I believe I have run into similar problems in the past.

Note, in many cases, the UEFI firmware will not verify the GRUB binary
itself, but will verify the SHIM against certificates in the UEFI
databases. On a standard system, Ubuntu doesn't have their own cert in
the UEFI key databases. The SHIM will verify the UBUNTU-signed GRUB
image against certificates embedded in the SHIM itself.

Anyway, after seeing your post and doing some more searching I came across this:
https://git.kernel.org/cgit/linux/kernel/git/jejb/sbsigntools.git/log/

It appears that James Bottomley has some really recent code for sbsign
up on kernel.org. I'm about to give it a shot myself and hope it fixes
the problem.

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https://bugs.launchpad.net/bugs/1551629

Title:
  sbsign generates invalid grub signatures

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