When trying to update the Offline Address book in Outlook 2010 the Send/Receive Progress window opens, shows progress to about 20% then just sits there forever. It never completes. This is after finding posts regarding turning off SSL on OAB. With SSL enabled it fails right away. This issue started because the owner of the company has a MacBook Pro and the Global Address List will not populate on his laptop. Through investigations I found that the OAB was not updating correctly. I can open the Address Book and see every user but when I try to update it, it fails.