Microsoft Support has an article on offline address books which may be helpful in this situation..appears you have cached mode turned on (it is by default on the clients) The Outlook Social connector (Free with Outlook 2010/2013) will do what you are asking for.
It scans your contacts and makes updates based on information in the GAL.
Remember, if you are looking at the Global Address List in Outlook then you are NOT looking at the Servers Global Address List*.
I know this is old, but it's the first search result in Google and doesn't have a proper answer. Fourth, you will receive a dialogue box for any matching / existing contacts. Local contacts always trump Active Directory contacts, and do not update when changes happen in AD (by design). For now, I've written an Outlook plugin that performs these steps automatically for the company I work for. Not the nicest way as in - why isn't this default?!It addresses business continuity, emergency preparedness, DR, productivity, and employee reachability.Closely integrated with Microsoft Exchange Server and Outlook, the blog will be of interest to IT administrators, architects and managers with hundreds or thousands of smartphones.Outlook clients on other machines do have a complete GAL including all newly-created users. Note for Mac Users: Mac versions of Outlook do not connect to the Exchange server in the same way as PC versions.