Issues with OABs not updating

Question

We are running 2 exchange 2010 servers (1 for client access, 1 for mailboxes) Recently we set up GALsync to pull a bunch of users over from a partner company and they now show up in our AD as contacts. 
The issue is when running outlook in cached mode, they don't show up.
When not in cached mode they do show up. 
I've forced updates on the OAB in exchange and downloaded new GAL from outlook however neither has worked.
When I go into Exchange management Console, and go to Organization Configuration-Mailbox-Offline Address Book it says that the OAB has been updated with todays date, however when I go to the local files on the server they haven't been updated since the 4th
of Jan. 
*Note-GALsync was set up and contacts were brought over on the 15th of Jan. 

Answer 1

This is just a matter of troubleshooting OABGEN (Offline Address Book Generation) issues.  You might want to start with the following:
Confirm that the OAB Generation server is up-to-date with Exchange 2010 SP3 RU4
OAB Generation server is properly running on the server (http://technet.microsoft.com/en-us/library/bb125184(v=exchg.141).aspx)...maybe even move it to the other server
Confirm that the OABGen distribution is working properly (http://technet.microsoft.com/en-us/library/bb123710(v=exchg.141).aspx)
Make sure that the users are not trying to use an old or invalid Offline Address Book.  Most environment just use 1 OAB and set it on all Mailbox Databases (http://technet.microsoft.com/en-us/library/aa996345(v=exchg.141).aspx)
Open Exchange Management Shell and run the following commands.  If you see any warnings, fix the object!
(Get-Mailbox -resultsize unlimited).count
(Get-DistributionGroup -resultsize unlimited).count
(Get-MailContact -resultsize unlimited).count
Turn up diagnostic logging for the Offline Address Book generation (http://technet.microsoft.com/en-us/library/dd335139(v=exchg.141).aspx) and then update the OAB (http://technet.microsoft.com/en-us/library/aa997684(v=exchg.141).aspx)
Review the event logs on the generation server and look for any reason why the OAB would not generate
This is just the start...but usually points you in the right direction for what the issue is.
Good luck