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I would like to setup GRUB on a USB where it detects automatically the available OS installations on the machine that it is plugged into...

This could be useful if you messed up your default GRUB menu on a computer and would like to boot into the machine w/out booting Live-OS. Or if you have multiple Live-OS installations on a USB-Drive and would like to add/remove different installations w/out needing to update grub manually.

I know that Grub2 has a OS-prober feature that looks for other installations on the hard-drive, but will that work in either of the scenarios listed above?

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Actually, someone already made this :)

SugerGrub2Disk is your friend.

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