A method includes acquiring an image of a cutter on a drill bit, determining a cutter dull condition based on the image of the cutter using a machine-learning method, wherein the machine-learning method is trained using a set of training images and a set of known cutter dull conditions, wherein each of the set of known cutter dull conditions is associated with one or more of a set of cutters depicted in the set of training images and determining a cutter degradation severity based the image of the cutter. The method also includes generating bit modification instructions based the cutter dull condition and the cutter degradation severity.