Send As from a shared mailbox stopped working

I have created a Shared Mailbox a few months ago and gave one use full access rights and send as permissions. This worked perfectly since it was created. On Friday, the user started getting:
Delivery has failed to these recipients or groups:
You can't send a message on behalf of this user unless you have permission to do so. Please make sure you're sending on behalf of the correct sender, or request the necessary permission.
If the problem continues, please contact your helpdesk.
There have been no changes made to any of the rights or permissions anywhere. The shared mailbox properties still show this user in the full access and send as list. The shared accounts address is available in the GAL so that is not an issue.
Any ideas would be appreciated. I could probably recreate this mailbox, but would rather fix the issue or at least know what happened in case it does it again.
Nick Laurino

Hi,
Have you tried removing and then re-adding the permission for the user? Worth a try when such issue occurs.
As the administrator, you may want to verify that the user actually does have "Send-As" permission on the shared mailbox. To do that,
Open the Exchange Management Console on the Server
Navigate to Recipient Configuration > Mailbox and right click the Shared Malibox
Select "Manage Send As Permission"
Check that the user is listed in the permissions
To solve the issue on the client side, delete the offline address book and allow Outlook to recreate it.
Close Outlook
Delete the Offline Address Book folder
It can be found under "C:\users\{username}\AppData\Local\Microsoft\Outlook\Offline Address Books"
Open Outlook and it will download a fresh copy of the Offline Address Book
I hope this can be helpful.
Thanks,
Melon Chen
Forum Support
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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.
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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
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I'm experiencing an issue regarding the sent items from a shared mailbox.
The users would like the items Sent on Behalf of a shared mailbox to be saved within this shared mailbox.
At this moment, the Sent Items are saved in the users own mailbox.
We have a single Microsoft Exchange Server 2010 (Version 14.3 Build 123.4) and Users connecting the Exchange Server are using Microsoft Outlook 2007 (12.0.6680.5000) SP3 MSO.
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I am using a shared mailbox (with a disabled account) where I get sent items and also deleted items placed in the right folders.
I think it’s just a matter of how you configure Outlook. It works well for me in both Outlook 2010 and Outlook 2013, cached mode and also online mode. You can add a shared mailbox to your Outlook profile in at least two ways where one of them doesn’t work
but the other does.
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configured”. After restarting Outlook you will find the shared mailbox below your own in the left pane.
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Messages sent from a shared mailbox aren't saved to the Sent Items.

Messages sent from a shared mailbox aren't saved to the Sent Items.
In my enviroment , I have Exchange 2010 and Outlook 2007 - i have a shared mailbox called
ServiceDesk. I have added this mailbox to user "Mike" and given mike "Send as Permission" .
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Below is a similar solution to my problem but i do not want to make any changes to my registry. Please any other solution to this?
http://www.msoutlook.info/question/278
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Hi,
This is maybe the wrong forum for this question, but anyway;
Thie site you were pointing out's solution is valid.
Please look in to the following KB article that describes the steps needed to solve this issue. A hotfix package (which you might not need and a a "fixit" dowload for it, but will also change the registry key.
http://support.microsoft.com/kb/972148
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