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Mystery of the sent item!

Mystery of the sent item!

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There are many scenarios and business requirements that are addressed by the use of the Send As, Send on Behalf of and Full Mailbox Access capabilities. These permissions can be easily assigned using the Exchange Management Console or the Exchange Management Shell. The particular permissions of interest for this blog post are the Send As and the Send on Behalf of permissions. Once these permissions are assigned, every e-mail that is sent using either one of these permissions is saved in the Sent Items folder of the sender, by default. The ability to change this behavior using a registry key, the DelegateSentItemsStyle is discussed in KB953804 for Outlook 2003 and KB972148 for Outlook 2007. When the DelegateSentItemsStyle registry key value is set to ‘1’, the behavior changes and the items are now saved in the Sent Items folder of the mailbox that the permissions were assigned for. As an example if User 1 has Send As permissions on User 2’s mailbox, whenever User 1 send as e-mail as User 2, the item is saved in the Sent Items folder of User 2, instead of User 1’s Sent Items Folder. One of the requirements for this registry key to work correctly is to run Outlook in cached mode. If you run Outlook in Online Mode, the results are inconsistent.

We are introducing a major change with Exchange Server 2010 SP2 RU4. To explain the change, let me first set the stage with an example. The user “Delegate” has been assigned Full Mailbox Access and Send As permissions to the user “Manager” mailbox. This is accomplished using the below powershell cmdlets.


Add-ADPermission -identity Manager -User Delegate -ExtendedRights "Send As”

Add-MailboxPermission Manager -User Delegate -AccessRights FullAccess -InheritanceType all

With Exchange Server 2010 SP2 RU3 and lower, whenever Delegate would use Send As permissions and send an e-mail to any user, the item would show up in the Sent Items Folder of Delegate. With Exchange Server 2010 SP2 RU4, this behavior changes. We can now make a copy of the e-mail in the Sent Items folder of the Manager Mailbox. To achieve this functionality we are introducing 2 new powershell cmdlets;




A sample default output of the Get-MailboxSentItemsConfiguration is below. This has been executed against the Manager mailbox


[PS] C:\Windows\system32>Get-MailboxSentItemsConfiguration Manager

RunspaceId                  : 38eb470d-f92d-4381-afa0-5bb7b8741e02

SendAsItemsCopiedTo         : Sender

SendOnBehalfOfItemsCopiedTo : Sender

Identity                    :

IsValid                     : True


Note, the values for SendAsItemsCopiedTo and SendOnBehalfOfItemsCopiedTo. Both attributes have the default value of Sender. The attributes can be configured with any one of two possible values; Sender (Default) or SenderAndFrom 

Let me quickly explain what each of these values mean


  • Sender (Default) – This value is the default and will imply that all e-mails sent using Send As or Send on Behalf of permissions are saved only in the Sent Items folder of the Sender (in our case, Delegate user)
  • SenderAndFrom – This value implies that e-mails sent using Send As or Send on Behalf of permissions are saved in the Sent Items folder of the Sender and the mailbox on which the permissions are assigned (in our case, both Delegate user and Manager user)


Now, I will use the Set-MailboxSentItemsConfiguration and set the Manager Mailbox SendAsItemsCopiedTo attribute value to SenderAndFrom

[PS] C:\Windows\system32>Set-MailboxSentItemsConfiguration Manager -SendAsItemsCopiedTo SenderAndFrom

[PS] C:\Windows\system32>Get-MailboxSentItemsConfiguration Manager

RunspaceId                  : 38eb470d-f92d-4381-afa0-5bb7b8741e02

SendAsItemsCopiedTo         : SenderAndFrom

SendOnBehalfOfItemsCopiedTo : Sender

Identity                    :

IsValid                     : True

Once this change is made, all e-mails that Delegate user sends using Send As permissions on the Manager user will show up in the Sent Items folder of both, Manager and Delegate. An important point to note is that we no longer require the DelegateSentItemsStyle registry key to be present or set with a value. We also do not require that Outlook be configured to be running in Cached Mode. This change allows Outlook to be running in Online Mode to achieve the required functionality.


