Comment 55 for bug 1991606

Ok, via LP: #2018519, here is a test case.

$ mkdir /tmp/home
$ export HOME=/tmp/home
$ sudo apt install dput python3-pip python3-distro-info
$ pip3 install -U setuptools
$ dput
Traceback (most recent call last):
  File "/usr/bin/dput", line 33, in <module>
    sys.exit(load_entry_point('dput===1.1.0ubuntu2', 'console_scripts', 'execute-dput')())
  File "/usr/bin/dput", line 25, in importlib_load_entry_point
    return next(matches).load()
  File "/usr/lib/python3.10/importlib/metadata/__init__.py", line 171, in load
    module = import_module(match.group('module'))
  File "/usr/lib/python3.10/importlib/__init__.py", line 126, in import_module
    return _bootstrap._gcd_import(name[level:], package, level)
  File "<frozen importlib._bootstrap>", line 1050, in _gcd_import
  File "<frozen importlib._bootstrap>", line 1027, in _find_and_load
  File "<frozen importlib._bootstrap>", line 1006, in _find_and_load_unlocked
  File "<frozen importlib._bootstrap>", line 688, in _load_unlocked
  File "<frozen importlib._bootstrap_external>", line 883, in exec_module
  File "<frozen importlib._bootstrap>", line 241, in _call_with_frames_removed
  File "/usr/share/dput/dput/dput.py", line 33, in <module>
    from .helper import dputhelper
  File "/usr/share/dput/dput/helper/dputhelper.py", line 17, in <module>
    import pkg_resources
  File "/tmp/home/.local/lib/python3.10/site-packages/pkg_resources/__init__.py", line 3327, in <module>
    def _initialize_master_working_set():
  File "/tmp/home/.local/lib/python3.10/site-packages/pkg_resources/__init__.py", line 3301, in _call_aside
    f(*args, **kwargs)
  File "/tmp/home/.local/lib/python3.10/site-packages/pkg_resources/__init__.py", line 3339, in _initialize_master_working_set
    working_set = WorkingSet._build_master()
  File "/tmp/home/.local/lib/python3.10/site-packages/pkg_resources/__init__.py", line 629, in _build_master
    ws.require(__requires__)
  File "/tmp/home/.local/lib/python3.10/site-packages/pkg_resources/__init__.py", line 966, in require
    needed = self.resolve(parse_requirements(requirements))
  File "/tmp/home/.local/lib/python3.10/site-packages/pkg_resources/__init__.py", line 827, in resolve
    dist = self._resolve_dist(
  File "/tmp/home/.local/lib/python3.10/site-packages/pkg_resources/__init__.py", line 852, in _resolve_dist
    if dist is None or (dist not in req and replace_conflicting):
  File "/tmp/home/.local/lib/python3.10/site-packages/pkg_resources/__init__.py", line 3204, in __contains__
    return self.specifier.contains(item, prereleases=True)
  File "/tmp/home/.local/lib/python3.10/site-packages/pkg_resources/_vendor/packaging/specifiers.py", line 902, in contains
    item = Version(item)
  File "/tmp/home/.local/lib/python3.10/site-packages/pkg_resources/_vendor/packaging/version.py", line 197, in __init__
    raise InvalidVersion(f"Invalid version: '{version}'")
pkg_resources.extern.packaging.version.InvalidVersion: Invalid version: '1.1.0ubuntu2'
$

I still think the better answer is "don't mix pip with your system install". But this is at least a test case that satisfies my constraint from above.