On MacOS I am looping through the source folder of pdf's and checking the destination folder if the there is an existing subfolder with the same name as the file. I am encountering a problem when I run the program it goes directly to my else statement even though the subfolder I know exists. I have tested this on Windows and it works fine but for some reason I can't get it to run successfully on mac. The only thing I can think of is because of the .DS_Store hidden file type that is hanging this up. Here's my existing code import shutil import os from pathlib import Path source = '/Users/miram/Library/CloudStorage/OneDrive-Company/Docs/Test_SRCDirectory' dest = '/MAIN/Building-D1D-RFS2' fileword_target = "CRATE" #File Rename for file in Path(source).iterdir(): name = file.stem.split(fileword_target)[0].rstrip() subdir = Path(dest, name) print(f"Checking subdir: {subdir}") #Move file into folder that matches name variable if subdir.exists(): destination = Path(subdir, file.name) shutil.move(file, destination) print(f"{name} have been moved.") else: print(f"Folder not found for {name}") my files I am moving look like this: filename L1 CRATE D1D which the .stem/.strip should give me my subfolder name that I am searching for in the destination folder. Continue reading...