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Since there is no --debugger flag you need to run:

rdebug script/runner lib/scripts/something.rb

That will open an debugging IRB right away, like this:

require File.dirname(__FILE__) + '/../config/boot'
(rdb:1) _

Enter c to continue and reach your actual debugger call. Then, debug away.

If nothing happens for you: Make sure ruby-debug is available in the Gemfile and you require it.