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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.

3

Answers


  1. Chosen as BEST ANSWER

    I figured it out. What I needed to do was to purge the apps, and delete ~/.local/lib/python3.8. This was the step that I'd been missing.

    So in the end, the fix was:

    sudo apt purge python3 python3-pip python3-openssl
    rm -rf ~/.local/lib/python3.8
    sudo apt install libssl-dev libffi-dev python3 python3-pip python3-openssl
    

    Then, I could run python -m pip install --upgrade pip without error.

    This solution is only suitable for Ubuntu in WSL.

    It's what I run, but follow up for other users has confirmed that it can completely break any installed desktop environments.


  2. 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

    Login or Signup to reply.
  3. Another solution would be to simply pip remove the pyOpenSSL and then install it again:

    pip uninstall pyOpenSSL
    pip install pyOpenSSL
    
    Login or Signup to reply.
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