Many important managerial outcomes hinge on the co-occurrence of multiple uncertain events, a situation termed “conjunctive risk.” Whereas the past behavioral literature on this topic has examined how people decide whether to enter situations with conjunctive risk, this paper studies how decision-makers manage conjunctive risk that they already face. In a series of experiments, we study an underexplored decision-making strategy that can lead to predictable bias, specifically, excessive prioritization of one’s biggest problem. The bias manifests predominantly in attentive decision-makers and, in some cases, reverses for inattentive decision-makers. In this work, we elucidate a novel way in which managers’ choices may differ systematically according to whether they are managing risk or choosing between risks, even when those decisions are formally equivalent.