There's been many studies around the concept "how do you get expertise? In what field can you actually develop expertise?" such as Naturalistic Decision Making [1] [2]. The wisdom from there can be applied to the question of automation.
If your task is for example, to pilot a preset route with stable condition and very low surprise, you will fall for the "getting too comfortable" trap and we tend to start to get lazy(or efficient) and offload the mental effort and skills atrophy. A common workaround to this is to have regular training(deliberate practice) that introduce the "tricky" situation to keep the skill up. Problem ofc arises when people don't keep this up.
This can be seen in the diagnostic performance differences between junior and senior doctors, not always in the favor to the senior [3]. If you add a layer of automation but the insight gathered by working on that layer is great (and falls off) then deliberate practice start to become a requirement
[1] https://commoncog.com/putting-mental-models-to-practice/