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"Send on Behalf of" does not work when sending to external email addresses

"Send on Behalf of" does not work when sending to external email addresses
Asked by: msidnam
We have Exchange 2010 and Outlook 2010. I've noticed that if users have delegate access to  a mailbox and they send an email to someone internal it will say <user> on Bahalf Of <owner>.

However, if they send and email to an external recipient it will just say the owners name. On one of the tests sending to outlook.com if we click the arrow next to the FROM it will shows <user> on Behalf Of <owner>. But on another mailbox it doesnt show it. Is this by design or can i change a setting to say "On Behalf Of" when sending externally as well?

I'm also getting an error when adding or removing delegates. It says it cannot activate the Send-On-Behalf-List, Operation failed for one mailbox.
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msidnam
Asked:
msidnam
1 Solution
 
EEhotlineCommented:
Send on Behalf of requires the client to support it, exchange to exchange. Some external clients can see the additional information in the headers and display the information, if the external sources use Exchange, it will work. If you mail a non-exchange system, the behavior cannot be predicted.
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