Ever since I made an automatic publishing infrastructure for highlight.js releases… there wasn't a single time when it really worked automatically as planned!
There was always something: directory structure changes that require updates to the automation tool itself, botched release tagging, out of date dependencies on the server, our CDN partners having their own bugs with automatic updates, etc. In my own words:
You can't really automate anything. You just shift maintenance from your thing to your automation tools.— Ivan Sagalaev (@isagalaev) October 9, 2014
But! It still makes sense because by introducing automation you can do more complex things at the next level and keep maintenance essentially constant. In fact, if your maintenance is much lower than you can afford it means that you don't do enough interesting stuff :-).