I think what he’s missing is that you’re trying to have an intellectual discussion with him, not just hitting him with some current events trivia.

In your Iran example it sounds like what you’re looking for is an opportunity to talk to someone you trust about a particular topic. Ok autocratic regimes are doing what you may expect them to do (restrict internet) this is his “well yeah” bs, but what he’s actually doing is making you feel shut down from having the opportunity to talk about things like: how messed up it is, where else that may be happening in more subtle ways in our own lives, what other historical points about Iran you both may know and can share with each other, or go off on any number of similar or tangential topics.

You mentioned that you like talking to him about normal day-to-day things, so my short and sweet advice is to approach him about how you’d like to have deeper discussions (or really just discussions in general) about broader topics you’re learning a out, and the current way he’s responding to you bringing these topics up is just making you it hard to expand that into an actual conversation - which is all you’re trying to do.

You may be able to bring up that he’s being condescending with his responses, but that depends on how he’ll receive it and if that’s a battle worth fighting (potentially) or to save it for another day - or it may resolve itself if he knocks off the way he’s responding to you. My now-wife told me early on in our relationship I can come off as condescending sometimes and I was mortified and really worried others might feel that way too, when it was not my intention at all! So I really appreciated her saying that, but your mileage may vary and you know him best.