.Net is running somehow in wine but as you can see it's quite unstable http://appdb.winehq.org/objectManager.php?sClass=application&iId=2586 But I was trying to say that any external dependency which isn't installed on targeted OS in default, isn't good at all. So your Starter-app won't work on Win XP in case that user had not previously installed .Net by himself. But who knows what percentage of people have installed .Net and which version. If you will be compiling with .Net v4 then in desktop with .Net v3 the app won't work afaik. And about Mono, there are rumors for some time that mono is dead and from my experience almost no-one uses Mono at Unix-like desktops. Wine is wrapper to C/C++ Win API so if you will be developing this Starter in C/C++ then you will be out of this mess. And for Windows users there won't be any dependecy as well. But it's only my personal opinion.