Math can be difficult, and for those with high levels of mathematics-anxiety (HMAs), math is associated with tension, apprehension, and fear. But what underlies the feelings of dread effected by math anxiety? Are HMAs’ feelings about math merely psychological epiphenomena, or is their anxiety grounded in simulation of a concrete, visceral sensation – such as pain – about which they have every right to feel anxious? We show that, when anticipating an upcoming math-task, the higher one’s math anxiety, the more one increases activity in regions associated with visceral threat detection, and often the experience of pain itself (bilateral dorso-posterior insula). Interestingly, this relation was not seen during math performance, suggesting that it is not that math itself hurts; rather, the anticipation of math is painful. Our data suggest that pain network activation underlies the intuition that simply anticipating a dreaded event can feel painful. These results may also provide a potential neural mechanism to explain why HMAs tend to avoid math and math-related situations, which in turn can bias HMAs away from taking math classes or even entire math-related career paths.