It looks like 'winetricks dotnet20' and current wine is good enough that .net support isn't quite the limiting factor anymore! See http://bugs.winehq.org/show_bug.cgi?id=8499 http://bugs.winehq.org/show_bug.cgi?id=12457 http://bugs.winehq.org/show_bug.cgi?id=12458 for three sizeable apps that actually put up their GUIs, at least briefly. MySQL Workbench actually runs well enough to explore the GUI.