This paper presents a swept envelope approach to determining the optimal tool orientation for five-axis tool-end machining. The swept profile of the cutter is determined based on the tool motion. By analyzing the swept profile against the part geometry, four types of machining errors (local gouge, side gouge, rear gouge, and global collision) are identified. The tool orientation is then corrected to avoid such errors. The cutter’s swept envelope is further constructed by integrating the intermediate swept profiles, and can be applied to NC simulation and verification. This paper analyzes the properties of the swept profile of a general cutter in five-axis tool-end machining. The relation of the swept profile, the part geometry, the tool motion, and the machining errors is developed. Therefore, the error sources can be detected early and prevented during tool path planning. The analytical results indicate that the optimal tool orientation occurs when the curvature of the cutter’s swept profile matches with the curvature of the local part surface. In addition, the optimal cutting direction generally follows the minimum curvature direction. Computer illustrations and example demonstrations are shown in this paper. The results reveal the developed method can accurately determine the optimal tool orientation and efficiently avoid machining errors for five-axis tool-end machining.