Just a minor point, Dragon is very good at taking potentially unmasking photos off of PHO, if Emma thought quickly and downloaded the pic I could see it though.
Interesting chapter, I'm not completely sure about Calvert playing Cantos speed Chess with his Civ ID though, if for example Armsmaster was clever and told Clockblocker to tag SS and keep her tagged till he arrived (because she's obviously a gigantic flight risk in this situation), then confined her and interrogated her, and she, being a 16 year old girl after all, let any of this slip, he would be outed in short order. Hell if she's recaptured at *any* point, there's a risk it comes out. That's exactly the kind of knowledge he carefully compartmentalized in canon.
It is explicable however if he's keeping a safe timeline and he's planning on seeing if he can pull a fast one, quickly. If whatever plan he has takes less than 24 hours or so, and leaves SS very dead at the end of it, than I could see him taking the risk.