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Doesn't that just compare the page on the proxy to the page stored on the hard drive temporary internet folder, rather than comparing the proxy page to the source server page?
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Yep, that's exactly what it does... there is no way (that I know of) for ensuring you don't ever get outdated content that is cached on a proxy by doing something locally - apart from not using a proxy where possible
The only way I know off is setup your own proxy server remotely and use that to access pages, and set it up to always not cache content which is what I have done. Make sure you dont use a http port otherwise the traffic will still get intercepted.