The key to this problem was that I had insserv installed and controlling my boot scripts. I ran the following commands, and was able to continue/complete the upgrade: sudo update-bootsystem-insserv restore sudo apt-get remove insserv Reading package lists... Done Building dependency tree Reading state information... Done The following packages will be REMOVED: insserv 0 upgraded, 0 newly installed, 1 to remove and 1 not upgraded. 20 not fully installed or removed. After this operation, 270kB disk space will be freed. Do you want to continue [Y/n]? (Reading database ... 153407 files and directories currently installed.) Removing insserv ... Processing triggers for man-db ... Setting up netbase (4.34ubuntu2) ... Setting up ifupdown (0.6.8ubuntu19) ... Removing any system startup links for /etc/init.d/loopback ... Setting up ntpdate (1:4.2.4p4+dfsg-7ubuntu5) ... Installing new version of config file /etc/network/if-up.d/ntpdate ... Setting up ubuntu-minimal (1.140) ... Setting up libwww-perl (5.820-1) ... Setting up librpc-xml-perl (0.64-1) ... Setting up apparmor-utils (2.3+1289-0ubuntu14) ... Setting up ppp (2.4.5~git20081126t100229-0ubuntu2) ... Installing new version of config file /etc/init.d/pppd-dns ... Setting up pppconfig (2.3.18ubuntu2) ... Installing new version of config file /etc/init.d/dns-clean ... Setting up telnet (0.17-36) ... Setting up exim4-base (4.69-9ubuntu1) ... Installing new version of config file /etc/cron.daily/exim4-base ... Installing new version of config file /etc/init.d/exim4 ... Setting up exim4-daemon-light (4.69-9ubuntu1) ... * Starting MTA [ OK ] Setting up bsd-mailx (8.1.2-0.20081101cvs-2ubuntu1) ... Setting up lftp (3.7.8-1) ... Installing new version of config file /etc/lftp.conf ... Setting up libfinance-quote-perl (1.13-4) ... Setting up mailx (1:20081101-2ubuntu1) ... Setting up network-manager (0.7.1~rc4.1.cf199a964-0ubuntu2) ... Installing new version of config file /etc/dbus-1/system.d/NetworkManager.conf ... Installing new version of config file /etc/dbus-1/system.d/nm-dhcp-client.conf ... Installing new version of config file /etc/dbus-1/system.d/nm-dispatcher.conf ... Installing new version of config file /etc/dbus-1/system.d/nm-system-settings.conf ... Installing new version of config file /etc/dbus-1/system.d/nm-avahi-autoipd.conf ... Installing new version of config file /etc/init.d/NetworkManager ... Removing any system startup links for /etc/init.d/NetworkManager ... /etc/rc0.d/K01NetworkManager /etc/rc1.d/K01NetworkManager /etc/rc2.d/S06NetworkManager /etc/rc3.d/S06NetworkManager /etc/rc4.d/S06NetworkManager /etc/rc5.d/S06NetworkManager /etc/rc6.d/K01NetworkManager Adding system startup for /etc/init.d/NetworkManager ... /etc/rc2.d/S50NetworkManager -> ../init.d/NetworkManager /etc/rc3.d/S50NetworkManager -> ../init.d/NetworkManager /etc/rc4.d/S50NetworkManager -> ../init.d/NetworkManager /etc/rc5.d/S50NetworkManager -> ../init.d/NetworkManager Setting up network-manager-gnome (0.7.1~rc4.1-0ubuntu2) ... Installing new version of config file /etc/xdg/autostart/nm-applet.desktop ... Installing new version of config file /etc/dbus-1/system.d/nm-applet.conf ... Setting up ubuntu-desktop (1.140) ... Setting up gnucash (2.2.6-2ubuntu5) ... Processing triggers for libc6 ... ldconfig deferred processing now taking place