Mystery of the sent item!


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 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!

Comments (46)

  1. Anonymous says:

    @a-c: I am working on trying to get Outlook 2003 setup for testing (sigh.. it has been a long time since I even looked at OL 2003 :)) I will keep you posted on what I find. But, if it helps any; I have tested this with cached mode on OL 2007 and OL 2010, it works as we expect. You do not need the delegatesentitemsstyle registry key to be present and the items are populated in the "manager" mailbox in my example…

  2. Anonymous says:

    GarW: I do not think that this is available for O365 yet, but I am checking and if anything changes I will be sure to post.

  3. Anonymous says:

    @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

  4. Anonymous says:

    @Pavan: I will be posting updates as they are available

    @a-c: I will investigate this as well, but do you have the delegatesentitemsstyle registry key present on the machine that you are testing on, if yes… can you try and remove that key, test again and report back? Thanks!

  5. Anonymous says:

    @STP: Exactly what is not working and can you provide the output of the get-mailboxsentitemsconfiguration? Also, if your user mailbox and the shared mailbox are in different AD Sites there is a reported issue that this does not work. We are investigating and I will update the post once we have more details

  6. Anonymous says:

    Can this also be used for the deleted items? There is the "DelegateWasteBasketStyle" registry option. But that doesn't work with an online mailbox.

  7. Anonymous says:

    @Alberto Diaz: Essentially this setting will take effect only when the user'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

  8. Anonymous says:

    Great feature, my users have been asking for this for a long time! I can finally make them happy! Thank you.

    Anyway, I had a strange problem: I set "Sender and From" in both "SendAsItemsCopiedTo" and "SendOnBehalfOfItemsCopiedTo" settings for a given mailbox, and it worked for a delegate, while not for another. After some investigations, I figured out that the delegate which was ok had Outlook in online mode, the one which was not working had Outlook in cached mode. Switching to online mode solved the problem and the sent message was placed in both "Sent Items" folders as expected. As a countercheck, I switched back to cached mode and the problem reappeared.

    We are still using Outlook 2003 (with latest SP and updates). Exchange version is 2010 SP2 RU4.

    Is this a bug, or a behavior "by design", or a specific issue with Outlook 2003? Or what else?

    A.

  9. Anonymous says:

    Thank you, this is a very welcome and nice feature.

  10. Anonymous says:

    How long we need to wait for Get-MailboxSentItemsConfiguration in Exchange 2013? – It’s really a missing feature for our customers!

  11. Anonymous says:

    @sachinshah55: no, the registry key is not present. Thank you in advance for your efforts investigating this.

  12. Anonymous says:

    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.

  13. Anonymous says:

    @Rajkumar. Sorry for the late reply but….THANKS !!

  14. Anonymous says:

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

  15. Anonymous says:

    I'm having exactly the same issue as harrie where  a Distribution Group has "SendOnBehalf" permission on a delegated mailbox and the individual members are al set to "SenderAndFrom" the mail will NOT be placed in the Sent Items of the delegated mailbox. This is for shared mailboxes in my case

    Only when I give the individual members "SendOnBehalf" permission, does it work.

  16. Anonymous says:

    camlost: You are correct, this requires that the permission be already assigned, it works for both, send as and send on behalf, as you will see in my output of get-mailboxsentitemsconfiguration, you can set it for both. HTH

  17. Anonymous says:

    No, this does not work for deleted items. The fix is only for Sent Items

  18. Anonymous says:

    @Lannar: This setting is put in place for possible use in the future. At this time, we do not have any details to share around how we may implement this in a future release.

  19. Anonymous says:

    @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

  20. camlost says:

    If I understand it, it is necessary to assign the sender the Send As permission and full mailbox access. On the other hand, this allows users to send messages anonymously – recipient will not be able to recognize who sent  message to him.

    Or is this feature available even in case of Send On Behalf, i.e in case of delegate access? (This would be MUCH better for us. ;-))

  21. GarW says:

    Is this functionality available in Office365?

  22. STP says:

    i have tried installing SP2 RU4 , but still the issue exists

    STP

  23. Pavan says:

    I was absolutely able to reproduce the issue with mailbox and shared mailbox in different AD sites. Please update.

  24. Alberto Diaz says:

    Hi,

    Is there any way to disable the "Sent Items" option in OWA? In our organization, we don't use Outlook and don't want the final user to be able to change this setting.

