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Interesting, and somewhat weird - I haven't had any issues with any of the 4.x kernel upgrades in the past. In either case, I'm now using a USB drive to host /boot/ and nothing else, and it works (still using grub/mbr). Since I don't have UEFI booting setup, I don't think it's worth messing with...

EDIT: I "fixed" this by plugging in a USB drive and putting BOOT and grub on the USB drive instead of booting from the ZFS pool. It's sufficient for now but still curious to know why 5.x kernel would fail when 4.x worked. I just upgraded 4 machines to Proxmox 6.x. Three booted fine, except for...

Are you running Proxmox on ZFS? I had issues with this where when I did large writes (such as running a backup) it would hang and require a hard reboot. When I removed the swap (didn't need it anyway, it was barely used), the hanging went away. As a new user I can't post links but Google for...