Automating the monitoring of machine tools poses a significant challenge, with previous studies relying on machine vision to address this issue, primarily focusing on measuring specific tool wear using custom algorithms. In this study, we introduce an automated tool wear monitoring process capable of assessing wear across various tools. Utilizing deep neural network models for image classification and segmentation, our proposed process effectively masks areas where tool wear occurs. The image classification model selects the best-performing backbone model based on the highest F1 score. To account for varying depths-of-cut lines among different tools in the masked area, we introduce an algorithm that utilizes the Hough transform to determine the horizontal angle with the cut line. By systematically measuring the maximum flank wear of diverse tools, including indexable, ball, and solid endmills, using this method, we can replace conventional manual processes. This approach can be extended and automated for various machine tools, offering substantial potential for enhancing manufacturing tool monitoring processes.