So here's the problem we had. User has offline files on his H: drive (Home drive), so that he can access them while traveling. If the user boots up his laptop and logs in, and THEN connects via VPN or work wireless, he can't access his H: drive at all. He can still see his offline files, but they stay offline and all other files are not accessible. Also if he disconnects his laptop goes to a meeting then comes back and docks he is unable to get access to his H: drive until he reboots. The only way to get the files back online and have access to the rest of his H: drive is to log-in WHILE having a live network connection to the office. After a bit of research I found the answer via mcseRob (See link below).
The short version is that the user needs read access to the folder that the share is pointed to, not just a sub-folder that his H: drive is pointing to. Windows checks to see if the files are back online by checking the share itself! So when it checks and doesn't have read access to the share it thinks the files are still offline. So a quick fix is to give all users read access to the share itself.
For our situation we ONLY give read access to the share and not all the sub folders below. This does allow everyone to see the sub-folder names, which may reveal user names. But follow the link below for some possible fixes to that problem.
Source: http://social.technet.microsoft.com/Forums/windows/en-US/dccf79c0-af86-43e9-99c6-20a21c22c38c/offline-files-the-work-offlinework-online-button-disappears-from-windows-explorer-after-the?forum=w7itpronetworking
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