Pocket milling has been regarded as one of the most widely used operations in machining. The surface quality of the machined pockets is an essential aspect of any engineering and medical applications. In the current study, rotary ultrasonic machining (RUM) was applied for milling micro-pockets on alumina (Al2O3) ceramic. The objective of this research was to analyze the effect of the tool overlapping parameters on the surface roughness, surface morphology and the profiles of the machined pockets. Subsequently, the effect of different tool path strategies was analyzed on the surface quality and the material removal rate (MRR) of the machined pockets. A scanning electron microscope is used for analyzing the tool wear mechanisms. The experimental results provide evidence that the surface roughness, surface morphology and the MRR have been significantly affected by the considered tool overlapping and the tool path strategies. Furthermore, among the selected tool overlapping parameters (5–25%) and the tool path strategies, the best surface roughness (Ra = 0.155 μm and Rt = 1.432 µm) of the machined pockets can be found at 20% of the tool overlapping with a mix of uni-directional and zigzag tool path strategy.