Depressingly common. And also depressingly futile to argue against sometimes.
Person tries to automate something they don't understand. They come up with simple, elegant "solution" that fails to address half of what the task involves. When presented people are, naturally, "what about X?", where X is important and addressed in the previous solution, and not at all addressed in the simpler, more elegant new solution.
Cue blog post where automator complains about how "management" piled on "edge cases" "at the last minute".
I know I've been guilty of this. The only solution I've found--be humble and ask as many questions as you can. (I guess working in the job for a few months is another solution, but sometimes that is a luxury you can't afford.)
Too often someone with an automation mindset will see an task and decide that it can be automated without actually understanding half of what the task involves.