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This may be a bug fixed since the versions you're running. I'm not seeing it with Wing on macOS or Windows and there have been relatively recent fixes to I/O buffering.

Note that if you set Python Options under the Debug/Execute tab of Project Properties then omitting -u may cause this. That tells Python to run in un-buffered mode. We specify that option by default but it's possible for the user to override this.

Please let us know if this does not help.