I imagine it would have dinged you for going through Kuwait, where there is a road, instead of heading straight across the desert of Iraq.
The game is literally named "Travel". So it's annoying that it penalizes you for your knowledge of traveling between places. It would have been much cooler if they had leaned in to that and prioritized routes that you could actually do on public land/sea transport.
That's way more interesting to me than being able to look at a map and notice that Brazil does in fact have borders with both Colombia and Argentina (one of which is non-navigable).
Just saying that most people don't know international traveling routes at all, and so for most people, this is a fun little game that makes total sense.
Maybe if you had tried yesterday (Bangladesh to Yemen), you'd found it clearer.