Comment 29 for bug 173721

"Shift with numeric keypad keys works as in MS Windows".
It takes an effect immediately but after reboot it behaves
like it wasn't set (but it is still checked in the layout options
dialog).

After doing some testing, I' not sure this is a race condition described in previous comments.

I tested System/Admin/Login Window with Enable Automatic Login enabled.
A reboot caused the "Shift with numeric keypad keys works as in MS Windows" to be broken.

I then tested System/Admin/Login Window with Enable Timed Login with 30, 60 and 90 second pauses before login.
A reboot caused the "Shift with numeric keypad keys works as in MS Windows" to be broken.

I then disabled the Automatic Login and logged in manually, both immediately and after a period of time.
In both cases, a reboot caused the "Shift with numeric keypad keys works as in MS Windows" to work properly.

In my case I was running Ubuntu 8.04 as a VMWare client on a Dell Inspiron 1721 Windows host running Vista.

So - for me at least, a temporary solution was to turn off the automatic login.
Not sure what a manual login would be running that the automatic is not, but there seems to be a difference.