The article investigates the typical conditions of gear rim machining in pilot production using end cylindrical milling cutters. A testing methodology is proposed to simulate gear rim machining conditions through rolling with a cutter under minimal cutting depth and thickness. The wear of the cutter is measured up to the point of cutting edge failure, and a correlation between edge failure and cutter rotation eccentricity is established. The limitations of manual data collection methods are identified. It is demonstrated that during manufacturing, the cutters exhibit significantly higher precision compared to the deviations present in the milling system. Experimental evidence confirms that when cutting edge oscillation occurs due to rotation eccentricity, the cylindrical profile of the cutter transforms into a series of hyperboloids. Furthermore, it is determined that while cutter tooth wear under rotation eccentricity is generally uniform, the most engaged tooth experiences accelerated wear proportional to the magnitude of edge oscillation at a given point.