I have a rather strange problem. I manage a network of about 35 Mac, and we all recently switched from Mail.app to Outlook 2011 (Please don't debate this, I've already had this conversation ad nauseum) We are using network home directories (NHD) server from a Windows file server over the SMB protocol.
The problem I'm having is Spotlight does not function inside of Outlook. But ONLY inside of Outlook. The global Spotlight can find all email and contacts with Outlook, but the embedded Spotlight cannot. As a test, I took one of my users and switched them from a network home directory to a portable home directory (PHD) (this means the home folder was copied to the local hard drive). This resulted in a working Spotlight within Outlook, as soon as I switched the user back to an NHD, however, it stopped working.
I have already tried erasing the Spotlight index and killing the process to force re-indexing. I have exhausted all Spotlight troubleshooting, and since the global is working that is obviously not the issue. I believe it has something to do with the Spotlight plugin Microsoft wrote that is located in /Library/Spotlight.