As more entrepreneurial experiences are integrated into engineering programs, students are faced with new challenges they need help in managing. While previous research has identified entrepreneurial activities that engineering students struggle with, the antecedents of these difficulties have not been directly investigated. Drawing on an ethnographic study in a project-based entrepreneurship course, this paper investigates difficulties as caused by both cognitive conflicts and cultural clashes. The findings suggest that difficulties with entrepreneurial activities do not necessarily stem from lack of entrepreneurial capabilities on behalf of students, they can just as well stem from legitimate conflicts of interest that students and teachers need to navigate. As such, difficulties cannot always be solved by students learning more about entrepreneurship. As shown in the study, collaborative and externally oriented learning activities – mainstays of project-based entrepreneurship courses – particularly contribute to putting competing social demands on students.