Email stuck in outbox if sending mail from a shared mailbox

Hi,
Some user mailboxes have recently been migrated from Exchange 2003 to Exchange 2010. Shared mailboxes are located on Exchange 2003 still for the time being.
Some users have send as permissions to a shared mailbox. In Outlook the users are logged in as themselves and using the from field send an email from the shared mailbox.
The email is sent and delivered to its recipient.
The email is however stuck in the outbox of the users mailbox.
I have tried recreating the Outlook profile, windows profile and using a different PC, but the mails still get stuck in the outbox.
If outlook is changed to use cached mode then the emails are delivered. We don't want customers using cached mode though.
If I migrate the shared mailbox to Exchange 2003 I still have the problem.
If I migrate the users mailbox to Exchange 2003 then the problem goes away.
On the Laptop I am testing this on it is Windows 7, Office 2003. I have also tested on another computer with Windows 7 and Outlook 2007. Outlook safe mode doesn;t help or turning off windows firewall.
Has anyone experienced a similar issue?
Regards
Matt

Hi,
Based on your description, I found this kb below:
http://support.microsoft.com/kb/2703723/en-us
This problem occurs when all the following conditions are true:
Your Outlook profile is configured in online mode (not cached Exchange mode).
You have the DelegateSentItemsStyle registry value set to 1.
There is no resolution to this problem other than to either switch your profile to cached Exchange mode or set the DelegateSentItemsStyle registry value to zero (0).
Note If you set DelegateSentItemsStyle=0 in the registry, email messages that you send from a shared mailbox will be copied to
your Sent Items folder and not the Sent Items folder of the shared mailbox.
Important
This section, method, or task contains steps that tell you how to modify the registry. However, serious problems might occur if you modify the registry incorrectly. Therefore, make sure that you follow these steps carefully. For added protection, back up the
registry before you modify it. Then, you can restore the registry if a problem occurs. For more information about how to back up and restore the registry,
http://windows.microsoft.com/en-US/windows7/Back-up-the-registry
1.Exit Outlook.
2.Start Registry Editor.
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
Allow.
3.Locate and then select the following registry key:
HKEY_CURRENT_USER\Software\Microsoft\Office\x.0\Outlook\Preferences
（Note In this key path, the placeholder x.0represents 15.0 for Outlook 2013, 14.0 for Outlook 2010, 12.0 for Outlook 2007, and
11.0 for Outlook 2003.）
4.Select the DelegateSentItemsStyle value.
5.On the Edit menu, click Modify.
6.Type 0, and then click OK.
7.Exit Registry Editor.
8.Start Outlook.
Regards,
Melon Chen
TechNet Community Support
It's recommended to download and install
Configuration Analyzer Tool (OffCAT), which is developed by Microsoft Support teams. Once the tool is installed, you can run it at any time to scan for hundreds of known issues in Office
programs.

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I have done the troubleshooting but I didn't find any problem at server side. I will send you mail also with all EXBPA report and as well DC, HC and Mailbox servers' Application Log and System Log.
Below are the questions's answers which was asked by you:
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I am not able to open the MS Outlook. Please check all details in this thread : http://social.technet.microsoft.com/Forums/en-US/exchange2010/thread/c491c5c7-7d6f-48ff-97fa-6bf83d94e53c
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I have run the EXBPA and didn't see any critical Problem. I have took the screen shot and report. Please have a look in below screen shot link:
a. http://cid-31ba948d0da4d57e.skydrive.live.com/self.aspx/.Public/EXBPA.docx                                                                            - Final Report
b. http://cid-31ba948d0da4d57e.skydrive.live.com/self.aspx/.Public/ExBPA.BaseLine.200906270226501077.data.xml                        - Baseline Health Check
c. http://cid-31ba948d0da4d57e.skydrive.live.com/self.aspx/.Public/ExBPA.Connectivity%20Test.200906270223318201.data.xml      - Connectivity Check
d. http://cid-31ba948d0da4d57e.skydrive.live.com/self.aspx/.Public/ExBPA.Health%20Check.200906270125477730.data.xml            - Health Check with 2 Hr. Baseline option
e. http://cid-31ba948d0da4d57e.skydrive.live.com/self.aspx/.Public/ExBPA.Permission%20Check.200906270224343377.data.xml      - Permission Report
The error which I received in EXBPA, that allready ignored by you and told that it is bug in EXBPA. Have a look here: http://social.technet.microsoft.com/Forums/en-US/exchange2010/thread/d4bb03bb-db84-4a8b-83ba-19937d7dcacf
3.     Please check application log, whether any error event logged there. They could come from ADAccess related error or etc.
I didn't see any ADAccess event on the server. For this I have left my lab PC open and I will check again.
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I am facing this problem with all users (7 users). Anyway I moved one user from one server Mailbox Database (2mbx2010) to Other Server Mailbox Database (mbx2010). After that
a) Rebooted the Workstation
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c) Delete the Old MS Outlook Profile
d) Create New profile for same user without any problem.
e) Tried to login in MS Outlook and got the same error. : http://social.technet.microsoft.com/Forums/en-US/exchange2010/thread/c491c5c7-7d6f-48ff-97fa-6bf83d94e53c
f) Open the OWA successfully for Same user.
g) Tried to send mail but again mail went to Drafts Folder.
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mailbox via OWA to test the issue.
I tried you suggested option, but sorry it also couldn't help.
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   b) http://cid-31ba948d0da4d57e.skydrive.live.com/self.aspx/.Public/WDC2010%7C_SYSTEMEVENT.evtx          - DC/GC System Log
   c) http://cid-31ba948d0da4d57e.skydrive.live.com/self.aspx/.Public/HC2010%7C_APPLICATION.evtx              - Hub/Client Application Log
   d) http://cid-31ba948d0da4d57e.skydrive.live.com/self.aspx/.Public/HC2010%7C_SYSTEM.evtx                      - Hub/Client System Log
   e) http://cid-31ba948d0da4d57e.skydrive.live.com/self.aspx/.Public/MBX2010%7C_Application.evtx                - Mailbox Application Log
   f) http://cid-31ba948d0da4d57e.skydrive.live.com/self.aspx/.Public/MBX2010%7C_System.evtx                      - Mailbox System Log
There will be some error log you will be that the system is not able to communicate with DC/DC, MBX or HC at everyday around 3 AM or some time 6 PM Evening also. These error came because I have installed VM on Windows 7 Workstation and after 45 min or one hrs. if I don't work on PC, then pc goes to sleep. so you may ignore these alerts.
I hope my answer will give you some clue and I expect more help from your side.
With Best Regards
Shambhu Sharma

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