TFS 2010: check file on open

I have a number of projects that include certain files that I use to create block diagrams, etc. (* .graphml, * .doc, * .docx, to be precise). While I am installing the files for "opening with" the appropriate editor, I have to manually check them in TFS to make them "writable." There seems to be a way for TFS to check files automatically, as is done for code, xml, etc. How can i achieve this?

Note:
My TFS settings are set to "automatically check" files, but to no avail.

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TFS 2012 Local Workspaces.

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