When this happens to me it makes me question my design.

If the AI doesn’t understand it, chances are it’s counter-intuitive. Of course not all LLM’s are equal, etc, etc.

Then again, I have a rough idea on how I could implement this check with some (language-dependent) accuracy in a linter. With LLM's I... just hope and pray?

I'd agree with that but in the JS world, there's a lot of questionable library designs that are outside of my control.