Film products are widely applicable as the main components of traditional flexible packaging products as well as high-tech electronic products. As the range of applicability expands and becomes more modernized, the required quality level also increases. In most cases, products are delivered to the customer in rolls. These rolls sometimes produce quality problems. This study considered the fixed bending region (FBR) of roll-type film products. The FBR can cause several quality problems such as wrinkles or mis-windings. To avoid second-phase quality problems, the horizontal oscillating technique is often used for winding. This paper presents a simulation model of the winding oscillation to determine the optimal oscillation width to avoid FBR-related problems and improve thickness smoothness.