After getting frustrated with ruby debug on 1.9.3, I realized that pry-nav and pry-stack-explorer are an excellent replacement for ruby-debug. After using pry for a while, I doubt I will return to using irb and ruby-debug.
As the author of pry-nav, I'm really glad to see more people using it! Thanks and please file issues if you get any odd behavior. I've been trying to improve the tracing.
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)