Abstract: The present invention is a system and method for cropping and annotating images on a touch sensitive display device or other handheld device, including the following steps: (a) displaying an image of the image file to be cropped/annotated; (b) receiving an first input from a user designating a first point in the image defining a corner of a crop/annotation rectangle; (c) receiving a second input from the user designating a second point in the image defining an opposite corner of the crop/annotation rectangle; and (d) cropping and/or annotating the image from the first point to the second point of the crop/annotation rectangle. The present invention may be used in digital cameras, Apple iPhones®, hand-held devices that inspectors may use to annotate photographs taken to substantiate statements of problems found during industrial inspections, and in other purposes.