Information Technology (IT) curricula's strong application component and its focus on user centeredness and team work require that students experience directly real-world projects for real users of IT solutions. Although the merit of this IT educational tenet is universally recognized, delivering collaborative and experiential learning has its challenges. Reaching out to identify projects formulated by actual organizations adds significantly to course preparation. There is a certain level of risk involved with delivering a useful solution while, at the same time, enough room should be allowed for students to experiment with, be wrong about, review, and learn. Challenges pertaining to the real-world aspect of problem-based learning are compounded by managing student teams and assessing their work such that both individual and collective contributions are taken into account. Finally, the quality of the project releases is not the only measure of student learning. Students should be given meaningful opportunities to practice, improve, and demonstrate their communication and interpersonal skills. In this paper we present our experience with two courses in which teams of students worked on real-world projects involving three external partners. We describe how each of the challenges listed above has impacted the course requirements, class instruction, team dynamics, assessment, and learning in these courses. Course assessment and survey data from students are linked to learning outcomes and point to areas where the collaborative and experiential learning model needs improvement.