urllib3>=2.0 does not work with system Python on macOS · Issue #3020 · urllib3/urllib3 · GitHub
The removal of LibreSSL support in urllib3 2.0 makes it impossible to be used with the system Python on macOS. What are you recommending to macOS users that do not want to or are not allowed to use a Homebrew version of Python? In our Python packages that use requests / urllib3, we will now either have to pin urllib3 to =2.0. That is the case that issue describes as "The combination of the above three is very unlikely.", but that is exact
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