Unable to install get-pip.py 2.7 due to SSL error

Question

We are using Python 2.7.3 and trying to install the compatible pip. Downloaded from https://bootstrap.pypa.io/pip/2.7/get-pip.py. When installing getting the below error.

Can someone help how to fix this error.

C:\Python27>python get-pip.py
DEPRECATION: Python 2.7 reached the end of its life on January 1st, 2020. Please upgrade your Python as Python 2.7 is no longer maintained. pip 21.0 will drop support for Python 2.7 in January 2021. More details about Python 2 support in pip can be found at https://pip.pypa.io/en/latest/development/release-process/#python-2-support pip 21.0 will remove support for this functionality.
c:\users\malai\appdata\local\temp\tmpe98lt9\pip.zip\pip\_vendor\urllib3\util\ssl_.py:424: SNIMissingWarning: An HTTPS request has been made, but the SNI (Server Name Indication) extension to TLS is not available on this platform. This may cause the server to present an incorrect TLS certificate, which can cause validation failures. 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
c:\users\malai\appdata\local\temp\tmpe98lt9\pip.zip\pip\_vendor\urllib3\util\ssl_.py:164: 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
WARNING: Retrying (Retry(total=4, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, '_ssl.c:504: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol'),)': /simple/pip/
c:\users\malai\appdata\local\temp\tmpe98lt9\pip.zip\pip\_vendor\urllib3\util\ssl_.py:164: 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
WARNING: Retrying (Retry(total=3, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, '_ssl.c:504: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol'),)': /simple/pip/
c:\users\malai\appdata\local\temp\tmpe98lt9\pip.zip\pip\_vendor\urllib3\util\ssl_.py:164: 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
WARNING: Retrying (Retry(total=2, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, '_ssl.c:504: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol'),)': /simple/pip/
c:\users\malai\appdata\local\temp\tmpe98lt9\pip.zip\pip\_vendor\urllib3\util\ssl_.py:164: 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
WARNING: Retrying (Retry(total=1, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, '_ssl.c:504: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol'),)': /simple/pip/
c:\users\malai\appdata\local\temp\tmpe98lt9\pip.zip\pip\_vendor\urllib3\util\ssl_.py:164: 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
WARNING: Retrying (Retry(total=0, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, '_ssl.c:504: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol'),)': /simple/pip/
c:\users\malai\appdata\local\temp\tmpe98lt9\pip.zip\pip\_vendor\urllib3\util\ssl_.py:164: 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:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol'),)) - skipping
ERROR: Could not find a version that satisfies the requirement pip<21.0 (from versions: none)
ERROR: No matching distribution found for pip<21.0

Answer 1

The problem with Python 2.7.3 is that it was linked with very old OpenSSL, 0.9.8, I suspect. To work around the SSL problem download distributions manually and install them without accessing PyPI. Download https://files.pythonhosted.org/packages/b2/40/4e00501c204b457f10fe410da0c97537214b2265247bc9a5bc6edd55b9e4/setuptools-44.1.1.zip (it's the last version that supports Python 2) and https://files.pythonhosted.org/packages/53/7f/55721ad0501a9076dbc354cc8c63ffc2d6f1ef360f49ad0fbcce19d68538/pip-20.3.4.tar.gz (again, the last version supporting Python 2). Extract both archives and install using the command

python setup.py install

PS. Please be warned that you're still using old Python with old OpenSSL so you can never access PyPI running pip install. You always need to download all packages and install them using pip install --no-index.

Answer 2

Python 2.7.3 is too old. Upgrade to at least 2.7.9 or better to the latest one, 2.7.18.