Real-world design settings can be complex, ill-structured, open and typically uncertain and/or ambiguous about their goals and solution paths. This study contributes to understanding how to work with these types of problems in a course project setting. The main objective of the study is to identify, propose and validate a set of practical guidelines for dealing with ill-structured, open-problem project assignments in courses that teach design engineering or design development planning. A literature review identifies key practices for proposing the guidelines, which are then validated by intervening in an engineering project management master's course. The intervention took place during the COVID-19 lockdown restrictions with 12 project groups created from 105 enrolled students. During the validation, qualitative and quantitative feedback was gathered from the students, and the results provide positive evidence for achieving the objective. Key to this outcome was the combination of the self-regulation of learning, co-regulation of learning and socially shared regulation of learning. In this sense, the proposed guidelines look promising for redesigning university courses that deal with open problems, thus enhancing students' capacity for handling uncertainty and ambiguity.