Running the Windows version of IDA Pro on Wine can be a bit troublesome: Every single time I'm reinstalling it, I'm spending way too much time fixing the same quirks, so this time I took notes!

Installing Python

Since IDA Pro 7.0, the bundled python's architecture is x64, and has some troubles during its installation process: when asked to chose where to install it, the next button isn't working.

The solution is to ignore python's installation, complete IDA Pro's one, download the latest release of Python2.7 for x64, and launch it in quiet mode, via msiexec /i python-2.7.13.amd64.msi /q.

You can now use IDA Pro with IDAPython.

Fixing IDA Pro's annoying behaviour with regard to multi-screens

IDA Pro uses Qt (namely 5.X since IDA Pro 6.9), meaning that on Wine it's affected by QTBUG-43439: Broken menu/combo dropdown positioning in multiple monitor setup when running under wine, also tracked via Bug 37709 in Wine.

The easiest way to fix this annoying behaviour is to ~~monkey patch Qt~~ use Wine's explorer, to create a virtual desktop so that IDA Pro won't have to fiddle with our screens, with something like this:

$ wine explorer /desktop=IDA,1920x1080 .wine/drive_c/Program\ Files/IDA\ 7.2/ida.exe