I'm not sure if this is what you are looking for, but you can try the disable-pry , which will iterate automatically throughout the loop without leaving the session. Another option (although not big for long loops) is to use exit or Ctrl + D , which iterates through one loop of the loop. You will need to re-enter it until your cycle is complete, however this will allow you to hit another breakpoint if your goal.
For a little more control, you can add another gem, such as byebug or pry-byebug .
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