One thing that struck me about the hospital scene between Dean and Castiel in SPN 4.16, which I think many have mentioned, is how Dean was likening Castiel's role to John's when he tells him not to disappear leaving just cryptic remarks behind. Dean felt betrayed by that act of John's, and I think he felt betrayed by Castiel in this episode. Castiel didn't literally send Dean back to hell, but he did put him back there mentally. And both he and John have asked Dean to perform tasks that are unknowable and likely to result in failure. Dean had no idea how to protect Sam from himself, and still doesn't. He also has no idea how to set things right with the seals.
In either case, his failure results in a kind of apocalypse.
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