Messages stuck in Outbox

Hi there,

Environment is Exchange 2013 CU2 and Office Outlook 2013 latest patches.
Primary mailbox is the users one, connected in online mode.
I added a shared mailbox as a new mailbox inside this profile. (i did not attach it to the users mailbox)
It is a seperate second exchange mailbox next to the users one.
The user has "Full Access" and "Send-As" rights on this shared mailbox.

Now afer some time the users gets an error when sending emails from that shared mailbox.
The error is 0x8004010F and is mostly related to pst issues and offline/cache-mode.
And suddenly later or maybe after restart of Outlook the messages are sent.

What i had to achieve with this configuration, is that the user is able to send emails from this mailbox and all the processed items have to stay inside the shared mailbox.
"DelegateSentItemsStyle" and "Get-MailboxSentItemsConfiguration" is not part of Outlook or Exchange 2013 anymore as it seems.

Does anyone had this problem before or has any idea how to workaround this?

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Simon Butler (Sembee)ConsultantCommented:
First - CU2 is no longer supported.
You need to keep up to date. The earliest you can be now is SP1, so I would recommend that you upgrade to Exchange 2013 SP1 first and see if the problems continue.

PsymoniousAuthor Commented:
I know that CU2 is no longer supported, but there are some dependencies that do not allow me to upgrade at the moment. I hope i can soon upgrade to CU6.

But in general, would you choose the same configuration to achieve this or have you any other suggestion?
Simon Butler (Sembee)ConsultantCommented:
The configuration you have posted is what I would do. There aren't any other options.
However as for further troubleshooting, I wouldn't even bother until the server is up to date, at least on SP1. Many people, myself included, don't even consider Exchange 2013 close to production ready until SP1.

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PsymoniousAuthor Commented:
I will review this behaviour after i upgraded to CU6 within the next 1-2 weeks and come back to this discussion.

Thank you so far.
PsymoniousAuthor Commented:
We finally updated our Exchange Server and Cilents to latest patchlevel.
Sadly we still have that weird issue with messages stuck in Outbox.

Any additional ideas how we can analyze/fix it?
Simon Butler (Sembee)ConsultantCommented:
Messages stuck in the Outbox are usually an indication of a problem with the Transport Service. Lack of disk space, AV scanning something it shouldn't be etc.


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