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Re:What's New in Ruby 2.1 [pdf] by thedevelopment on Wednesday November 27, 2013 @04:53PM (#6811403)
I believe the debugger is broken in Ruby-2.0, and you should use byebug instead.

There are pry wrappers for byebug - https://github.com/deivid-rodriguez/pry-byebug - maybe that'll work?

Re:What's New in Ruby 2.1 [pdf] by andyl on Wednesday November 27, 2013 @07:00PM (#6812152)
Yesss - that worked. Tip of the day - thanks a ton !!