ok, found the issue. I think if you followed the zol ubuntu administration guide (https://github.com/zfsonlinux/zfs/wiki/Ubuntu-18.04-Root-on-ZFS), which is only using a debootstrap, you are using mawk and not gawk, which is why the regexp don't match and find your kernel.
Traditional ubuntu installations have gawk by default (higher priority for the awk alternative), this is why we didn't spot it. I'm unsure on how to fix those yet, but meanwhile, to unblock you, you can install gawk. ** Summary changed: - update-grub fails on zfs with root and boot datasets + update-grub fails on zfs with root and boot datasets when using mawk ** Changed in: grub2 (Ubuntu) Status: New => Triaged -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1834095 Title: update-grub fails on zfs with root and boot datasets when using mawk To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/grub2/+bug/1834095/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs