This article reconsiders the problem of human freedom in the wake of David Bentley Hart’s That All Shall Be Saved. It renews and reasserts the crisis of every human freedom’s eternal destiny. With insights from Maurice Blondel, Bernard Lonergan, and Hans Urs von Balthasar, the article makes a case for distinctive conceptions of human freedom, divine agency, and the problem of hell. The article closes by reading Theo-Drama as a map marking places for further theological exploration.