While this is generally an issue with pipx, it is likely to come up with pre-commit hooks (since the underlying binaries should be installed with pipx). The issue is the error Bad Interpreter No Such File or Directory when running a pipx-installed application, like poetry or black. This happens on MacOS because of a broken symlink between the application-specific binary path and the Python binary actually being used (I’ve found this to be a brew issue, specifically). This can be fixed with pipx reinstall-all, which will uninstall and reinstall all pipx applications with working symlinks to the appropriate Python binaries.