Python: Sort a Messy Downloads Folder by Year and Month

📎 This article includes 2 downloadable practice files ↓

Thousands of files in one Downloads or Scans folder? This script files them into 2019/06-Jun style folders automatically.

from pathlib import Path
from datetime import datetime
import shutil

SOURCE = Path(r"C:\Users\me\Downloads")
DRY_RUN = True                       # set to False to actually move files

for f in SOURCE.iterdir():
    if not f.is_file():
        continue
    when = datetime.fromtimestamp(f.stat().st_mtime)
    target = SOURCE / str(when.year) / when.strftime("%m-%b")
    target.mkdir(parents=True, exist_ok=True) if not DRY_RUN else None
    dest = target / f.name
    n = 1
    while dest.exists():                                   # never overwrite
        dest = target / f"{f.stem} ({n}){f.suffix}"
        n += 1
    print(("WOULD MOVE " if DRY_RUN else "MOVED ") + f.name, "->", dest.relative_to(SOURCE))
    if not DRY_RUN:
        shutil.move(str(f), str(dest))

How it works

• st_mtime is the last-modified time — for downloads that is usually when the file arrived.
• The while dest.exists() loop adds (1), (2)… instead of overwriting duplicates.
• Dry run first: read the printed plan, then set DRY_RUN = False.

Schedule it weekly with Windows Task Scheduler and the folder stays tidy on its own.