ImportError: cannot import name HTTPSHandler using PIP

Question

Facing an HTTPSHandler error while installing python packages using pip, following is the stack trace,

--------desktop:~$ pip install Django==1.3
Traceback (         


        

Answer 1

Homebrew

This was probably caused by an upgrade to Mavericks. Here's how I fixed it.

Update OpenSSL

#make a copy of the existing library, just in case
sudo cp /usr/bin/openssl /usr/bin/openssl.apple

# update openssl 
brew update
brew install openssl
brew link --force openssl

# reload terminal paths
hash -r

Reinstall Python

Python 3

brew uninstall python3

brew install python3 --with-brewed-openssl

Python 2

brew uninstall python

brew install python --with-brewed-openssl

This answer consolidates all the Stack Exchange answers and comments I found, and is based mostly on this Apple Stack Exchange answer.