Recently while troubleshooting some "Cannot work Offline" cases i realized sometimes the Go Offline process doesn't work as expected and leave the MSCRM_MSDE local database empty even if, during Go Offline, everything goes fine and CRM UI shows how many records get downloaded successfully, etc.....
The issue is, if you don't download the "System Records" successfully on the client while going offline, your offline client will not work at all because we need informations such as the one in OrganizationUIBase, SystemUserBase, etc... will working offline.
The reason why Go Offline process is not working and is not showing any error is not clearly identified, however if you follow the following very good kb entirely you should get rid of it anyways.
KB916165 Error message when you try to go offline in the Microsoft Dynamics CRM laptop client for Outlook: "Failed move data for entity <EntityName> during action saInsert, countRows=<CountNumber>. Contact your system administrator for assistance"
METHOD 4 is crucial and solves this problem, but 90% of our customer are reluctant to do that, there is no reason to be afraid, the repair do not break any customization in place and takes around 10 minutes plus a reboot to complete.
The only thing you need to take care of before a repair is having a backup of your report and of your CRM Hotfixes because the repair will reset these.
Thus... I decided to monitor if we have some data in MSDE when generating the client report, here is what is shows when you have a laptop client offline.
+ MSCRM_MSDE Database Content Information
|-AccountBase Table Row Count: 0
|-ContactBase Table Row Count: 0
|-SystemUserBase Table Row Count: 8
|-UserSettingsBase Table Row Count: 6
|-OrganizationUIBase Table Row Count: 157
Here if you have nothing inside SystemUserBase table and go offline seemed to have worked fine, you have a general problem and need to repair CRM installation.
Hope this helps