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I attempted to upgrade pip from 9.x to 19.3.1. Initially, this traceback prompts just when issuing pip. Now it happens when attempting pip list/install/uninstall. I've tried a few things including the solution here: 'pip install' fails for every package ("Could not find a version that satisfies the requirement")

The curl command in this also generates the same traceback.

I've tried sudo easy_install -U pip and that allowed me to run pip without the traceback but I still have the traceback when attempting to list/install/uninstall.

Here is the traceback:

Traceback (most recent call last):
  File "<stdin>", line 22318, in <module>
  File "<stdin>", line 198, in main
  File "<stdin>", line 83, in bootstrap
  File "/var/folders/zz/n8qtr4fd7pq4c0wgpswz2xf40000gq/T/tmp4UTKAc/pip.zip/pip/_internal/commands/install.py", line 23, in <module>
  File "/var/folders/zz/n8qtr4fd7pq4c0wgpswz2xf40000gq/T/tmp4UTKAc/pip.zip/pip/_internal/cli/req_command.py", line 20, in <module>
  File "/var/folders/zz/n8qtr4fd7pq4c0wgpswz2xf40000gq/T/tmp4UTKAc/pip.zip/pip/_internal/network/session.py", line 17, in <module>
  File "/var/folders/zz/n8qtr4fd7pq4c0wgpswz2xf40000gq/T/tmp4UTKAc/pip.zip/pip/_vendor/requests/__init__.py", line 97, in <module>
  File "/var/folders/zz/n8qtr4fd7pq4c0wgpswz2xf40000gq/T/tmp4UTKAc/pip.zip/pip/_vendor/urllib3/contrib/pyopenssl.py", line 46, in <module>
  File "/Library/Python/2.7/site-packages/OpenSSL/__init__.py", line 8, in <module>
    from OpenSSL import rand, crypto, SSL
  File "/Library/Python/2.7/site-packages/OpenSSL/rand.py", line 11, in <module>
    from OpenSSL._util import (
  File "/Library/Python/2.7/site-packages/OpenSSL/_util.py", line 6, in <module>
    from cryptography.hazmat.bindings.openssl.binding import Binding
  File "/Library/Python/2.7/site-packages/cryptography/hazmat/bindings/openssl/binding.py", line 182, in <module>
    Binding.init_static_locks()
  File "/Library/Python/2.7/site-packages/cryptography/hazmat/bindings/openssl/binding.py", line 139, in init_static_locks
    cls._ensure_ffi_initialized()
  File "/Library/Python/2.7/site-packages/cryptography/hazmat/bindings/openssl/binding.py", line 134, in _ensure_ffi_initialized
    cls._register_osrandom_engine()
  File "/Library/Python/2.7/site-packages/cryptography/hazmat/bindings/openssl/binding.py", line 99, in _register_osrandom_engine
    _openssl_assert(cls.lib, cls.lib.ERR_peek_error() == 0)
  File "/Library/Python/2.7/site-packages/cryptography/hazmat/bindings/openssl/binding.py", line 43, in _openssl_assert
    errors
cryptography.exceptions.InternalError: Unknown OpenSSL error. Please file an issue at https://github.com/pyca/cryptography/issues with information on how to reproduce this.

MacOS version: 10.14.6

openssl version: LibreSSL 3.0.2 (brew installed and added to PATH in .zshrc)

pip version: pip 19.3.1 from /Library/Python/2.7/site-packages/pip-19.3.1-py2.7.egg/pip (python 2.7)

ooTestifyoo
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