https://github.com/pypa/pip/issues/5367
There is similar issue on github. I think that we have to provide python3-distutils for 3.6? I've just downgraded it with python3-distutils_3.6.6-1_all.deb and pipenv worked. $ sudo dpkg -i /tmp/downloads/python3-distutils_3.6.6-1_all.deb dpkg: warning: downgrading python3-distutils from 3.7.2-3 to 3.6.6-1 (Reading database ... 351861 files and directories currently installed.) Preparing to unpack .../python3-distutils_3.6.6-1_all.deb ... Unpacking python3-distutils (3.6.6-1) over (3.7.2-3) ... Setting up python3-distutils (3.6.6-1) ... pipenv --python 3.6 Creating a virtualenv for this project… Using /usr/bin/python3.6m (3.6.8) to create virtualenv… ⠋Running virtualenv with interpreter /usr/bin/python3.6m Using base prefix '/usr' New python executable in /tmp/pipenv-test/.venv/bin/python3.6m Also creating executable in /tmp/pipenv-test/.venv/bin/python Installing setuptools, pkg_resources, pip, wheel...done. Virtualenv location: /tmp/pipenv-test/.venv $ So, I guess when Debian dropped 3.6 support, python3-distutils also removed 3.6? -- yashi