The best way to manage python dependencies is with pip-compile

https://gist.github.com/hynek/5e85706cee589a204251b333595853...

    update-deps:
    	pip-compile --upgrade --generate-hashes --output-file requirements/main.txt requirements/main.in
    	pip-compile --upgrade --generate-hashes --output-file requirements/dev.txt requirements/dev.in
    
    init:
    	pip install --editable .
    	pip install --upgrade -r requirements/main.txt  -r requirements/dev.txt
    	rm -rf .tox
    
    update: update-deps init    

    .PHONY: update-deps init update