here is the manual reproduction

root@ubuntu:~# /etc/kernel/postinst.d/zz-update-grub 4.4.0-64-generic 
/boot/vmlinuz-4.4.0-64-generic
Generating grub configuration file ...
Warning: Setting GRUB_TIMEOUT to a non-zero value when GRUB_HIDDEN_TIMEOUT is 
set is no longer supported.
Found linux image: /boot/vmlinuz-4.4.0-64-generic
Found initrd image: /boot/initrd.img-4.4.0-64-generic
Found linux image: /boot/vmlinuz-4.4.0-62-generic
Found initrd image: /boot/initrd.img-4.4.0-62-generic
done

root@ubuntu:~# df -m /
Filesystem     1M-blocks  Used Available Use% Mounted on
/dev/vda3           1777  1510       154  91% /

root@ubuntu:~# resize2fs /dev/vda3
resize2fs 1.42.13 (17-May-2015)
Filesystem at /dev/vda3 is mounted on /; on-line resizing required
old_desc_blocks = 1, new_desc_blocks = 131
The filesystem on /dev/vda3 is now 548404992 (4k) blocks long.

root@ubuntu:~# df -m /
Filesystem     1M-blocks  Used Available Use% Mounted on
/dev/vda3        2013606  1507   1926382   1% /

root@ubuntu:~# /etc/kernel/postinst.d/zz-update-grub 4.4.0-64-generic 
/boot/vmlinuz-4.4.0-64-generic
Generating grub configuration file ...
grub-probe: error: unknown filesystem.

** Description changed:

  don't really know if this is a resize2fs problem or a grub problem.
  But we discovered it when trying to cloud-init bootstrap a node with larger 
than 2 TB disk.
- 
  
  Create a virtual or a physical node with more than 2TB disk.
  install ubuntu cloud image on disk.
  boot and let cloud init run it's course, after that grub2 os-probe will fail 
with this error message:
  grub-probe: error: unknown filesystem.
+ 
+ Have tested this in both trusty and xenial

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https://bugs.launchpad.net/bugs/1666853

Title:
  grub-probe when fs is larger than 2tb

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