Confronting a more powerful rival can be a risky proposition. This paper integrates prospect theory into the growing Neoclassical Realist (NCR) literature to identify the conditions under which decision makers are most likely to accept foreign policy risks. I argue that decision makers governing regimes with low levels of political counterframing are more likely to settle into a dominant loss frame when their external security environment erodes. This increases the probability that they will initiate disputes with more powerful adversaries. To assess this proposition, I conduct a test of weaker state confrontation grounded in a NCR framework that utilizes the insights from prospect theory. Data come from the postwar era and support my hypothesis. Loss frames exert influence over the decision to initiate risky foreign policy strategies in regimes in which political counterframing is absent.