Now, I think there’s a curious implication here. Remember when Andy one-shot the Archon? Good times, right? Well, when that happened, Andy’s will was suppressed by the Domination Runes on his Armor.
I think the Jailer is also perpetually under influence of Domination Magic. I think the runes tattooed on his flesh are basically the Eternal Ones’ use of the thing, and what it does is: It suppresses the Jailer’s will to leave.
A lot of people have questioned: If the Jailer’s minions can just fly out of the Maw, why can’t they carry the Jailer with them? And I think that’s the answer. The Domination Magic cast on the Jailer stops him from trying to leave. It even stops him from doing something like ordering his minions to drag him out.
So he has to escape through the cracks of the magic. He has to break the hold on him by doing things that he isn’t forbidden to do. And that’s why his methods seem so roundabout and overly complicated. There are lots of obstacles to his plans that we can’t even see because the obstacles are in his brain.
That’s just a hypothesis, but it would explain lots of plot holes of Shadowlands.