Let me first apologize if this is in the wrong forum, it may fit in the Outlook connector as well, but I chose here.
Two users are experiencing the same issue. The issue is that when you try to run through enterprise activation the address book fails. Let me go into more detail on each case.
Case 1: User is running a World edition blackberry and when syncing the address book simply said "Syncing failed" and the sync was completed without the full import of the address book.
Case 2: User is running a Tour. "Address Book Database failed to sync" was the error thrown. If you don't disable wireless address book sync from the "Address Book>Options" menu then you can get some serious issues on the Tour - 1000+ contacts with the same name, inability to alter settings in address book options, can't search your address book, requires handheld wipe.
After digging into these two cases I realized that both users, when I exported their contacts, had extra columns that were populated. This came from exporting their contacts from Outlook and using it with Palm and moving it through different contact management solutions. Also "0/0/00" or "00-00-000" was populated in many of their contacts birthdays. So I have set out to clean their address book exports and re-import them, whether that will fix the problem or not is to-be-determined.
I have a decent walkthrough to clean one of these lists with minimal effort and without loosing much data that I will post after I confirm that this issue is resolved by cleaning the address book. I also have the mysql commands to remove a specific user's address book.
So I created a test address book and populated one contact with every option available to zimbra. When I exported this list I was left with 46 columns (I will list these later, if I manage to fix the problem). I then created my own custom column and populated it for that user. I did an import and export of this list, all successful, and the unrecognized column was preserved by zimbra. I was even able to search for the hidden field using zimbra by using "#fieldname:stringsearch"