I found that this was due to System76 Pop!_OS kernels having gotten
installed, which also explains when those were installed why I problems
booting them and had to manually boot to the 5.0 signed kernel.
Something to be aware of is that the System76 PPA is not just for their
DDE but for the entire system.

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https://bugs.launchpad.net/bugs/1854115

Title:
  package grub-efi-amd64-signed 1.128.1+2.04-1ubuntu12.1 failed to
  install/upgrade: installed grub-efi-amd64-signed package post-
  installation script subprocess returned error exit status 1

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