Unfortunately using pry-nav with pry has some limitations that ruby-debug doesn't: 1. It doesn't seem to work in some cases (like putting binding.pry in a Proc.new { ... } 2. On Windows, binding.pry works when directly embedded in a ruby script, but when put into code such as a Rails controller or model then several things don't work properly ('whereami' will show it doesn't have context.. though this works fine on Linux)
For these reasons, I still find ruby-debug better for actual debugging (when step/next are necessary) and pry better for inspecting state at a particular moment in time (but I can just call pry from the ruby-debug in that case)