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tymccoy

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Sending Emails from Different Email Addresses from the Same Exchange Server

I have received a request from the owner of our company who owns multiple companies asking the ability to send and reply to messages specific to one of his secondary companies using that companies domain name due to governmental regulations etc.  
Currently he has one primary email account which all of his company emails from the various companies go to one exchange server.  So if some wants to send him an email bob@abc.com, bob@xyz.com, bob@mno.com etc... all the emails go to bob@abc.com and he replies back to all of the messages from bob@abc.com, but now when he receives or sends an email from bob@xyz.com he needs to use bob@xyz.com.
The owner of the company does not want to constantly be opening and closing outlook throughout the day, but want to manage his emails from the large number of companies he owns from one Outlook session.  
Originally I thought I would be forced to take out bob@xyz.com out of his email allias and establish a separate account for bob@xyz.com and give delegate rights to his primary account bob@abc.com, but I can't seem to get this to work although I went through the following kb article on Microsoft's website http://support.microsoft.com/kb/291626  but when the primary email bob@abc.com sends a message on behalf of bob@xyz.com I get an undeliverable message immediately saying the following Delivery has failed to these recipients or distribution lists:
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.
Does anyone have any suggestions on how to approach this issue in which I am not thinking of right now, or knows why even when I go through the exact procedure listed by Microsoft "MANY TIMES NOW USING MANY ACCOUNTS" that it fails.  Could the issue on sending on behalf be a setting that is on the exchange server its self?

Thanks
ty
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DerekStone

Try configuring:
Active Directory Users and Computers | Right click on user | Properties | Exchange General | Delivery Options | Send on behalf
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Alan Hardisty
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Thanks DerekStone and Alanhardisty for your responses.
Derek I did try what you said previously with no luck on my test account but it does work for others users in different email addresses on the server.  "Kind of interested why its doing that but I have bigger issues to deal with besides my own curiosity."
Alan I did see the link previously and did go through it prior to posting with no luck, but then when you mentioned smtp relaying I realized what I was doing wrong and was not setting up the outbound account to use authentication.  So you win the wonderful prize of thanks for your help and 500 points which I hope you do not spend all in one spot ;-)
I'll try not to spend them all at once!  Thanks : )

Alan
Don't forget to close the question down by clicking on the "Accept As Solution" or Accept Multiple Solutions" buttons by the comment or comments that helped you solve the problem.

Thanks

Alan