Can't Send As (From) alias

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RPitchford

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Outlook version
Outlook 2010 64 bit
Email Account
Exchange Server 2007
My Exchange server (2007) is set up to send and receive messages for several domains.
Each user/mailbox has an alias for each domain. Incoming email for each domain is delivered as expected.
However, a user is unable to send a message (generates a bounce with a permissions error) with From set to one of their aliases - only messages From the address that is selected as the Reply (default) address will be delivered. Changing the Reply address allows the user to send as the selected alias.
The only workaround I have been able to find is to add another user account/mailbox and give them cross permissions, but this is messy at best and consumes extra licenses. A support case was opened with Microsoft at one point, but they had no solution. A friend tested this in an Exchange 2010 environment and found the same problem.
Has anyone encountered this and found a better workaround?

Thanks, Roy
 
Are the addresses all assigned to one mailbox? This is expected behavior - Exchange always uses the default. You could use shared mailboxes with full access permission - they don't consume licenses - but it gets messy if you have a lot of addresses. Replies will properly use the correct address. Another option is using distribution groups or gal contacts - instructions are here: http://www.slipstick.com/office-365/send-messages-secondary-office-365-exchange-addresses/
 
Yes, all the addresses are aliases on the same mailbox. Yes, that is pretty much what the Microsoft support tech said, only I think he worded it using "by design". Of course I would expect Exchange to use the Default by default, but to not allow the use of an alias as the From address is just a bit beyond comprehension. I wish someone could give me some sort of a reason as to why this is necessary or desirable.
I appreciate your suggested alternatives, but this is such a huge amount of work to have to do to work around something that should not require any additional effort (beyond maybe selecting a box to turn this behavior on or off).
Anyone at Redmond listening?!?
 
I decided to try the Contact method, but I got stuck at delivering the messages to the right mailbox (Mailflow). The directions you provided were for Office 365 Exchange and were a bit difficult to follow in my Exchange 2007 context. Do you have any similar write ups I could look at that would fit 2007 a little better?

Thanks, Roy
 
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