Dear All,
I thought I would share a fix for a related issue here just in case someone has a similar issue to mine.
I recently ran into the same "Outlook wont search" issue and tried the re-indexing tricks mentioned to no avail.
Initialy some emails would be searched but not all of them them.
After my first attempt to re-index only my contacts became visible during outlook searches but not the mail messages.
Eventually I figured out what was happening.
I use several VM's on my Mac and somehow my Outlook file associations on my Outlook message files changed for some weird reason to an application on one of the VM.
This obviously did not affect Outlook itself or older indexed items but no new emails would be indexed and thus come up in the search. After the first re-index attempt none of the older indexed items would search either.
Once I set the program association for the message files back to Outlook all of my messages became searchable again.
Hope this helps someone!
Cheers
PS:
Your messages are stored here for Office 2011:
\Documents\Microsoft User Data\Office 2011 Identities\Main Identity\Data Records\Messages\