rb:43:in `block in <top (required)>'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:205:in `call'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:205:in `block in execute'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:200:in `each'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:200:in `execute'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:158:in `block in invoke_with_call_chain'
/Users/boris/.rvm/rubies/ruby-1.9.3-p194/lib/ruby/1.9.1/monitor.rb:211:in `mon_synchronize'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:151:in `invoke_with_call_chain'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:176:in `block in invoke_prerequisites'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:174:in `each'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:174:in `invoke_prerequisites'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:157:in `block in invoke_with_call_chain'
/Users/boris/.rvm/rubies/ruby-1.9.3-p194/lib/ruby/1.9.1/monitor.rb:211:in `mon_synchronize'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:151:in `invoke_with_call_chain'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:176:in `block in invoke_prerequisites'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:174:in `each'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:174:in `invoke_prerequisites'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:157:in `block in invoke_with_call_chain'
/Users/boris/.rvm/rubies/ruby-1.9.3-p194/lib/ruby/1.9.1/monitor.rb:211:in `mon_synchronize'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:151:in `invoke_with_call_chain'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:176:in `block in invoke_prerequisites'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:174:in `each'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:174:in `invoke_prerequisites'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:157:in `block in invoke_with_call_chain'
/Users/boris/.rvm/rubies/ruby-1.9.3-p194/lib/ruby/1.9.1/monitor.rb:211:in `mon_synchronize'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:151:in `invoke_with_call_chain'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/task.rb:144:in `invoke'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/application.rb:116:in `invoke_task'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/application.rb:94:in `block (2 levels) in top_level'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/application.rb:94:in `each'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/application.rb:94:in `block in top_level'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/application.rb:133:in `standard_exception_handling'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/application.rb:88:in `top_level'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/application.rb:66:in `block in run'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/application.rb:133:in `standard_exception_handling'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/lib/rake/application.rb:63:in `run'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@global/gems/rake-0.9.2.2/bin/rake:33:in `<top (required)>'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@apps2/bin/rake:23:in `load'
/Users/boris/.rvm/gems/ruby-1.9.3-p194@apps2/bin/rake:23:in `<main>'
Tasks: TOP => nginx => native_support => ext/ruby/ruby-1.9.3-x86_64-macosx//passenger_native_support.bundle => ext/ruby/ruby-1.9.3-x86_64-macosx//Makefile

Answer 1

1. Looks like you’re using RVM. So go ahead and recompile ruby

rvm uninstall 1.9.3
rvm install 1.9.3

1. Reinstall the passenger Gem
2. Make sure to include the .conf files for your virtual hosts, which the upgrade to Mountain Lion probably clobbered

In my case I added the following line to the end of my httpd.conf file:

Include /etc/apache2/passenger_pane_vhosts/*.conf