Trusting relationships are both valuable and risky. Where the risks are high and the fears of betrayal are also high, it might seem rational to try to mitigate the risks, while still enjoying the benefits of the trusting relationship, by forming a contingency plan. A contingency plan—in the sense I am interested in—involves contingent punishments for defection, which are primarily meant to encourage the trusted partner to act trustworthily. I argue, however, that such contingency plans suffer from an internal tension wherein the contingency planner both seeks and undermines a particular level (or kind) of trust. There are two problems in particular, either of which is sufficient to undermine trusting relationships: one, the planner fails to see the trusted partner as sincerely engaged in the trusting relationship, and two, the planner separates herself out from the trusting relationship by seeing her flourishing as separate from her partner’s (or, even worse, as dependent on her partner’s harm). Continency plans, then, are not just about the future; they cast a moral shadow on what we are doing now.