Little is known about the stressors of working in covert and undercover policing roles and the impact these can have on the health and psychological well-being of police officers. Extant literature focuses upon the social impact of undercover and covert policing in a democratic society, especially in relation to policing political groups. Presented here are the results of an exploratory study into the lives of former police officers who have engaged in various forms of covert/undercover policing. Utilising semi-structured interviews, in a five-participant case-study design, this research investigates the impact that covert and undercover policing has on the well-being of former officers who have undertaken this role, and how they utilised coping strategies. Data were thematically analysed using Braun and Clarke’s framework (Braun and Clarke 2006). Findings were consistent in that fear of violence was a large factor that impacted the well-being and personal relationships of undercover officers. The paper concludes by outlining pertinent suggestions for future research and considers the implications for covert policing.