When Sitecore receives a media request it goes through a few key steps to convert the URL in to a form it can use: Sitecore identifies that the request is for a media item because the path begins with a media prefix defined in the web.config. www.website.com /~/media /Images/kitten.jpg The prefix is removed and replaced with the root of the media library. /media library / Images/kitten.jpg The file extension is removed. /media library/Images/kitten