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Say you have some file on your windows system.

Is there a simple way or tool which can mark this file as not uploadable to some other machine over the internet?

All applications on the system can only read this file locally, but it must not leave the system boundary.

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There really isn't any way to stop a file that can be accessed from being copied. If the file can be opened (e.g. in a text editor), then it can be saved to another file from there, copied to the clipboard, have screenshots made of it to another file, or have pictures of the displayed file taken with another device. Granted, those options become increasingly extreme, but the only way to truly secure the files is to keep them from being accessed by anyone who would have any reason to copy them off of the machine.

This is covered in the answer to this post: https://serverfault.com/questions/408992/secure-remote-rdp-worker-prevent-file-transfer

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