Make sure to "trust" all websites that need to be trusted.  
https://stackoverflow.com/questions/49324802/pip-always-fails-ssl-verification

Example:  
python -m pip install --trusted-host pypi.python.org --trusted-host 
files.pythonhosted.org --trusted-host pypi.org --upgrade pip

"blocking outbound traffic". Seems very restrictive. You should talk with the 
IT department and ask about running "pip install".      
And... the mail server itself isn't going to function without permitted 
firewall traffic.
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