Depends on the criticalality of getting this right without errors is, how often this deploy is going to be run, and how much time is needed to deliver this. I'

Depends on the criticalality of getting this right without errors is, how often this deploy is going to be run, and how much time is needed to deliver this. I'm not sure what Chaos Monkey is, but I come from an operations background, where I moved to a devops role, and automating the infrastructure builds. Testing is essential. There is no need to differentiate best practices if you're coding for the application or the infrastructure. As you said, checking each state of the deployment should be done, I'll do pre-checks to make sure the filesystems have the needed space for the MW component, etc. I'll check each phase, and break down the phases via functions much like a developer would for application development. This helps keep my code reusable, and easy to read for other admins. It's much easier to rerun/correct one function that fails on a deployment than have to go through the entire setup again. I'd write the test in whatever language is doing the deploy, as I test while it's deploying. From there, it's good to have some type of audit you can run against your infrastructure, to check versions, mount points, and changes. It can be a mess when someone updates one server, but the rest are slightly different. You'd be surprised how often this happens and eventually development environment looks different than prod, and people are wondering why the applications behaving differently. I can go into more detail later on, but hope that gives you a feel for it! BTW, I'm at a large enterprise so these deployments and installs are on an enterprise scale, which makes it worth getting it right in the automation piece, as the person running it isn't always an expert on the automation, or the infrastructure itself. Get it right the first time or log what broke will save a lot of head aches later on.