We updated/can update the setuptools version, which should fix the breakage?

Possibly.

I just tried to write a test for this (test_warning.py):

def test_pip_works_with_warnings_as_errors(script):
    script.environ['PYTHONWARNINGS'] = 'error'
    script.pip("--version", expect_stderr=False)

I think it should work, but right now I'm getting random test suite failures locally and I don't know why. I've just done the branch rename thing, maybe something happened there, or maybe there are test failures on main at the moment (I saw some PRs about fixing CI against main, but I think they were lint). Anyway, I don't have time to get my dev environment fixed up at the moment, so if someone else wants to add that test, feel free.

I do think that we should have the test, if only to ensure that the ensurepip PR doesn't break (because that's nearly always a last minute or after-the-fact part of the release in my experience, at which point finding out that the CPython tests fail is, shall we say, "unwelcome" 🙂)

If the test runs fine now, then I guess we might have already fixed the issue, but a quick manual test suggests not:

❯ pip --version                 
pip 21.1.dev0 from d:\work\projects\pip\src\pip (python 3.9)
PS 14:02 (.venv) [Git: main] 00:02.474 D:\Work\Projects\pip
❯ python -We -m pip --version
Traceback (most recent call last):
  File "d:\work\projects\pip\src\pip\_vendor\packaging\version.py", line 57, in parse
    return Version(version)
  File "d:\work\projects\pip\src\pip\_vendor\packaging\version.py", line 298, in __init__
    raise InvalidVersion("Invalid version: '{0}'".format(version))
pip._vendor.packaging.version.InvalidVersion: Invalid version: 'setuptools'

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "C:\Users\Gustav\AppData\Local\Programs\Python\Python39\lib\runpy.py", line 197, in _run_module_as_main
    return _run_code(code, main_globals, None,
  File "C:\Users\Gustav\AppData\Local\Programs\Python\Python39\lib\runpy.py", line 87, in _run_code
    exec(code, run_globals)
  File "d:\work\projects\pip\src\pip\__main__.py", line 21, in <module>
    from pip._internal.cli.main import main as _main
  File "d:\work\projects\pip\src\pip\_internal\cli\main.py", line 9, in <module>
    from pip._internal.cli.autocompletion import autocomplete
  File "d:\work\projects\pip\src\pip\_internal\cli\autocompletion.py", line 10, in <module>
    from pip._internal.cli.main_parser import create_main_parser
  File "d:\work\projects\pip\src\pip\_internal\cli\main_parser.py", line 8, in <module>
    from pip._internal.cli import cmdoptions
  File "d:\work\projects\pip\src\pip\_internal\cli\cmdoptions.py", line 23, in <module>
    from pip._internal.cli.parser import ConfigOptionParser
  File "d:\work\projects\pip\src\pip\_internal\cli\parser.py", line 12, in <module>
    from pip._internal.configuration import Configuration, ConfigurationError
  File "d:\work\projects\pip\src\pip\_internal\configuration.py", line 21, in <module>
    from pip._internal.exceptions import (
  File "d:\work\projects\pip\src\pip\_internal\exceptions.py", line 7, in <module>
    from pip._vendor.pkg_resources import Distribution
  File "d:\work\projects\pip\src\pip\_vendor\pkg_resources\__init__.py", line 3252, in <module>
    def _initialize_master_working_set():
  File "d:\work\projects\pip\src\pip\_vendor\pkg_resources\__init__.py", line 3235, in _call_aside
    f(*args, **kwargs)
  File "d:\work\projects\pip\src\pip\_vendor\pkg_resources\__init__.py", line 3264, in _initialize_master_working_set
    working_set = WorkingSet._build_master()
  File "d:\work\projects\pip\src\pip\_vendor\pkg_resources\__init__.py", line 574, in _build_master
    ws = cls()
  File "d:\work\projects\pip\src\pip\_vendor\pkg_resources\__init__.py", line 567, in __init__
    self.add_entry(entry)
  File "d:\work\projects\pip\src\pip\_vendor\pkg_resources\__init__.py", line 623, in add_entry
    for dist in find_distributions(entry, True):
  File "d:\work\projects\pip\src\pip\_vendor\pkg_resources\__init__.py", line 2061, in find_on_path
    path_item_entries = _by_version_descending(filtered)
  File "d:\work\projects\pip\src\pip\_vendor\pkg_resources\__init__.py", line 2034, in _by_version_descending
    return sorted(names, key=_by_version, reverse=True)
  File "d:\work\projects\pip\src\pip\_vendor\pkg_resources\__init__.py", line 2032, in _by_version
    return [packaging.version.parse(part) for part in parts]
  File "d:\work\projects\pip\src\pip\_vendor\pkg_resources\__init__.py", line 2032, in <listcomp>
    return [packaging.version.parse(part) for part in parts]
  File "d:\work\projects\pip\src\pip\_vendor\packaging\version.py", line 59, in parse
    return LegacyVersion(version)
  File "d:\work\projects\pip\src\pip\_vendor\packaging\version.py", line 127, in __init__
    warnings.warn(
DeprecationWarning: Creating a LegacyVersion has been deprecated and will be removed in the next major release

Sorry, that really is all I have time to do on this for now.

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