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>The “disable cache” checkbox in the developer tools seems to do nothing

I've the same issue. It works sometimes and other times it doesn't.

You need to keep the pane open for it to have an effect. The relevant SO thread: http://stackoverflow.com/questions/5690269/disabling-chrome-...

I actually like this behavior but obviously you need to know about it for it to seem reasonable :-)

Yes, I'm aware of that. But sometimes even keeping the dev tools open doesn't clear the cache. Probably it's some bug.