Richard, as you didn't use 'apport' or 'ubuntu-bug' when creating this
bug report I'm unsure if what you are reporting applies to me or not as
your report doesn't include any version information.
I have Ubuntu 18.04 and Ubuntu 19.04 installed on this laptop which has
two disks /dev/sda and /dev/sdb. Using Ubuntu 18.04 I can install grub,
update grub and boot to either installation without any problem.

>From Ubuntu 18.10 (now upgraded to Ubuntu 19.04) any attempt to update
grub seemed to fail as I could only boot to the existing kernel and not
to the newly installed kernel. I have seen this on more than one
occasion.

If this is an example of what you are reporting and something that has
been an issue since the 18.04 release then I can confirm the bug report.

There's a reference to my issue at:
https://ubuntuforums.org/showthread.php?t=2403574&p=13808168&viewfull=1#post13808168

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https://bugs.launchpad.net/bugs/1803805

Title:
  grub-pc fails to install on the last of multiple devices

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