I was about to file a new BUG Report.

I did a quick fix and uploaded to one of my Repositories:
https://github.com/luckylinux/grub-
scripts/commit/59f90b0f751fb1241b0243dc5700522ffe73bf8e

Basically you need to add one mount / umount command for the /usr
Dataset whenever the / and/or /etc Dataset is mounted.

One Command is probably NOT needed as it generates an "unmount Error",
but the other seems to be.

Any change of getting this (FINALLY !) Fixed and Upstreamed ?

Thanks

Before Fix:
========================================================================================================
root@LiveUbuntu02:/# update-grub
Sourcing file `/etc/default/grub'
Sourcing file `/etc/default/grub.d/lubuntu-grub-theme.cfg'
Generating grub configuration file ...
/etc/grub.d/10_linux_zfs: 403: .: cannot open 
/tmp/zfsmnt.NYQsLe/etc/os-release: No such file
Warning: os-prober will not be executed to detect other bootable partitions.
Systems on them will not be added to the GRUB boot configuration.
Check GRUB_DISABLE_OS_PROBER documentation entry.
Adding boot menu entry for UEFI Firmware Settings ...
done
========================================================================================================


After Fix:
========================================================================================================
root@LiveUbuntu02:/# update-grub
Sourcing file `/etc/default/grub'
Sourcing file `/etc/default/grub.d/lubuntu-grub-theme.cfg'
Sourcing file `/etc/default/grub.d/zfs.cfg'
Generating grub configuration file ...
Found linux image: vmlinuz-6.8.0-35-generic in rpool/ROOT/ubuntu
Found initrd image: initrd.img-6.8.0-35-generic in rpool/ROOT/ubuntu
Found linux image: vmlinuz-6.5.0-14-generic in rpool/ROOT/ubuntu
Found initrd image: initrd.img-6.5.0-14-generic in rpool/ROOT/ubuntu
umount: /tmp/zfsmnt.Q0TA2T/usr: not mounted.
Found linux image: vmlinuz-6.8.0-35-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_frequent-2023-12-31-1715
Found initrd image: initrd.img-6.8.0-35-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_frequent-2023-12-31-1715
Found linux image: vmlinuz-6.5.0-14-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_frequent-2023-12-31-1715
Found initrd image: initrd.img-6.5.0-14-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_frequent-2023-12-31-1715
umount: /tmp/zfsmnt.Q0TA2T/usr: not mounted.
Found linux image: vmlinuz-6.8.0-35-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_hourly-2023-12-31-1717
Found initrd image: initrd.img-6.8.0-35-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_hourly-2023-12-31-1717
Found linux image: vmlinuz-6.5.0-14-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_hourly-2023-12-31-1717
Found initrd image: initrd.img-6.5.0-14-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_hourly-2023-12-31-1717
umount: /tmp/zfsmnt.Q0TA2T/usr: not mounted.
Found linux image: vmlinuz-6.8.0-35-generic in rpool/ROOT/ubuntu@install
Found initrd image: initrd.img-6.8.0-35-generic in rpool/ROOT/ubuntu@install
Found linux image: vmlinuz-6.5.0-14-generic in rpool/ROOT/ubuntu@install
Found initrd image: initrd.img-6.5.0-14-generic in rpool/ROOT/ubuntu@install
umount: /tmp/zfsmnt.Q0TA2T/usr: not mounted.
Found linux image: vmlinuz-6.8.0-35-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_frequent-2023-12-31-1730
Found initrd image: initrd.img-6.8.0-35-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_frequent-2023-12-31-1730
Found linux image: vmlinuz-6.5.0-14-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_frequent-2023-12-31-1730
Found initrd image: initrd.img-6.5.0-14-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_frequent-2023-12-31-1730
umount: /tmp/zfsmnt.Q0TA2T/usr: not mounted.
Found linux image: vmlinuz-6.8.0-35-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_frequent-2023-12-31-1745
Found initrd image: initrd.img-6.8.0-35-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_frequent-2023-12-31-1745
Found linux image: vmlinuz-6.5.0-14-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_frequent-2023-12-31-1745
Found initrd image: initrd.img-6.5.0-14-generic in 
rpool/ROOT/ubuntu@zfs-auto-snap_frequent-2023-12-31-1745
umount: /tmp/zfsmnt.Q0TA2T/usr: not mounted.
/etc/grub.d/10_linux_zfs: 406: .: cannot open 
/.zfs/snapshot/20240619_fix_nested_zfs_datasets/etc/os-release: No such file
Warning: os-prober will not be executed to detect other bootable partitions.
Systems on them will not be added to the GRUB boot configuration.
Check GRUB_DISABLE_OS_PROBER documentation entry.
Adding boot menu entry for UEFI Firmware Settings ...
done
========================================================================================================


EDIT 1: on one system, my proposed fix performed correctly. On another one, it 
failed with
========================================================================================================
/etc/grub.d/10_linux_zfs: 406: .: cannot open 
/.zfs/snapshot/20240619_fix_nested_zfs_datasets/etc/os-release: No such file
========================================================================================================

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https://bugs.launchpad.net/bugs/1899372

Title:
  update-grub 10_linux_zfs fails when /usr is a separate filesystem

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