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This addresses an issue raised by @CaseyFeist during code review: Updating pip for pipenv users or requiring them to update without a heads up won't be a good experience (our version is old enough that they'll need to uninstall and reinstall pipenv locally to successfully update). If you can refactor this to stay pinned to current version for pipenv users only, I should be able to accept this (and the related project updates). https://github.com/heroku/heroku-buildpack-python/pull/833#issuecomment-537758441