Mac OSX version 10.12 - There was a problem confirming the ssl certificate: [SSL: TLSV1_ALERT_PROTOCOL_VERSION] tlsv1 alert protocol version (_ssl.c:590) - skipping
This is a common issue I have seen in Mac OSX when I try to use pip. eg:sudo pip install -t lib -r requirements.txt Could not fetch URL https://pypi.python.org/simple/google-api-python-client/: There was a problem confirming the ssl certificate: [SSL: TLSV1_ALERT_PROTOCOL_VERSION] tlsv1 alert protocol version (_ssl.c:590) - skipping However the reason for the problem is pip version update with relevant to underlying OSX infrastructure. You have to identify which version of pip is there within mac OS. Run brew install python Unversioned symlinks `python`, `python-config`, `pip` etc. pointing to `python3`, `python3-config`, `pip3` etc., respectively, have been installed into