The possible methods of determining the cutting force—due to the great practical importance of knowing the force—have long been and are still intensively studied areas of cutting theory. In milling, cutting is a series of successive short material removals. During force measurement in such cases, the transient process that can be detected at the beginning of the process can influence the nature of the entire cutting cycle. The present study reports on the research, the aim of which was to explore the dynamic process of cutting force measurement in intermittent cutting. The measurements were made during face milling of C-steel and highly alloyed steel (X5CrNi 18–10). The milling head contained a single insert, with which the disturbing interaction of the multiple cutting edges was eliminated. As a result of the work, a method suitable for examining the close relationship between the initial transient nature of the milling cycle and the decay, as well as a mathematical model for the decay process, was developed. The model was validated with cutting experiments and measurements. The achieved results can be used to better understand the process of chip removal and to determine the actual power requirements of milling works.