How do I allow a user to "Send As" to both replies and to new mail?

In a SBS 2003 Exchange environment, I am trying to setup User A to have Send As permissions for User B.  So far I have been able to allow User A to be able to reply to existing messages from User B with the Send As permission in Outlook 2003.  When trying to create a new e-mail to Send As User B, User A gets an Undeliverable message error that says that they do not have permission to send to the recipient when the recpeient is not a user on the network.

User A has Send As permissions for User B in the Security Tab in AD. What other permissions need to be set to allow for this?
TriYoungAsked:
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Joseph DalyCommented:
You may also want to read over this article about the send as permission as well.

http://www.cryer.co.uk/brian/msexchange/exch_howto_grant_send_as.htm
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Joseph DalyCommented:
To allow this you need to enable the send on behalf of permission.

http://www.cryer.co.uk/brian/msexchange/exch_howto_grant_send_on_behalf_of.htm
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oztrodamusCommented:
If I remember correctly you need to assign full control permission to the mailbox via the security tab in the mailbox properties in Exchange. I believe what you are seeing is the result of a relay deny, which is what I would expect in what you are trying to do.
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TriYoungAuthor Commented:
That article was actually one of the first places I looked.  I tried setting the Send As permission according to this article.  I had also read someplace else that exchange can take several hours to update the permissions before they take effect.  After two days, the problem has not changed.  I have even gone as far as giving User A Full Control in security and exchange permissions to see if this would allow it and it has not.  I have actually been able to recreate this scenario with two of my clients, so I am assuming I am either missing a step in the process somewhere but I can't find it.
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Malli BoppeCommented:
Give the user full access and ask him to use OWA to open the USERb mailbox.Now he just just be able to send new emails and reply emails form USERB mailbox.Don't need to worry about SENDAS permissions or
You can create new outlook profile on USERA machine for USERB mail but just use the USERA credentails.This should also work.
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TriYoungAuthor Commented:
It should be possible to have both mailboxes within the same profile in outlook.  I was trying to avoid having to have the user open multiple profiles or OWA just to create a new e-mail for user B.  As I said earlier within the same profile, they can replay to messages coming in, they just can't initiate messages going out.  I have this setup in my office and working, however as an administrator, my permissions are different than most users.  I have two different customers that have this similar issue.  I will compare our settings to what they have and create a test user on our network to see what the differences are.
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TriYoungAuthor Commented:
I have been able to recreate this scenario on 3 separate and unassociated networks running Exchange 2003 via SBS.  The only differences I have seen so far have been that Domain Admins set to be user A are able to send and reply to messages as another.  When not Domain admins, they can reply only but not send new messages.

If the mailbox rights within advanced exchange properties of User B are set so that Everyone has all the listed permissions checked except for associated external account , then it works without being a Domain Admin.  The problem with that is then anyone could essentially get in and mess with User B's e-mail.  Further testing on this is needed to see what I can actually give them access to and still be allowed to initiate a Send As e-mail.
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oztrodamusCommented:
Hi TriYoung,

I'm a bit confused. You mention both Domain Admins and Domain Admin. I don't know if this is a typo, but it does make me wonder if your tyring to assign Send As rights to a Group account, and I don't think you can. To be more specific I don't believe Exchange will bifurcate the group to determine if the user you're trying to Send As is a memebr. It will only look at the Group account and treat it as the user. Remember Groups can have email addresses as well as a user. Therefore, eventhough you can assign the group permission to Send As that does not give the memebers of the group the right to Send As.
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Malli BoppeCommented:
Try recreating the outlook profile, delete nk2 and ost files as well and also do not use cached mode.
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TriYoungAuthor Commented:
The key thing I missed is that the server needed to be restarted for the change to take effect.
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