Troubleshooting OpenSSL Compatibility in Python 2.7 on Mac OS X

Python utilizes OpenSSL for secure communication. The version of OpenSSL used by Python may vary depending on the system configuration. When encountering inconsistencies between OpenSSL versions used by the terminal and Python, such as upgrading OpenSSL without seeing the update reflected in Python, addressing the linkage is crucial.

To update OpenSSL, follow the steps described in the referenced article (http://rkulla.blogspot.kr/2014/03/the-path-to-homebrew.html). Here's a summary:

• Install the updated OpenSSL version using Homebrew:

  brew update
  brew install openssl

• Link the new OpenSSL version:

  brew link openssl --force 

• Install a new version of Python that links to the Homebrew-installed OpenSSL:

  brew install python --with-brewed-openssl    

• Create a symbolic link to the new Python binary:

  sudo ln -s /usr/local/Cellar/python/2.7.8_2/bin/python /usr/local/bin/python  

After these steps, verify that the installed OpenSSL version is being used by Python:

python --version  
Python 2.7.8

python -c "import ssl; print ssl.OPENSSL_VERSION"
OpenSSL 1.0.1j 15 Oct 2014

If this procedure resolves the issue, you can apply a similar approach to Ubuntu 12.04 once a solution is available for that platform.