In recent years, various reasons for improvement of performance and efficiency in ultrasonic vibration–assisted machining processes have been reported, which were mostly descriptive and without sufficient analytical and empirical proofs. Among the different machining processes, the least amount of experimental data and analytical relations exist about ultrasonic-assisted milling. In this article, for the first time in ultrasonic-assisted milling, we have determined the times of tool–workpiece engagement and their separation from each other in each vibration cycle and then investigated the influence of vibration amplitude and cutting speed on tool–workpiece effective engagement in ultrasonic-assisted milling. Contrary to ultrasonic-assisted turning, cutting time in each vibration cycle in ultrasonic-assisted milling is different from each other. With the aid of comprehensive experiments at tool–workpiece engagement angles smaller than 90°, we have proved that the main reason for average cutting force decrease in ultrasonic-assisted milling compared with conventional milling is the separation of tool and workpiece that occurs in a portion of each vibration cycle, and other factors such as change of friction behavior have less importance. At investigated tool–workpiece engagement angles, experimental and analytical results agree with each other.