Problems with Cached Exchange mode losing emails in the sentmail folder

bazianm used Ask the Experts™
I am working with a hosted Exchange 2007 server and Outlook 2003. For some time when operating in chached exchange mode there has been  an issue with emails that were sent not appearing in the sent mail folder.   This problem has persisted through migration to a brand new workstation, and through the  migration from one host on exchange 2003 to another host using exchange 2007.   In the prossess of diagnosing this error we took the user off of chached exchange mode and the problem no longer occurred.
In speaking to the tech support at out exchange host it has been suggested that the issue is most likely on the local system, on the workstations in question.
The systems in question are using Windows XP Professional (all up to date), Trend Micro Office Scan as the anti virus protection, and PGP Universal Satalite for encryption.
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My first suspicion was something to do with Junk Email filters because they are supposedly only applied on the client-side (Outlook 2003 for example) when the program is running in Cached Exchange mode.  So I would like at the user's approved and blocked senders lists and also encourage them to check e-mail using Outlook Web Access (OWA) if it is available within the I.T. enviorment in question.

I wondered whether there might be a corrupted "offline" (.OST) file in Outlook that could be contributing to this issue, but the most relevant document I could locate using [Junk Mail corrupted] (4 hits), [online offline corrupted] (6 hits):

However, the behavior in this case seems to only be an intermittent lag between the Inbox or Sent folder being synchronized when online versus offline.  I revised the Microsoft Knowledge Base search criteria I was using to [online offline message synchronization] and found: (15 hits)
"Synchronizing e-mail messages with an OST does not update the Sent Items folder when you use Outlook 2003 or Outlook 2002 to work offline"

I believe the file this is referring to is "outlook.ost" and within Win XP it is typically located in:
C:\Documents and Settings\%username%\Local Settings\Application Data\Microsoft\Outlook

If the above document does not help, I recommend noting the size and date stamp of the "outlook.ost" file, closing Outlook, renaimg it "outlook.OLD", removing the user's Profile from the "Mail" applet in the Win Xp Control Panel of their computer and re-adding (recreating it) a new profile.  This will probably result in a new, much smaller "outlook.ost" file being created.

Good luck!
(answer from Not-a-MCSE/MVP)

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