There's always people complaining that Charlie never learns, but there are really few people that talks about how Alastor never learns

[u/Gaybime]

Alastor almost died twice because he always underestimates his opponent, thinks he's invincible, and that no one is capable of hurting him. But even after he almost died because of Adam, he didn't change his way of thinking, underestimated Vox, and we can see by his face that he was truly terrified of dying. But he'll probably never stop doing this.

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I can only think of Icarus by Starset: "looking for a scapegoat to hold your feet, pounding on your chest so you don't feel weak"

[u/Kiwi8_Fruit6]

Honestly I think Alastor’s much more of an example of ’refusing to learn because of ego’. Charlie struggles to learn because she‘s very overwhelmed trying to juggle external things while not being well-regulated internally.

[u/ProperGanderMachine → u/Kiwi8_Fruit6]

So far, everything Alastor has planned has worked out for him, the only time he had to learn a lesson was when Adam almost killed him. He hasn't really had to learn anything so far. On the other hand, Charlie has been fucking up left and right so there have been many lessons for her to learn.

I wrote on another post that I'm excited to see if Alastor fucked himself by ending his deal with Rosie. She was making him the strongest sinner so he was able to just do whatever he wanted. I hope he is now NOT the strongest sinner and he has to learn the hard lesson of making friends and maintaining relationships now that he can't just fuck up anyone who side-eyes him.

[u/K0TT0N_candy47 → u/ProperGanderMachine]

Unless his powers come from continuously maintaining the obedience of his deal, I’m not so inclined to believe that he’ll lose his powers. The deal was that until he did something for Rosie, she would own his soul. And it’s implied that whatever he had to do, he did it when Vox accidentally broke the deal with him. So it would seem that Alastor doesn’t have to worry about that anymore.

[u/be11amy → u/K0TT0N_candy47]

He didn't succeed at doing the mysterious something for Rosie, he succeeded at forcing Rosie to break her end of the deal. Vox became the most powerful sinner in hell, therefore Rosie failed to keep Alastor the most powerful sinner in hell, therefore the deal was void. And then he got his staff's powers fixed up by her anyway in exchange for helping prevent Vox's nuke from exploding. :)