Versions no longer available with Python 3.10

[nickvanderstel]

We've been using setuptools 81.0.0 with our CI for a few months now, but this morning we were no longer able to install that version, and the latest available version reported by pip is 21.0.0. Any reason why python 3.10 would no longer have access to the more recent releases?

Update: this appears to be isolated to one machine, but we're not sure why this sudden behavior, as we didn't update anything over the past couple of days.

One thing I noticed is that running pip install -vv setuptools==81.0.0 stops fetching links from pypi at version 21. It isn't skipping more recent versions.

[sueun-dev]

yeah, Python 3.10 itself doesn't look like the reason.

I tried this in a fresh Python 3.10.20 venv and pip install --no-cache-dir setuptools==81.0.0 installs 81.0.0; an unpinned upgrade resolves to 82.0.1. PyPI also still lists 81.0.0 as Requires-Python >=3.9, non-yanked, with a py3-none-any wheel.

The update about -vv stopping at version 21 is the interesting bit. If pip isn't even seeing links after 21, it's probably reading a stale/truncated simple-index response or a mirror/proxy/cache, not rejecting 81 for Python compatibility.

I'd try forcing the real index and bypassing cache on that machine:

python -m pip install --no-cache-dir -i https://pypi.org/simple 'setuptools==81.0.0'
python -m pip config debug

If that works, check PIP_INDEX_URL, global pip config, and any CI/package-proxy cache in front of PyPI.

[cjmeyer]

@sueun-dev, I am seeing the exact same thing as @nickvanderstel. I tried your suggestion but still got an error:

ERROR: Could not find a version that satisfies the requirement setuptools==81.0.0

This followed by a whole list of versions ranging from 0.6b1 to 21.0.0. It then ends with the following error:

ERROR: No matching distribution found for setuptools==81.0.0

[sueun-dev]

@cjmeyer I rechecked that path a bit harder. On a clean Python 3.10.20 venv, this still installs for me:

python -m pip install --isolated --no-cache-dir -i https://pypi.org/simple 'setuptools==81.0.0'

The weird part is the list ending around 21.0.0. On the live PyPI simple page, setuptools-81.0.0 is present, but it's near the very end of a pretty large page. Right now I get about 534k bytes back, with 21.0.0 around offset 173k and 81.0.0 around offset 532k.

So I'd check whether that machine is getting a truncated/cached simple-index page, even when -i is set:

python - <<'PY'
import urllib.request
body = urllib.request.urlopen('https://pypi.org/simple/setuptools/', timeout=20).read().decode()
print(len(body))
print(body.find('setuptools-21.0.0'))
print(body.find('setuptools-81.0.0'))
print(body[-40:])
PY

python -m pip config debug
python -m pip debug --verbose

If the 81.0.0 offset is -1, or the response is way smaller than ~534k, that'd explain the pip output: pip isn't rejecting 81.0.0 for Python 3.10, it's never seeing that link. At that point I'd look for a proxy, package mirror, CI cache, or a no-index / find-links setting that -i alone doesn't override.

[cjmeyer]

@sueun-dev, running the above; it prints the following 3 numbers:

534141
173279
531897

I also tried to use curl to grab https://pypi.org/simple/setuptools as well as just using a browser to access it. In both cases I got a list of versions that went from 0.6b1 to 82.0.1.

[nickvanderstel]

I want to point out that @cjmeyer and I are dealing with this on the same machine, and I believe we have now seen issues with packages other than setuptools. We did make sure all OS packages were up to date and rebooted the server, but we're still seeing the same behavior.

To add to what @cjmeyer already provided, when running the following command:

python -m pip config debug

Nothing interesting was returned, all the fields were false so it doesn't look like we're getting a bad config somewhere.

[webknjaz]

And -vvvvv? Check what APIs pip hits, I guess? And older/newer pip versions.

[cjmeyer]

It appears that whatever was causing the issue has now resolved itself over the weekend.

[gistrec]

This looks more like an index/configuration issue than a Python 3.10 compatibility issue.

setuptools==81.0.0 is published on PyPI and supports Python >=3.9, so Python 3.10 should not by itself limit resolution to 21.0.0.

