reinstall-all reinstalls everything but pipx

[jaraco]

Describe the bug
I find I have to invoke reinstall-all after each Python update (#633). When I do, I see that pipx fails to reinstall with the error:

⛔ Error, the python executable would be deleted! Change it using the --python option or PIPX_DEFAULT_PYTHON environment variable.
...
The following package(s) failed to reinstall: pipx

This issue happened a few weeks ago and again today when I upgraded to Python 3.11.3 (using homebrew on macOS ARM).

Side note: I'm forced to pipx reinstall xonsh as that's the application that stops working after a Python upgrade. I notice that pipx still runs, and I didn't keep track of what happens to the other pipx-installed applications after the Python upgrade.

How to reproduce

 $ pipx reinstall-all --verbose
pipx >(setup:801): pipx version is 1.2.0
pipx >(setup:802): Default python interpreter is '/Users/jaraco/.local/pipx/venvs/pipx/bin/python'
pipx >(upgrade:91): Upgrading shared libraries in /Users/jaraco/.local/pipx/shared
upgrading shared libraries...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/shared/bin/python -m pip --disable-pip-version-check install --upgrade pip setuptools wheel
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/oathtool
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/oathtool
uninstalled oathtool! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/oathtool
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/oathtool/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/shared/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/oathtool/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: oathtool
installing oathtool...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/oathtool/bin/python -m pip install oathtool
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 38ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: oathtool
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/oathtool.
  installed package oathtool 2.3.1, installed using Python 3.11.3
  These apps are now globally available
    - oathtool
done! ✨ 🌟 ✨
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/git-fame
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/git-fame
uninstalled git-fame! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/git-fame
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/git-fame/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/git-fame/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: git-fame
installing git-fame...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/git-fame/bin/python -m pip install git-fame
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 56ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: git-fame
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/git-fame.
  installed package git-fame 2.0.1, installed using Python 3.11.3
  These apps are now globally available
    - git-fame
done! ✨ 🌟 ✨
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/cherry_picker
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/cherry-picker
uninstalled cherry-picker! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/cherry-picker
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/cherry-picker/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/cherry-picker/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: cherry-picker
installing cherry-picker...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/cherry-picker/bin/python -m pip install cherry-picker
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 65ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: cherry-picker
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/cherry_picker.
  installed package cherry-picker 2.1.0, installed using Python 3.11.3
  These apps are now globally available
    - cherry_picker
done! ✨ 🌟 ✨
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/flake8
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/flake8
uninstalled flake8! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/flake8
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/flake8/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/flake8/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: flake8
installing flake8...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/flake8/bin/python -m pip install flake8
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 37ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: flake8
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/flake8.
  installed package flake8 6.0.0, installed using Python 3.11.3
  These apps are now globally available
    - flake8
done! ✨ 🌟 ✨
⛔ Error, the python executable would be deleted! Change it using the --python option or PIPX_DEFAULT_PYTHON environment variable.
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/reno
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/reno
uninstalled reno! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/reno
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/reno/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/reno/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: reno
installing reno...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/reno/bin/python -m pip install reno
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 43ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: reno
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/reno.
  installed package reno 4.0.0, installed using Python 3.11.3
  These apps are now globally available
    - reno
done! ✨ 🌟 ✨
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/xon.sh
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/xonsh
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/xonsh-uptime
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/xonsh-cat
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/xonsh-uname
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/xonsh
uninstalled xonsh! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/xonsh
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/xonsh/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/xonsh/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: xonsh[ptk]
installing xonsh from spec 'xonsh[ptk]'...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/xonsh/bin/python -m pip install xonsh@git+https://github.com/xonsh/xonsh xonsh[ptk]
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 32ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: xonsh[ptk]
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/xonsh.
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/xonsh-cat.
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/xonsh-uname.
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/xonsh-uptime.
  installed package xonsh 0.13.4, installed using Python 3.11.3
  These apps are now globally available
    - xon.sh
    - xonsh
    - xonsh-cat
    - xonsh-uname
    - xonsh-uptime
done! ✨ 🌟 ✨
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: jaraco-clipboard
installing jaraco-clipboard...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/xonsh/bin/python -m pip install jaraco-clipboard
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 1142ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: jaraco-clipboard
  injected package jaraco-clipboard into venv xonsh
