I've tried asking this questions in numerous other places and so far I've had no response, so I'm hoping someone here will be able to help.

I rebooted my server last week and when I tried to remove old kernels it was stopping when trying to update grub. I ran update-grub2 on its own and I get:

Generating grub configuration file ...
grub-probe: error: not a directory.

fdisk -l shows:

Disk /dev/sda: 111.8 GiB, 120034123776 bytes, 234441648 sectors
Units: sectors of 1 * 512 = 512 bytes
Sector size (logical/physical): 512 bytes / 512 bytes
I/O size (minimum/optimal): 512 bytes / 512 bytes
Disklabel type: dos
Disk identifier: 0x31337774

Device     Boot     Start       End  Sectors Size Id Type
/dev/sda1  *         2048  52430847 52428800  25G 83 Linux
/dev/sda2        52430848 146802687 94371840  45G 83 Linux

Running grub-probe -v -d /dev/sda1 produces this:
grub-probe: info: adding `hd0' -> `/dev/sda' from device.map.
grub-probe: info: adding `hd1' -> `/dev/sdb' from device.map.
grub-probe: info: adding `hd2' -> `/dev/sdc' from device.map.
grub-probe: info: adding `hd3' -> `/dev/sdd' from device.map.
grub-probe: info: Cannot stat `/dev/disk/by-id/usb-Seagate_Backup+_Hub_BK_NA8TT3NB-0:0', skipping. grub-probe: info: Cannot stat `/dev/disk/by-id/usb-Seagate_Expansion_NA84KDR3-0:0', skipping.
grub-probe: info: /dev/sda1 is present.
grub-probe: info: Looking for /dev/sda1.
grub-probe: info: /dev/sda is a parent of /dev/sda1.
grub-probe: info: /dev/sda1 starts from 2048.
grub-probe: info: opening the device hd0.
grub-probe: info: drive = 0.
grub-probe: info: the size of hd0 is 234441648.
grub-probe: info: drive = 0.
grub-probe: info: the size of hd0 is 234441648.
grub-probe: info: Scanning for DISKFILTER devices on disk hd0.
grub-probe: info: Scanning for mdraid1x devices on disk hd0.
grub-probe: info: Scanning for mdraid09 devices on disk hd0.
grub-probe: info: Scanning for mdraid09_be devices on disk hd0.
grub-probe: info: Scanning for dmraid_nv devices on disk hd0.
grub-probe: info: Scanning for ldm devices on disk hd0.
grub-probe: info: scanning hd0 for LDM.
grub-probe: info: no LDM signature found.
grub-probe: info: Scanning for lvm devices on disk hd0.
grub-probe: info: no LVM signature found.
grub-probe: info: Scanning for DISKFILTER devices on disk hd0.
grub-probe: info: Scanning for mdraid1x devices on disk hd0.
grub-probe: info: Scanning for mdraid09 devices on disk hd0.
grub-probe: info: Scanning for mdraid09_be devices on disk hd0.
grub-probe: info: Scanning for dmraid_nv devices on disk hd0.
grub-probe: info: Scanning for ldm devices on disk hd0.
grub-probe: info: scanning hd0 for LDM.
grub-probe: info: no LDM signature found.
grub-probe: info: Scanning for lvm devices on disk hd0.
grub-probe: info: no LVM signature found.
grub-probe: info: Scanning for DISKFILTER devices on disk hd0.
grub-probe: info: Scanning for mdraid1x devices on disk hd0.
grub-probe: info: Scanning for mdraid09 devices on disk hd0.
grub-probe: info: Scanning for mdraid09_be devices on disk hd0.
grub-probe: info: Scanning for dmraid_nv devices on disk hd0.
grub-probe: info: Scanning for ldm devices on disk hd0.
grub-probe: info: scanning hd0 for LDM.
grub-probe: info: no LDM signature found.
grub-probe: info: Scanning for lvm devices on disk hd0.
grub-probe: info: no LVM signature found.
grub-probe: info: Scanning for DISKFILTER devices on disk hd0.
grub-probe: info: Scanning for mdraid1x devices on disk hd0.
grub-probe: info: Scanning for mdraid09 devices on disk hd0.
grub-probe: info: Scanning for mdraid09_be devices on disk hd0.
grub-probe: info: Scanning for dmraid_nv devices on disk hd0.
grub-probe: info: Scanning for ldm devices on disk hd0.
grub-probe: info: scanning hd0 for LDM.
grub-probe: info: no LDM signature found.
grub-probe: info: Scanning for lvm devices on disk hd0.
grub-probe: info: no LVM signature found.
grub-probe: info: Partition 0 starts from 2048.
grub-probe: info: /dev/sda1 is present.
grub-probe: info: Looking for /dev/sda1.
grub-probe: info: /dev/sda is a parent of /dev/sda1.
grub-probe: info: /dev/sda1 starts from 2048.
grub-probe: info: opening the device hd0.
grub-probe: info: drive = 0.
grub-probe: info: the size of hd0 is 234441648.
grub-probe: info: drive = 0.
grub-probe: info: the size of hd0 is 234441648.
grub-probe: info: Scanning for DISKFILTER devices on disk hd0.
grub-probe: info: Scanning for mdraid1x devices on disk hd0.
grub-probe: info: Scanning for mdraid09 devices on disk hd0.
grub-probe: info: Scanning for mdraid09_be devices on disk hd0.
grub-probe: info: Scanning for dmraid_nv devices on disk hd0.
grub-probe: info: Scanning for ldm devices on disk hd0.
grub-probe: info: scanning hd0 for LDM.
