Systems and methods according to the present invention provide techniques to automatically crop an image to a desired size. Automating the cropping process, while at the same time providing a high quality, cropped image, can be accomplished by employing a comprehensive approach that includes one or more of contextual cropping (e.g., basing cropping decisions on elements within the image to be cropped itself), training the cropping mechanism (e.g., using previously cropped versions of the same image or related images) and multiple operational modes (e.g., selecting one of a plurality of different cropping techniques for cropping a particular image).