Over the past two months I’ve had a look at two different sites running on WordPress that were running on Windows Servers. In both cases, the sites were having issues, and in both cases, they could not get simple functionality they wanted to work on the servers and ended up moving to Linux hosting.
Does WordPress run on Windows? Yes, most definitely. I can attest that I’ve run serveral installations going back to the old 1.x days. The problem is this: even though you can get a core installation of WP running, there are alot of plugins that simply will not work on a Windows server.
The big thing that comes to mind is this: why even bother messing with a Windows Server? The WordPress package is built to run on Linux, and even if you don’t want to setup your own server, you can certainly get a competently hosted account in the $3.99 a month range. There we know the plugins we want will run.
My feeling is this: yes, it runs on Windows, but I have yet to see a situation where I didn’t have some strange problem that took time to diagnose which was related the use of that platform. If you like chasing phantoms around a server, then maybe this is a project for you. I personally have better things to do.
So in the future, my general rule is this: no Windows servers for WordPress. If you want my help, it’s going to move to Linux first.