Abstract Interest in the influences on and strategies to mitigate boredom has grown immensely. Boredom emerges in contexts in which people have difficulty paying attention, such as underchallenging relative to optimally challenging conditions. The current study probed contextual influences on peoples' experience of boredom by manipulating the order with which people performed easy and optimally challenging conditions of a task ( N = 113). We measured frontal alpha asymmetry (FAA) and theta/beta as neural correlates of self‐regulatory and attentional control processes, respectively. Results showed self‐reported boredom was higher in the easy condition when the optimal condition was completed before it. Similarly, participant's FAA shifted rightward from the first to the second task when the optimal condition was completed prior to the easy condition, indicating that self‐regulatory processes were strongly engaged under these context‐specific conditions. Theta/beta was lower during the easy relative to the optimal condition, regardless of the task order, indicating that maintaining attention in the easy condition was more difficult. No relations between perceptions of the task and neural correlates were observed. Exploratory analyses revealed higher levels of variability in FAA and theta/beta were associated with less enjoyment and more boredom, respectively. We speculate these observations reflect the less consistent engagement of self‐regulatory and attentional control and, in turn, might play a role in peoples' subjective experience. We discuss the implications of our findings for our understanding of influences on and strategies to mitigate boredom, as well as how attentional and self‐regulatory processes operate under conditions boredom typically emerges.