Why is ASP.NET MVC asking me to re-authenticate for .PNG files but not .gifs or .jpegs?

IIS can serve content directly without passing the request to ASP.NET. I suspect in your case that IIS is set to serve GIF and JPG but not PNG. See for example http://mvolo.

Com/blogs/serverside/archive/2006/11/10/Stopping-hot_2D00_linking-with-IIS-and-ASP.NET. Aspx for a discussion on the topic. See also http://www.microsoft.com/technet/prodtechnol/WindowsServer2003/Library/IIS/4c840252-fab7-427e-a197-7facb6649106.mspx?mfr=true .

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