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I am looking for a way to make a Live USB with Persistence that can be run headless (i.e. by a bash script, therefor with no GUI interaction), either from Mac OS or Ubuntu.

I need this to be able to program multiple USB drives easily for my students.

I managed to make a Live USB from Mac, either by using UNetbootin (even if I did not manage to make the persistence work) or by using the dd command. However, I did not manage to make it persistent without the use of a GUI tool.

Do you guys know how I could do that ?

Thanks !

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If you using dd to copy a USB set up with persistence, I don't see why that doesn't work if the USBs don't have bad blocks.
If you want to add persistence to a USB created from the ISO, just add the word "persistent" to the kernel line (linux...) in both grub.cfg (for UEFI machines) and the /syslinux/txt.cfg (or isolinux/txt.cfg) files. Also create a file named casper-rw of up to 4G on the root of the USB and put an ext4 filesystem in it.e.g.:

dd if=/dev/zero of=casper-rw bs=1M  count=1024
mkfs.ext4 -F -O^has_journal -L casper-rw casper-rw

If your USBs are big, you can use a partition labeled "casper-rw" insted of the file to avoid the 4G limit of files in FAT filesystems.

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