Send As permission not working - Exchange 2010

Trying to allow a user to send as from a distribution list on Exchange 2010. I ran the following command:
Add-ADPermission -identity "Algentis - HR" -user mwong -AccessRights ExtendedRight -ExtendedRights "Send as"
The users gets an access denied NDR error message in Outlook (both cached and non-cached mode) as well as OWA. Here is the exact NDR:
Delivery has failed to these recipients or groups:
[email protected]
You can't send a message on behalf of this user unless you have permission to do
so. Please make sure you're sending on behalf of the correct sender, or request
the necessary permission. If the problem continues, please contact your
helpdesk.
Please help!

 Try to send mail through OWA, it may work. If it is, then it's Outlook issue.
Solution: Have user update the offline address book (click Send/Receive tab, click Send/Receive groups and select Download Address Book). Better yet,
1) Close Outlook
2) Delete the offline address book folder under “C:\Users\username\AppData\Local\Microsoft\Outlook\Offline Address Books”  (I assume it’s Windows 7 computer, look under C:\documents and settings\username\…. for XP computers).
3) Open Outlook and let it download new OAB.
Other Possibilities are,
1) You just gave “Send-As” permission for the user. Then, you have to wait for few hours. (you may restart Information Store to take effect the permission right away, who wants to do it?
2) User’s Outlook got bad/outdated cached contact information. Search for *.NK* files under user’s profile and delete it. Obviously Close the Outlook first before you delete the *.NK* files.
Please check this from your end & if you face any issue or have any query please let me know.
Check the below mentioned link for your reference.
http://anandthearchitect.wordpress.com/2011/07/17/exchange-2010-you-cant-send-a-message-on-behalf-of-this-user-unless-you-have-permission-to-do-so/

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