I encountered the same issue, and I’d like to share what worked for me.

When I explicitly set the input and output for Pry like this:

Pry.config.input = STDIN
Pry.config.output = STDOUT
binding.pry

I was able to interact with the Pry session normally inside Docker.

However, I also noticed one important thing:

If I exit the Pry session by pressing Ctrl + D, then the next time I hit binding.pry, it sometimes doesn’t stop properly or ignores input.

To avoid this problem, I recommend using the exit command inside Pry to leave the session gracefully. That way, Pry continues to behave correctly in future debugging sessions.

Hope this helps others facing the same issue!