This article describes an exploratory investigation of the risk perceptions of experts and novices in relation to helicopter operations, under conditions where the participants are matched on various characteristics previously found to affect perceptions, such as demographic, gender, and background factors. The study reports considerable evidence of perceptual differences between the two participant groups (i.e., expert pilots and candidate pilots). We find that the experts' perceptions of relative risks are more veridical, in terms of their higher correlation with the true relative frequencies. A significant positive correlation between the flight hours and the contextual risk-taking tendency is also shown, leading the experienced pilots' choices toward risky alternatives in scenarios—a potential result of their overconfidence based on superior task performance. Possible explanations are offered for the findings and potential avenues for future research are identified.