Our service learning research includes assessment of reflective assignments done by students who apply theoretical knowledge in practical, real-life contexts by working with actual clients. For many of these students our classes are a departure from traditional forms of learning, and a challenge to their ability to apply what they know in often very unpredictable situations. The reflective assignments, which include field notes and journal entries, are designed to 1) train the professional competencies of client case management, writing and recording and 2) foster a sustained commitment to learning and professional development. This paper will describe several teaching and learning issues related to reflective writing which we have encountered in our students' work, and outline our plans to address them as we continue to promote critical thinking and reflection as important skills for our students to master.