Reflection is crucial for aspiring teachers, yet many pre-service teachers (PSTs) struggle to grasp its true meaning. This study explores how PSTs deconstruct their initial reflections and re-signify their understanding based on challenges encountered in real-world practicum settings. Additionally, it examines how the facilitator supported the PSTs’ reflections over time. Over the course of a year in the physical education teacher education context, six PSTs, along with the first author, who fulfilled dual roles as external facilitator and researcher, engaged in three iterative Action Research (AR) cycles. Within each AR cycle, the external facilitator explored the authentic teaching challenges faced by PSTs, offering individualized support while unpacking reflection concepts. Data were collected through focus group interviews, reflective journals from the PSTs, and the observation of participants by the external facilitator, which provided contextual field notes on the PSTs’ teaching–learning experiences. Our findings emphasize the need to initially understand PSTs’ views on reflection. This serves as a starting point for deconstructing the three concepts outlined in our theoretical framework, through the scrutiny of PSTs’ real teaching–learning experiences. This process facilitated a resignification, leading to an advanced comprehension of reflection among the PSTs. The study emphasizes the value of integrating this approach into systemic teacher education reforms and suggests extending training and mentorship to cooperating teachers.