Public bug reported:

I have an external drive which I am booting from.
when running grub-install after update-grub, it fails.
$ sudo grub-install /dev/sdb
source_dir doesn't exist. Please specify --target or --directory

$ mount
/dev/sdb6 on / type ext4 (rw,errors=remount-ro)
...

As a rusult of this, there is no option to boot from the newest
installed kernels at the grub boot menu.  It must be possible to hand
edit something, but grub-install is supposed to work.

I don't mind repeating information that has been provided on the forum already. 
 If anyone wants to look there though:
http://ubuntuforums.org/showthread.php?t=2200335&page=4&p=12911643#post12911643
also: 
http://askubuntu.com/questions/408076/update-grub-doesnt-help-boot-new-kernels-on-external-drive

package: grub2-common: /usr/sbin/grub-install

1.) $ lsb_release -rd
Description:    Ubuntu 13.10
Release:        13.10

2.) $ apt-cache policy grub2-common
grub2-common:
  Installed: 2.00-19ubuntu2.1
  Candidate: 2.00-19ubuntu2.1
  Version table:
 *** 2.00-19ubuntu2.1 0
        500 http://us.archive.ubuntu.com/ubuntu/ saucy-updates/main amd64 
Packages
        100 /var/lib/dpkg/status
     2.00-19ubuntu2 0
        500 http://us.archive.ubuntu.com/ubuntu/ saucy/main amd64 Packages

3.) I expected to be able to install the new boot options found by update-grub
4.)  instead I received an error: source_dir doesn't exist. Please specify 
--target or --directory

This is a security vulnerability to the extent that there is a security
vulnerability driving the update to newer kernels, and this impedes the
use of the new and improved kernels.

** Affects: ubuntu
     Importance: Undecided
         Status: New

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https://bugs.launchpad.net/bugs/1273054

Title:
  grub-install fails when using external drive /dev/sdb

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