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Looks like root SSL certificates shipped with Jessie have become stale.
Pip fails to interact with PyPI:
$ ./.venv/bin/python -m pip install --upgrade "pip<19.2" "setuptools<44.0" "wheel<0.34"
Cannot fetch index base URL https://pypi.python.org/simple/
<...>
No distributions at all found for pip<19.2 in ./.venv/lib/python3.4/site-packages
Jessie has reached EOL in 2018, Jessie LTS in 2020.
Even though Jessie ELTS is still supported, we will drop support now.
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