Python "pip install " is failing with AttributeError: 'module' object has no attribute 'SSL_ST_INIT'

I ran into this issue as well. The solution proposed to run pip doesn't work because pip is broken too! I found this solved it for me:

sudo python -m easy_install --upgrade pyOpenSSL

This installed version 17.3.0 which was an upgrade to the (stock python-openssl on xenial) version ?0.15.1?. Note the massive change in version it could be they dropped the leading 0. in later versions.

Anyway, after that, pip and ansible started to work again.

I did the following which seemed to fix the error, not sure if it's the correct way, but it did fix the error on my machine:

I first backed up the directories below, recommend you do same.

rm -rf /usr/lib/python2.7/dist-packages/OpenSSLrm -rf /usr/lib/python2.7/dist-packages/pyOpenSSL-0.15.1.egg-infosudo pip install pyopenssl

I couldn't uninstall it because every time I ran pip I got the same error you did: 'module' object has no attribute 'SSL_ST_INIT'.

After the above my pip now works and more importantly my ansible now works (which was broken by my previous updates).

Not sure if it will work on your system, and removing things out of band, like I did, is risky at best, so as a warning, I would say, your mileage may vary with my kludgy fix, use caution!

Below method worked for me, I am using Ubuntu 20.04 and wanted to install Objection for Runtime manipulation and dynamic analysis of iOS apps.

Short Background:

I noticed that when I fired pip3 install objection in terminal it gave me same error as you but the directory path was little bit different.In my case it was related to python3.8, so I did following things

Solution:

rm -rf /home/smshrimant/.local/lib/python3.8/site-packages/OpenSSL/sudo rm -rf /usr/local/lib/python3.8/dist-packages/OpenSSL/