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One of the major problem which prevent the migration to Ruby 1.9 is the lack of the porting of ruby-debug. 
 Here the steps I followed to made it working on my MacBook with Multiruby: 
 
sudo gem install rake-compiler ruby_core_source --no-rdoc --no-ri 
sudo gem install ruby-debug19 --no-rdoc --no-ri 
 I hope it works for you too!

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