(May 2020) so this piece is out of date. I use pipenv on one of my projects, including (in combination with direnv) for setting up my local dev environment on

(May 2020) so this piece is out of date. I use pipenv on one of my projects, including (in combination with direnv) for setting up my local dev environment on macOS and as part of CI/CD for deploying into a Docker container based on one of the Python images. The project doesn't have a huge number of dependencies, but pipenv has worked well. The only time I fought with it was over its PyUp safety checks, but "pipenv check" is opt-in anyway. For most of my other projects, I install from either a setup.py or requirements file using pip, often driven by a Makefile. Again, deploying into Linux, but using macOS for local development, again with direnv. In 20 years of professional Python development on mostly small-to-medium size projects, I've never had any issues I can recall getting packages installed. Conversely, I semi-regularly fight with cocoapods, npm and gems.