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 On Wed, Feb 17, 2016 at 2:45 PM, Debian Bug Tracking System < ow...@bugs.debian.org> wrote: > Thank you for filing a new Bug report with Debian. > > This is an automatically generated reply to let you know your message > has been received. > > Your message is being forwarded to the package maintainers and other > interested parties for their attention; they will reply in due course. > > Your message has been sent to the package maintainer(s): > Axel Beckert <a...@debian.org> > > If you wish to submit further information on this problem, please > send it to 815...@bugs.debian.org. > > Please do not send mail to ow...@bugs.debian.org unless you wish > to report a problem with the Bug-tracking system. > > -- > 815021: http://bugs.debian.org/cgi-bin/bugreport.cgi?bug=815021 > Debian Bug Tracking System > Contact ow...@bugs.debian.org with problems >