rb-ruby-debug

• If not done already, install MacPorts.
• To install rb-ruby-debug, run the following command in macOS terminal (Applications->Utilities->Terminal)
  
  sudo port install rb-ruby-debug Copy
• To see what files were installed by rb-ruby-debug, run:
  
  port contents rb-ruby-debug Copy
• To later upgrade rb-ruby-debug, run:
  
  sudo port selfupdate && sudo port upgrade rb-ruby-debug Copy

The MacPorts Project uses a system called Trac to file tickets to report bugs and enhancement requests. Though anyone may search Trac for tickets, you must have a GitHub account in order to login to Trac to create tickets.