Automated electronic document design systems and methods for appropriately sizing and positioning uploaded user images into predefined image areas in a product design being created in a Web environment. For an image that is not to be cropped when incorporated into the design, the image is sized to fit within the selected image area and positioned in the image area according to a predefined anchor location. The aspect ratio of the original image is maintained. For an image that is available for cropping when incorporated into the design, the image is sized and cropped to create a version of the image that fills the image container.