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reinstall-all fixes most issues

The following command should fix many problems you may encounter as a pipx user:

pipx reinstall-all

This is a good fix for the following problems:

  • System python was upgraded and the python used with a pipx-installed package is no longer available
  • pipx upgrade causes issues with old pipx-installed packages

pipx has been upgraded a lot over the years. If you are a long-standing pipx user (thanks, by the way!) then you may have old pipx-installed packages that have internal data that is different than what pipx currently expects. By executing pipx reinstall-all, pipx will re-write its internal data and this should fix many of issues you may encounter.

Note: If your pipx-installed package was installed using a pipx version before and you want to specify particular options, then you may want to uninstall and install it manually:

pipx uninstall <mypackage>
pipx install <mypackage>

Diagnosing problems using list

pipx list

will not only list all of your pipx-installed packages, but can also diagnose some problems with them, as well as suggest solutions.

Specifying pipx options

The most reliable method to specify command-line options that require an argument is to use an =-sign. An example:

pipx install pycowsay --pip-args="--no-cache-dir"

Another example for ignoring ssl/tls errors:

pipx install termpair --pip-args '--trusted-host --trusted-host --trusted-host --trusted-host'"

Check for PIP_* environment variables

pipx uses pip to install and manage packages. If you see pipx exhibiting strange behavior on install or upgrade, check that you don't have special environment variables that affect pip's behavior in your environment.

To check for pip environment variables, execute the following depending on your system:

Unix or macOS

env | grep '^PIP_'

Windows PowerShell

ls env:PIP_*

Windows cmd

set PIP_

Reference: pip Environment Variables

pipx log files

Pipx records a verbose log file for every pipx command invocation. The logs for the last 10 pipx commands can be found in $XDG_STATE_HOME/pipx/logs or user's log path if the former is not writable by the user.

For most users this location is ~/.local/state/pipx/logs, where ~ is your home directory.

Debian, Ubuntu issues

If you have issues using pipx on Debian, Ubuntu, or other Debian-based linux distributions, make sure you have the following packages installed on your system. (Debian systems do not install these by default with their python installations.)

sudo apt install python3-venv python3-pip

Reference: Python Packaging User Guide: Installing pip/setuptools/wheel with Linux Package Managers

macOS issues

If you want to use a Pipx-installed package in a shebang (a common example is the AWS CLI), you will likely not be able to, because the binary will be stored under ~/Library/Application Support/pipx/. The space in the path is not supported in a shebang. A simple solution is symlinking ~/Library/Application Support/pipx to ~/Library/ApplicationSupport/pipx, and using that as the path in the shebang instead.

mkdir $HOME/Library/ApplicationSupport
ln -s $HOME/Library/Application\ Support/pipx $HOME/Library/ApplicationSupport/pipx

Does it work to install your package with pip?

This is a tip for advanced users. An easy way to check if pipx is the problem or a package you're trying to install is the problem, is to try installing it using pip. For example:

Unix or macOS

python3 -m venv test_venv
test_venv/bin/python3 -m pip install <problem-package>


python -m venv test_venv
test_venv/Scripts/python -m pip install <problem-package>

If installation into this "virtual environment" using pip fails, then it's likely that the problem is with the package or your host system.

To clean up after this experiment:

rm -rf test_venv

Pipx files not in expected locations according to documentation

Pipx versions after 1.2.0 adopt the XDG base directory specification for the location of PIPX_HOME and the data, cache, and log directories. Version 1.2.0 and earlier use ~/.local/pipx as the default PIPX_HOME and install the data, cache, and log directories under it. To maintain compatibility with older versions, pipx will automatically use this old PIPX_HOME path if it exists. For a map of old and new paths, see Installation.

In Pipx version 1.5.0, this was reverted for Windows and MacOS. It defaults again to ~/.local/pipx on MacOS and to ~\pipx on Windows.

If you have a pipx version later than 1.2.0 and want to migrate from the old path to the new paths, you can move the ~/.local/pipx directory to the new location (after removing cache, log, and trash directories which will get recreated automatically) and then reinstall all packages. For example, on Linux systems, PIPX_HOME moves from ~/.local/pipx to ~/.local/share/pipx so you can do this:

rm -rf ~/.local/pipx/{.cache,logs,trash}
mkdir -p ~/.local/share && mv ~/.local/pipx ~/.local/share/
pipx reinstall-all

For moving the paths back after 1.5.0, you can perform the same steps, switching the paths around.