When machining miniaturized components, the contact conditions between the tool and the workpiece exhibit very small contact areas that are on the order of 10−5 mm2. Under these conditions, extremely high contact stresses are generated, and it is not clear whether macroscopic theories for the chip formation, cutting forces, and friction mechanisms are applicable. For this reason, the present investigation has focused on creating a basic understanding of the frictional behavior in very small scale machining processes so that evaluations of standard macroscale models could be performed. Specialized machining experiments were conducted on 70/30 brass materials using high-speed steel tools over a range of speeds, feeds, depths of cut, and tool rake angles. At each operating condition studied, the friction coefficient and the shear factor τk were obtained. Based on the experimental results, it was determined that the standard macroscopic theory for analyzing detailed friction mechanisms was insufficient in very small scale machining processes. An approach that utilized the shear factor, in contrast, was found to be better for decoupling the physical phenomena involved. Utilizing the shear factor as an analysis parameter, the parameters that significantly influence the friction in microscale machining processes were ascertained and discussed.