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I love Python. I think it is a very productive language for prototyping, pedagogy, and experimentation with a mature ecosystem to support you as you take your shit code ideas to production. However, in all my years using it, I could never get to upgrade pip, its preferred package manager, inside a virtualenv without problems. And that frustrates me.

The story starts with one of the first things you tell Python noobs before they pwn their own system and blame it all on hallowed Python: use virtualenvs. I’m not sure if this applies to Windows users (or if the concept of virtualenvs even applies to Windows users) but for *nix users, this advice makes sense since Python is often used by your system for other, more-important-than-your-side-projects, OS-y things it does. This is why Python often comes pre-packaged with the system and why you should use virtualenvs: the last thing you want is to upgrade the datetime library which your NTP daemon is using only to find out that said daemon relies on a particular quirk of that datetime library version to function properly. And so virtualenvs.

I do not intend to discuss how virtualenvs work, but suffice it to say that it does magic so that the libraries your projects need are isolated. If that whole story about NTP daemons and datetime above just flew over your head, at least appreciate how nice it is to have your dependencies isolated like that; alexandria could not see PyGame, and PyGame Objects could not see Flask, and yet I develop them on the same machine. It tingles that part of my brain which makes me put my glass/cup down at different spots on the table every time after I take a sip so that I end up with liquid circles touching each other but not overlapping. An ordered world is just so zen.

(Although I should note that I’ve long given up making PyGame work consistently with virtualenvs across the machines I use. Nowadays, I just containerize the whole thing to find almost the same peace of mind.)

Anyway, I’m beginning to digress. To proceed with the story, there comes a time when issuing pip commands inside a virtualenv results to the following warning:

(origin3) chad@scheherazade:~$ pip freeze
You are using pip version 8.1.2, however version 10.0.1 is available.

And, well, who does not want free updates? Not to mention when the software involved is not just free but also open-source. And have I told you that this free and open-source software is part of the ecosystem of my favorite programming language? Up-update and away, I say!

(origin3) chad@scheherazade:~$ pip install --upgrade pip
Collecting pip
  Using cached
Installing collected packages: pip
  Found existing installation: pip 8.1.2
    Not uninstalling pip at /home/chad/.venvburrito/lib/python2.7/site-packages/pip-8.1.2-py2.7.egg, outside environment /home/chad/.virtualenvs/origin3
Successfully installed pip-8.1.2

Err…okay, that did not really work. But not to worry! The beauty of using FOSS is that help is almost always available online. Especially on StackOverflow, a pillar of modern software engineering. Which leads us to the following words of wisdom:

pip is just a PyPI package like any other; you could use it to upgrade itself the same way you would upgrade any package:

~Cairnarvon on StackOverflow

But, but…Cairnarvon good sir, said instructions not working is what exactly set me on this quest! Then again, no one else is complaining that the accepted answer does not really work so I guess I’m the idiot here.

Thankfully, there are more words of wisdom in StackOverflow. If one option does not work, you have options. Fortunate then that this idiot can read. Since “pip is just a PyPI package”, it stands to reason that you can also upgrade it using its totally-not-sexy sibling of a package manager, easy_install.

Now, the other thing you tell Python noobs, maybe even before you tell them about virtualenvs, is to use pip over easy_install because reasons. So at this point, I am conflicted: one of the most ingrained teachings in my being is to use pip over easy_install but I have also been told to use updated software packages as much as possible. The latter urge wins out so I end up doing naughty things…

(origin3) chad@scheherazade:~$ easy_install pip
Searching for pip
Best match: pip 10.0.1
Adding pip 10.0.1 to easy-install.pth file
Installing pip3.6 script to /home/chad/.virtualenvs/origin3/bin
Installing pip3 script to /home/chad/.virtualenvs/origin3/bin
Installing pip script to /home/chad/.virtualenvs/origin3/bin

Using /home/chad/.virtualenvs/origin3/lib/python3.5/site-packages
Processing dependencies for pip
Finished processing dependencies for pip

…with good results:

(origin3) chad@scheherazade:pydagogical$ pip --version
pip 10.0.1 from /home/chad/.virtualenvs/origin3/lib/python3.5/site-packages/pip (python 3.5)

Or maybe not.

Bolstered by my enlightenment that you can upgrade pip using easy_install, I proceed to spin up new virtualenvs, just to savor the feeling of having an upgraded pip at last.

(spam) chad@scheherazade:~$ pip freeze
Traceback (most recent call last):
  File "/home/chad/.virtualenvs/spam/bin/pip", line 7, in 
    from pip._internal import main
ImportError: No module named 'pip._internal'

Thankfully, as a Professional Software Engineer with Years in the Industry, I can confidently read and debug the source code of the tools I am using. So I figured out that I should change line 7 of

# -*- coding: utf-8 -*-
import re
import sys
from pip._internal import main
if __name__ == '__main__':
    sys.argv[0] = re.sub(r'(-script\.pyw|\.exe)?$', '', sys.argv[0])


from pip import main

And everything should work fine and dandy again…

…except for the pip version:

(spam) chad@scheherazade:~$ pip --version
pip 8.1.2 from /home/chad/.venvburrito/lib/python2.7/site-packages/pip-8.1.2-py2.7.egg (python 3.5)

I remember first encountering this all the way back at 2012, under, I think, 10.04 Lucid Lynx. But back then, I had a potato for a computer–the kind which weeps against Eclipse–and Ubuntu isn’t as polished as it is now. But, for crying out loud, it is 2018, I am on machines with glorious i7 processors and at least 16GB of RAM and this shit is still a thing.

At this point, Python has gone from a language whose ecosystem just works to a time waster to rival all the times I had to manually type public static void main(String[] args) just to test a damn Java behavior. I call it quits and I’m just happy I even have virtualenvs with a working pip installation.

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