We're currently running continuous automated functional tests against the CI builds of our software. This is done on a variety of Windows based machines (around 10-15 boxes or VMs), to identify version-specific problems.
The pain starts when we want to upgrade let's say the flash plugin deployed on all those machines, we're currently doing it all manually since I was told a automatic solution is usually feasible when you want to deploy it on 20+ machines which are ideally as identical as possible.
Also we need certain programs to have a specific configuration (a simple example would be the default webpage in IE).
Are you aware of any tool that supports managing applications and setting in that kind of heterogeneous environment?