Modal Security is an increasingly discussed proposed necessary condition on undermining defeat. Modal Security says, roughly, that if evidence undermines (rather than rebuts) one’s belief, then one gets reason to doubt the belief's safety or sensitivity. The primary interest of the principle is that it seems to entail that influential epistemological arguments, including Evolutionary Debunking Arguments against moral realism and the Benacerraf-Field Challenge for mathematical realism, are unsound. The purpose of this paper is to critically examine Modal Security in detail. We develop and discuss what we take to be the strongest objections to the principle. One of the aims of the paper is to expose the weakness of these objections. Another is to reveal how the debate over Modal Security interacts with core problems in epistemology — including the generality problem, and the distinction between direct and indirect evidence.