I am running the below commands in the Mac terminal. How can I upgrade the pip version? I am getting below error messages:
option 1:
aspa@LM-M527128 ~ % python -m pip install pip --upgrade
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 Please upgrade your Python as Python 2.7 is no longer maintained.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.
WARNING: Retrying (Retry(total=4, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, u'[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)'),)': /simple/pip/
WARNING: Retrying (Retry(total=3, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, u'[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)'),)': /simple/pip/
WARNING: Retrying (Retry(total=2, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, u'[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)'),)': /simple/pip/
WARNING: Retrying (Retry(total=1, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, u'[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)'),)': /simple/pip/
WARNING: Retrying (Retry(total=0, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, u'[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)'),)': /simple/pip/
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, u'[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)'),)) - skipping
Requirement already up-to-date: pip in /Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/site-packages (20.2.4)
WARNING: You are using pip version 20.2.4; however, version 20.3.4 is available.
You should consider upgrading via the '/Library/Frameworks/Python.framework/Versions/2.7/Resources/Python.app/Contents/MacOS/Python -m pip install --upgrade pip' command.
option 2:
aspa@LM-M527128 ~ % sudo pip install -U pip
Password:
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.
WARNING: The directory '/Users/aspadmanabhan/Library/Caches/pip' or its parent directory is not owned or is not writable by the current user. The cache has been disabled. Check the permissions and owner of that directory. If executing pip with sudo, you may want sudo's -H flag.
WARNING: Retrying (Retry(total=4, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, u'[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)'),)': /simple/pip/
WARNING: Retrying (Retry(total=3, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, u'[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)'),)': /simple/pip/
WARNING: Retrying (Retry(total=2, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, u'[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)'),)': /simple/pip/
WARNING: Retrying (Retry(total=1, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, u'[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)'),)': /simple/pip/
WARNING: Retrying (Retry(total=0, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLError(1, u'[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)'),)': /simple/pip/
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, u'[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)'),)) - skipping
Requirement already up-to-date: pip in /Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/site-packages (20.2.4)
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, u'[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:727)'),)) - skipping
aspadmanabhan@LM-MAA-40527128 ~ %
question from:
https://stackoverflow.com/questions/65891005/getting-ssl-certificate-error-while-upgrading-the-pip 
