ngl with everything from episode 9 I’m more and more convinced that Caleb signed up to the army. Not like, brass tacks model soldier sign up. But – poor as anything, just needs a goddamn job? I believe it. He signed up, it was shit, he deserted. Just based on the info we learned about the Dwendalian Empire overall, as well as a touch of Caleb backstory and the consistent disenfranchisement with the empire. Especially with the element of poverty: being a soldier is a lot cheaper than being a scholar. 

idk, this will probably be wrong. But I do think in some shape or form that Caleb/Caleb’s family fell foul of the empire/army. WHO KNOWS