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I recently upgraded from Ubuntu 21.10 to 22.04 and the process went smoothly without reporting any errors.

Whenever I try to run a system update dpkg raises the following error relating to the old linux-image:

/etc/grub.d/bin/grubcfg_proxy: error while loading shared libraries: libcrypto.so.1.1: cannot open shared object file: No such file or directory
run-parts: /etc/kernel/postrm.d/zz-update-grub exited with return code 127
dpkg: error processing package linux-image-5.13.0-39-generic (--remove):
installed linux-image-5.13.0-39-generic package post-removal script subprocess returned error exit status 1
dpkg: too many errors, stopping
Errors were encountered while processing:
linux-image-5.13.0-39-generic
Processing was halted because there were too many errors.
E: Sub-process /usr/bin/dpkg returned an error code (1)

dpkg shows a status of remove and Half:

rH linux-image-5.13.0-39-generic 5.13.0-39.44 amd64 Signed kernel image generic

The following is in the dpkg log:

2022-04-25 11:15:54 startup packages remove
2022-04-25 11:15:54 status half-installed linux-image-5.13.0-39-generic:amd64 5.13.0-39.44
2022-04-25 11:15:54 remove linux-image-5.13.0-39-generic:amd64 5.13.0-39.44 <none>
2022-04-25 11:15:55 startup archives unpack

I have tried to re-install the libssl1.0 package but I get the same error as above as dpkg tries to remove the old linux-image first. I have also tried to purge the image but it raises the same error as above too.

sudo apt purge  linux-image-5.13.0-39-generic

I cannot re-install the old image as it not installable.

sudo apt install --reinstall  linux-image-5.13.0-39-generic

The following packages have unmet dependencies:
 linux-image-5.13.0-39-generic : Depends: linux-modules-5.13.0-39-generic but it is not installable
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  • you played with grub-customizer?
    – nobody
    Apr 27, 2022 at 17:04
  • Please askubuntu.com/questions/1168054/… repair grub first.
    – nobody
    Apr 27, 2022 at 17:10
  • Thank you @nobody I did have grub-customizer installed and I used it to clean up grub a long time ago - it did not cause any issues. I will try to repair grub but I currently do not have locate installed and cannot use it to find the libssl1.0.0 location, any suggestions? I cannot remove the grub-customizer package until I have fixed this.
    – Interrupt
    Apr 27, 2022 at 17:30
  • Please see the solution(s) in my bug report: bugs.launchpad.net/ubuntu/+source/ubuntu-release-upgrader/+bug/…
    – Batwam
    Apr 28, 2022 at 17:06

1 Answer 1

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We need to fix the missing libssl1.1 library manually. Please head over to the official Debian package library online and download the binary package that matches your system: https://packages.debian.org/stretch/libssl1.1

You will then need to run the following command to install libssl1.1:

sudo dpkg --install libssl1.1*.deb

After this the missing dependencies should be fixed and you can then clean out the linux-image

sudo apt purge <linux-image-name-to-remove>
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  • That’s how I fixed is as well, I did however download it from the Ubuntu Impish repo: packages.ubuntu.com/impish/libssl1.1
    – Batwam
    Apr 28, 2022 at 17:34
  • 1
    Thank you @Batwam. It is probably better to grab the libssl package from the correct distro (Impish).
    – Interrupt
    Apr 28, 2022 at 18:16

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