Question: I'm having an error when installing/updating any pip module in python3. Purging and reinstalling pip and every package I can thing of hasn't helped. Here's the error that I get in response to running python -m pip install --upgrade pip specifically (but the error is the same for attempting to install or update any pip module): Traceback (most recent call last): File "/usr/lib/python3.8/runpy.py", line 194, in _run_module_as_main return _run_code(code, main_globals, None, File "/usr/lib/python3.8/runpy.py", line 87, in _run_code exec(code, run_globals) File "/usr/lib/python3/dist-packages/pip/__main__.py", line 16, in <module> from pip._internal.cli.main import main as _main # isort:skip # noqa File "/usr/lib/python3/dist-packages/pip/_internal/cli/main.py", line 10, in <module> from pip._internal.cli.autocompletion import autocomplete File "/usr/lib/python3/dist-packages/pip/_internal/cli/autocompletion.py", line 9, in <module> from pip._internal.cli.main_parser import create_main_parser File "/usr/lib/python3/dist-packages/pip/_internal/cli/main_parser.py", line 7, in <module> from pip._internal.cli import cmdoptions File "/usr/lib/python3/dist-packages/pip/_internal/cli/cmdoptions.py", line 24, in <module> from pip._internal.exceptions import CommandError File "/usr/lib/python3/dist-packages/pip/_internal/exceptions.py", line 10, in <module> from pip._vendor.six import iteritems File "/usr/lib/python3/dist-packages/pip/_vendor/__init__.py", line 65, in <module> vendored("cachecontrol") File "/usr/lib/python3/dist-packages/pip/_vendor/__init__.py", line 36, in vendored __import__(modulename, globals(), locals(), level=0) File "<frozen importlib._bootstrap>", line 991, in _find_and_load File "<frozen importlib._bootstrap>", line 975, in _find_and_load_unlocked File "<frozen importlib._bootstrap>", line 655, in _load_unlocked File "<frozen importlib._bootstrap>", line 618, in _load_backward_compatible File "<frozen zipimport>", line 259, in load_module File "/usr/share/python-wheels/CacheControl-0.12.6-py2.py3-none-any.whl/cachecontrol/__init__.py", line 9, in <module> File "<frozen importlib._bootstrap>", line 991, in _find_and_load File "<frozen importlib._bootstrap>", line 975, in _find_and_load_unlocked File "<frozen importlib._bootstrap>", line 655, in _load_unlocked File "<frozen importlib._bootstrap>", line 618, in _load_backward_compatible File "<frozen zipimport>", line 259, in load_module File "/usr/share/python-wheels/CacheControl-0.12.6-py2.py3-none-any.whl/cachecontrol/wrapper.py", line 1, in <module> File "<frozen importlib._bootstrap>", line 991, in _find_and_load File "<frozen importlib._bootstrap>", line 975, in _find_and_load_unlocked File "<frozen importlib._bootstrap>", line 655, in _load_unlocked File "<frozen importlib._bootstrap>", line 618, in _load_backward_compatible File "<frozen zipimport>", line 259, in load_module File "/usr/share/python-wheels/CacheControl-0.12.6-py2.py3-none-any.whl/cachecontrol/adapter.py", line 5, in <module> File "<frozen importlib._bootstrap>", line 991, in _find_and_load File "<frozen importlib._bootstrap>", line 975, in _find_and_load_unlocked File "<frozen importlib._bootstrap>", line 655, in _load_unlocked File "<frozen importlib._bootstrap>", line 618, in _load_backward_compatible File "<frozen zipimport>", line 259, in load_module File "/usr/share/python-wheels/requests-2.22.0-py2.py3-none-any.whl/requests/__init__.py", line 95, in <module> File "<frozen importlib._bootstrap>", line 991, in _find_and_load File "<frozen importlib._bootstrap>", line 975, in _find_and_load_unlocked File "<frozen importlib._bootstrap>", line 655, in _load_unlocked File "<frozen