Trying to pathlib instead of os.path

[bowlofred]

You are assuming that if it's not a file that it must be a directory. But that's not the case. It might not exist at all. You've only given the filename to Path, not the entire path. So it's not looking in mydir for the files, it's looking in your current directory. When it's not found, is_file() returns False.

Change line 4 to something like dr = pathlib.Path(mydir, esb)

An alternative that is similar:

import pathlib
import os

mydir = 'C:\\02'
for file_object in pathlib.Path(mydir).iterdir():
    if file_object.is_dir():
        print(f"{file_object} is a Directory")
    elif file_object.is_file():
        print(f"{file_object} is a File")
    else:
        print(f"{file_object} is neither file nor directory.")