usrbinenv python3 checks that the version of the projects bundled in ensurepip are the latest versions available usr bin env python3 checks that the version of the projects bundled in ensurepip are the latest versions available
import ensurepip
import json
import urllib.request
import sys


def main():
    outofdate = False

    for project, version in ensurepip._PROJECTS:
        data = json.loads(urllib.request.urlopen(
            "https://pypi.org/pypi/{}/json".format(project),
            cadefault=True,
        ).read().decode("utf8"))
        upstream_version = data["info"]["version"]

        if version != upstream_version:
            outofdate = True
            print("The latest version of {} on PyPI is {}, but ensurepip "
                  "has {}".format(project, upstream_version, version))

    if outofdate:
        sys.exit(1)


if __name__ == "__main__":
    main()