Chapter 6 situates John Milton’s major works – Paradise Lost, Paradise Regained, and Samson Agonistes – in relation to abiding conflicts over fiscal policy prompted by the Civil War and its aftermath. Milton was actively critical of the Commonwealth’s management of fiscal policy and voiced his fear about the fiscal impact of a restored monarchy. Though fiscal concerns are largely occluded from his poetry, Milton’s depiction of war and its effects continues this critique by dramatizing the disastrous consequences of security imaginaries organized around the violently expansive accumulation of wealth. Milton’s metasecurity dilemma arises in his poetry as a question about how to value people and circumstances correctly, about the relevant criteria to use to orient oneself ethically and politically within catastrophic realities. His poems thus highlight Milton’s deep uncertainty about how to define safety or about what kinds of collective security might be possible in such a disoriented moment.