I have become genuinely convinced that Jockington being FRIEND or in some way connected to the Tail of Hell is entirely possible. I don't think it would be narratively satisfying and I don't know why Toby would write it that way but it's hard to ignore so many connections. That being said, I'm so hyped for Chapter 5 and I really hope we get more Asgore and (maybe) some characterization of the six (seven?) human souls from UNDERTALE in some way. I just think it'd be neat.