High speed milling (HSM) has great potential use in die/mold cutting, but traditional machining plans do exploit HSM capabilities effectively. An important consideration in HSM is to limit cutting force variations, and one way to do so is to reduce cutter-workpiece engagement (CWE) variations. CWE is measured as the area of the tool instantaneously engaged with the part. Estimating CWE as a function of the tool path requires repeated, expensive computations. This paper develops algorithms for a discretized computational model to make CWE computations for arbitrary shaped parts.