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Outlook Exchange "Send on Behalf" Permission not working

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Last Modified: 2016-09-07
Exchange Server 2010
Windows Server 2008r2

I have set up the permission in "Mailflow ->Delivery Options" and the "Manage send as Permission" tool on the account that I want the user to be able to send from. This was set up by someone else on another account and it worked fine, I copied their setup and for some reason it just doesnt work. Every time the user tries to send an email as this account they recieve the message saying they dont have permission. It has been more than 24hrs since I set this up so I think there has been plenty of time for the settings to update accross the network.

Any ideas?
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