As Aaron suggested I also think you installed your printer with the usb backend 
instead of the hp backend. hp-toolbox GUI needs the hp backend to work!
Run the following command to find out which backend you use:
$ lpstat -v
The recommend way for installing a printer in Dapper using gnome-cups-manager 
is described here: 
https://help.ubuntu.com/community/HpPrinterInstallationAndMaintenanceDapper

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hplip cannot find DeskJet 5440 printer, despite CUPS's claims to the contrary
https://launchpad.net/bugs/49107

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