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This study seeks to examine a twofold break that can be observed in Schelling’s treatise on human freedom. The first break, a classic yet essential one, is Schelling’s argument for the positivity of evil within the complex relation uniting humankind and God in reference to the obscure principle. This positivity of evil is directly contrary to a tradition that generally favoured understanding evil as a simple absence of good, as a fault or lack. The second break, less immediate yet significantly identifiable, concerns the positivity of the risk of evil itself. Such a risk is never stated explicitly, yet it emerges from the new reading of the Investigations proposed in this article. In order to uncover the positivity of the risk of evil, we need to grasp precisely the right way of understanding the positivity of evil itself: namely as the positivity of a very precise metaphysical finality.