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Gotcha. I would be open to something like this (as long as the maintenance footprint isn't too large), but I don't think I'm prepared to work on it myself. I'll leave this open in case anyone would like to try prototyping it.
Some open questions:
Does this work if the service is running as a different user?
Is there some existing program that could open the PTY, so Shawl would only need some minor adjustments to play nice with that program, rather than implementing the full functionality in Shawl itself?
PTY was supported since Windows 10: https://learn.microsoft.com/en-us/windows/console/creating-a-pseudoconsole-session
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