Hi Ophir (2021.10.19_10:59:43_+0000)
> Running pypy3 -m ensurepip on Debian returns an AssertionError. 

Thanks for the bug, that shouldn't happen.

What should happen is that it prints the error message:

> ensurepip is disabled in Debian/Ubuntu for the system python.
>
> Python modules for the system python are usually handled by dpkg and apt-get.
>
>    apt-get install python3-<module name>
>
> Install the python3-pip package to use pip itself.  Using pip together
> with the system python might have unexpected results for any system
> installed module, so use it on your own risk, or make sure to only use
> it in virtual environments.

However:

> Running get-pip.py <https://bootstrap.pypa.io/get-pip.py> does not
> change the error.

I can't reproduce that, get-pip.py works for me, and leaves me with a
functional pip.

SR

-- 
Stefano Rivera
  http://tumbleweed.org.za/
  +1 415 683 3272

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