Hi. Random emails get stuck in Outbox when viewing another user's mailbox as shared/additional mailbox. The user person viewing the shared/additional mailbox has their Outlook configured in either cached or online mode. It makes no difference, in that they see "stuck" emails in the shared mailbox's Outbox. Additionally, when in cache mode, the "Download shared folders" is set to UNchecked. With regards to the user who is the one actually sending the email, their Outlook is always set for cache mode. The Outlook of the actual user sending the email appear to be fine. The Outbox is clear and they see the email(s) in their Sent Items. In fact, the actual email is received by the intended recipient. I am not sure if the problem is with Outlook or Exchange? Our user's are using the latest and most up-to-date version of Outlook 2010 (both 32 and 64-bit). We only started noticing this to be an issue or frequent enough to notice it when we moved the user's to our Exchange 2010 server. We have 2 CAS servers and 1 Mailbox server. All are running Exchange 2010 version 14.02.0247.005, and Windows Server 2008 R2 SP1 64-bit. The only difference is that the 2 CAS servers are Windows Standard, while Mailbox server is Windows Enterprise. Thanks in advance for any help/insight. ~m

Hi , Please click Send/Receive all Folders and review . Please test in Outlook safe mode. By the way, do all email accounts in a same outlook profile ? Wendy Liu TechNet Community Support

Hi , Please test on owa Open another mailbox and verify. Have you tried open shared mailbox from another user ? What about repairing Outlook ? Wendy Liu TechNet Community Support

Had the same issue with our system until we installed RU4 for Service pack 2. http://support.microsoft.com/kb/2632409 Setting the sent items save location to "Sender and From" instead of just "Sender" solved the issue for us. Seemed for us it was an issue with Exchange not being able to file the email after it was sent (checks showed the message actually was sent but just got stuck in the outbox)

Wendy Liu, Clicking Send/Receive all folders makes no difference, and neither does running Outlook in safe mode. To clarify, Outlook is running a single profile (i.e. primary account), and within this profile there is a shared/additioanl mailbox (i.e. secondary account). ~m

Jon_R, Thanks, but you misunderstand. Let me clarify. I have my Outlook profile configured so that my account is the primary. Within my account I have full access via shared/additional mailbox feature to another user's mailbox (i.e. secondary account). The user who own's the secondary account on my profile sends emails from his own Outlook profile as the primary. I am able to view it. From time to time (intermittent, meaning not every time) emails that he sends out appears to be stuck in my Outlook "view" but in his Outlook they are not stuck and in fact go to his Sent Items and is delivered. Now NEW INFO: It almost seems like the emails he sends out are the last ones before he closes Outlook, turns of computer or it goes to sleep/hibernation mode. It almost feels like the message does get sent/delivered, but my shared view does not sync up yet, so it appears stuck? Because when he turns his Outlook back on then it has enough time to propogate/sync. Does that makes sense? And if so, is there is a fix to this latency of synching a shared/additional mailbox?

We have RU4 for Exchange SP2 installed, ran the cmdlet Set-MailboxSentItemsConfiguration <SharedMailbox> -SendAsItemsCopiedTo SenderAndFrom, but no change for us. Items sent from delegates are delivered, but the mail sits in the shared mailbox's Outbox.

Owa is fine. It looks exactly like the shared mailbox when opened from their own Outlook profile. Outlook as well as OWA does not show the stuck email item(s) in the Outbox. In fact, the email(s) are actually being delivered. They only appear to be stuck when being viewed from Outlook as a shared mailbox. Yes, opened shared mailbox from another user and same problem. Yes, performed repair using scanpst.exe, but problem still exists. What's happening is the primary user is in cache mode, they send an email it goes out and then they immediately close Outlook. It appears that when they close Outlook immediately, the Outbox does not have enough time to sync when viewed as a shared mailbox. Once the primary user goes back to their Outlook, it then has enough time to sync/propogate and the Outbox then becomes clear on the shared mailbox view. How do we eliminate or minimize the time it takes for Outbox to sync so the shared mailbox view does not give the false positive of the email not going out?