I had the same issue whn upgrading from 17.10 to 18.04 and used the
following workaround:

cd /boot
mkdir unsigned
mv vmlinuz-4.10.0-40-generic vmlinuz-4.10.0-42-generic 
vmlinuz-4.13.0-46-generic unsigned/
apt-get upgrade 

and voila problem solved :-)

It seems that unsigned kernels are left in the /boot directory (not used
it seems) which prevents the grub update mechanism to happen correctly.
So I think the "design" is wrong and that unsigned kernel in SB mode
should just be ignored and shouldn't prevent the postinstall to proceed.

Just my 0.02€ and YMMV of course

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https://bugs.launchpad.net/bugs/1788727

Title:
  upgrade crashing due to unsigned kernels

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