In .NET 4.0, simply exposing a resource via a StaticFileHandler does not enable it to be served. This undocumented change causes 'unmodified' files from being retrieved via an ImageResizer provider.
The workaround is to specify StaticFileHandler for those requests, a la
<system.webServer>
<handlers>
<add name="StaticGifImages" path="*.gif" verb="*" type="System.Web.StaticFileHandler" />
<add name="StaticPngImages" path="*.png" verb="*" type="System.Web.StaticFileHandler" />
<add name="StaticJpgImages" path="*.jpg" verb="*" type="System.Web.StaticFileHandler" />
</handlers>
</system.webServer>