receiving order data, where the order data specifies a first personalization element;

constructing a geometric model for the customized jewelry item;

scaling the first personalization element to proper size;

projecting the first personalization element onto a three dimensional surface of the geometric model; and

converting the geometric model into a set of machinery instructions for a milling machine compensating for cutter geometry;

wherein the cutter geometry is tapered or cylindrical; and

wherein the step of converting the geometric model into a set of machining instructions comprises:

obtaining a plurality of machining patterns and associated cutting tools;

generating a first set of curves that define a first two dimensional toolpath based on cutter geometry for a first machining pattern from the plurality of machining patterns;

projecting the first two dimensional toolpath onto a surface of the customized item to generate a first resulting toolpath; rotating the first three dimensional toolpath by a first angle associated with the surface of the customized item to obtain a first resulting toolpath;

repeating steps of generating, projecting and rotating for a second machining pattern from the plurality of machining patterns to obtain a second resulting toolpath;

appending the second resulting toolpath to the first resulting toolpath to generate a master toolpath; and

converting coordinates from the master toolpath to a generic format file; wherein each of the steps is executed by one or more processors.