On the affected machine I would check:

1. Show what index pip is actually using:

python -m pip config list -v
echo "$PIP_INDEX_URL"
echo "$PIP_EXTRA_INDEX_URL"

Also check any pip.conf / pip.ini files and CI-level environment variables.

2. Compare what pip sees from the configured index vs PyPI directly:

python -m pip index versions setuptools -vv
python -m pip index versions setuptools --index-url https://pypi.org/simple/ -vv

3. Try bypassing local cache and any configured mirror:

python -m pip install --no-cache-dir --index-url https://pypi.org/simple/ -vv setuptools==81.0.0

If the direct PyPI command succeeds, then something local is overriding or truncating the package index, for example a corporate mirror, proxy cache, or pip config on that one host.

If it still stops at 21.0.0, please share the full -vv output plus:

python -m pip --version
python -m pip debug --verbose

That should show whether pip is filtering candidates locally or simply not receiving newer candidates from the index.

[nickvanderstel]

There was no difference in the versions reported by any of the commands. Here is the output of all the commands:

python -m pip config list -v

For variant 'global', will try loading '/etc/xdg/pip/pip.conf'
For variant 'global', will try loading '/etc/pip.conf'
For variant 'user', will try loading '/home/<user>/.pip/pip.conf'
For variant 'user', will try loading '/home/<user>/.config/pip/pip.conf'
For variant 'site', will try loading '/home/<user>/<work>/.direnv/python-3.10.12/pip.conf'

The following commands returned nothing:

echo "$PIP_INDEX_URL"
echo "$PIP_EXTRA_INDEX_URL"

python -m pip index versions setuptools -vv

* https://pypi.org/simple/setuptools/
Fetching project page and analyzing links: https://pypi.org/simple/setuptools/
Getting page https://pypi.org/simple/setuptools/
Found index url https://pypi.org/simple
Looking up "https://pypi.org/simple/setuptools/" in the cache
Request header has "max_age" as 0, cache bypassed
Starting new HTTPS connection (1): pypi.org:443
https://pypi.org:443 "GET /simple/setuptools/ HTTP/1.1" 304 0

python -m pip index versions setuptools --index-url https://pypi.org/simple/ -vv

1 location(s) to search for versions of setuptools:
* https://pypi.org/simple/setuptools/
Fetching project page and analyzing links: https://pypi.org/simple/setuptools/
Getting page https://pypi.org/simple/setuptools/
Found index url https://pypi.org/simple/
Looking up "https://pypi.org/simple/setuptools/" in the cache
Request header has "max_age" as 0, cache bypassed
Starting new HTTPS connection (1): pypi.org:443
https://pypi.org:443 "GET /simple/setuptools/ HTTP/1.1" 304 0

python -m pip install --no-cache-dir --index-url https://pypi.org/simple/ -vv setuptools==81.0.0
pip_verbose_1.txt

python -m pip --version

pip 22.0.2 from /home/<user>/<work>/.direnv/python-3.10.12/lib/python3.10/site-packages/pip (python 3.10)

python -m pip debug --verbose
pip_verbose_2.txt

[webknjaz]

This is interesting:

