Updating OpenSSL in Python 2.7: Understanding the Dependency and Resolution

In Python 2.7, the behavior of OpenSSL integration can be confusing, as the programming language interacts with the system's OpenSSL installation. Here's how OpenSSL works in Python 2.7 and how to resolve issues related to version updates:

Python's Reliance on OpenSSL

By default, Python 2.7 picks up OpenSSL from the system's environment. When you import the ssl module, Python checks the system's OpenSSL installation and uses its version.

OpenSSL Version Update Issue

The problem arises when you manually update OpenSSL on the system. While your terminal shows the updated version, Python continues using the older version. This is because the OpenSSL dynamic library (.dylib) used by Python still points to the old version.

Solution for macOS

1. Follow the instructions provided in the link: http://rkulla.blogspot.kr/2014/03/the-path-to-homebrew.html

2. Upgrade OpenSSL using Homebrew:

   brew update
   
   brew install openssl

3. Link the new OpenSSL version:

   brew link openssl --force

4. Install Python with brewed OpenSSL:

   brew install python --with-brewed-openssl

5. Create a symbolic link to the new Python version:

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

Now, Python will use the updated OpenSSL version.

Solution for Ubuntu

A definitive solution for Ubuntu 12.04 is still pending, but here are some potential steps you can try:

1. Install the latest OpenSSL version:

   sudo apt-get update
   
   sudo apt-get install openssl

2. Update the shared library:

   sudo ldconfig

3. Reinstall Python:

   sudo apt-get remove python
   
   sudo apt-get install python

4. Check the OpenSSL version:

   python -c "import ssl; print ssl.OPENSSL_VERSION"

Hopefully, these instructions will help you update OpenSSL in Python 2.7 and resolve any version mismatch issues you encounter.