Naturalistic observations of two fifth-year surgical trainees in the OR revealed that they struggled with specific tasks during several seemingly straightforward laparoscopic surgical procedures. Retrospective think-aloud reports of the trainees and their attending surgeons on those tasks in video clips and NASA-TLX ratings further shed lights on trainees' specific challenges. Results showed that trainees' inadequate cognitive skills rather than poor technical skills could be their greatest hindrance in performing those tasks. Specifically, the trainees seemed to focus their attention on immediate urgent tasks and failed to plan strategically for action sequences or manipulations. NASA-TLX results further showed that trainees and attending surgeons differed in their perceptions of effort, performance, and frustration in performing those isolated tasks. These preliminary data suggested that a gap exists between trainees and the more experienced surgeons on their attention allocation strategies, which may indicate the need to emphasize cognitive skills training such as multitasking during the practice of surgical skills outside the OR.