Sending "From" as another e-mail won't work (sort of)

Delivery has failed to these recipients or groups:
Fake Name <mailto:fname@gmail.com>
You can't send a message on behalf of this user unless you have permission to do so. Please make sure you're sending on behalf of the correct sender, or request the necessary permission. If the problem continues, please contact your helpdesk.

A user gets the above message (I replaced real name with Fake Name, that's the recipient's name) after they try changing the "From" address to an address they have full Access and Send permission access as (granted in the Exchange console).

However, they do not get such an error message if they specify the same "From" address by choosing "From" button and then "other address" and selecting the e-mail from their local contacts (I added it to their local contacts).

garryshapeAsked:
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Getsum_BloodlustCommented:
where did you apply the "send as" permission?
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apache09Commented:
I beleive only the contacts from the global address list (Exchange Address List)
Will allow you to use From:

If you are chooing an address in the personal contact list, this may be interpreted by Outlook/Exchange as a Non Exchange Address.

Especially if its details differs from that in Exchange's Global Address list.

Any reason why the user is using the personal contacts list vs the Global Address list?
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garryshapeAuthor Commented:
@Getsum
I applied the permissions in Exchange Management Console by right-clicking the mailbox and choosing "Manage Send As Permissions" and adding the user there (as well as the 'Manage Full Access Permission'). And in the properties of the mailbox under Mail Flow Settings > Delivery Options > and granting Send on behalf to the user there.

@apache09
When we try typing out the e-mail in the "From" field, click OK, then type up and send a message, it comes back with that "You can't send a message on behalf of this user unless you have permission to do so" message.

However, if I right-click that e-mail and add to her contacts, then go send a new e-mail and instead of typing out the e-mail in the "From", I click the From button and select the e-mail from the Contacts list, and typing out/sending an e-mail from that address sends out fine.
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apache09Commented:
Ahh think i see what the issue s here

In outlook there are two permissions

1 - send as someone else - DOne by providing Full Access to exchange mailbox in AD
2 - Send on Behalf - This can be granted through Delegate Permissions in the Delegators Profile.

Could be the person is listed as a delegate on the Mialbox but with limited permission to Send on Behalf
Check the delegates and the users permissions
Check they have editor rights to the Inbox
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garryshapeAuthor Commented:
I guess I would have to open Outlook and create a profile with the e-mail to see its Delegates.
It's a brand new mailbox, though, not intended for an end-user to use. It's a new mailbox setup to send/receive, I just wanted to give at least 1 user access to open/view it, and also Send As it.
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apache09Commented:
Considering when you open it, there should be no delegates listed then.

If this is the case add the person
Give them Full Delegate Access to the MailBox (Editor)
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