Abstract: Systems, computer-implemented methods, and computer program products for planning of a cutting boundary for removal of a diseased region of an anatomy, such as a bone tumor. A cutting surface is placed relative to the diseased region in a virtual model. An optimization algorithm specifies an optimization criterion that minimizes an amount of healthy region to be removed by the cutting surface and initializes candidate solutions to influence characteristics of the cutting surface. The optimization algorithm identifies a candidate solution that satisfies the optimization criterion and modifies characteristics of the cutting surface based on the identified candidate solution. The cutting boundary is defined relative to diseased region in the virtual model based on the modified cutting surface. The cutting boundary can be registered to the anatomy for constraining operation of a surgical tool in response to interaction of the surgical tool with the registered cutting boundary.