Multiple email addresses under one exchange account

I currently have multiple domains on my exchange server. There is a user that want's to have two different email address under the same exchange account. She wants to be able to send email from both email addresses. I have setup both email addresses under her profile. She can email from the original (main domain) email address, but when she changes the from address to the other email address she gets an undeliverable message "you can't send messages on behalf of this user. Before someone answers my request, make sure you remember, I only have one exchange account for this user with two email addresses. So there aren't any permission/sharing to allow.
Joe MAsked:
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Asif BacchusI.T. ConsultantCommented:
Your best bet is to setup another user with a separate mailbox.  So userA has domainA and userB has domainB.  Now, grant userA full access (or at least SendAs and ReceiveAs) to userB's mailbox.  If you'd like, you can also setup userB to forward all mail to userA and use OWA/Outlook rules to sort the mail into different folders, etc.  Now, when the user selects the from address they will be able to send using the other email address as the return address.

Sorry, I don't know any way of doing what you are trying to do using only aliases as you have configured, I'm pretty sure you have to use this multiple mailbox method.

Good luck :-)
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Joe MAuthor Commented:
Thank you for you reply. I should have mentioned I've already offered that option to the user, but she densest want to have two different mailboxes.
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Asif BacchusI.T. ConsultantCommented:
I'm not sure she has a choice :-)

You can make the whole thing transparent to her.  Simply forward all email from mailboxB to mailboxA (don't keep a copy in mailboxB if you don't want to) and then setup OWA (exchange) or Outlook rules to put all mail 'from' mailboxB in a separate folder in mailboxA.  She won't even need to know she has a separate mailbox, it's solely something the exchange admin has to be aware of.  From her perspective, she is just changing the 'from' address in Outlook as she is already trying to do anyways.  All of her mail will appear and be managed in mailboxA.

Does that make sense?
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Joe MAuthor Commented:
Thank you again for your reply. I have setup the new user and forward emails to her, and allow send email on the new users behalf, but she is getting an undeliverable message. Any thoughts why she is getting the error message?
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Asif BacchusI.T. ConsultantCommented:
She is receiving an undeliverable message or a message she cannot send on behalf of the user?  How did you set the Send As permission?  What version of Exchange are you using?
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Joe MAuthor Commented:
Message "you can't send a message on behalf of this user"
Exchange 2010
Under Mail Flow settings
Delivery Options
Grant this permission to: her user account
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Asif BacchusI.T. ConsultantCommented:
Ah, yes that will only grant Send on Behalf, not Send As.  If your user is changing the 'from' address in Outlook then she is attempting to Send As (not on Behalf).  Simple fix.  In EMC, right-click on the new user account and choose "Manage Send As Permission"  Add her user account and follow the wizard.  See if that fixes the problem.
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Joe MAuthor Commented:
I have already added her account to Manage send as permission. I'm going to remove "Send on behalf" and I hope that fixes the issue.
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Asif BacchusI.T. ConsultantCommented:
Just as a note, remember that replication has to occur for the permission to take effect,  especially if the user is in cached mode in Outlook.  Also remember that neither address can be hidden from the address lists.  If you want to forego the replication period you can just restart the Microsoft Exchange Information Store service.
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Joe MAuthor Commented:
I do have it hide from the directory. Do I need to un-hide it from the directory in order for the use to send as the other user?
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Asif BacchusI.T. ConsultantCommented:
Absolutely, yes.  You can reference this on technet if you'd like.  But basically, the address has to be resolvable from within Outlook in order to either Send on Behalf or Send As.  Since it's hidden, it cannot be resolved via the GAL and that is the issue.  Un-hide it, test, and let me know if that solves the problem.

I know it looks a little... undesirable... to have the alternate mailbox shown in the directory, but unfortunately that's just way it is.
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Joe MAuthor Commented:
Thank you for all the help.
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Asif BacchusI.T. ConsultantCommented:
Glad you got it figured out.
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