Skipping link: not a file: https://pypi.org/simple/setuptools/
Given no hashes to check 0 links for project 'setuptools': discarding no candidates
ERROR: Could not find a version that satisfies the requirement setuptools==81.0.0 (from versions: 0.6b1, 0.6b2, 0.6b3, 0.6b4, 0.6rc1, 0.6rc2, 0.6rc3, 0.6rc4, 0.6rc5, 0.6rc6, 0.6rc7, 0.6rc8, 0.6rc9, 0.6rc10, 0.6rc11, 0.7.2, 0.7.3, 0.7.4, 0.7.5, 0.7.6, 0.7.7, 0.7.8, 0.8, 0.9, 0.9.1, 0.9.2, 0.9.3, 0.9.4, 0.9.5, 0.9.6, 0.9.7, 0.9.8, 1.0, 1.1, 1.1.1, 1.1.2, 1.1.3, 1.1.4, 1.1.5, 1.1.6, 1.1.7, 1.2, 1.3, 1.3.1, 1.3.2, 1.4, 1.4.1, 1.4.2, 2.0, 2.0.1, 2.0.2, 2.1, 2.1.1, 2.1.2, 2.2, 3.0, 3.0.1, 3.0.2, 3.1, 3.2, 3.3, 3.4, 3.4.1, 3.4.2, 3.4.3, 3.4.4, 3.5, 3.5.1, 3.5.2, 3.6, 3.7, 3.7.1, 3.8, 3.8.1, 4.0, 4.0.1, 5.0, 5.0.1, 5.0.2, 5.1, 5.2, 5.3, 5.4, 5.4.1, 5.4.2, 5.5, 5.5.1, 5.6, 5.7, 5.8, 6.0.1, 6.0.2, 6.1, 7.0, 8.0, 8.0.1, 8.0.2, 8.0.3, 8.0.4, 8.1, 8.2, 8.2.1, 8.3, 9.0, 9.0.1, 9.1, 10.0, 10.0.1, 10.1, 10.2, 10.2.1, 11.0, 11.1, 11.2, 11.3, 11.3.1, 12.0, 12.0.1, 12.0.2, 12.0.3, 12.0.4, 12.0.5, 12.1, 12.2, 12.3, 12.4, 13.0.1, 13.0.2, 14.0, 14.1, 14.1.1, 14.2, 14.3, 14.3.1, 15.0, 15.1, 15.2, 16.0, 17.0, 17.1, 17.1.1, 18.0, 18.0.1, 18.1, 18.2, 18.3, 18.3.1, 18.3.2, 18.4, 18.5, 18.6, 18.6.1, 18.7, 18.7.1, 18.8, 18.8.1, 19.0, 19.1, 19.1.1, 19.2, 19.3, 19.4, 19.4.1, 19.5, 19.6, 19.6.1, 19.6.2, 19.7, 20.0, 20.1, 20.1.1, 20.2.2, 20.3, 20.3.1, 20.4, 20.6.6, 20.6.7, 20.6.8, 20.7.0, 20.8.0, 20.8.1, 20.9.0, 20.10.1, 21.0.0)
ERROR: No matching distribution found for setuptools==81.0.0
Exception information:
Traceback (most recent call last):
  File "/home/<user>/<work>/.direnv/python-3.10.12/lib/python3.10/site-packages/pip/_vendor/resolvelib/resolvers.py", line 348, in resolve
    self._add_to_criteria(self.state.criteria, r, parent=None)
  File "/home/<user>/<work>/.direnv/python-3.10.12/lib/python3.10/site-packages/pip/_vendor/resolvelib/resolvers.py", line 173, in _add_to_criteria
    raise RequirementsConflicted(criterion)
pip._vendor.resolvelib.resolvers.RequirementsConflicted: Requirements conflict: SpecifierRequirement('setuptools==81.0.0')

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/home/<user>/<work>/.direnv/python-3.10.12/lib/python3.10/site-packages/pip/_internal/resolution/resolvelib/resolver.py", line 94, in resolve
    result = self._result = resolver.resolve(
  File "/home/<user>/<work>/.direnv/python-3.10.12/lib/python3.10/site-packages/pip/_vendor/resolvelib/resolvers.py", line 481, in resolve
    state = resolution.resolve(requirements, max_rounds=max_rounds)
  File "/home/<user>/<work>/.direnv/python-3.10.12/lib/python3.10/site-packages/pip/_vendor/resolvelib/resolvers.py", line 350, in resolve
    raise ResolutionImpossible(e.criterion.information)
pip._vendor.resolvelib.resolvers.ResolutionImpossible: [RequirementInformation(requirement=SpecifierRequirement('setuptools==81.0.0'), parent=None)]

The above exception was the direct cause of the following exception:

