Field trips to augment in class learning hold valuable learning opportunities and can be transformative when observing context is important to understanding complex issues such as mental health and addiction. However, student reflections papers written after participating in the field trip were reviewed over a five-year period and identified that this form of experiential learning also resulted in harm to some social work students. Using a phenomenological approach (van Manen, 1990) to secondary data analysis, 53 papers identified four clusters of meanings related to discomfort, appreciation/ambivalence/regret, personal experiences of trauma and power. These individual experiences collectively raised larger questions around social work pedagogy and how educators should prepare students when confronted with distressing situations. We wondered to what degree witnessing such conditions became either a transformative experience as described by Rone (2008) or re-enacted individual experiences of past trauma. With field experience a pedagogical cornerstone to a career in Social Work, we advocate for ethically balancing between safeguarding students from feeling acute distress or re-experiencing trauma as a result of field trips, while ensuring they are professionally prepared to enter the profession upon graduation.