done! ✨ 🌟 ✨
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: keyring
installing keyring...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/xonsh/bin/python -m pip install keyring
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 76ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: keyring
  injected package keyring into venv xonsh
done! ✨ 🌟 ✨
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: xontrib-vox
installing xontrib-vox...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/xonsh/bin/python -m pip install xontrib-vox
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 46ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: xontrib-vox
  injected package xontrib-vox into venv xonsh
done! ✨ 🌟 ✨
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/blurb
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/blurb
uninstalled blurb! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/blurb
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/blurb/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/blurb/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: blurb
installing blurb...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/blurb/bin/python -m pip install blurb
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 24ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: blurb
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/blurb.
  installed package blurb 1.1.0, installed using Python 3.11.3
  These apps are now globally available
    - blurb
done! ✨ 🌟 ✨
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/keyring
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/keyring
uninstalled keyring! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/keyring
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/keyring/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/keyring/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: keyring
installing keyring...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/keyring/bin/python -m pip install keyring
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 37ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: keyring
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/keyring.
  installed package keyring 23.13.1, installed using Python 3.11.3
  These apps are now globally available
    - keyring
done! ✨ 🌟 ✨
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/stubtest
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/mypy
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/mypyc
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/dmypy
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/stubgen
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/mypy
uninstalled mypy! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/mypy
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/mypy/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/mypy/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: mypy
installing mypy...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/mypy/bin/python -m pip install mypy
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 46ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: mypy
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/dmypy.
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/mypy.
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/mypyc.
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/stubgen.
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/stubtest.
  installed package mypy 1.2.0, installed using Python 3.11.3
  These apps are now globally available
    - dmypy
    - mypy
    - mypyc
    - stubgen
    - stubtest
done! ✨ 🌟 ✨
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/hg
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/mercurial
uninstalled mercurial! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/mercurial
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/mercurial/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/mercurial/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: mercurial
installing mercurial...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/mercurial/bin/python -m pip install mercurial
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 29ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: mercurial
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/hg.
  installed package mercurial 6.4, installed using Python 3.11.3
  These apps are now globally available
    - hg
done! ✨ 🌟 ✨
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: dulwich
installing dulwich...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/mercurial/bin/python -m pip install dulwich
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 39ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: dulwich
  injected package dulwich into venv mercurial
done! ✨ 🌟 ✨
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: hg-evolve
installing hg-evolve...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/mercurial/bin/python -m pip install hg-evolve
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 26ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: hg-evolve
  injected package hg-evolve into venv mercurial
done! ✨ 🌟 ✨
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: hg-git
installing hg-git...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/mercurial/bin/python -m pip install hg-git
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 40ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: hg-git
  injected package hg-git into venv mercurial
done! ✨ 🌟 ✨
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: mercurial-keyring
installing mercurial-keyring...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/mercurial/bin/python -m pip install mercurial-keyring
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 52ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: mercurial-keyring
  injected package mercurial-keyring into venv mercurial
done! ✨ 🌟 ✨
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/tox-to-nox
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/nox
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/nox
uninstalled nox! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/nox
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/nox/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/nox/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: nox
installing nox...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/nox/bin/python -m pip install nox
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 45ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: nox
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/nox.
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/tox-to-nox.
  installed package nox 2022.11.21, installed using Python 3.11.3
  These apps are now globally available
    - nox
    - tox-to-nox
done! ✨ 🌟 ✨
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/http
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/httpie
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/https
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/httpie
uninstalled httpie! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/httpie
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/httpie/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/httpie/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: httpie
