Poetry Fails to Install/Update more-itertools on macOS

[rjmoggach]

When running poetry self add poetry-plugin-shell, Poetry attempts to update more-itertools (from 10.5.0 -> 10.6.0), but fails with the error:

Command '['/opt/homebrew/Cellar/poetry/2.0.1/libexec/bin/python', 
'/opt/homebrew/Cellar/poetry/2.0.1/libexec/lib/python3.13/site-packages/virtualenv/seed/wheels/embed/pip-24.3.1-py3-none-any.whl/pip', 
'uninstall', 'more-itertools', '-y']' returned non-zero exit status 1.

The error indicates that more-itertools is not installed, yet Poetry still tries to uninstall it, leading to a failure.

Expected Behavior

Poetry should correctly detect whether more-itertools is installed and handle the update properly. If it’s not installed, it should install it rather than attempting an uninstall.

Environment Details

• OS: macOS (Apple Silicon)
• Python Version: 3.13.1 (Installed via Homebrew)
• Poetry Version: 2.0.1
• Package Manager: Homebrew
• Virtualenv: Poetry-managed

Steps to Reproduce

brew install python@3.13
curl -sSL https://install.python-poetry.org | python3 -
poetry self add poetry-plugin-shell

Suggested Fix

• Poetry should check if a package is installed before attempting to uninstall it.
• Ensure Poetry respects system-installed packages and does not conflict with Homebrew-managed dependencies.

[rjmoggach]

Full Shell Output:

Keep in mind I've done all the digging and more-itertools is not installed anywhere... brew, pip, poetry... I've deleted venv... cleared cache...

poetry self add poetry-plugin-shellellar/python@3.13/3.13.1/Frameworks/Python.framework/Versions/3.13/lib/python3.13/subprocess.py:577 in run
  - Updating certifi (2024.12.14 -> 2025.1.31)
  - Updating more-itertools (10.5.0 -> 10.6.0): Failed

  CalledProcessError

  Command '['/opt/homebrew/Cellar/poetry/2.0.1/libexec/bin/python', '/opt/homebrew/Cellar/poetry/2.0.1/libexec/lib/python3.13/site-packages/virtualenv/seed/wheels/embed/pip-24.3.1-py3-none-any.whl/pip', 'uninstall', 'more-itertools', '-y']' returned non-zero exit status 1.

  at /opt/homebrew/Cellar/python@3.13/3.13.1/Frameworks/Python.framework/Versions/3.13/lib/python3.13/subprocess.py:577 in run
       573│             # We don't call process.wait() as .__exit__ does that for us.
       574│             raise
       575│         retcode = process.poll()
       576│         if check and retcode:
    →  577│             raise CalledProcessError(retcode, process.args,
       578│                                      output=stdout, stderr=stderr)
       579│     return CompletedProcess(process.args, retcode, stdout, stderr)
       580│
       581│

The following error occurred when trying to handle this error:


  EnvCommandError

  Command ['/opt/homebrew/Cellar/poetry/2.0.1/libexec/bin/python', '/opt/homebrew/Cellar/poetry/2.0.1/libexec/lib/python3.13/site-packages/virtualenv/seed/wheels/embed/pip-24.3.1-py3-none-any.whl/pip', 'uninstall', 'more-itertools', '-y'] errored with the following return code 1

  Output:
  Found existing installation: more-itertools 10.5.0
  error: uninstall-no-record-file

  × Cannot uninstall more-itertools 10.5.0
  ╰─> The package's contents are unknown: no RECORD file was found for more-itertools.

  hint: The package was installed by brew. You should check if it can uninstall the package.


  at /opt/homebrew/Cellar/poetry/2.0.1/libexec/lib/python3.13/site-packages/poetry/utils/env/base_env.py:342 in _run
      338│                 output = subprocess.check_output(
      339│                     cmd, stderr=stderr, env=env, text=True, encoding=encoding, **kwargs
      340│                 )
      341│         except CalledProcessError as e:
    → 342│             raise EnvCommandError(e)
      343│
      344│         return output
      345│
      346│     def execute(self, bin: str, *args: str, **kwargs: Any) -> int:

Cannot install more-itertools.

[rjmoggach]

My working solution:

brew uninstall poetry
brew install pipx
pipx install poetry
poetry self add poetry-plugin-shell

Will leave to devs to close or investigate further.

[ericapisani]

@rjmoggach Thanks for posting this. I ran into this exact same issue doing routine updates and your solution worked like a charm ✨