OK, I nuked everything and started again from scratch. $ sudo apt-get install wine1.5 Then used Winetricks to install Mono-2.8.2 and vcrun2010. (figured newer is better) Installed Quickbooks 2012 from CD (via the confusingly titled WINE Uninstall Software) Everything crashed midway through the install - both the WINE installer and the QB installer. Am I having fun yet? :)