installing httpie...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/httpie/bin/python -m pip install httpie
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 87ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: httpie
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/http.
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/httpie.
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/https.
  installed package httpie 3.2.1, installed using Python 3.11.3
  These apps are now globally available
    - http
    - httpie
    - https
done! ✨ 🌟 ✨
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/fab
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/fabric
uninstalled fabric! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/fabric
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/fabric/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/fabric/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: fabric
installing fabric...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/fabric/bin/python -m pip install fabric
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 41ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: fabric
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/fab.
  installed package fabric 3.0.0, installed using Python 3.11.3
  These apps are now globally available
    - fab
done! ✨ 🌟 ✨
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: jaraco-fabric
installing jaraco-fabric...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/fabric/bin/python -m pip install jaraco-fabric
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 49ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: jaraco-fabric
  injected package jaraco-fabric into venv fabric
done! ✨ 🌟 ✨
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: keyring
installing keyring...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/fabric/bin/python -m pip install keyring
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 51ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: keyring
  injected package keyring into venv fabric
done! ✨ 🌟 ✨
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/pyproject-build
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/build
uninstalled build! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/build
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/build/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/build/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: build
installing build...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/build/bin/python -m pip install build
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 37ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: build
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/pyproject-build.
  installed package build 0.10.0, installed using Python 3.11.3
  These apps are now globally available
    - pyproject-build
done! ✨ 🌟 ✨
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/virtualenv
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/virtualenv
uninstalled virtualenv! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/virtualenv
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/virtualenv/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/virtualenv/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: virtualenv
installing virtualenv...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/virtualenv/bin/python -m pip install virtualenv
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 42ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: virtualenv
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/virtualenv.
  installed package virtualenv 20.21.0, installed using Python 3.11.3
  These apps are now globally available
    - virtualenv
done! ✨ 🌟 ✨
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/black-primer
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/blackd
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/black
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/black
uninstalled black! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/black
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/black/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/black/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: black
installing black...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/black/bin/python -m pip install black
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 44ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: black
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/black.
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/blackd.
  installed package black 23.3.0, installed using Python 3.11.3
  These apps are now globally available
    - black
    - black-primer
    - blackd
done! ✨ 🌟 ✨
pipx >(uninstall:132): removed file /Users/jaraco/.local/bin/pyoxidizer
pipx >(rmdir:55): removing directory /Users/jaraco/.local/pipx/venvs/pyoxidizer
uninstalled pyoxidizer! ✨ 🌟 ✨
creating virtual environment...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pipx/bin/python -m venv --without-pip /Users/jaraco/.local/pipx/venvs/pyoxidizer
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pyoxidizer/bin/python -c import sysconfig; print(sysconfig.get_path('purelib'))
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pyoxidizer/bin/python --version
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: pyoxidizer
installing pyoxidizer...
pipx >(run_subprocess:173): running /Users/jaraco/.local/pipx/venvs/pyoxidizer/bin/python -m pip install pyoxidizer
pipx >(run_subprocess:173): running <fetch_info_in_venv commands>
pipx >(get_venv_metadata_for_package:316): get_venv_metadata_for_package: 26ms
pipx >(_parsed_package_to_package_or_url:147): cleaned package spec: pyoxidizer
pipx >(_symlink_package_apps:111): Force is true. Removing /Users/jaraco/.local/bin/pyoxidizer.
  installed package pyoxidizer 0.24.0, installed using Python 3.11.3
  These apps are now globally available
    - pyoxidizer
done! ✨ 🌟 ✨
The following package(s) failed to reinstall: pipx

I reproduced that over and over.

Expected behavior

Pipx should be able to reinstall itself, at least on non-Windows machines. Or if it's not possible for some technical reason, it should account for this edge case and direct the user with some way to reinstall it.

I see there is guidance about "Change the [python executable]", but I have no idea what I'd change it to, as I've never specified it before.

I've installed pipx using:

pip-run pipx -- -m pipx install pipx

Where pip-run resolves to the Python 3.11 bin directory where it's installed.

I can use pip-run to side-load pipx and use that to reinstall pipx:

 $ pip-run pipx -- -m pipx reinstall pipx
uninstalled pipx! ✨ 🌟 ✨
  installed package pipx 1.2.0, installed using Python 3.11.3
  These apps are now globally available
    - pipx
done! ✨ 🌟 ✨

[jaraco]

While revisiting #633, I observed that setting PIP_DEFAULT_PYTHON (#633 (comment)) appears to work around this issue too. After setting it to $(which python3), the error goes away and pipx reinstall-all now works without error.

Is that the best recommendation? If so, should pipx be advertising this setting as a recommended one for all users?