Ball-end milling process is widely used in the die and mold manufacturing because of suitable one for the machining of free-form surface. During the process, the pencil cutting operation can be adopted before finish cut to eliminate overload in uncut area caused by large diameter of ball-end mill. The ball-end mill cutter for the pencil cutting is easily deflected by cutting force due to the long and thin shape, and the tool deflection in pencil cutting is one of the main reason of the machining errors in a free-form surface. The purpose of this study is to find the characteristics of deflected cutter trajectory by constructing measurement system with eddy-current sensor. It was found that the severe reduction of corner radius produced the overcut during the plane cutting. Up cutting method induced the overcut both plane and slope cutting, but down cutting one induced the undercut. From the experiments, down cutting with upward cutting path can generate the small undercut surface.