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As mentioned in the article, this has already been explored with the "ensurepip" approach.

And it wasn't the only thing at the language summit that proposed expanding that approach: there was a discussion of carrying time zone updates in the same way, by shipping something with the interpreter that works but allowing updates from PyPI. http://pyfound.blogspot.com/2019/05/paul-ganssle-time-zones-...

So I think the development community / target audience at the language summit already understands the pros and cons of the suggested approach and the technical route to get there. (For an end user, my guess is the experience will be that anything in the Python 3.x standard library today will still be in the Python 3.x standard library, but you'll have to `pip install` a newer version if you want more features, and you get the benefit of being able to `pip install` something from the standard library where you previously couldn't.)

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