Sent messages stay in Outbox in Outlook, but messages go out. In Webmail messages can be sent. OL 2010/Exchange 2007
We have a very strange issue, which affects only one user: The user can send mails from Outlook 2010. Mails are delivered. However in Outlook they still show up in the Outbox as unsent. If the user logs on to OWA, the mails can still be seen in the Outbox, but are sent (and moved to the "sent items" correctly, when clicked on "send" in the outbox again. We've deleted the Outlook Profile and re-created it from scratch. We've even deleted his whole Windows Profile. The problem still exists. Outlook is Version 2010 (no Service Packs yet) Exchange Server is Version 2007, SP1, Rollup Pack 9 The user is not in offline mode and the caching mode has been disabled. We're especially puzzled, since it affects only one user - everybody else can work just fine.
September 7th, 2010 3:35pm

Does the problem follow the user to another machine? If not then wipe the machine. I find only three things work with Outlook issues - new Outlook profile, new Windows profile, wipe the machine. Simon.Simon Butler, Exchange MVP. http://blog.sembee.co.uk , http://exbpa.com/
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September 7th, 2010 3:45pm

Maybe move his mailbox to another mailbox store and see if that fixes anything.
September 8th, 2010 3:03am

"Wipe the machine" is not an option - it's a shared Citrix environment, everybody else working on this environment doesn't have the problem -just one user. We've deleted the users profile completely and re-created it. The problem still exists
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September 8th, 2010 10:40am

As an update: We've installed SP3 on all Exchange servers tonight just to be on the safe side. However this also didn't solve the problem. The best practice analyzer doesn't find any trouble.
September 8th, 2010 10:42am

We will try that.
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September 8th, 2010 10:45am

And the issue is same on all your citrix servers?Jonas Andersson MCTS: Microsoft Exchange Server 2007/2010 | MCITP: EMA 2007/2010 | MCSE/MCSA Blog: http://www.testlabs.se/blog
September 8th, 2010 12:08pm

"Wipe the machine" is not an option - it's a shared Citrix environment, everybody else working on this environment doesn't have the problem -just one user. We've deleted the users profile completely and re-created it. The problem still exists It would have helped if you mentioned the very important point that it was a Citrix based environment. Failing to mention an important point like that doesn't help anyone trying to assist you. Simon.Simon Butler, Exchange MVP. http://blog.sembee.co.uk , http://exbpa.com/
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September 8th, 2010 12:13pm

And the issue is same on all your citrix servers? Jonas Andersson MCTS: Microsoft Exchange Server 2007/2010 | MCITP: EMA 2007/2010 | MCSE/MCSA Blog: http://www.testlabs.se/blog Also, when did the issue appear? You need to think if there are any logic between this error and maybe a patch/update installation etc.... every change is important in this troubleshooting Jonas Andersson MCTS: Microsoft Exchange Server 2007/2010 | MCITP: EMA 2007/2010 | MCSE/MCSA Blog: http://www.testlabs.se/blog
September 8th, 2010 12:16pm

The fact that Outlook is running in a Citrix environment is only confusing people, but for completeness I can shortly describe the setup: The Citrix environment is streamed from a "read-only" Image so there is no way that users can change anything in the Outlook binary path and we can therefore positively exclude the option, that any Outlook binaries are corrupted, since all users are using the same. Users are using a different server in the Citrix farm every time they log in, but it doesn't make a difference, since they're all streamed from the same image. All Citrix servers are rebooted every night, so they're behaving like a completely fresh setup server (no temp files or the like). User profiles are mounted from a DFS share. So this leave only two possible sources for the problem: a) the Exchange Server b) the User profile Since we've already completely deleted the user's profile and started with a new profile, we're quite sure, that this is not the source of the problem. All tools we tried to run on the server to check the database (like the BPA) didn't show anything. Also the Logs are clean, except an Event ID 9639 (Source MSExchangeIS Mailbox Store), but we're not sure if this is related. The text of the Event implies, that the problem will solve itself ("A link to a message has been removed from spooler queue because the message was not found in the database. No further actions are required.") We tried to move the user's mailbox to a different mailbox store in the meantime. Didn't help either.
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September 8th, 2010 12:32pm

Hi, Since the symptom only occurs on certain user mailbox and it does not occur via OWA, we can eliminate the Exchange server cause. If Exchange server has some problem, the symptom will occur on each mailbox in the same environment. This issue can occur by incompatible third party programs or incorrect Office Outlook 2010 settings. If the issue is caused by Office 2010 setting, you may need create a new thread in Office 2010 forum. At this stage, I suggest you temporarily turn off firewall and antivirus program on the problematic user’s machine to check the result. If the issue persists, please try the following steps. Perform a clean boot to disable third party application. Note: A Clean Boot will allow us to isolate any device drivers or programs that are loading at startup that may be causing a conflict with other device drivers or programs that are installed in your computer. a) Start the machine on the problematic machine and type MSCONFIG.EXE in Run Command in Start menu. b) In the Services tab, click "Hide All Microsoft Services" and click "Disable All". c) In the Startup tab, click "Disable All". Click OK. (This will temporarily prevent third-party programs from running automatically during start-up.) d) Restart the computer. Does the problem still persist? If the problem does not occur, it indicates that the problem is related to one application or service we have disabled. You can use the MSCONFIG tool again to re-enable the disabled item one by one to find out the culprit. If the sent email still exists in Outbox, please uninstall Office 2010 and reinstall it or install Office 2007 for a test. Meanwhile, it’s highly recommended to create an Office Outlook thread. Hope this helps. Novak Wu-MSFT
September 10th, 2010 8:14am

At this stage, I suggest you temporarily turn off firewall and antivirus program on the problematic user’s machine to check the result. If the issue persists, please try the following steps. Perform a clean boot to disable third party application. Note: A Clean Boot will allow us to isolate any device drivers or programs that are loading at startup that may be causing a conflict with other device drivers or programs that are installed in your computer. You're not aware, that this is a shared Citrix environment...
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September 10th, 2010 12:18pm

Anyway you can have this user logon to a different machine other than the citrix server and test if the problem follows him?
September 10th, 2010 2:08pm

As Andy was mentioned, it’s highly recommended to logon the mailbox with another machine to check the result. Novak Wu-MSFT
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September 13th, 2010 5:28am

Solved. It was a profile issue. The default-user, from which the new profile was created was corrupt.
September 21st, 2010 10:14am

in my case, if the user's default inbox folder is not the exchange mailbox, will have this happen
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September 21st, 2010 12:30pm

Doubt you are still following this thread i have the same exact problem what in he default-user profile was currupt. i am having the same "exact" issue.
April 27th, 2012 3:55pm

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