My guess would be, that the 'recordfail' flag
was set in the 'grubenv' file, and that, somehow, it didn't get reset
after the system was booted.
You see, the Ubuntu menu entries in the grub.cfg file all include
a 'recordfail' line, which will execute the 'recordfail' function
that is defined earlier on in the file. The function will set the
'recordfail' flag to 1, and save that to the 'grubenv' file.
Once the system boots successfully, it is supposed to clear the
flag again; this actually happens in the '/etc/init.d/grub-common'
script.
Next time the time-out doesn't work, I suggest you look in the
'/boot/grub/grubenv' file first, and check if it includes a
'recordfail=1' line.
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