The user accounts are not part of any protected groups in AD.

The user accounts are not part of any protected groups in AD. Did they used to be? Is security inheritance disabled on those accounts?

The two accounts are brand new and were never part of any build-in security groups. I don't believe security inheritence has been disabled at this time.

Check to see if those accounts are protected by the adminsdholder object: http://technet.microsoft.com/en-us/library/2009.09.sdadminholder.aspx Adfind.exe -b DC=domain,DC=com -f "&(objectcategory=person)(samaccountname=*)(admincount=1)" -dn Adfind: http://www.joeware.net/freetools/tools/adfind/index.htm

Hi rcanderson, Any updates on this issue? Do you follow the document given by Andy to check on the adminsdholder object? This issue often occurs when you accounts are protected by the adminsdholder object. Here is a similar thread, hope can give you some help: "send as" permission being removed exchange 2007 http://social.technet.microsoft.com/Forums/en-US/exchangesvrgeneral/thread/c75869ad-e1b6-4b5d-8e72-ac3d7b8381dc Thanks, Evan Please remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.