Traceback (most recent call last):
  File "/home/<user>/<work>/.direnv/python-3.10.12/lib/python3.10/site-packages/pip/_internal/cli/base_command.py", line 165, in exc_logging_wrapper
    status = run_func(*args)
  File "/home/<user>/<work>/.direnv/python-3.10.12/lib/python3.10/site-packages/pip/_internal/cli/req_command.py", line 205, in wrapper
    return func(self, options, args)
  File "/home/<user>/<work>/.direnv/python-3.10.12/lib/python3.10/site-packages/pip/_internal/commands/install.py", line 339, in run
    requirement_set = resolver.resolve(
  File "/home/<user>/<work>/.direnv/python-3.10.12/lib/python3.10/site-packages/pip/_internal/resolution/resolvelib/resolver.py", line 103, in resolve
    raise error from e
pip._internal.exceptions.DistributionNotFound: No matching distribution found for setuptools==81.0.0
Removed build tracker: '/tmp/pip-req-tracker-9v3gh8ys'

If the depresolver only sees versions up until 21.0.0, maybe it doesn't load the entire https://pypi.org/simple/setuptools/. I thought that maybe this was somehow related to the urllib3 hardening (I recall one case where the server would report the content length header differing from the actual HTTP response body bytes served; I've also checked that curl -v --http1.1 -s https://pypi.org/simple/setuptools/ | wc -c - actually corresponds to Content-Length: 534141 on my machine), but you seem to be running old enough toolchain that wouldn't have it. Although, it's unclear where you get your Python 3.10.12 — some downstream builds might have patches that appeared upstream in later versions.

Have you checked your ls -l /etc/xdg/pip/pip.conf /etc/pip.conf ~/.pip/pip.conf ~/.config/pip/pip.conf ~/*/.direnv/python-3.10.12/pip.conf and tail /etc/xdg/pip/pip.conf /etc/pip.conf ~/.pip/pip.conf ~/.config/pip/pip.conf ~/*/.direnv/python-3.10.12/pip.conf?

The last upstream security release of Python 3.10 is 3.10.20 — you may want to try upgrading or get the same 3.10.12 from a different source.

Personally, I'd try to stick a breakpoint() into /home/<user>/<work>/.direnv/python-3.10.12/lib/python3.10/site-packages/pip/_vendor/resolvelib/resolvers.py:173 and go from there. I often do this when I have to figure out the context of why some deps behave they way they do. Pdb is your friend. You could go up the stack and see what HTTP response pip sees, actually.

Also, add --no-deps to your install / download subcommands — if this is scoped to installing one project, you probably want to have the depresolver skip looking into the transitive deps.

---

FWIW, it's not reproducible on my machine with the exact CPython version (installed via pyenv) in a virtualenv with

$ cat ~/.config/pip/pip.conf   
[global]
user = false
require-virtualenv = true

[install]
use-pep517 = true

$ pyenv install 3.10.12
Downloading Python-3.10.12.tar.xz...
-> https://www.python.org/ftp/python/3.10.12/Python-3.10.12.tar.xz
Installing Python-3.10.12...
Installed Python-3.10.12 to ~/.pyenv/versions/3.10.12

$ pyenv virtualenv 3.10.12 setuptools-5236-repro-py3.10.12

$ pyenv shell setuptools-5236-repro-py3.10.12

$ python -V
Python 3.10.12

$ python -m pip uninstall setuptools
Found existing installation: setuptools 65.5.0
Uninstalling setuptools-65.5.0:
  Would remove:
    ~/.pyenv/versions/3.10.12/envs/setuptools-5236-repro-py3.10.12/lib/python3.10/site-packages/_distu
tils_hack/*
    ~/.pyenv/versions/3.10.12/envs/setuptools-5236-repro-py3.10.12/lib/python3.10/site-packages/distut
ils-precedence.pth
    ~/.pyenv/versions/3.10.12/envs/setuptools-5236-repro-py3.10.12/lib/python3.10/site-packages/pkg_re
sources/*
    ~/.pyenv/versions/3.10.12/envs/setuptools-5236-repro-py3.10.12/lib/python3.10/site-packages/setupt
ools-65.5.0.dist-info/*
    ~/.pyenv/versions/3.10.12/envs/setuptools-5236-repro-py3.10.12/lib/python3.10/site-packages/setupt
ools/*
Proceed (Y/n)? y
  Successfully uninstalled setuptools-65.5.0

