Problem: E-mails that reside in the Outbox are not synchronized with the Exchange server when in Cached Exchange Mode.
More explanation on the problem:
If an e-mail is sent in non-cached mode (online mode) in Outlook 2003 with the option to deliver the message at a future date the following will happen:
1. The e-mail will be sent to the exchange server and reside in the outbox until it is to be delivered. Once the time is reached the e-mail will be sent even if the client is not open. (It's working when outlook client is close)
2. The e-mail will not appear in the outbox if Outlook is switched to cached mode.
If the e-mail is sent in cached mode with Outlook 2003 and the option set to deliver the message at a future date to following will happen.
1. The e-mail resides on the clients .ost file until it gets delivered
2. The e-mail will not be sent unless the Outlook client is opened in cached mode.
3. The e-mail will not appear in the outbox if Outlook is switched to online mode.
4. The e-mail will not appear in the outbox in the OWA client.
I found some information on synchronisation task for outlook 2003 who let appear the outbox is not synchronize
When Outlook 2003 synchronizes with an Exchange Server 2003 computer, Outlook 2003 uses an intelligent learning algorithm that is transparent to you. This algorithm puts higher synchronization priority on the folders that you use most frequently. This behavior gives you an optimal user experience. Outlook 2003 synchronizes folders in the following order (until you have been using Outlook long enough to train a synchronization priority):
1. Utility folders (common views, views, and security settings)
6. All other folders (defined by the user)
7. Sent Items
8. Deleted Items
9. Public Folder Favorites (added by the user)
Any idea how to synchronize the outbox folder contain in the OST file to synchronize with the server outbox folder, to allw users to send mail later without disable cached-mode
P-S.: My offline synchronization option include to synchronize the outbox folder