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sudo wrote

As far as PDFs go, the Tor people recommend only opening the ones you downloaded after disconnecting your computer from the internet. That way, they can't automatically try to fetch some resource from the web, and de-anonymize you in the process. There's probably some way to modify a PDF viewer so that it never tries to fetch online content, but I haven't bothered to do that yet. It'd be a good project for someone here to work on.