Ned Deily <n...@python.org> added the comment:

Thanks for the report.  I have to agree that the behavior is a little bit 
counterintuitive but I believe everything is working as designed and 
documented.  It all comes down to the fact that the ensurepip module is only 
concerned with the version of pip bundled with the python release; ensurepip 
deliberately does not check PyPI for a newer version of pip.  As documented, 
venv calls ensurepip after creating a new venv so the pip that is installed 
there is the one released with ensurepip. To get the latest version of pip, you 
would need to run (in the activated venv):

python3 -m pip install --upgrade pip

just as you needed to do to upgrade the system-wide instance of python3 to the 
latest pip.

https://docs.python.org/3/library/venv.html#creating-virtual-environments
  "Unless the --without-pip option is given, ensurepip will be invoked
   to bootstrap pip into the virtual environment."

https://docs.python.org/3/library/venv.html#creating-virtual-environments
  "Note: This module does not access the internet [...]"

----------
nosy: +ned.deily

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<https://bugs.python.org/issue40940>
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