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How do I update/upgrade pip itself from inside my virtual environment?

python
venv
pip
package-management
Alex KataevbyAlex Kataev·Jan 19, 2025
TLDR

To upgrade pip, run:

python -m pip install --upgrade pip # Injects latest pip directly into your veins.

Execute it from within your virtual environment to upgrade to the newest pip version.

The Comprehensive Guide

The Anatomy of the upgrade command

This command, python -m pip install --upgrade pip, specifically invokes the Python you're using to run the pip update. This ensures that the pip associated with that instance is targeted, which is especially critical in virtual environments.

The Misstep: Something you should not do

Never attempt to use pip update or pip update pip. It's a classic 'rookie move' — these commands simply don't exist in the pip lexicon. The --upgrade flag is the correct method for this action, upgrading pip to its latest and greatest iteration.

The Offbeat Path: Alternate Upgrade Methods

Remember, there's more than one way to skin a cat. While pip install --upgrade pip is the standard approach, the easy_install -U pip command can also upgrade pip within a virtual environment.

Special Measures for Windows

Windows users, this one's for you. Prepend the upgrade command with py -m, like so: py -m pip install --upgrade pip. It acts as a sort of 'spell of protection' against any potential conflicts with the Python version in play.

Confirmation Round: Checking the Upgraded Version

Much like a dog returns to its vomit... return to your pip with pip --version after the upgrade, and bask in the glory of the upgraded version announcement.

The Hardship of Debian's Version

Working with a Debian-based system? The system's package manager might be slinging an outdated version of pip. Take the reins and upgrade beyond what's given; newer pip features might just demand it.

Reaching for the sky: Skipping the Middleman

If you're the kind of person who loves being the first to own the latest gadget, fetch pip directly from the source using get-pip.py or curl. Instructions are provided in the official pip documentation — consider it as your treasure map.

Pinpoint Precision: Installing a Specific Version

To install a specific version, say 'hello' to the following format: python -m pip install pip==VERSION. Be sure to swap out VERSION with your desired version number — no free rides here.

Beyond Pip: Don't Forget Your Other Tools

Your Python toolbox isn't all about pip. After updating pip, you can wield it to update your other weapons of choice — requests, numpy, flask, your pick of the litter.

Aftercare Protocol: Restart Terminals and Editors

Upgrades can stir the pot. Weed out any chance of path and version-related hassles by giving the terminal and code editor a quick restart; consider it a mandatory post-upgrade cooldown.

Cache Conundrums: Bypass Caching During Installation

Some might call cache' a blessing, others a curse. To eschew any conflicts with old package versions, you can install packages with the --no-cache-dir flag:

pip install --no-cache-dir package_name # No old versions allowed at this party!

References