IT system development, integration, deployment, and administration benefit significantly from free and open source software (FOSS) tools and services. Affordability has been a compelling reason for adopting FOSS in computing curricula and equipping computing labs with support infrastructure. Using FOSS systems and services, however, is just the first step in taking advantage of how FOSS development principles and practices can impact student learning in IT degree programs. Above all, FOSS development of IT systems requires changes to how students, instructors, and other contributors work collaboratively and openly and get involved and invested in project activities. In this paper I examine the challenges to engage students in FOSS development projects proposed by real clients. A six-week course project revealed problems with adopting FOSS development and collaboration across different activities and roles that student team members have assumed. Despite these problems, students have showed a genuine and strong interest in gaining more practice with FOSS development. FOSS development teaching was further refined in two other courses to learn about adequate teaching strategies and the competencies that students achieve when they participate in FOSS development of IT systems.