Under pressure, people often prefer what is familiar, which can seem safer. We show that such familiarity-favoring can lead to choices precisely contrary to the source of felt pressure, thus exacerbating, rather than mitigating, its negative consequences. In Experiment 1, time-pressure increased choices to complete a longer but incidentally familiar task-option, resulting in increased felt stress during task-completion. In Experiment 2, pressure to reach a performance benchmark in a chosen puzzle increased participants‟ choices of an incidentally familiar puzzle that both augured and delivered objectively worse performance (i.e., fewer points obtained). This occurred even when familiarity was established through unpleasant prior experience akin to a devil you know preference under pressure, whereas such negatively familiar options were disfavored in pressure-free situations. These results demonstrate how pressure-induced flights to familiarity can sometimes aggravate rather than ameliorate pressure, and can occur even when available evidence points to the sub-optimality of familiar options.