importlib._bootstrap>", line 618, in _load_backward_compatible File "<frozen zipimport>", line 259, in load_module File "/usr/share/python-wheels/urllib3-1.25.8-py2.py3-none-any.whl/urllib3/contrib/pyopenssl.py", line 46, in <module> File "/home/patrick/.local/lib/python3.8/site-packages/OpenSSL/__init__.py", line 8, in <module> from OpenSSL import crypto, SSL File "/home/patrick/.local/lib/python3.8/site-packages/OpenSSL/crypto.py", line 3268, in <module> _lib.OpenSSL_add_all_algorithms() AttributeError: module 'lib' has no attribute 'OpenSSL_add_all_algorithms' Error in sys.excepthook: Traceback (most recent call last): File "/usr/lib/python3/dist-packages/apport_python_hook.py", line 72, in apport_excepthook from apport.fileutils import likely_packaged, get_recent_crashes File "/usr/lib/python3/dist-packages/apport/__init__.py", line 5, in <module> from apport.report import Report File "/usr/lib/python3/dist-packages/apport/report.py", line 32, in <module> import apport.fileutils File "/usr/lib/python3/dist-packages/apport/fileutils.py", line 12, in <module> import os, glob, subprocess, os.path, time, pwd, sys, requests_unixsocket File "/usr/lib/python3/dist-packages/requests_unixsocket/__init__.py", line 1, in <module> import requests File "<frozen importlib._bootstrap>", line 991, in _find_and_load File "<frozen importlib._bootstrap>", line 975, in _find_and_load_unlocked File "<frozen importlib._bootstrap>", line 655, in _load_unlocked File "<frozen importlib._bootstrap>", line 618, in _load_backward_compatible File "<frozen zipimport>", line 259, in load_module File "/usr/share/python-wheels/requests-2.22.0-py2.py3-none-any.whl/requests/__init__.py", line 95, in <module> File "<frozen importlib._bootstrap>", line 991, in _find_and_load File "<frozen importlib._bootstrap>", line 975, in _find_and_load_unlocked File "<frozen importlib._bootstrap>", line 655, in _load_unlocked File "<frozen importlib._bootstrap>", line 618, in _load_backward_compatible File "<frozen zipimport>", line 259, in load_module File "/usr/share/python-wheels/urllib3-1.25.8-py2.py3-none-any.whl/urllib3/contrib/pyopenssl.py", line 46, in <module> File "/home/patrick/.local/lib/python3.8/site-packages/OpenSSL/__init__.py", line 8, in <module> from OpenSSL import crypto, SSL File "/home/patrick/.local/lib/python3.8/site-packages/OpenSSL/crypto.py", line 3268, in <module> _lib.OpenSSL_add_all_algorithms() AttributeError: module 'lib' has no attribute 'OpenSSL_add_all_algorithms' Original exception was: Traceback (most recent call last): File "/usr/lib/python3.8/runpy.py", line 194, in _run_module_as_main return _run_code(code, main_globals, None, File "/usr/lib/python3.8/runpy.py", line 87, in _run_code exec(code, run_globals) File "/usr/lib/python3/dist-packages/pip/__main__.py", line 16, in <module> from pip._internal.cli.main import main as _main # isort:skip # noqa File "/usr/lib/python3/dist-packages/pip/_internal/cli/main.py", line 10, in <module> from pip._internal.cli.autocompletion import autocomplete File "/usr/lib/python3/dist-packages/pip/_internal/cli/autocompletion.py", line 9, in <module> from pip._internal.cli.main_parser import create_main_parser File "/usr/lib/python3/dist-packages/pip/_internal/cli/main_parser.py", line 7, in <module> from pip._internal.cli import cmdoptions File "/usr/lib/python3/dist-packages/pip/_internal/cli/cmdoptions.py", line 24, in <module> from pip._internal.exceptions import CommandError File "/usr/lib/python3/dist-packages/pip/_internal/exceptions.py", line 10, in <module> from pip._vendor.six import iteritems File "/usr/lib/python3/dist-packages/pip/_vendor/__init__.py", line 65, in <module> vendored("cachecontrol") File "/usr/lib/python3/dist-packages/pip/_vendor/__init__.py", line 36, in vendored __import__(modulename, globals(), locals(), level=0) File "<frozen importlib._bootstrap>", line 991, in _find_and_load File "<frozen importlib._bootstrap>", line 975, in _find_and_load_unlocked File "<frozen importlib._bootstrap>", line 655, in _load_unlocked File "<frozen importlib._bootstrap>", line 618, in _load_backward_compatible File "<frozen zipimport>", line 259, in load_module File "/usr/share/python-wheels/CacheControl-0.12.6-py2.py3-none-any.whl/cachecontrol/__init__.py", line 9, in <module> File "<frozen importlib._bootstrap>", line 991, in _find_and_load File "<frozen importlib._bootstrap>", line 975, in _find_and_load_unlocked File "<frozen importlib._bootstrap>", line 655, in _load_unlocked File "<frozen importlib._bootstrap>", line 618, in _load_backward_compatible File "<frozen zipimport>", line 259, in load_module File "/usr/share/python-wheels/CacheControl-0.12.6-py2.py3-none-any.whl/cachecontrol/wrapper.py", line 1, in <module> File "<frozen importlib._bootstrap>", line 991, in _find_and_load File "<frozen importlib._bootstrap>", line 975, in _find_and_load_unlocked File "<frozen importlib._bootstrap>", line 655, in _load_unlocked File "<frozen importlib._bootstrap>", line 618, in _load_backward_compatible File "<frozen zipimport>", line 259, in load_module File "/usr/share/python-wheels/CacheControl-0.12.6-py2.py3-none-any.whl/cachecontrol/adapter.py", line 5, in <module> File "<frozen importlib._bootstrap>", line 991, in _find_and_load File "<frozen importlib._bootstrap>", line 975, in _find_and_load_unlocked File "<frozen importlib._bootstrap>", line 655, in _load_unlocked File "<frozen importlib._bootstrap>", line 618, in _load_backward_compatible File "<frozen zipimport>", line 259, in load_module File "/usr/share/python-wheels/requests-2.22.0-py2.py3-none-any.whl/requests/__init__.py", line 95, in <module> File "<frozen importlib._bootstrap>", line 991, in _find_and_load File "<frozen importlib._bootstrap>", line 975, in _find_and_load_unlocked File "<frozen importlib._bootstrap>", line 655, in _load_unlocked File "<frozen importlib._bootstrap>", line 618, in _load_backward_compatible File "<frozen zipimport>", line 259, in load_module File "/usr/share/python-wheels/urllib3-1.25.8-py2.py3-none-any.whl/urllib3/contrib/pyopenssl.py", line 46, in <module> File "/home/patrick/.local/lib/python3.8/site-packages/OpenSSL/__init__.py", line 8, in <module> from OpenSSL import crypto, SSL File "/home/patrick/.local/lib/python3.8/site-packages/OpenSSL/crypto.py", line 3268, in <module> _lib.OpenSSL_add_all_algorithms() AttributeError: module 'lib' has no attribute 'OpenSSL_add_all_algorithms'  I'm running Ubuntu 20.04 in WSL. Python openssl is already installed. sudo apt install python3-openssl Reading package lists... Done Building dependency tree Reading state information... Done python3-openssl is already the newest version (19.0.0-1build1). 0 upgraded, 0 newly installed, 0 to remove and 0 not upgraded.  My assumption is that I need to re-install some stuff, but I'm not sure what. I've tried the obvious stuff like python3-openssl, libssl-dev, libffi-dev, and python3-pip itself and python3 alltogether.

Answer: As version 39.0.0 presented this bug, downgrading the cryptography package solves this, without purging or touching your OS. pip install cryptography==38.0.4 to downgrade from 39.0.0 which presented this error EDIT per @thomas, The error is a result of incompatibility between cryptography and pyopenssl, so if possible, also upgrading to openssl>22.1.0 should work: pip install -U pyopenssl cryptography