Cannot "Send As" a distribution list in Exchange 2010

I'm trying to enable some of our users to send email as one of our distribution lists in Exchange 2010, and I cannot get it to work. 
I have granted the users "send as" permissions on the distribution group in ADUC, both individually and as members of a security group. I also did the same using the "Add-AdPermission" PowerShell cmdlet.
I have ensured that the distribution list is visible to the GAL.
I have cleared Outlook's nickname cache.
I have tried waiting the specified two hours for Exchange settings to update, and I have also rebooted the Exchange server itself. 
I continue to get bounce messages with "You can't send a message on behalf of this user unless you have permission to do so."
What can I try next? 
Thanks,
Jason

Hi Jason,
I have a test in my lab. Here is the steps for your reference:
1. Open Active Directory Users and Computers on Domain Controller. Click Users -> right click the distribution group -> click Properties -> click Security.
2. Add the user that you want to grant "Send As" permission to the list. Allow the "Send As" permission.
3. Click Apply, and then Ok.
Besides, we need to wait some minutes to take it effect.
Hope it helps.
If you need further assistance, please feel free to let me know.
Best regards,
Amy
Amy Wang
TechNet Community Support

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