I am experiencing a problem with a user where it seems that previously synced email messages and contacts that were recently restored from a backup are not syncing to the server from the user's Outlook client. Here are the specs first:

Windows 7 OS (32Bit)
Office 2010
Zimbra ZCO Client: 6.0.6058.8
Zimbra Server: 6.0.3_GA_1915.UBUNTU8
***I'd like to include the ZCO files, but I am not sure where is safest to place them.***

Background:
User moved to this machine from Office 2003/Windows XP. Originally the installers installed the ZCO client and synced down the mailbox and calendar, contacts and tasks to this machine. Everything seemed fine. Then, it looks like the installer and the user decided to delete all of the mail folders, contacts, calendar, etc. from the Outlook client. They then re-imported all of the mail, contacts, calendar, etc. back into the Outlook Client. Basically it looks like they decided to restore the folders and messages from a backup directly into the Outlook Client.

What seems to be happening is that new messages are syncing between the server and outlook and vice versa.
The Calendar is syncing between the server and Outlook and vice versa.
All old email including those inside folders are not syncing back up to the server.

It almost seems like the server thinks that these messages are already sync'd or something. So it will not sync them.

So, in summary:
New messages sync properly between the server and Outlook and vice versa.
The Calendar actually is syncing properly.
The folder hierarchy appears to have synced between the server and Outlook and vice versa.
Old email will not sync from Outlook to the server.

I have 2 ZCO files that I can provide.

The user has 800Mb of data to sync back up to the server. It has been about 8 hours since the user and the installer did their changes. Maybe it just takes time or something?

Any thoughts on what I should do to fix this?

***I'd like to include the ZCO files, but I am not sure where is safest to place them.***