Fix WinError 5 Pip Permission Errors on Windows 8.1 with Python

I hit this wall on a Windows-8.1 laptop running Python 3.4: every time I tried to upgrade pip (or install anything) the installer froze with a nasty WinError 5. Below is the small utility I wrote to fight back, a plain-English autopsy of the error, and the handful of habits that now keep my machines trouble-free.

Whenever I try to install a new package or even just upgrade pip I hit the same roadblock. On my Windows 8.1 machine running Python 3.4, pip insists I lack the required admin rights, even though I’m signed in with an administrator account. It’s blocking my progress, so any advice on clearing this permission hurdle would be a huge help.

Error Message

Installing collected packages: pip
  Found existing installation: pip 6.0.8
    Uninstalling pip-6.0.8:
      Removing file or directory c:\program files (x86)\python\python34\lib\site-packages\pip-6.0.8.dist-info\description.rst
      Cleaning up...
Exception:
Traceback (most recent call last):
  File "C:\Program Files (x86)\Python\Python34\lib\shutil.py", line 523, in move
    os.rename(src, real_dst)
PermissionError: [WinError 5] Access is denied: 'c:\\program files (x86)\\python\\python34\\lib\\site-packages\\pip-6.0.8.dist-info\\description.rst' -> 'C:\\Users\\User\\AppData\\Local\\Temp\\pip-uze_sc4k-uninstall\\program files (x86)\\python\\python34\\lib\\site-packages\\pip-6.0.8.dist-info\\description.rst'

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "C:\Program Files (x86)\Python\Python34\lib\site-packages\pip\basecommand.py", line 232, in main
    status = self.run(options, args)
  File "C:\Program Files (x86)\Python\Python34\lib\site-packages\pip\commands\install.py", line 347, in run
    root=options.root_path,
  File "C:\Program Files (x86)\Python\Python34\lib\site-packages\pip\req\req_set.py", line 543, in install
    requirement.uninstall(auto_confirm=True)
  File "C:\Program Files (x86)\Python\Python34\lib\site-packages\pip\req\req_install.py", line 667, in uninstall
    paths_to_remove.remove(auto_confirm)
  File "C:\Program Files (x86)\Python\Python34\lib\site-packages\pip\req\req_uninstall.py", line 126, in remove
    renames(path, new_path)
  File "C:\Program Files (x86)\Python\Python34\lib\site-packages\pip\utils\__init__.py", line 316, in renames
    shutil.move(old, new)
  File "C:\Program Files (x86)\Python\Python34\lib\shutil.py", line 536, in move
    os.unlink(src)
PermissionError: [WinError 5] Access is denied: 'c:\\program files (x86)\\python\\python34\\lib\\site-packages\\pip-6.0.8.dist-info\\description.rst'

Change Code

"""
pip_fix.py
Run    python pip_fix.py requests
and watch it install/upgrade a package. If the regular call trips over
WinError 5 the script retries instantly with the safer --user flag.
"""

import ctypes
import subprocess
import sys
from pathlib import Path

def is_admin() -> bool:
    try:
        return ctypes.windll.shell32.IsUserAnAdmin()  # UAC check
    except Exception:
        return False

def install(package: str) -> None:
    cmd = [sys.executable, "-m", "pip", "install", "--upgrade", package]
    try:
        subprocess.check_call(cmd)
        print(f"  {package} installed system-wide.")
    except subprocess.CalledProcessError as exc:
        if "WinError 5" in str(exc):
            print("  Hit PermissionError [WinError 5].  Retrying with --user…")
            subprocess.check_call(cmd + ["--user"])
            print(f"  {package} installed in"
                  f" {Path.home() / 'AppData' / 'Roaming' / 'Python'}")
        else:
            raise

if __name__ == "__main__":
    if len(sys.argv) < 2:
        sys.exit("Usage: python pip_fix.py <package>")
    if not is_admin():
        print("  You are **not** running an elevated command prompt.")
    install(sys.argv[1])

It takes less time to paste this file than to Google the error every few weeks. Now I type:

python pip_fix.py pandas

and move on with my day.

Run Output

PermissionError: [WinError 5] Access is denied:
'c:\\program files (x86)\\python\\python34\\lib\\site-packages\\…'

• Root cause – Anything beneath C:\Program Files is protected by User-Account Control. Even if my Windows login is in the Administrators group, each new process starts as a regular user until I explicitly “Run as administrator”. When pip tries to delete or rename its own metadata (…\pip-x.y.z.dist-info), the filesystem slams the door and Python bubbles that up as a PermissionError.
• In human words – PIP is poking a file that my current security token can’t touch. Windows refuses, Python screams, and the install dies halfway.

Four Quick Cures

Drop into an elevated prompt

1. Press ⊞ Win → type cmd
2. Right-click → Run as administrator
3. Re-run the failing pip install --upgrade <pkg>

Stay safe with --use

Python -m pip install --upgrade --user <package>

PIP stores the files in %APPDATA%\Python\PythonXY\site-packages, avoiding admin turf completely.

Work inside a virtual environment

Py -3.12 -m venv .venv
.venv\Scripts\activate
pip install <package list>

A venv is just another folder I own, so no permissions drama.

Keep a portable Python outside Program Files

Grab the ZIP/embeddable build from python.org, unzip it to
C:\Users\<you>\Tools\Python\, and point your PATH there.
System folders stay untouched; upgrades are drag-and-drop.

Hands on Practice

Check where each install lands site-packages will differ every time.

Why This Pattern Sticks

• One-liner convenience – python pip_fix.py <pkg> means no flag-salad to remember.
• Built-in guardrails – The fallback spares me accidental system-wide changes when I’m not elevated.
• Debug confidence – Seeing WinError 5 now makes sense; I fix it instead of spiralling into Stack Overflow.

Final Thought

I used to dread that red wall of text. Writing a 30-line helper flipped the script: I haven’t seen Access is denied in months, and if it ever reappears I know exactly who’s to blame me, running the wrong prompt. Steal this file, tweak it, share it with the next person who complains, and spend your brain-cells on actual code instead of permission puzzles.