A culture of automation is such a cornerstone of DevOps, one of it’s oldest, most famous tropes is “automate ALL the things”. But are there things we maybe shouldn’t automate? What if how we go about automating things is actively causing us pain in the form of incidents? We’ll take a look at some of the impacts and challenges pervasive automation has presented for engineers and operations, along with some important considerations when automating our complex, living socio-technical systems, as well as some strategies to cope with these “ironies of automation.”