Not sure if you found your answer on the JetBrains forum, but if not, this is what works for me in RubyMine 3.2.4.
My config.ru looks like this:
require './app' run Sinatra::Application
In a simple app.rb file, place the breakpoint on the line "Hello World" below:
get '/' do "Hello World" end
Just right-click the app.rb or config.ru file and select "Debug" application "" from the context menu. If you are loading a page, you must click the break point.
Hope this helps.
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