In an effort to understand the nature of perceptual expertise in laparoscopic surgery, we interviewed 20 surgeons, using videotape footage of a challenging laparoscopic gallbladder removal case. Early data analysis showed that certain perceptual cues along with accepted surgical methods were important for supporting the confidence level needed to proceed laparoscopically when risk was present. Staff (expert) surgeons in this sample decided to convert to an open procedure less frequently than residents. They also were able to “see” meaningful perceptual cues more frequently than the residents. Staff surgeons were more likely to make specific predictions and inferences about the patient’s disease from the available perceptual information. To varying extents, all of the surgeons indicated the importance of monitoring whether events were outside their personal comfort boundary. This research supports a focus on perceptual abilities as well as metacognitive abilities in surgical training.