I recently set up Outlook on a different machine at home. Everything went great, I imported my calendar, contacts.
Then the PC locked up and I hard to do a hard re-boot. After that (I think the sequence of events is correct), now outlook won't do the intelligence when I start to type in someone's e-mail address, not even for people in my contacts list.
I have a check-mark in "Suggest Names in To, Cc, and Bcc fields", as well as a checkmark in "Automatic name checking".