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I'm storing some data in the RootFolder.Properties for a bunch of subsites, sub-subsites and sub-sub-subsites. On the parent site(s), I want to roll up that data, security trimmed for the user. (All are in the same site collection)

Obviously, looping over all SPWebs would be terribly expensive. There is the Content Query WebPart, which I assume does something a lot more effective. Does anyone know what it actually does under the hood, and if I can leverage that to roll up known SPWeb.RootFolder.Properties?

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No, the Content Query Web Part cannot query such properties! I would recommend that you instead create and use a SharePoint list for storing you data. That can be queried with security trimming and all by the CQWP.

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