Incoming Mail Received by Server but Delayed to Inbox

I'm getting reports from multiple users that emails that are being sent to them are not showing up in their Outlook client for hours or even days later.

When I looked at one specific message, I could see that it was received by our Barracuda Spam Firewall on May 17th at 20:12.  The message header also shows May 17th around the same time.

Next, I went to the Exchange toolbox and ran the message tracking utility.  It also shows the EventID's for RECEIVE, EXPAND, TRANSFER and DELIVER were all on May 17th around the same time, shortly after the Barracuda received the message from our ISP.

The header and message tracking tells me that we're not having an email receipt problem, and mail is flowing properly into our system.  But, the user said it just showed up in their Outlook 2007 client the morning of May 19th, almost 2 days later!  This user was in the office on May 18th and using Outlook all day, but swears the message was not in her inbox until the 19th.  Other users are reporting similar scenarios.

This is only happening on a few messages, not all messages to these users.  And it's not just one user having this issue, so I don't think it's a problem with a specific computer or client install.  As a result, I did not create new profiles for these users or reinstall Outlook.

Outlook 2007 clients are all running in cached mode (bottom right status bar says "Connected to Microsoft Exchange").

Any ideas?
Chad_J_LemmerAsked:
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Manpreet SIngh KhatraConnect With a Mentor Solutions Architect, Project LeadCommented:
Humm if there was a one time issue i think that could be due to some activity that was happeing on the server (for Example that the Trend micro has the task of first scaning and then forwarding the mails to users, if it is updating itself and then takes time to re-start its task from the background to start scanning and then delivering the mails, so in this kind of a scenario it would take time).
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Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
Check with the AV on the server as there is nothing that would deliver some emails today and some 2 days later.
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Chad_J_LemmerAuthor Commented:
There is no AV software running on the server.
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Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
From the message header can you also verify where it took more time to get delivered.
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Chad_J_LemmerAuthor Commented:
All dates and times in the header show May 17th, which is when our server received the message.

It appears to be a problem with the Outlook client getting the message.  What's strange is that I've had multiple users report the problem, so it's not just happening to one user.
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Manpreet SIngh KhatraSolutions Architect, Project LeadCommented:
yeah was there anyupdates to AV's on the clients or anything else that might have caused the issue. Also we dont know if the mails were delivered to the server and were stuck on the server for some reason inthe queues and restarting the services that resolved. May be something happened on the server end.
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Chad_J_LemmerAuthor Commented:
Possible, I guess.  Trend is auto-updating, and we run WSUS to keep our clients patched.
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Chad_J_LemmerAuthor Commented:
Trend isn't running on our Exchange server, only the clients.  And none of our servers are using WSUS to receive updates.  

It appears to be a one-time thing, since I haven't received any other reports from users.  Very strange indeed.  I'm guessing we'll never know for sure.

Thanks for you suggestions.
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