Upon further inspection of the log, I realised that the issue occurs when /etc/grub.d/bin/grubcfg_proxy is being run but this file is not part of grub itself. Looking through the package contents, it looks like grubcfg-cfg is included in grub-customizer which is installed on my system so, this is perhaps actually and issue with the grub-customizer package?
It looks like it is not the first time this package has this kind of compatibility issues: https://askubuntu.com/questions/1168054/how-to- fix-kernel-issue-after-upgrading-from-18-10-to-19-04 -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1969353 Title: Apt/Grub issue with 22.04 Upgrade (Missing libcrypto.so.1.1) To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/ubuntu-release-upgrader/+bug/1969353/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs
