I found out how to fix the issue using this link.
https://linuxconfig.org/installation-of-deb-kernel-in-debian-chroot-environment
update-grub fails silently in chroot unless these mounts are done:
mount -o bind /proc ${prefix}/proc
mount -o bind /proc ${prefix}/dev
This is an upstream issue. I'll make a patch and submit there.
Cheers!
Brandon Bradley
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