Illithids are tough for me, because they're ostensibly genius level intellect villains and I do not possess a genius level intellect.
Personally I've long taken the "genius-level intellect doesn't mean you're 'smart' (in the colloquial sense), sensible, or particularly good at anticipating the behaviour of others in real terms" approach, because, frankly, I've known enough people with that level of intellect, and accompanying qualifications that it's pretty obvious the being incredibly intelligent never makes you
generally brilliant, it makes you very good at a fairly narrow range of things that you're focused on (and there are some things it benefits more than others). This was interestingly notable in videogames and wargames too - the sort of person who literally sees a dozen moves (or more!) ahead in chess might deal with a basic feint well in say, Starfleet Battles, immediately recognising it and not taking the bait, but equally might get completely wrecked by a slightly more unorthodox or risky strategy, and whilst they might be better than most at assessing the likely the result of an attack, or anticipating how much energy they'd have left after a manuever, the sheer complexity of the situation destroys the ability to "go chess mode" on it. And let's not even start on videogames, even ones they purported to be good at!
Genius-level monsters should be well-prepared and shouldn't fall for bog-standard tricks, but they will never have anticipated everything, and they probably won't understand their opponents anywhere near as they think they do. They should be pretty good at things they care about, but I doubt most Illithids are very interested in "tactical combat against humanoids", because that's trivial for them most of the time and likely don't really have to make much an effort with most of their victims. Likewise most dragons seem like they'd have an astonishing knowledge of history, geography (local or otherwise), the provenance of artifacts/coins/etc. but because fighting is not particularly difficult or interesting for them, probably they're not actually particularly smart tactically (and overconfidence/arrogance are very real issues, especially for the kind of being that defines the notion of the kind of pride that comes before a fall!). Fear the very rare dragon who has actually obsessed about war and conquest for centuries - that's the guy who is the big bad of a campaign!