Some problems just bother you more than others. Are extreme insight experiences more likely when working on such problems? Insight research typically focuses on whether or not an insight occurs, but no research has been found that empirically explores predictors of variability in insight experience. To fill this gap, online survey data were collected from Amazon Mechanical Turk workers (N = 253) and professionals contacted through Zoomerang (N = 246). A scale was created to measure the bothersome state, or mental itch, as participants had experienced it while trying to solve a challenging problem at work. The mental itch score accounted for variance in insight experience beyond intrinsic motivation and ideational behavior scores. An interaction between mental itch and ideation was also observed in explaining insight experience—specifically, ideation accounted for extreme insight experiences only when participants were also experiencing a strong mental itch while working on the problem. Findings also suggested that 1 mechanism through which a mental itch facilitates extreme insight experiences is through an obsessive passion for solving the problem. Key implications of this research are that (a) more research should study insight experiences as they naturally occur, and (b) measuring mental itch experience in all insight research (in experimental and natural settings) would help to increase the comparability and generalizability of different research findings.