Dealing with SSL HandShake failure with Python Requests (_ssl.c:590)

I was working with Requests trying to talk to a REST api when I encountered this SSL HandShake error. It was fairly easy to replicate because it happens every time I tried talking to a HTTPS endpoint or resource. It didn't matter if it was a GET or POST action. I suspect it'd be the same for other actions like PATCH or DELETE.

So what's the fix? Uninstall-install then maybe an update or upgrade.

1. I updated Python to 2.7.11. You might not need to do this if your up-to-date. 
2. I uninstalled requests. - $ pip uninstall requests
3. I uninstalled urllib3. - $ pip uninstall urllib3
4. Installed crypto dependencies or libs. This is where it gets hairy.
   
   First I had to update my machine's openSSL library. This could range from easy to hair pulling hard. Thankfully, I had brew on my machine so it was relatively easy.
   
   Anyhow you'll want to see this from the terminal after the update.
   
   

   $ openssl version
   OpenSSL 0.9.8zh 14 Jan 2016
   

   
   After you'll need to run this command:
   
   

   $ pip install pyopenssl ndg-httpsclient pyasn1
   

   
    This installs the rest of the crypto dependencies.
   
5. I installed urllib3 back. - $ pip install urllib3
   I also installed urllib3[secure]. - $ pip install urllib3[secure]
   You might not need the secure version but I covering all the bases.
   
6.  Install requests back. - $ pip install requests
   Same deal with urllib3, you might also want to install request with security.
   
   $ pip install request[security]

Why this works? I suspect that there's an installation-time check for either urllib3 (or requests) for the crypto stuff that keeps things from working without the uninstall-reinstall.