I'm closing this as not a bug. If the process limits DOS paths to MAX_PATH, then checking os.path.isfile() should not be special cased to support longer DOS paths because calling open() on such a path will raise FileNotFoundError. My suggestion in msg314126 to have stat() fall back on querying the directory in this case is too magical, even if it does make os.stat() more consistent with os.listdir() and the stat result from os.scandir().