In accordance with various aspects of the present invention, a system and method for automated generating of a cutting curve on a surface is provided. In accordance with an exemplary embodiment, a computer-implemented method for automated generating of a cutting curve on a gingival surface to facilitate cutting of an aligner material comprises the defining of initial gingival curves along the line around a tooth (LAT) on a patient's jaw, including within an interproximal area between teeth. The initial gingival curves are replaced with a modified, dynamic cutting curve comprising an offset adjustment configured to minimize weakening of a region of the aligner material within the interproximal area. This process for generating a modified, dynamic cutting curve within an interproximal area can be suitably applied or continued for each of other the teeth and interproximal areas between those teeth to define a complete dynamic cutting curve. The resulting complete dynamic cutting curve can then be output for conversion into machine executable code to facilitate cutting of the aligner material.