Objective: A ‘cancer care observation’ (CCO) empathy training is described. This study examined psychiatry trainees’ experience of CCO and cancer patients’ experience of being observed. Method: Trainees were paired with consenting patients undergoing cancer treatment; they observed a number of cancer treatment sessions and chronicled their experiences. The observations were discussed in supervision. Semi-structured interviews were conducted with trainees and observed patients. Observation journals and transcribed interviews were analysed using qualitative description. Results: Seven trainees participated. Three themes emerged: patients used trainees to support themselves while trainees struggled with role identities; CCO extends trainees’ professional awareness and can benefit patients; and staff reactions were mixed. Trainees developed wide-ranging, empathic insights into cancer and hospital care experiences. No patient regarded CCO as intrusive. Conclusions: Trainees garnered insights from CCO as they generated clinical hypotheses, learnt about professional boundaries and gained first-hand experience of unconscious mental processes based on their empathic connections. CCO lends itself to psychiatry and, potentially, other medical trainees.