Python Error When Installing ez_setup.py "could not create SSL/TLS secure channel"

Question

Python version: 2.7.13

OS: Windows Server 2012

I'm following this tutorial to set up Python environment

When I attempt to execute

python ~\Desktop\ez_setup.py

I get

Exception calling "DownloadFile" with "2" argument(s): "The request was aborted: Could not create SSL/TLS secure
channel."
At line:1 char:106
+ [System.Net.WebRequest]::DefaultWebProxy.Credentials = [System.Net.CredentialCac ...
+ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
    + CategoryInfo          : NotSpecified: (:) [], MethodInvocationException
    + FullyQualifiedErrorId : WebException

I tried enabling SSL and TLS based on this link and restarting the Server, but no luck

Answer 1

As a workaround you can use the --insecure flag, although it doesn't fix the SSL error.

Source: Github Setuptools Issues