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Send As and Send On Behalf Of Problems

Exchange 2007, Outlook 2010.

After assigning "Send As" permissions to a mailbox, users report that they receive an NDR when trying to Send As the account that they have Send As permissions for.  These users also have Full Access to the mailbox.

The NDR error message:

You are not allowed to send this message because you are trying to send on behalf of another sender without permission to do so. Please verify that you are sending on behalf of the correct sender, or ask your system administrator to help you get the required permission.

I've waited over 72 hours after setting this permission (and opened and closed Outlook), and Outlook in cached mode still will not "update" this permission.  If you look at a domain controller, the Send As permissions are confirmed to have been propgated by looking at attribute editor.

If I put Outlook in Online mode, all of a sudden the permission works correctly and you can Send As without problems.  Put Outlook back into Cached mode, and you can't Send As as it produces an NDR.  If I go to OWA as https://mail.domain.com/owa/email@address.com and Send As from OWA, it works.

Other strange symptoms that may be related:

If a user currently has Send On Behalf Of permission and you take away Send On Behalf Of and add Send As instead (for instance the user decides they don't want their name to show up), Outlook will just give them a Pop Up error message (not an NDR) that says "You do not have permission to Send On Behalf Of this user"  (well, duh, I'm trying to SEND AS).

I've seen A LOT of conflicting information regarding whether or not Exchange caches AD permissions and what the mechanics of that are.  I'd like to figure out a straight answer for why these Send As and Send on Behalf issues happen and what I can do to work around it.  Rebuilding .OST files every time a user wants Send As permission isn't really a good workaround for me, and switching a user from Send on Behalf of to Send As or vice-versa seems to be broken right now.


Basically, the bottom line is this:

#1:  When I assign Send As permissions, Outlook clients in Cached Mode never find out about it and always give the NDR unless they are put in Online mode or a new .OST is created, even if you wait 72 hours and re-open Outlook.

#2:  If a user used to have Send As permissions and you remove that and assign Send On Behalf Of permissions instead, Outlook/Exchange doesn't seem to be able to learn that this change has been made.  Outlook in Online mode will continue to Send As, and Outlook in offline mode will continue to result in the same NDR you get when trying to Send As.




Anyone have any insight on this?
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Rajkumar Duraisamy
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Hello Friends, I just found a solution which worked for me. This may sound stupid but it works
GoTo--> File--> Options and change the User Name to the User who got the permission to Send as