I'm also using Debian; have been since Wheezy. I also template my VMs with Packer/Ansible though, so in the event it gets too messy or annoying to fix, I just e

I'm also using Debian; have been since Wheezy. I also template my VMs with Packer/Ansible though, so in the event it gets too messy or annoying to fix, I just export the pool and import it to a new VM. The last issue I had was that linux-headers didn't get installed with the kernel update, so DKMS couldn't build on them. I assumed they were a dependency for zfs-dkms, but no.