This time I got it while running dpkg-reconfigure -aup low.

When it crashed I got the bug.

run-parts: executing /etc/kernel/postinst.d/nvidia-common
Running depmod.
update-initramfs: Generating /boot/initrd.img-2.6.27-4-generic
cpio: ./sbin/udevtrigger: Cannot stat: No such file or directory
Not updating initrd symbolic links since we are being updated/reinstalled 
(2.6.27-4.6 was configured last, according to dpkg)
Not updating image symbolic links since we are being updated/reinstalled 
(2.6.27-4.6 was configured last, according to dpkg)
Running postinst hook script /sbin/update-grub.
Searching for GRUB installation directory ... found: /boot/grub
Searching for default file ... found: /boot/grub/default
Testing for an existing GRUB menu.lst file ... found: /boot/grub/menu.lst
Searching for splash image ... none found, skipping ...
Found kernel: /boot/vmlinuz-2.6.27-4-generic
Found kernel: /boot/last-good-boot/vmlinuz
Found kernel: /boot/vmlinuz-2.6.27-3-generic
Found kernel: /boot/memtest86+.bin
Updating /boot/grub/menu.lst ... done

Examining /etc/kernel/postinst.d.
run-parts: executing /etc/kernel/postinst.d/dkms
 * Running DKMS auto installation service for kernel 2.6.27-4-generic           
 *  vboxdrv (2.0.2)...                                                          vboxdrv (2.0.2): Already installed on this kernel.
                                                                         [ OK ]
run-parts: executing /etc/kernel/postinst.d/nvidia-common
update-initramfs: Generating /boot/initrd.img-2.6.27-3-generic
cpio: ./sbin/udevtrigger: Cannot stat: No such file or directory
update-initramfs: Generating /boot/initrd.img-2.6.27-4-generic
cpio: ./sbin/udevtrigger: Cannot stat: No such file or directory
 * PCMCIA bridge driver already present in kernel
mktexlsr: Updating /var/lib/texmf/ls-R-TEXMFMAIN... 
mktexlsr: Done.
 * Updating the system logo...                                                  /etc/init.d/linuxlogo: 60: cannot create /etc/issue.linuxlogo: Directory nonexistent
invoke-rc.d: initscript linuxlogo, action "restart" failed.
thomas@thomas-laptop:~$

I will try to reproduce this with valgrind.

thomas@thomas-laptop:~$ lsb_release -rd ; uname -a ; apt-cache policy linux linux-source-2.6.27 linux-headers-generic linux-image-generic
Description:	Ubuntu intrepid (development branch)
Release:	8.10
Linux thomas-laptop 2.6.27-4-generic #1 SMP Wed Sep 24 01:30:51 UTC 2008 i686 GNU/Linux
linux:
  Installed: 2.6.27.4.4
  Candidate: 2.6.27.4.4
  Version table:
 *** 2.6.27.4.4 0
        500 http://gb.archive.ubuntu.com intrepid/restricted Packages
        100 /var/lib/dpkg/status
linux-source-2.6.27:
  Installed: 2.6.27-4.6
  Candidate: 2.6.27-4.6
  Version table:
 *** 2.6.27-4.6 0
        500 http://gb.archive.ubuntu.com intrepid/main Packages
        100 /var/lib/dpkg/status
linux-headers-generic:
  Installed: 2.6.27.4.4
  Candidate: 2.6.27.4.4
  Version table:
 *** 2.6.27.4.4 0
        500 http://gb.archive.ubuntu.com intrepid/main Packages
        100 /var/lib/dpkg/status
linux-image-generic:
  Installed: 2.6.27.4.4
  Candidate: 2.6.27.4.4
  Version table:
 *** 2.6.27.4.4 0
        500 http://gb.archive.ubuntu.com intrepid/main Packages
        100 /var/lib/dpkg/status
thomas@thomas-laptop:~$