Long-term exposure to critical incidents can have a negative impact on officers’ well-being while affecting their capacity to maintain public safety. Operational flaws can, similarly, lead to hasty and incorrect decision-making; therefore, adequate briefing and debriefing systems are needed to facilitate the management of critical incidents. This study aimed to investigate the types of critical incidents and their impact on front-line officers’ well-being in light of the existing briefing and debriefing systems in Metro South African Police. A qualitative exploratory method was used to understand the impact of critical incidents and the Police officers’ perceptions of briefing and debriefing structures in the South African Metro Policing context. A total of 25 Metro Police officers were invited to share their experiences regarding their handling of critical incidents. The findings indicated that incidents involving mutilated victims or the death of a fellow police officer induced strong feelings of guilt and anger. Incidents with faceless crowds involving poor operational planning and execution strategies induced confusion, helplessness, frustration, and often humiliation. Participants were clearly fearful of appearing soft or inadequate in asking for help from their supervisors. Consequently, they remained reluctant to disclose their fears and concerns so as to avoid subsequent stigmatization in the absence of a systematic debriefing procedure. The current system of briefing and debriefing procedures cannot address the psychological and operational needs of the members of the police force. Internationally recognized briefing and debriefing systems must be urgently adjusted to and implemented within the South African policing landscape.