Sure, I'd expect the signal emulation in Windows to be incompatible in some way but this particular phenomenon I blame on buffering. It's very very likely that the "echo" will have finished its output before the Perl process gets scheduled again so by the time the while() starts the whole output is sitting in STDIN's buffer already. You could try spawning the Windows equivalent of "(echo one; sleep 1; echo two)" and kill()ing that.
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