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Just pry or with byebug? If the latter: https://github.com/deivid-rodriguez/byebug/issues/564
I feel your pain, u/2called_chaos -- so much that after being totally fed up with this kind of unreliable faff, I fixed it in a gem I maintain! Here's a video demo of your exact setup. You can see it broken and then working after simply adding the gem:
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