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Hidden Messages in Outbox

I have a couple users that have problems with the Outbox folder in their mailbox. We are running Exchange 2010 with Outlook 2007 clients. The problem we are seeing from a couple users is that messages are randomly piling up in the Outbox, but they are not visible. If I attach their mailbox to my profile I can see messages in the Outbox and can clear them out. The crazy thing about it is that the users say that the messages are being received by the destination even though the messages never make it to the Sent Items folder. It doesn't happen to all of their messages, only some of them. Also, there is nothing unique about the messages such as internal, external, small, large, etc. It is completely random. We have tried deleting the profile on the local machine without luck. Anyone have an idea?
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Chris Bottomley
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Tools | Options | Preferences tab | Email Options | Advanced Email Options:

In folders other than Inbox, save replies with original messages" is it checked and uncheck if so

If I can recall, there is a hotfix to deal with this issue. You must apply the hotfix the in Outlook box.

Let me see if I can find it.
I think I found it. See if this procedure fix your problem:
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chris - that box is unchecked.

rmrustice - I tried running the hotfix, but it said "The expected version of the product was not found on the system". I ran it on mine as well and get the same error. We must be patched beyond that hotfix.
I strongly suggest before trying t make any changes to the registry you check out the relatively simple post I made at the start.

Hey ho.

What happens if they search for the 'missing' emails ... can they find them anywhere?

You can create the registry value manually. This case was very common over here during beginning of the coexistence between Outlook 2007 and Exchange 2010. We openned a case in Microsoft and they instructed us to create the registry key.

Follow those steps and see if it works:

   1. Exit Outlook 2007.
   2. Start Registry Editor.
          * In Windows Vista, click Start, type regedit in the Start Search box, and then press ENTER.
            If you are prompted for an administrator password or for confirmation, type the password or click Continue.
          * In Windows XP, click Start, click Run, type regedit, and then click OK.
   3. Locate and then right-click the following registry subkey:
      HKEY_CURRENT_USER\Software\Microsoft\Office\12.0\Outlook\Cached Mode
   4. On the Edit menu, point to New, and then click DWORD Value.
   5. Type SendOne, and then press ENTER.
   6. Right-click SendOne, and then click Modify.
   7. In the Value data box, type 0, and then click OK.
   8. On the File menu, click Exit to exit Registry Editor.
If it works, you can create a Group Policy to distribute the configuration among your desktops.
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Found the answer eventually through my own troubleshooting and research.
For future reference, you are using a workaround, but has not solved the case. The problem you have is exactly like the KB I provided.