Just today I learned that a version of requests from August broke compatibility with a version of pip from February, which is packaged in ubuntu 14.04. (I was installing dependencies with apt and pip as root in a docker image.) (http://stackoverflow.com/questions/27341064/how-do-i-fix-imp...)

Meanwhile, openssl and bash, while getting security updates very recently, are in their very latest versions still compatible with programs from probably over 8 years ago.