Teachers’ experience of negative emotions has been associated with teacher turnover, a significant problem faced by many education systems around the world. This chapter aims to provide a deeper understanding of these phenomena through the appraisal of Bob, a novice secondary school teacher, who, despite having considered leaving the profession during a rough moment in his career, ultimately stays on after moving to a different school. The details of Bob’s appraisal are presented using an analytical approach that makes it possible to explore it in a holistic way. This examination shows the features of Bob’s appraisal both when he was experiencing negative emotions and considering dropping out of the profession and once he decided to continue. We find that, in Bob’s appraisal during the difficult period, his duties generate contradictions with actions by leadership and students, revealing a lack of leadership support and considerable student misbehaviour. Changing schools leads to some transformations in his appraisal: contradictions related to the lack of leadership support are overcome, and better student behaviour is noted. We discuss other studies that illustrate the positive impact of teacher reappraisal on professional development and teacher education and advocate for a collective effort to address the issues related to teacher distress and turnover through reappraisal.