Did you receive an email indicating that a critical service is deprecating support for TLSv1.0 or TLSv1.1? Even worse, is your app running ruby 1.9?

All hope is not lost! Let’s get you on TLSv1.2!

Background

Ruby 1.9.0 was first released on Christmas of 2007. Support for the 1.9 branch ended on February 23, 2015. It had a good run.

The 1.9 branch supported SSLv2, SSLv2.3, SSLv3 and TLSv1. Perfectly acceptable for the time. But 1.9 apps still exist, and the world of services around them are changing for PCI compliance and other valid security concerns.

Is your OpenSSL version, adequate?

#!/bin/sh openssl version

If the system is running an OpenSSL version >= 1.0.1 there is no immediate need to upgrade. Skip to the ruby section

If the system is running an OpenSSL version < 1.0.1 then you need to upgrade OpenSSL to support TLSv1.2

Upgrade OpenSSL

You now know that you must upgrade OpenSSL. I take zero responsibility for knowing your environment, so please investigate your appropriate procedures. Here are a few options for popular systems:

#!/bin/sh # Ubuntu 12.04 and newer sudo apt-get update sudo apt-get install --only-upgrade openssl libssl-dev # RedHat Enterprise v6 or CentOS sudo yum update openssl libcurl # OS X (using homebrew) brew update brew install openssl

Rebuild ruby

I currently enjoy using rbenv to manage my local and server ruby installations. Check to ensure that your version of rbenv can install your desired ruby version

#!/bin/sh rbenv install -l

Are you ready for the big show?! The following assumes that we’re attempting to build ruby version 1.9.2-p180.

#!/bin/sh # rbenv rbenv install --force --patch 1.9.2-p180 < < ( curl -sSL https://gist.githubusercontent.com/crftr/7a8f8873fcb1469c1d02c572e00a13a9/raw/ee187756fbc855ec7447d1a476515a2c443260d1/openssl_tls_1.2.patch ) rbenv rehash # for users of RVM rvm install 1.9.2-p180 --patch https://gist.githubusercontent.com/crftr/7a8f8873fcb1469c1d02c572e00a13a9/raw/ee187756fbc855ec7447d1a476515a2c443260d1/openssl_tls_1.2.patch

Let’s test!

The following curl command will return HTML and JavaScript if and only if the server can communicate over TLSv1.2

#!/bin/sh curl --tlsv1 .2 https://www.google.com

For our ruby test we will use HTTParty. It’s tried and true. If it’s available try the following in a ruby REPL of your choice

# IRB, the Rails console, or whatever is appropriate for your app require 'httparty' HTTParty . get ( 'https://www.google.com' , ssl_version: :TLSv1_2 , debug_output: $stdout )

Final notes

Let’s be honest, running ruby 1.9 is risky. It is in your best interest to upgrade as soon as possible. But legacy apps exist in the wild. I hope that all critical applications eventually receive the attention and upgrades they deserve – but only do so after adequately planning the procedure. There’s no need to rush through an upgrade for the TLS support.

Happy hacking!