grub-probe: info: no LDM signature found.
grub-probe: info: Scanning for lvm devices on disk hd0.
grub-probe: info: no LVM signature found.
grub-probe: info: Scanning for DISKFILTER devices on disk hd0.
grub-probe: info: Scanning for mdraid1x devices on disk hd0.
grub-probe: info: Scanning for mdraid09 devices on disk hd0.
grub-probe: info: Scanning for mdraid09_be devices on disk hd0.
grub-probe: info: Scanning for dmraid_nv devices on disk hd0.
grub-probe: info: Scanning for ldm devices on disk hd0.
grub-probe: info: scanning hd0 for LDM.
grub-probe: info: no LDM signature found.
grub-probe: info: Scanning for lvm devices on disk hd0.
grub-probe: info: no LVM signature found.
grub-probe: info: Scanning for DISKFILTER devices on disk hd0.
grub-probe: info: Scanning for mdraid1x devices on disk hd0.
grub-probe: info: Scanning for mdraid09 devices on disk hd0.
grub-probe: info: Scanning for mdraid09_be devices on disk hd0.
grub-probe: info: Scanning for dmraid_nv devices on disk hd0.
grub-probe: info: Scanning for ldm devices on disk hd0.
grub-probe: info: scanning hd0 for LDM.
grub-probe: info: no LDM signature found.
grub-probe: info: Scanning for lvm devices on disk hd0.
grub-probe: info: no LVM signature found.
grub-probe: info: Scanning for DISKFILTER devices on disk hd0.
grub-probe: info: Scanning for mdraid1x devices on disk hd0.
grub-probe: info: Scanning for mdraid09 devices on disk hd0.
grub-probe: info: Scanning for mdraid09_be devices on disk hd0.
grub-probe: info: Scanning for dmraid_nv devices on disk hd0.
grub-probe: info: Scanning for ldm devices on disk hd0.
grub-probe: info: scanning hd0 for LDM.
grub-probe: info: no LDM signature found.
grub-probe: info: Scanning for lvm devices on disk hd0.
grub-probe: info: no LVM signature found.
grub-probe: info: Partition 0 starts from 2048.
grub-probe: info: /dev/sda1 is present.
grub-probe: info: Looking for /dev/sda1.
grub-probe: info: /dev/sda is a parent of /dev/sda1.
grub-probe: info: /dev/sda1 starts from 2048.
grub-probe: info: opening the device hd0.
grub-probe: info: drive = 0.
grub-probe: info: the size of hd0 is 234441648.
grub-probe: info: drive = 0.
grub-probe: info: the size of hd0 is 234441648.
grub-probe: info: Scanning for DISKFILTER devices on disk hd0.
grub-probe: info: Scanning for mdraid1x devices on disk hd0.
grub-probe: info: Scanning for mdraid09 devices on disk hd0.
grub-probe: info: Scanning for mdraid09_be devices on disk hd0.
grub-probe: info: Scanning for dmraid_nv devices on disk hd0.
grub-probe: info: Scanning for ldm devices on disk hd0.
grub-probe: info: scanning hd0 for LDM.
grub-probe: info: no LDM signature found.
grub-probe: info: Scanning for lvm devices on disk hd0.
grub-probe: info: no LVM signature found.
grub-probe: info: Scanning for DISKFILTER devices on disk hd0.
grub-probe: info: Scanning for mdraid1x devices on disk hd0.
grub-probe: info: Scanning for mdraid09 devices on disk hd0.
grub-probe: info: Scanning for mdraid09_be devices on disk hd0.
grub-probe: info: Scanning for dmraid_nv devices on disk hd0.
grub-probe: info: Scanning for ldm devices on disk hd0.
grub-probe: info: scanning hd0 for LDM.
grub-probe: info: no LDM signature found.
grub-probe: info: Scanning for lvm devices on disk hd0.
grub-probe: info: no LVM signature found.
grub-probe: info: Scanning for DISKFILTER devices on disk hd0.
grub-probe: info: Scanning for mdraid1x devices on disk hd0.
grub-probe: info: Scanning for mdraid09 devices on disk hd0.
grub-probe: info: Scanning for mdraid09_be devices on disk hd0.
grub-probe: info: Scanning for dmraid_nv devices on disk hd0.
grub-probe: info: Scanning for ldm devices on disk hd0.
grub-probe: info: scanning hd0 for LDM.
grub-probe: info: no LDM signature found.
grub-probe: info: Scanning for lvm devices on disk hd0.
grub-probe: info: no LVM signature found.
grub-probe: info: Scanning for DISKFILTER devices on disk hd0.
grub-probe: info: Scanning for mdraid1x devices on disk hd0.
grub-probe: info: Scanning for mdraid09 devices on disk hd0.
grub-probe: info: Scanning for mdraid09_be devices on disk hd0.
grub-probe: info: Scanning for dmraid_nv devices on disk hd0.
grub-probe: info: Scanning for ldm devices on disk hd0.
grub-probe: info: scanning hd0 for LDM.
grub-probe: info: no LDM signature found.
grub-probe: info: Scanning for lvm devices on disk hd0.
grub-probe: info: no LVM signature found.
grub-probe: info: Partition 0 starts from 2048.
grub-probe: info: opening hd0,msdos1.
grub-probe: info: drive = 0.
grub-probe: info: the size of hd0 is 234441648.
grub-probe: error: not a directory.

Every other partition on that drive end with it saying ext2.

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