The debug gem's binding.break creates break point but no console prompt

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I have a Rails 7 application using gem "debug", platforms: %i[ mri mingw x64_mingw ] for debugging. I am also using WSL2 and Windows Terminal on Windows 11 for my development environment in case that's part of the issue I'm about to describe.

If I try setting a binding.break, breakpoint in my application it breaks correctly but doesn't give me a console prompt. I'm not sure if there is something I'm not doing as this gem is new to me. I'm attaching an example output from my Puma output.

Update: Also should note that when using this in my tests, it does work as expected.

Another Update: I noticed that the break points work if I use rails s to start the server but not when I use bin/dev.

Another Update: Here is the bin/dev file contents.

#!/usr/bin/env bash

if ! command -v foreman &> /dev/null
then
  echo "Installing foreman..."
  gem install foreman
fi

foreman start -f Procfile.dev

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