We examined the role of cognitive ability in moderating the effects of occlusion on quasi-driving performance. Two experiments were conducted where we tested for executive function (EF) ability (shifting, updating, and inhibition), before presenting a one-dimensional pedal tracking task with a cognitive secondary task (N-back). The first experiment used self-paced occlusion (SPO), and the second experiment used forced occlusion (FO). The results showed strong individual differences. With SPO, we found that higher updating ability led to worse pedal tracking performance, likely because of insufficient visual sampling. In contrast, higher updating ability in FO was related to better pedal tracking stability. Our findings suggest that people with higher cognitive ability may sometimes carry out insufficient visual sampling when driving, either because they are more prone to distraction by cognitive tasks or because they are overly confident in their ability to manage the primary task with lower amounts of visual information.