This paper presents and evaluates an active dual-sensor autofocusing system that combines an optical vision sensor and a tactile probe for autofocusing on arrays of small holes on freeform surfaces. The system has been tested on a two-axis test rig and then integrated onto a three-axis computer numerical control (CNC) milling machine, where the aim is to rapidly and controllably measure the hole position errors while the part is still on the machine. The principle of operation is for the tactile probe to locate the nominal positions of holes, and the optical vision sensor follows to focus and capture the images of the holes. The images are then processed to provide hole position measurement. In this paper, the autofocusing deviations are analyzed. First, the deviations caused by the geometric errors of the axes on which the dual-sensor unit is deployed are estimated to be 11 μm when deployed on a test rig and 7 μm on the CNC machine tool. Subsequently, the autofocusing deviations caused by the interaction of the tactile probe, surface, and small hole are mathematically analyzed and evaluated. The deviations are a result of the tactile probe radius, the curvatures at the positions where small holes are drilled on the freeform surface, and the effect of the position error of the hole on focusing. An example case study is provided for the measurement of a pattern of small holes on an elliptical cylinder on the two machines. The absolute sum of the autofocusing deviations is 118 μm on the test rig and 144 μm on the machine tool. This is much less than the 500 μm depth of field of the optical microscope. Therefore, the method is capable of capturing a group of clear images of the small holes on this workpiece for either implementation.