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In ruby-debug, when a user sets a breakpoint that ends up executed by a later-created thread, then nothing will happen.
The only solution that I have at this point is to always set RUBY_EVENT_VM for all living threads every time the hook proc is called. I've tried to optimize this and failed; the cost of figuring out accurately if there's a new thread is always greater than the brute-force method of just always forcing the flags to be updated.
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This issue was solved with changeset r27033.
Mark, thank you for reporting this issue.
Your contribution to Ruby is greatly appreciated.
May Ruby be with you.