$ python -m pip install pip==22.0.2
Collecting pip==22.0.2
  Downloading pip-22.0.2-py3-none-any.whl (2.1 MB)
     ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ 2.1/2.1 MB 14.6 MB/s eta 0:00:00
Installing collected packages: pip
  Attempting uninstall: pip
    Found existing installation: pip 23.0.1
    Uninstalling pip-23.0.1:
      Successfully uninstalled pip-23.0.1
Successfully installed pip-22.0.2

$ python -m pip list                
Package Version
------- -------
pip     22.0.2
WARNING: You are using pip version 22.0.2; however, version 26.1.2 is available.
You should consider upgrading via the '~/.pyenv/versions/setuptools-5236-repro-py3.10.12/bin/python -m pip install --upgrade pip' command.

$ python -m pip download --no-deps --no-cache-dir --index-url https://pypi.org/simple/ setuptools==81.0.0
Looking in indexes: https://pypi.org/simple/
Collecting setuptools==81.0.0
  Downloading setuptools-81.0.0-py3-none-any.whl (1.1 MB)
     ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ 1.1/1.1 MB 12.5 MB/s eta 0:00:00
Saved ./setuptools-81.0.0-py3-none-any.whl
Successfully downloaded setuptools
WARNING: You are using pip version 22.0.2; however, version 26.1.2 is available.
You should consider upgrading via the '~/.pyenv/versions/setuptools-5236-repro-py3.10.12/bin/python -m pip install --upgrade pip' command.

