This research examines factors contributing to professional misconduct among registered health professionals in New Zealand. It seeks to understand more about the factors contributing to situations where health professionals fail to recognize and manage situations that result in disciplinary action. A multiple case study approach was used to analyze New Zealand Health Practitioners Disciplinary Tribunal (HPDT) cases published between 2012 and 2015. Data were developed from 33 case reports published full text on the HPDT website involving practitioners who had been found guilty of professional misconduct. Findings were developed from the research data both deductively and inductively, creating theoretical interpretations grounded in an iterative process of cross-case synthesis. The findings show three core themes that are present in the analysis of cases, including failure to “benchmark” best practice, inability to moderate behavior, and inability to reflect and learn with colleagues. Key factors contributing to the failure to recognize and manage professional situations indicated a “Perfect Storm” that gathered around professional, personal, and organizational issues. Professional isolation, lack of knowledge and skill, challenging client situations; personal stress, neediness, or “stuckness”; and organizational factors such as high acuity/demand, all contributed to this Perfect Storm. Health practitioners and their colleagues should notice moments when their own or others behavior is inappropriate or unreasonable in the context of a client’s care, particularly responses that are a recurring pattern. Ongoing education about professional issues is an essential requirement for the health workforce as more complex demands and work roles impact on practitioners.