I noticed that even simple things on my stupid Windows 8 that I got stuck with thanks to the aggressive addiction policies of Newegg/ASUS/Microsoft wouldn’t even properly search my Outlook contacts. Forget the cutesy interface I need my computer to allow me to do business efficiently. Don’t get me going on charms and having to move the mouse and click repeatedly to do what a simple start menu did. (I have installed a 3rd party start menu)
The fix was simple but just one more tedious step in what shouldn’t be broken to begin with.
The fix in my case consisted of opening Outlook, going to File>Options>Search>Indexing Options and removing Outlook from the index.
Then close Outlook and make sure it completely closes by waiting or checking with taskmanager.
Open Outlook and re-add Outlook to the Index.