You'll want to make sure you have a recent gcc; see http://wiki.winehq.org/Wine64 As a general rule, taking programs shipped with Windows and trying to run them in Wine is not a good test of anything. They are not like normal programs. Maybe notepad and calc used to be simple, but I'm not so sure that's the case in Windows 7. Your error is caused by an unimplemented function, which is nothing to do with the architecture. That particular error tends to show up in .NET programs that use WIC. I'm pretty sure that if you compile a 64-bit PE notepad or calc from Wine's codebase, those programs will work. I think the fact that 7zip and Putty work is an indication that the simplest of 64-bit programs do run, and the basic architecture is working. I would guess that if you have a program that is compiled for 32-bit and 64-bit from a shared codebase, it's not using any MS components when it runs in Wine, its installer works, and it's not using typelibs, the architecture probably won't be very important.