If you've ever gotten errors like this the solution is simple, you need i386 enabled on your 64-bit install because wine depends on some 32-bit x86 libraries: dpkg --add-architecture i386 apt update apt install wine After that it will install just fine. apt install wine Reading package lists... Done Building dependency tree Reading state information... Done........

This is sure simple if you follow the guide but it took a lot of hacking around to make this work on Debian/Ubuntu! Now before you ask why bother running wine and python, the reason is because Python executables are NOT cross-platform. If you run pyinstaller in Linux, that binary will only run on Linux and the same if you do it in Windows. So it is preferable if you have a single environment that you can create Linux and Windows binaries from rather than running 2 separate........

Solution: Aptitude is very smart and fixed the issues it was because of nvidia cuda and opencl and nothing else suggested or hinted this using apt sudo aptitude install wine The following NEW packages will be installed: ocl-icd-libopencl1{ab} ocl-icd-libopencl1:i386{ab} wine wine1.6 wine1.6-amd64{a} wine1.6-i386:i386{a} The following packages will be REMOVED:........

After an upgrade wine wouldn't open anything, not even the pre-installed notepad. There are no wine logs and nothing is mentioned in any standard log file about why. I finally decided to run wine from the shell and see what's going on: wine client error:0: version mismatch 398/402. Your wineserver binary was not upgraded correctly, or you have an older one somewhere in your PATH. Or maybe the wrong wineserver is still running?........