It looks like things are worse than I thought. Once I install python3-setuptools, even though the `docker` module now imports successfully, running `docker.from_env()` fails with the following: Python 3.12.3 (main, Apr 10 2024, 05:33:47) [GCC 13.2.0] on linux Type "help", "copyright", "credits" or "license" for more information. >>> import docker >>> docker.from_env() Traceback (most recent call last): File "/usr/lib/python3/dist-packages/docker/api/client.py", line 214, in _retrieve_server_version return self.version(api_version=False)["ApiVersion"] ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ File "/usr/lib/python3/dist-packages/docker/api/daemon.py", line 181, in version return self._result(self._get(url), json=True) ^^^^^^^^^^^^^^ File "/usr/lib/python3/dist-packages/docker/utils/decorators.py", line 46, in inner return f(self, *args, **kwargs) ^^^^^^^^^^^^^^^^^^^^^^^^ File "/usr/lib/python3/dist-packages/docker/api/client.py", line 237, in _get return self.get(url, **self._set_request_timeout(kwargs)) ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ File "/usr/lib/python3/dist-packages/requests/sessions.py", line 602, in get return self.request("GET", url, **kwargs) ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ File "/usr/lib/python3/dist-packages/requests/sessions.py", line 589, in request resp = self.send(prep, **send_kwargs) ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ File "/usr/lib/python3/dist-packages/requests/sessions.py", line 703, in send r = adapter.send(request, **kwargs) ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ File "/usr/lib/python3/dist-packages/requests/adapters.py", line 486, in send resp = conn.urlopen( ^^^^^^^^^^^^^ File "/usr/lib/python3/dist-packages/urllib3/connectionpool.py", line 791, in urlopen response = self._make_request( ^^^^^^^^^^^^^^^^^^^ File "/usr/lib/python3/dist-packages/urllib3/connectionpool.py", line 497, in _make_request conn.request( TypeError: HTTPConnection.request() got an unexpected keyword argument 'chunked' During handling of the above exception, another exception occurred: Traceback (most recent call last): File "", line 1, in File "/usr/lib/python3/dist-packages/docker/client.py", line 96, in from_env return cls( ^^^^ File "/usr/lib/python3/dist-packages/docker/client.py", line 45, in __init__ self.api = APIClient(*args, **kwargs) ^^^^^^^^^^^^^^^^^^^^^^^^^^ File "/usr/lib/python3/dist-packages/docker/api/client.py", line 197, in __init__ self._version = self._retrieve_server_version() ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ File "/usr/lib/python3/dist-packages/docker/api/client.py", line 221, in _retrieve_server_version raise DockerException( docker.errors.DockerException: Error while fetching server API version: HTTPConnection.request() got an unexpected keyword argument 'chunked' This is https://github.com/docker/docker-py/issues/3113, an issue reported about a year ago. Per the urllib3 maintainer, who commented on the bug: > I can confirm however that docker-py is not compatible with urllib3 2.0. Since requests will soon allow it, docker-py should modify setup.py to use urllib3 >= 1.26.0, < 2.0.0 or fix the bug. So, simply installing python3-setuptools won't be enough. The module code itself either needs patches, or it needs upgrading to a new upstream version. Per https://github.com/docker/docker-py/issues/3113#issuecomment-1536476705, the issue was fixed upstream starting with version 6.1.0.