➜ python -m pip index versions setuptools
WARNING: pip index is currently an experimental command. It may be removed/changed in a future release without prior warning.
setuptools (82.0.1)
Available versions: 82.0.1, 82.0.0, 81.0.0, 80.10.2, 80.10.1, 80.9.0, 80.8.0, 80.7.1, 80.6.0, 80.4.0, 80.3.1, 80.2.0, 80.1.0, 80.0.1, 80.0.0, 79.0.1, 79.0.0, 78.1.1, 78.1.0, 78.0.2, 78.0.1, 77.0.3, 77.0.1, 76.1.0, 76.0.0, 75.9.1, 75.8.2, 75.8.1, 75.8.0, 75.7.0, 75.6.0, 75.5.0, 75.4.0, 75.3.4, 75.3.3, 75.3.2, 75.3.1, 75.3.0, 75.2.0, 75.1.0, 75.0.0, 74.1.3, 74.1.2, 74.1.1, 74.1.0, 74.0.0, 73.0.1, 73.0.0, 72.2.0, 72.1.0, 71.1.0, 71.0.4, 71.0.3, 71.0.2, 71.0.0, 70.3.0, 70.2.0, 70.1.1, 70.1.0, 70.0.0, 69.5.1, 69.5.0, 69.4.2, 69.4.1, 69.3.1, 69.2.0, 69.1.1, 69.1.0, 69.0.3, 69.0.2, 69.0.1, 69.0.0, 68.2.2, 68.2.1, 68.2.0, 68.1.2, 68.1.0, 68.0.0, 67.8.0, 67.7.2, 67.7.1, 67.7.0, 67.6.1, 67.6.0, 67.5.1, 67.5.0, 67.4.0, 67.3.3, 67.3.2, 67.3.1, 67.2.0, 67.1.0, 67.0.0, 66.1.1, 66.1.0, 66.0.0, 65.7.0, 65.6.3, 65.6.2, 65.6.1, 65.6.0, 65.5.1, 65.5.0, 65.4.1, 65.4.0, 65.3.0, 65.2.0, 65.1.1, 65.1.0, 65.0.2, 65.0.1, 65.0.0, 64.0.3, 64.0.2, 64.0.1, 64.0.0, 63.4.3, 63.4.2, 63.4.1, 63.4.0, 63.3.0, 63.2.0, 63.1.0, 63.0.0, 62.6.0, 62.5.0, 62.4.0, 62.3.4, 62.3.3, 62.3.2, 62.3.1, 62.3.0, 62.2.0, 62.1.0, 62.0.0, 61.3.1, 61.3.0, 61.2.0, 61.1.1, 61.1.0, 61.0.0, 60.10.0, 60.9.3, 60.9.2, 60.9.1, 60.9.0, 60.8.2, 60.8.1, 60.8.0, 60.7.1, 60.7.0, 60.6.0, 60.5.0, 60.4.0, 60.3.1, 60.2.0, 60.1.1, 60.1.0, 60.0.5, 60.0.4, 60.0.3, 60.0.2, 60.0.1, 60.0.0, 59.8.0, 59.7.0, 59.6.0, 59.5.0, 59.4.0, 59.3.0, 59.2.0, 59.1.1, 59.0.1, 58.5.3, 58.5.2, 58.5.1, 58.5.0, 58.4.0, 58.3.0, 58.2.0, 58.1.0, 58.0.4, 58.0.3, 58.0.2, 58.0.1, 58.0.0, 57.5.0, 57.4.0, 57.3.0, 57.2.0, 57.1.0, 57.0.0, 56.2.0, 56.1.0, 56.0.0, 54.2.0, 54.1.3, 54.1.2, 54.1.1, 54.1.0, 54.0.0, 53.1.0, 53.0.0, 52.0.0, 51.3.3, 51.3.2, 51.3.1, 51.3.0, 51.2.0, 51.1.2, 51.1.1, 51.1.0, 51.0.0, 50.3.2, 50.3.1, 50.3.0, 50.2.0, 50.1.0, 50.0.3, 50.0.2, 50.0.1, 50.0.0, 49.6.0, 49.5.0, 49.4.0, 49.3.2, 49.3.1, 49.3.0, 49.2.1, 49.2.0, 49.1.3, 49.1.2, 49.1.1, 49.1.0, 49.0.1, 49.0.0, 48.0.0, 47.3.2, 47.3.1, 47.3.0, 47.2.0, 47.1.1, 47.1.0, 47.0.0, 46.4.0, 46.3.1, 46.3.0, 46.2.0, 46.1.3, 46.1.2, 46.1.1, 46.1.0, 46.0.0, 45.3.0, 45.2.0, 45.1.0, 45.0.0, 44.1.1, 44.1.0, 44.0.0, 43.0.0, 42.0.2, 42.0.1, 42.0.0, 41.6.0, 41.5.1, 41.5.0, 41.4.0, 41.3.0, 41.2.0, 41.1.0, 41.0.1, 41.0.0, 40.9.0, 40.8.0, 40.7.3, 40.7.2, 40.7.1, 40.7.0, 40.6.3, 40.6.2, 40.6.1, 40.6.0, 40.5.0, 40.4.3, 40.4.2, 40.4.1, 40.4.0, 40.3.0, 40.2.0, 40.1.1, 40.1.0, 40.0.0, 39.2.0, 39.1.0, 39.0.1, 39.0.0, 38.7.0, 38.6.1, 38.6.0, 38.5.2, 38.5.1, 38.5.0, 38.4.1, 38.4.0, 38.3.0, 38.2.5, 38.2.4, 38.2.3, 38.2.1, 38.2.0, 38.1.0, 38.0.0, 37.0.0, 36.8.0, 