Understanding assigned tasks is an important skill for academic success. However, few studies have explored the accuracy of task understanding as it develops over the duration of a complex assignment. This study examined explicit, implicit, and socio-cultural aspects of task understanding in the context of an design project assigned to a third year class of Mechanical Engineering students. Specifically, this study examined: (1) the agreement between student and instructors task perceptions for the same complex engineering design task, and (2) changes in both instructor's and students' task perceptions from the beginning to the end of the task. Findings indicate that: (1) students' and instructor task-perceptions generally became more attuned over time, (2) instructor task-understanding evolved over time, and (3) socio-contextual aspects of task-understanding were highly correlated with task and course academic achievement.