Send-As Permissions Randomly Failing.

Exchange 2010 SP3 RU5
I have a group mailbox may users have Send-As permissions to. Sending messages as the mailbox is failing randomly for many of the users. For example, UserA sends 3 messages within 10min, one of the 3 messages bounces with the NDR shown below. UserA can send
more 10 messages the reset of the day without any issues. Then a few days later one of the messages he sends that day will bounce with the same type of NDR.
On average there are 100+ messages sent from this mailbox each day, and probably 2 will fail.
Any ideas on how to troubleshoot this would be appreciated.
Delivery has failed to these recipients or groups:
'[email protected]' <mailto:[email protected]>
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.
Diagnostic information for administrators:
Generating server:
[email protected]
#MSEXCH:MSExchangeIS:/DC=com/DC=Domain/DC=DSRoot:MBX01[578:0x000004DC:0x0000001D] #SMTP

Hi,
According to your description, I understand that the issue occurs randomly. Please double confirm the send as permission has been given for the users who have problems for sending from this mailbox.
How many users have been given send as permission? Please send a test email again from this mailbox to check whether the issue can be reproduced for the problematic user. If the issue doesn’t occur when resending a message from this mailbox
for the problematic user, please remove the send as permission for this user then add it back and
restart the Microsoft Exchange Information Store service to have a try.
Regards,
Winnie Liang
TechNet Community Support

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