Outlook Autocomplete is empty
Problem: Outlook does not suggest email addresses when typing in the To field of an email message. Outlook builds the suggestion list throughout the day, but 'forgets' the autocomplete list whenever Outlook is closed.
Solution:
Step 1. Empty the autocomplete list to remove the corrupted list that is causing the problem.
In Outlook, go to File --> Options. In the Mail section scroll down to the Send Messages section and click the button to "Empty Auto-Complete List".
Step 2. Rebuild the autocomplete list by almost sending a message to all of your contacts.
Open a new message.
On the Options tab, click Delay Delivery.
Check "Do not deliver before" and pick a date far in the future. (This will prevent the message from being sent immediately since we do not actually want to send a message to all of your contacts!)
Click the To button.
In the address book, for each desired contact list, select all the contacts and click To. (To select all, click the first contact in the list, scroll to the bottom, then while holding the shift key, click the last contact in the list.) The common contact folders to include are Contacts, Suggested Contacts, and Environmental Protection.
Once all the desired addresses are in the To field of the delayed message, click send. The message is not sent now, but moves to your Outbox folder.
Go to the Outbox folder and delete the email message sent in the previous step.
Addresses should now appear in the autocomplete suggestion list as you type in the To field of a new email message.