Project-based learning has been explored in a variety of contexts and different phases of education. Several implementation challenges are associated with project-based learning. Among these challenges is ensuring collaboration between students enrolled in a project assignment. The purpose of this study was to present several practical insights on how to tackle collaboration challenges in project-based learning. The study is based on the qualitative analysis of 67 reflections reports submitted by students who were enrolled in a project-based learning assignment in engineering education. The results suggest that collaboration challenges can be traced to priority conflicts between students as well as to the uncertainty in the project assignment. The results further suggest that these challenges can be successfully addressed by applying a structured project-management approach to planning, communication, and follow up. In addition, the findings suggest this structured approached should be supported by a mindset that recognizes the importance of adaptations and flexibility as the project develops. Moreover, the findings suggest that a collaboration environment based on inclusion, openness, and support enables students to respond to emerging problems and disagreements. The paper outlines several recommendations on how to improve students’ collaboration ability within project teams in the context of project-based assignments.