Why do I require multiple EOF (CTRL+Z) characters?

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This answer is unix-ish, but I think a similar phenonemon is happening on Windows. The underlying form of an EOF is a zero-length read. On interactive input devices (terminals), there is a special mechanism for having an EOF in the input stream, but if there’s already input to be read, it will be consumed along with that input (resulting a non-zero length read) and thus never noticed by the application. Only when the EOF occurs with no prior input buffered can it be noticed and acted upon by the application.

If you have access to a Linux (or other *nix) system, write a similar test program and run it under strace. Watch the underlying read calls that happen, and the reason for this otherwise-unintuitive behavior will make sense.

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