Chaos Engineering is a method of testing the resilience of systems, particularly Windows-based systems, by intentionally injecting faults and observing their behavior to enhance reliability and prevent outages. Originating from Netflix's transition to AWS, this practice has evolved into a scientific, safe approach even in production environments, addressing the limitations of traditional QA testing. With a significant portion of web applications running on Windows, Chaos Engineering is crucial for testing built-in fault tolerance features and understanding system reactions to failures. The article explores examples of Chaos Engineering applications on Windows Server, Microsoft SQL Server, and Microsoft Exchange Server, highlighting its role in simulating failover and capacity stress scenarios to ensure systems respond as expected. It advocates for planned outages or "FireDrills" to bolster team skills and system reliability, emphasizing that while Windows systems have robust support options, they also face greater risks without adequate testing. Gremlin's platform is recommended as a tool to help organizations identify and address availability risks in Windows environments, promoting resilient systems through comprehensive testing beyond traditional methods.