36.7.2, 36.7.1, 36.7.0, 36.6.1, 36.6.0, 36.5.0, 36.4.0, 36.3.0, 36.2.7, 36.2.6, 36.2.5, 36.2.4, 36.2.3, 36.2.2, 36.2.1, 36.2.0, 36.1.1, 36.1.0, 36.0.1, 35.0.2, 35.0.1, 35.0.0, 34.4.1, 34.4.0, 34.3.3, 34.3.2, 34.3.1, 34.3.0, 34.2.0, 34.1.1, 34.1.0, 34.0.3, 34.0.2, 34.0.1, 34.0.0, 33.1.1, 33.1.0, 32.3.1, 32.3.0, 32.2.0, 32.1.3, 32.1.2, 32.1.1, 32.1.0, 32.0.0, 31.0.1, 31.0.0, 30.4.0, 30.3.0, 30.2.1, 30.2.0, 30.1.0, 30.0.0, 29.0.1, 29.0.0, 28.8.1, 28.8.0, 28.7.1, 28.7.0, 28.6.1, 28.6.0, 28.5.0, 28.4.0, 28.3.0, 28.2.0, 28.1.0, 28.0.0, 27.3.1, 27.3.0, 27.2.0, 27.1.2, 27.1.0, 27.0.0, 26.1.1, 26.1.0, 26.0.0, 25.4.0, 25.3.0, 25.2.0, 25.1.6, 25.1.5, 25.1.4, 25.1.3, 25.1.2, 25.1.1, 25.1.0, 25.0.2, 25.0.1, 25.0.0, 24.3.1, 24.3.0, 24.2.1, 24.2.0, 24.1.1, 24.1.0, 24.0.3, 24.0.2, 24.0.1, 24.0.0, 23.2.1, 23.2.0, 23.1.0, 23.0.0, 22.0.5, 22.0.4, 22.0.2, 22.0.1, 22.0.0, 21.2.2, 21.2.1, 21.2.0, 21.1.0, 21.0.0, 20.10.1, 20.9.0, 20.8.1, 20.8.0, 20.7.0, 20.6.8, 20.6.7, 20.6.6, 20.4, 20.3.1, 20.3, 20.2.2, 20.1.1, 20.1, 20.0, 19.7, 19.6.2, 19.6.1, 19.6, 19.5, 19.4.1, 19.4, 19.3, 19.2, 19.1.1, 19.1, 19.0, 18.8.1, 18.8, 18.7.1, 18.7, 18.6.1, 18.6, 18.5, 18.4, 18.3.2, 18.3.1, 18.3, 18.2, 18.1, 18.0.1, 18.0, 17.1.1, 17.1, 17.0, 16.0, 15.2, 15.1, 15.0, 14.3.1, 14.3, 14.2, 14.1.1, 14.1, 14.0, 13.0.2, 13.0.1, 12.4, 12.3, 12.2, 12.1, 12.0.5, 12.0.4, 12.0.3, 12.0.2, 12.0.1, 12.0, 11.3.1, 11.3, 11.2, 11.1, 11.0, 10.2.1, 10.2, 10.1, 10.0.1, 10.0, 9.1, 9.0.1, 9.0, 8.3, 8.2.1, 8.2, 8.1, 8.0.4, 8.0.3, 8.0.2, 8.0.1, 8.0, 7.0, 6.1, 6.0.2, 6.0.1, 5.8, 5.7, 5.6, 5.5.1, 5.5, 5.4.2, 5.4.1, 5.4, 5.3, 5.2, 5.1, 5.0.2, 5.0.1, 5.0, 4.0.1, 4.0, 3.8.1, 3.8, 3.7.1, 3.7, 3.6, 3.5.2, 3.5.1, 3.5, 3.4.4, 3.4.3, 3.4.2, 3.4.1, 3.4, 3.3, 3.2, 3.1, 3.0.2, 3.0.1, 3.0, 2.2, 2.1.2, 2.1.1, 2.1, 2.0.2, 2.0.1, 2.0, 1.4.2, 1.4.1, 1.4, 1.3.2, 1.3.1, 1.3, 1.2, 1.1.7, 1.1.6, 1.1.5, 1.1.4, 1.1.3, 1.1.2, 1.1.1, 1.1, 1.0, 0.9.8, 0.9.7, 0.9.6, 0.9.5, 0.9.4, 0.9.3, 0.9.2, 0.9.1, 0.9, 0.8, 0.7.8, 0.7.7, 0.7.6, 0.7.5, 0.7.4, 0.7.3, 0.7.2
WARNING: You are using pip version 22.0.2; however, version 26.1.2 is available.
You should consider upgrading via the '~/.pyenv/versions/setuptools-5236-repro-py3.10.12/bin/python -m pip install --upgrade pip' command.

So I'd dig into how the env is different. Although, having a debugger would likely help expose better context (as I suggested above).

[nickvanderstel]

As @cjmeyer mentioned above, things started working this morning, and we're not sure why. One thing I noticed is that a venv I created on Friday would still exhibit the same behavior, but when I created a new one this morning, it worked fine.

Sorry that we weren't able to find the smoking gun, but I really appreciate all the help everyone has provided!