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CSS file not served by IIS 7.5 after multiple clear cache refreshes in a row in browser

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http://serverfault.com – We are experiencing an interesting issue with IIS 7.5 static caching and a css file. When we use IE to hit the page in question everything works fine - 200 OK on css file. When we refresh the page it works fine - 304 Not Modified on css file. When I refresh again with control key it reloads fine - 200 OK on css file. Now if I do a control key + refresh multiple times in a row really fast the css fails to load and in the developer tools network it says "Loading..." for the css file and it hangs never coming back. Any ideas? (HowTos)