Script to install ensurepip to Python. Works on macOS and Linux for Anaconda and classic python installs.

install_ensurepip.py

import os
import sys
import io
import tarfile
import urllib.request
import re


ARCHIVE_URL = 'http://d.pr/f/YqS5+'


print('Downloading ensurepip module archive...')
response = urllib.request.urlopen(ARCHIVE_URL)
data = response.read()
tar_f = tarfile.open(fileobj=io.BytesIO(data))

package_roots = [x for x in sys.path]
i = 1
for root in package_roots:
    print("{}.".format(i), root)
    i += 1
x = int(input("Choose installation directory (.../lib/pythonX.X)\n"))
while 1 > x or x > len(package_roots):
    x = int(input("Try again: "))
    
package_root = package_roots[x-1]

print('Extracting files to', package_root)
os.chdir(package_root)

try:
    tar_f.extractall()
except:
    print('Extraction failed! Please ensure you have appropriate '
          'permissions and try again. May you should use "sudo"?')
else:
    print('All done!\n')

Looks like something happened with the archive? Try to download manually and try to open with some other tool to verify