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As root, copy filesystem.squashfs to some empty dir, e.g.:

cp /mnt/target/casper/filesystem.squashfs /data/local/dev/ubuntu
cd /data/local/dev/ubuntu

Unpack the file then move it somewhere else (so you still have it as a backup):

unsquashfs filesystem.squashfs
mv filesystem.squashfs /data/local/dev/ubuntu/backup.filesystem.squashfs

Go in squashfs-root, add/modify as per your taste then recreate filesystem.squashfs:

cd /data/local/dev/ubuntu
mksquashfs squashfs-root filesystem.squashfs -b 1024k -comp xz -Xbcj x86 -e boot

copy the newly created filesystem.squashfs over the existing one on your USB drive, e.g.:

cp filesystem.squashfs /mnt/target/casper/filesystem.squashfs

then reboot and use your LIVE USB.

Note: the above commands are part of squashfs-tools.