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There seems to be an issue in your code when checking the If-Modfied-Since header. From what I can see in dotPeek, you check if If-Modified-Since is earlier than the newest file, and then return 304, if that is true. Shouldn't it be the other way around, that you return 304 if If-Modified-Since is later than the newest file? This means the code should read
if (dateTime.CompareTo(date) >= 0)
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