    Thanks in advance and regards

  25. Gijs says:

    Is there a planned date for fixing the From-Only option?

    This would really make me a very happy person!

  26. Teck says:

    I noticed that the "Sent Items" 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. 🙂

    Still, the "Sent Items" screen in the ECP appears in english.

  27. starman says:

    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 ?

  28. Patry says:

    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.

  29. Harrie says:

    Is it possible to make this work for a delegated Distribution Group as well?

    Whe a Dsitribution Group has "SendOnBehalf" permission on a delegated mailbox and the individual members are al set to "SenderAndFrom" the mail will NOT be placed in the Sent Items of the delegated mailbox.

    Only when I give the individual members "SendOnBehalf" permission, this option works fine.

    Will the be a workarround for this behaviour?

  30. Harrie says:

    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 "DelegateWasteBasketStyle"?

  31. Rajkumar says:

    Hi Sachin,

    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.

    We have one shared mailbox called "customers" 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 shifts…so the manager wants to calculate the sent count using this shared mailbox as "send as" of each users per shift basis for one day and this needs to be emailed automatically

  32. Rajkumar says:

    @Patry You can set this option for all the mailbox in databases are server using the below option

    Get-Mailbox -ResultSize Unlimited -Database "Database Name"| Set-MailboxSentItemsConfiguration -SendAsItemsCopiedTo SenderAndFrom

    Get-Mailbox -ResultSize Unlimited -Server "Server Name"| Set-MailboxSentItemsConfiguration -SendAsItemsCopiedTo SenderAndFrom

  33. Mike says:

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

  34. Lannar says:

    Can you elaborate as to why the 'From' setting is not supported?  Clearly something got missed here since the value exists but is not implemented.  When can we expect an update to resolve this?  

    Currently we have no way of having an item sent by a delegate go ONLY in the shared mailbox's sent items if they are using outlook 2010.

  35. Oystein says:

    Hi,

    you have the Exchange 2013 Rocks as subtitle, so assume you can explain a rocky way to get DelegateSentItemsStyle work again in Exchange 2013 CU2.

    And yes, I've noticed the command has been removed, but obviously a required function for anyone using Exchange as a group mailbox.

    And no, the Exchange 2013 shared mailboxes does not give the same result, neither does it support active sync from windows phones as being without password.

    Further the default sender as active mailbox selected does not work, neither does it remember last From addresses in Outlook 2013.

    All in all a real showstopper for upgrade from Exchange 2010.

    Please tell me you have a workaround that rocks, and hopefully not the manual registry setting of all clients.

    thanks

    Oystein

  36. Siddhartha Rao says:

    Need help in imorting multiple users to "Send as" for a mailbox.

    I have figured out on how to import multiple users for Full mailbox access

    foreach ($line in import-csv "path of the csv file"){Add-MailboxPermission -Identity "Mailbox name" -User $line.Name -AccessRights FullAccess}

    can you give me a similar code for send as?

  37. Siddhartha Rao says:

    Sorry for bothering you. but i belive i found the answer

    foreach ($line in import-csv "Path of the CSV file"){Add-ADPermission "Mailbox display name" -User $line.Name –

    Extendedrights "Send As"}

  38. Andy says:

    I tried to set this up and thought it was working correctly (sent items should be in both sender and from boxes).  It now appears that outbound messages are only going to the sender's "Outbox", not even their "Sent Items".  I have confirmed the emails are actually still being sent.  Ideas?

  39. Andy says:

    It appears that my problem was related to the "DelegateSentItemsStyle" regisry setting.  It was set to "1".  Please disregard my previous post.  Thanks.

  40. SamR says:

    "sachinshah55 20 Nov 2012 7:16 PM
    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."

    Do you know whether this fix has been published?

  41. StevenW says:

    Is there any way to make these changes in Exchange 2013?

  42. JacoH says:

    Is there any way to disable Set-Mailbox SentItemsConfiguration MailBox -SendAsItemsCopiedTo From ?

  43. Ulysse says:

    When do you plan to add this feature in Exchange 2013 ? Thx

  44. James Auman says:

    Did Exchange 2010 ever fix the issue where "SendAsItemsCopiedTo from" puts a copy of the email in both mailboxes’ sent items?

  45. PaulC says:

    Thank you so much for this, it was driving me mad a some users don’t have Outlook in Cached mode and as you stated it was erratic to say the least. The fact that I no longer have to amend each user’s Outlook is a real plus. You’re a star!