If a user's Outlook profile is not syncing:
Make sure you have completed all normal troubleshooting steps first (restart Outlook, restart PC, have user log in if you see "Need Password" on bottom right of Outlook). If none of the normal fixes appear to be working, and everything else besides Outlook is working on the computer, do the following--
Go to Control Panel > Mail > Show Profiles > Add
You will be prompted to enter a name for the new profile and then the user's username, password, and security questions. Once created, make sure to select the new profile created and click 'Apply".
Talk to the user after several hours have passed and if everything is fixed, delete the original profile and only leave the one that you created.