title: Best way to upgrade Python 2.7.4 to the latest 2.7.x on Windows
body: <p>I currently have on Windows 10 Python 2.7.4 (32-bit) which doesn't have pip. Now I wish to have pip to install additional modules and for that a newer 2.7.x with pip is required. I already tried to install pip with 2.7.4 but it didn't work and other sources indicate it's not even supported. What's the best way to upgrade to the latest Python 2.7.x so that my Windows environment does not get messed up? Can I just delete the old Python27 directory and install the new version in it or should I run some uninstall first? Windows Apps &amp; features list shows a couple of Python 2.7 modules which I've installed using .exe installers.</p>
  
  <p>Note: The project requires Python 2.7.x, therefore upgrading to Python 3.7.x is not an option.</p>
  
  <p>EDIT: I wish to upgrade Python also due to the error message outputted by <code>get-pip.py</code> which is directly telling a Python upgrade will solve it:</p>
  
  <pre><code>...\pip.zip\pip\_vendor\urllib3\util\ssl_.py:150: InsecurePlatformWarning: A true SSLContext object is not available. This prevents urllib3 from configuring SSL appropriately and may cause certain SSL connections to fail. You can upgrade to a newer version of Python to solve this. For more information, see https://urllib3.readthedocs.io/en/latest/advanced-usage.html#ssl-warnings
    Could not fetch URL https://pypi.org/simple/pip/: There was a problem confirming the ssl certificate: HTTPSConnectionPool(host='pypi.org', port=443): Max retries exceeded with url: /simple/pip/ (Caused by SSLError(SSLError(1, '_ssl.c:504: error:1407742E:SSL routines:SSL23_GET_SERVER_HELLO:tlsv1 alert protocol version'),)) - skipping
    Could not find a version that satisfies the requirement pip (from versions: )
  No matching distribution found for pip
  </code></pre>