Reflective capacity has been described as an essential characteristic of professionally competent clinical practice, core to ACGME competencies. Reflection has been recently linked to promoting effective use of feedback in medical education and associated with improved diagnostic accuracy, suggesting promising outcomes. There has been a proliferation of reflective writing pedagogy within medical education to foster development of reflective capacity, extend empathy with deepened understanding of patients' experience of illness, and promote practitioner well-being. At Alpert Med, "interactive" reflective writing with guided individualized feedback from interdisciplinary faculty to students' reflective writing has been implemented in a Doctoring course and Family Medicine clerkship as an educational method to achieve these aims. Such initiatives, however, raise fundamental questions of reflection definition, program design, efficacy of methods, and outcomes assessment. Within this article, we consider opportunities and challenges associated with implementation of reflective writing curricula for promotion of reflective capacity within medical education. We reflect upon reflection.