2nd Age Middle Earth thought: We know Sauron is a fan of long-range psychological attacks as he besieges a city. Do you think after 400 years of getting to know the people of Ost-in-Edhil, they were personal? Like, it’s not just Sauron camped on a nearby hill weaving a spell of fear and despair into the dark clouds that now flow out over your city, setting fell whispers loose in your dreams. It’s Sauron whom you once told, while tipsy at a Yule party 200 years ago, that you were still frightened of dogs after an incident in your childhood, or that you never felt like you’d truly lived up to your mother’s expectations, or… And now the Song he’s woven of hopeless terror has notes that sound like the howling of hungry hounds, or your mother’s disparaging sigh, or... And he’s doing that to everyone at once with all their different private doubts and fears.
Annatar: a great friend in that he’s an active listener, very good at remembering your favorite tea to drink when you’re down, or the book you mentioned reading to discuss with you a year later. Also, unfortunately, Sauron.