We recently struggled through figuring out how to make Drupal run on a Windows Server 2008 machine that was running IIS. Every Drupal site that we had dealt with prior to this was hosted on a Linux machine running Apache, MySQL and PHP, and so we needed to figure out what could be done differently to make it work on our in-house server, which was already running a production instance of ArcGIS Server under IIS7.

From the outset, we had two options: