Well. I've been using python personally since 2007, and it never broke with update (I still occasionally run scripts written for 2.5). Also, I am working as a python backend dev, dealing with hundreds of systems (we are deploying 270+ systems and supporting another 340 user built docker images built on top of py library), and no problems there either. In my previous job, I was doing deployment to 4000+ kiosk computers, and still, no problems with python breaking.

What was definitely problematic was the update from 2 to 3. Another problem may be dependency management (people not pinning dependencies). But the python itself? What does it even mean? Interpreter not starting?