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Exchange Send As Error Messages

I recently migrated to a new exchange 2010 sp3 server. All my clients are using Outlook 2010 sp1. We have a few shared mailboxes each department uses. I granted individual send as, full access permissions and send on behalf of in EMC.  It has been a month now and some users are receiving the below message:

Delivery has failed to these recipients or groups:

John Doe
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.

This happens when the user replies, reply all or sometimes creates a new email. Sometimes the message is received by the recipient. Other times I do not know. The users with the problem I deleted the .ost files and created a new email profile.
Since doing so there hasn't been any issues to the users who have had the problem YET. I do not want to recreate Outlook profiles for everyone, What else can I look at/check to see what is the issue? Did I do the correct thing by recreating the outlook profile?
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Avatar of Simon Butler (Sembee)
Simon Butler (Sembee)
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I will remove the send on behalf of, can you explain why it is intermittent and happens sporadically?
Hard to say. With both permsisions set you get odd results. It could be they are overwriting each other or generally causing problems depending on the replication.

Simon.
Noted, thank you.
@Sembee2 after removing send on behalf of permissions and keeping Full Access Permissions and Send As Permissions on Friday, today a user informs me that when he tried to send an email he received the error again. any other ideas?
Have you tested it for yourself? If the permissions are in place and there isn't a deny there (will be the case if the user is an Admin, Domain Admin or Power User) then it can be down to end user error.

Simon.