I have an item in the content tree that I only want to allow access to a specific role.
i.e
My initial plan was to add a 'DENY' against the 'Everyone' role, then add a 'ALLOW' against my role.
But as far as I can see this does not work because the 'DENY' of 'Everyone' will always trump the 'ALLOW' of my role?
What you want to do is break inheritance on the item so that any previous permissions that have been provided will be eliminated. Then, give permissions only to the role you want.
This will achieve the "Deny Everyone" you are attempting to do, but know that this means that if you try to apply a 'global' security higher in the tree you will need to repeat it at this level. For example, if you have a Content Admin role that can do anything anywhere, you would have to re-apply the Content Admin role on this item.
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