provisioning failing on pip dependencies

[ieaves]

Currently vagrant provision fails, erroring out with a wall of useless text. I can't track down the root cause but I am able to reach a solution.

Looking at this bug report from ansible ansible/ansible-modules-core#5347 I thought pip might be executing using the python 2 pip executable, and having reached a permission error elevated the pip permissioning to use sudo creating an ansible task of

• name: Install pip dependencies
  become: yes
  pip: executable="/usr/bin/pip3"
  chdir="{{ local_dev_path }}"
  requirements="{{ local_dev_path }}/{{ item }}"
  with_items:
  - requirements.txt

Attempting to provision with this modification will actually break pip causing all uses of pip to land with the following error:

ImportError: No module named 'packaging'

However, reinstalling pip directly through the get-pip script will correct the error. Re-installing pip through any other means does not appear to correct the issue

sudo -i
apt-get purge -y python3-pip
wget https://bootstrap.pypa.io/get-pip.py
python3 ./get-pip.py
apt-get install python3-pip

If you ssh into the box, update pip using the above and re-provision. Voila, provisioning will be successful.

As to why? Fuck if I know.