@@ -142,6 +142,20 @@ def create_if_needed(d):
        context.bin_name = binname
        context.env_exe = os.path.join(binpath, exename)
        create_if_needed(binpath)
        return context

    def create_configuration(self, context):
@@ -293,8 +307,8 @@ def _setup_pip(self, context):
        # We run ensurepip in isolated mode to avoid side effects from
        # environment vars, the current directory and anything else
        # intended for the global Python environment
-        cmd = [context.env_exe, '-Im', 'ensurepip', '--upgrade',
-                                                    '--default-pip']
        subprocess.check_output(cmd, stderr=subprocess.STDOUT)

    def setup_scripts(self, context):
@@ -394,11 +408,7 @@ def upgrade_dependencies(self, context):
        logger.debug(
            f'Upgrading {CORE_VENV_DEPS} packages in {context.bin_path}'
        )
-        if sys.platform == 'win32':
-            python_exe = os.path.join(context.bin_path, 'python.exe')
-        else:
-            python_exe = os.path.join(context.bin_path, 'python')
-        cmd = [python_exe, '-m', 'pip', 'install', '--upgrade']
        cmd.extend(CORE_VENV_DEPS)
        subprocess.check_call(cmd)


diff --git a/Misc/NEWS.d/next/Windows/2021-09-30-23-17-27.bpo-45337.qg7U_h.rst b/Misc/NEWS.d/next/Windows/2021-09-30-23-17-27.bpo-45337.qg7U_h.rst
@@ -0,0 +1,4 @@