Broken pip due to bad OpenSSL module

Question

whenever I run pip (python -m pip) I get the following error message:

  Traceback (most recent call last):
  File "/usr/bin/pip", line 11, in <module>
    load_entry_point('pip==20.0.2', 'console_scripts', 'pip')()
  File "/usr/lib/python3/dist-packages/pkg_resources/__init__.py", line 490, in load_entry_point
    return get_distribution(dist).load_entry_point(group, name)
  File "/usr/lib/python3/dist-packages/pkg_resources/__init__.py", line 2854, in load_entry_point
    return ep.load()
  File "/usr/lib/python3/dist-packages/pkg_resources/__init__.py", line 2445, in load
    return self.resolve()
  File "/usr/lib/python3/dist-packages/pkg_resources/__init__.py", line 2451, in resolve
    module = __import__(self.module_name, fromlist=['__name__'], level=0)
  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 "/usr/lib/python3/dist-packages/OpenSSL/__init__.py", line 8, in <module>
    from OpenSSL import crypto, SSL
  File "/usr/lib/python3/dist-packages/OpenSSL/crypto.py", line 1553, in <module>
    class X509StoreFlags(object):
  File "/usr/lib/python3/dist-packages/OpenSSL/crypto.py", line 1573, in X509StoreFlags
    CB_ISSUER_CHECK = _lib.X509_V_FLAG_CB_ISSUER_CHECK
AttributeError: module 'lib' has no attribute 'X509_V_FLAG_CB_ISSUER_CHECK'
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 "/usr/lib/python3/dist-packages/OpenSSL/__init__.py", line 8, in <module>
    from OpenSSL import crypto, SSL
  File "/usr/lib/python3/dist-packages/OpenSSL/crypto.py", line 1553, in <module>
    class X509StoreFlags(object):
  File "/usr/lib/python3/dist-packages/OpenSSL/crypto.py", line 1573, in X509StoreFlags
    CB_ISSUER_CHECK = _lib.X509_V_FLAG_CB_ISSUER_CHECK
AttributeError: module 'lib' has no attribute 'X509_V_FLAG_CB_ISSUER_CHECK'
Original exception was:
Traceback (most recent call last):
  File "/usr/bin/pip", line 11, in <module>
    load_entry_point('pip==20.0.2', 'console_scripts', 'pip')()
  File "/usr/lib/python3/dist-packages/pkg_resources/init.py", line 490, in load_entry_point
    return get_distribution(dist).load_entry_point(group, name)
  File "/usr/lib/python3/dist-packages/pkg_resources/init.py", line 2854, in load_entry_point
    return ep.load()
  File "/usr/lib/python3/dist-packages/pkg_resources/init.py", line 2445, in load
    return self.resolve()
  File "/usr/lib/python3/dist-packages/pkg_resources/init.py", line 2451, in resolve
    module = import(self.module_name, fromlist=['name'], level=0)
  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 "/usr/lib/python3/dist-packages/OpenSSL/init.py", line 8, in <module>
    from OpenSSL import crypto, SSL
  File "/usr/lib/python3/dist-packages/OpenSSL/crypto.py", line 1553, in <module>
    class X509StoreFlags(object):
  File "/usr/lib/python3/dist-packages/OpenSSL/crypto.py", line 1573, in X509StoreFlags
    CB_ISSUER_CHECK = _lib.X509_V_FLAG_CB_ISSUER_CHECK
AttributeError: module 'lib' has no attribute 'X509_V_FLAG_CB_ISSUER_CHECK'

I wanted to install requests but I got this error:

    /usr/lib/python3/dist-packages/secretstorage/dhcrypto.py:15: CryptographyDeprecationWarning: int_from_bytes is deprecated, use int.from_bytes instead
  from cryptography.utils import int_from_bytes
/usr/lib/python3/dist-packages/secretstorage/util.py:19: CryptographyDeprecationWarning: int_from_bytes is deprecated, use int.from_bytes instead
  from cryptography.utils import int_from_bytes

Then I wanted to fix it using this command:

pip3 list --outdated --format=freeze | grep -v '^\-e' | cut -d = -f 1 | xargs -n1 pip3 install -U

Now I always get this error saying that lib module lacks some var. I don't know what to do. I think that I should remove all pip packages which cause this, but I fear to completely brick my system. There seems to be something frozen also, but I don't know what this means.

How to fix this error?

Does this answer your question? module 'lib' has no attribute 'X509_V_FLAG_CB_ISSUER_CHECK' — Gilles 'SO- stop being evil', Oct 13 '22 at 13:11

score 2 · Answer 1 · answered May 23 '23 at 22:29

2

I had to remove pip and then install it again:

sudo apt remove python3-pip 
wget https://bootstrap.pypa.io/get-pip.py
sudo python3 get-pip.py

answered May 23 '23 at 22:29

user1046658

670

score 1 · Accepted Answer · answered Sep 22 '22 at 22:00

1

The following commands fixed this problem:

sudo apt update
sudo apt upgrade

answered Sep 22 '22 at 22:00

Max

31

score 0 · Answer 3 · answered Oct 03 '22 at 08:07

Possible solution is to upgrade using pip. Edit the crypto.py file and remove the offending line by commenting it out with a #

Then upgrade latest version of PyOpenSSL.

pip install pip --upgrade
pip install pyopenssl --upgrade

Now you can re-add the commented line again and it should be working

score 0 · Answer 4 · answered Dec 02 '23 at 20:01

This scenario typically happens when installing Pip packages globally, using sudo. As described in Pip issue 11795, this can easily break the system-wide Pip, and the "right way" is instead to install Pip packages always into virtual Python environments.

But first we have to clean up the mess. (The following assumes a Pip package install command caused the mess; if an apt command caused it, this is not the right solution for you.)

Replace the broken system-wide Pip with a local install (as already described in the answer by @user1046658):
```
sudo apt remove python3-pip
wget https://bootstrap.pypa.io/get-pip.py
sudo python3 get-pip.py
```
Use the new working Pip to uninstall the package that created the mess. For example, if installing Pip package certbot messed everything up, as it happened to me, use pip3-autoremove to uninstall it and all its unused dependencies:
```
sudo pip3 install pip3-autoremove
sudo pip3-autoremove certbot
```
Make sure the initial error message is gone by again executing python -m pip.
Switch back to a system-wide Pip. This is not strictly needed, but makes for a cleaner system as you know that all systemwide installed Python packages, including Pip itself, are installed via apt. The locally installed Pip version from above might be newer, but that is not necessary to have, as all Python applications that are not in the Ubuntu repos will be installed in virtual environments from now on, and thus bring their own version of Pip.
```
sudo pip3 uninstall pip
sudo apt install python3-pip
```
Make sure the initial error message is still gone, even when now using again Pip from the Ubuntu repos as initially: python -m pip.

score 0 · Answer 5 · answered Jan 19 '24 at 10:35

for me, the solution was reinstalling the openssl pip module globally.

Be warned that installing stuff via sudo pip might corrupt your system.

sudo update
sudo upgrade
sudo pip uninstall pyopenssl
sudo pip install pyopenssl

this reinstalled the latest versions and the warning disappeared

Broken pip due to bad OpenSSL module

5 Answers5

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