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Are there any plans for windows support?

At first glance it should already work if you provide the right programs (e.g. change scrot for some Windows screenshot program). Or is there a more serious incompatibility?

How much does this rely on scrot's features & flags? Would it be as simple as finding another command line screenshot tool that works on windows or would I need to update the flags?

It does not rely on the screenshot program at all, it only needs a set of image files to work on. So yes, I think any commandline tool would do for Windows.

One thing we have to care about is the ordering of command options. In the current implementation, it assumes that <command> <flag1> <flag2> ... <files>. So if a command working on Windows requires other ordering like <command> <files> <flag1> <flag2>, then we have to update the current implementation.