Mr Yotsumura, Sakamoto, and every assassin who grew attached to another person found themselves in this predicament. Shishiba should've learned. He only had himself to blame for caring.

He was still baffled by how this could even happen. It takes someone of a certain skill level to be targeted by the JAA. And Shishiba knew they could have his head for not performing his duty as an Order member, failing to kill a Class-A extermination target. He wondered what they'd do if they found out he was actively protecting that target. At this point, he's not even sure he could trust Osaragi with it.

"I'm back," Shishiba announced as he entered. He'd set up this small routine so you know it's him. If anyone enters without announcing their arrival, you attack. I need to teach them some self-defence or something... He looked around, waiting for you to pop out from wherever you were hiding.