UPDATE: 11/20/2012

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The issue with this not working for mailboxes in different AD Sites is resolved. A fix is available from Microsoft CTS for this issue. Please open a case and request the fix for this if you need it.

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;

Get-MailboxSentItemsConfiguration

Set-MailboxSentItemsConfiguration

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 three possible values; Sender (Default), SenderAndFrom or From

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)
• From – This value implies that e-mails sent using Send As or Send on Behalf of permissions are saved in the Sent Items folder of only the mailbox on which the permissions are assigned (in our case, Manager user)

IMPORTANT: At this time, the From value does not work as expected. It performs the same action that the SenderAndFrom value implies, which saves the e-mail in both, the Manager and Delegate Sent Items folder. We are NOT recommending that customers use the From value at this time. The intended functionality of this value is planned to be included in a future release of a RollUp or Service Pack for Exchange Server 2010.

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!