We are also introducing this as a self-service option for end users! Users will have the ability to use Outlook Web App (OWA) to set the values as well! Below is a screenshot of the Options in OWA.



IMPORTANT: For this to work, we require that all Client Access Server roles in the Site where the users Mailboxes are created be updated to Exchange Server 2010 SP2 RU4. We also require that all Mailbox Servers that host the mailboxes that require this functionality be updated to Exchange Server 2010 SP2 RU4

I hope that you find the information above useful!

  • <p>Is there a planned date for fixing the From-Only option?</p> <p>This would really make me a very happy person!</p>

  • <p>@Gijs: There is no planned date at this time for the From option to work as expected, which is to make a copy of the e-mail ONLY in the shared mailbox sent items folder. We strongly recommend that customers do NOT use this setting at this time. You should only use the SenderAndFrom setting</p>

  • <p>@Alberto Diaz: Essentially this setting will take effect only when the user&#39;s mailbox has been provided Full Mailbox Access or Send-As permissions to another user. I will investigate if it is possible to disable changing this setting in OWA and post back</p>

  • <p>I noticed that the &quot;Sent Items&quot; option in OWA does not seem to be localized (we are running a german environment). I double-checked to make sure that I installed the german version of the roll-up, which I did. :)</p> <p>Still, the &quot;Sent Items&quot; screen in the ECP appears in english.</p>

  • <p>I have been playing with Exchange 2013 RTM in my lab, and this long awaited feature is not there. It is not in the OWA interface and there is no powershell cmdlet called Get-MailboxSentItemsConfiguration either. Do you have any info regarding that ?</p>

  • <p>@starman: There are plans to port this feature over the Exchange 2013, we do not have an ETA at this time.</p>

  • <p>I have updated the blog post with information that the fix for cross site mailboxes is available. Please open a case with Microsoft and request the fix.</p>

  • <p>@Teck: I will check with the OWA team and let you know in localization of the screen for other languages and when it will be available and post back</p>

  • <p>Is it possible to set this option for a database or the server, to always use this option. Now it seems you have to do this for every existing and new mailbox.</p>

  • <p>Is it possible to make this work for a delegated Distribution Group as well?</p> <p>Whe a Dsitribution Group has &quot;SendOnBehalf&quot; permission on a delegated mailbox and the individual members are al set to &quot;SenderAndFrom&quot; the mail will NOT be placed in the Sent Items of the delegated mailbox.</p> <p>Only when I give the individual members &quot;SendOnBehalf&quot; permission, this option works fine.</p> <p>Will the be a workarround for this behaviour?</p>

  • <p>Is Microsoft developing simular functionality for the Deleted-Items in On-line mode, as already developed for Outlook in Cached mode with the registry setting &quot;DelegateWasteBasketStyle&quot;?</p>

  • <p>Hi Sachin,</p> <p>Is there any option that I can track and find all the emails that are sent from a shared mailbox using the Send As permission.</p> <p>We have one shared mailbox called &quot;customers&quot; and around 50 users are having send as permissions for that. All users have to reply back using this shared mailbox to all their customers. All users are sending emails 24*7 in 3 the manager wants to calculate the sent count using this shared mailbox as &quot;send as&quot; of each users per shift basis for one day and this needs to be emailed automatically</p>

  • <p>@Patry You can set this option for all the mailbox in databases are server using the below option</p> <p>Get-Mailbox -ResultSize Unlimited -Database &quot;Database Name&quot;| Set-MailboxSentItemsConfiguration -SendAsItemsCopiedTo SenderAndFrom</p> <p>Get-Mailbox -ResultSize Unlimited -Server &quot;Server Name&quot;| Set-MailboxSentItemsConfiguration -SendAsItemsCopiedTo SenderAndFrom</p>

  • <p>@Rajkumar. Sorry for the late reply but....THANKS !!</p>

  • <p>Just like Harrie, I&#39;d love to know if there will be a DelegateWasteBasketStyle feature added as well. With outlook 2013 coming out, I&#39;m cranking out our group policy settings and would like to not have to push those possibly not supported registry settings.</p>

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