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Hello, reposting this issue here <https://github.com/pantsbuild/pex/issues/2154>

We discovered this in pants when moving from 2.12 to 2.15 and traced it back to pex

Has anyone seen this before? :slightly_smiling_face:

The urllib3 2.0.0 release is a gift that keeps on giving. Breaking-change releases of fundamental packages always seem to cause all sorts of downstream issues...

I've been active on the issue. This appears to be a Pip bug since fixed. Use `--pip-version 23.1` or newer and no flake.

Aha, but to use `--pip-version` from Pants at all you must be on Pants 2.16.x+ and to get 23.1 or newer you must be on 2.17.x: <https://www.pantsbuild.org/v2.17/docs/reference-python#pip_version>