Categories Exchange 2010

Sent Items Behavior in Shared Mailboxes - Update

In the “Sent and Deleted Items Behavior in Shared Mailbox” tip we talked the behavior of sent e-mails in Outlook (Cached Mode) when an e-mail is sent using SendAs or Send-On-Behalf-Of permissions. For example, we said that if UserA (the delegate) sends an e-mail AS UserB (the manager or shared mailbox), the e-mail goes into UserA’s Sent Items folder instead of the folder in UserB’s mailbox.

This becomes more of a problem with shared mailboxes when there are multiple users accessing the same mailbox and they all need to be aware of e-mails sent from that mailbox.

But what about when using Outlook Web App [OWA] or Outlook in Online Mode?! With Exchange Server 2010 SP2 RU3 and lower, the behavior here is the same and there is simply no way of changing this... The good news is that this changes in Exchange Server 2010 SP2 RU4! Now OWA and Outlook can be configured to put the e-mail in the Sent Items folder of UserA, UserB or even both.

To configure this, two new PowerShell cmdlets were introduced:

  • Get-MailboxSentItemsConfiguration
  • Set-MailboxSentItemsConfiguration

The first one allows us to check the behavior of sent items for a mailbox (in our example, UserB). If we run this against UserB (the manager):

[PS] C:\>Get-MailboxSentItemsConfiguration UserB
RunspaceId                  : 0f8cb6b9-a3f4-4e43-ab08-d88e6356425d
SendAsItemsCopiedTo         : Sender
SendOnBehalfOfItemsCopiedTo : Sender
Identity                    :
IsValid                     : True

Here, we are interested in the values of the SendAsItemsCopiedTo and SendOnBehalfOfItemsCopiedTo attributes which are self-explanatory. Sender is the default value for both attributes but this can be configured to Sender, SenderAndFrom or From:

  • Sender - e-mails sent using SendAs or Send-on-Behalf-of permissions are saved only in the Sent Items folder of the Sender (UserA);
  • SenderAndFrom – e-mails sent using SendAs 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 example, both UserA and UserB);
  • From – e-mails sent using SendAs 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 example, UserB)

NOTE 1: the From value does not work as expected... It basically performs the same action as the SenderAndFrom value, meaning it saves the e-mail in both mailboxes. This is still the case in Rollup 5 v2.

NOTE 2: for some reason this feature does not seem to be present in Exchange 2013...

To configure e-mails sent using SendAs permissions to go to both mailboxes, we would use:

[PS] C:\>Set-MailboxSentItemsConfiguration UserB -SendAsItemsCopiedTo SenderAndFrom
[PS] C:\>Get-MailboxSentItemsConfiguration UserB
RunspaceId                  : 0f8cb6b9-a3f4-4e43-ab08-d88e6356425d
SendAsItemsCopiedTo         : SenderAndFrom
SendOnBehalfOfItemsCopiedTo : Sender
Identity                    :
IsValid                     : True

NOTE: if you are using Outlook, then the registry key fix mentioned in the beginning (DelegateSentItemsStyle) might over right this setting, so it recommended that it is removed!

Users can also configure this themselves now through OWA! By going to their settings, there is a new tab called Sent Items which allows them to set these values.

NOTE: in order for this to work properly, all Client Access Servers and Mailbox servers in the site where the users’ mailboxes are need to have at least RU4.

Nuno Mota

Nuno Mota is an Exchange MVP working as a Microsoft Messaging Specialist for a financial institution. He is passionate about Exchange, Lync, Active Directory, PowerShell, and Security. Besides writing his personal Exchange blog, LetsExchange.blogspot.com, he regularly participates in the Exchange TechNet forums and is the author of the book “Microsoft Exchange Server 2013 High Availability.”

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