Entourage not syncing 'Sent Items' withExchange 2003 server anymore

D

dimitriw

Version: 2008
Operating System: Mac OS X 10.5 (Leopard)
Processor: Intel
Email Client: Exchange

Hi all,

I have been looking around for a problem, but never found a solution anywhere. So I will post my own experience with the issue hoping some people can benefit from it.

I have Entourage 2008 running. It connects to my SBS 2003 server with Exchange 2003. All worked well until today.

I was preparing an email with a couple of Word documents (.doc) attached. Before I was actually going to send the message I wanted to check that the attachments were correct. Then I clicked the 'Send' button, but it appeared I had forgotten to close Word with an open attachment first.

Entourage complained it couldn't send the message and that I had to shut down Word first. So I did, and clicked the 'Send' button again.

Now Entourage complained about its database (can't remember the exact phrase anymore I'm afraid) and that I should restart Entourage and that I may have to rebuild it (the database).

I restarted Entourage. It recovered the mail I was trying to send, so I ended up with two of them in my Outbox. It automatically sent the first (the original one) and in the meantime I deleted the second so it wouldn't get sent as well. The message that was sent correctly showed up in my 'Sent Items' folder - in Entourage.

But NOT in Exchange (i.e. not in any other client, like Outlook, OWA or my mobile). And after that no other sent mails from Entourage would sync with the server anymore.

Luckily I was already suspicious about that e-mail with the documents attached. First I deleted the missing messages (the one that went wrong and all messages sent after it), so they moved to 'Delete Items'. Then I cleared the 'Sent Items' cache folder. I moved some message from 'Deleted Items' back to 'Sent Items'. Syncing worked without any problem.

Then I moved the 'problematic' message back. It wouldn't sync. Then I moved some more messages back. Those didn't sync with the server anymore either. I removed the 'problematic' message from the 'Sent Items' folder again. The other messages DID sync again. That one message apparently blocked the entire sync process.

In 'Deleted Items' I removed the attached documents from the e-mail. Then I moved it back to 'Sent Items'. The message got synced to the server, and other messages get synced as well.

So, it appears the problem was solved. It looks like one (or all) of the attachments was keeping Entourage from syncing the entire folder.
 
C

chado

I went through the same painful process only using Exchange 2007. Any luck finding a solution?
 

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