I've never seen a job I didn't want to automate. Sometimes it's worked out well, sometimes automation has turned a small nuisance into a big, fragile, free-time-eating monster nuisance. In this talk, I'll explore why we automate, when to automate, the hazards of automation and the - big - rewards of automation. I'm part of the team developing IBM's WebSphere Liberty application server. We've used a mix of off-the-shelf and home-rolled tools and processes to work smarter and more productively. I'll describe what we've learned as WebSphere has transitioned to DevOps and continuous delivery and why I still can't resist trying to automate all the things.