1. A method of generating embroidery data from image data, comprising: identifying an object from the image data, wherein the object corresponds to a contiguous portion of an image defined by the image data, and wherein the object defines an area to be embroidered and an area distinct from the object and entirely surrounded by an inside edge of the object; automatically identifying a singular region within the object; generating occluded boundary information associated with the singular region, wherein the occluded boundary information represents a merging of at least two regular regions of the object into a single continuous area to be embroidered; and generating the embroidery data based on the occluded boundary information.