Outlook 2010 on Windows 2008 R2 - Programmatic settings not working

I have a Windows 2008 server that I have Windows 2008 R2 on.  (Its also a Xenapp6.5) server.   I am using a third party software that calls Outlook 2010 to send an email.  Here is my problem.  If I select Never warn me of suspicious activity, the email is created and all is well.

If I select prompt me, the users get a prompt just like they are supposed to.  The problem I am having is I created a GPO and applied to the users container to automatically approve these notifications.  The third party software is looking for that setting in Outlook to be checked.  When I log in as a regular user this is what I see:

I need to have the 3rd radio button selected for everyone.  I have used the Outlook 2010 adm templates, I have set it in the registry and I still can't get that setting to be there.  I really need some help here!
Chad FranksSenior System EngineerAsked:
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David Johnson, CD, MVPOwnerCommented:
change it to a registry setting in your group policy (update)
Dirk KotteSECommented:
possible there is a "loopback Policy / replace" set at the Terminalserver OU that disable this Setting at the user-OU?
Check with "gpresult -h" or "rsop.msc" from within the user session if your Settings are active.

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Chad FranksSenior System EngineerAuthor Commented:
You were both right.  The registry setting worked, but I also had a loop back policy that was overwriting it.

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Windows Server 2008

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