Yeah. I can't say that the organizations we're doing enablement for are really "DevOps". We're mostly trying to get them moving in that direction (since they say that's where they want to be). The whole "self-sustaining deployments" and "infrastructure as code" thing is a hard row to hoe with a lot of the COTS software they want to use. So, while it's possible to automate many things — at least partially — you can definitely tell when you're working with (against?) a product that you can tell was never looked at with automated deployment in mind.
Attempts at automation often run smack into the wall of "GUI-oriented management". Most frequently, one can automate the baseline deployment of COTS software ...and even redeployment, but there's no good method to automate the configuration of much COTS software. I still remember one Java-based application I was automating, I'd located the file that contained its JDBC configuration. Was really pissed when, after sorting out how to pre-place a configured JDBC file, discovered that the application would simply blow away that file on first-start. Grr...
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