Pry
Pry tricks

binding.pry in external code

Simply monkey patch the method that you are interested in debugging:
def SomeGem::method
require 'pry'
binding.pry
super
end
You can even do this automatically for a list of methods you are interested in:
[:foo, :bar, :baz].each do |cb|
define_method cb do
require 'pry'
binding.pry
super
end
end

Get filtered stack trace

# at breakpoint
caller.select {|line| line.starts_with? '/your-app-dir' }
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binding.pry in external code
Get filtered stack trace