Many challenges exist that make it more difficult to safeguard networked environments properly. In this course, we'll start with an overview of security monitoring, and then dive into challenges related to encryption and network monitoring. We'll also explore attacker tactics, including detection evasion, data exfiltration, network traffic manipulation, and pivoting. Each section expands on the challenges these topics pose to effective security monitoring and information on how modern controls can detect and mitigate them. By the end, you’ll have a well-rounded understanding of the challenges in monitoring complex infrastructures, enhancing your ability to protect and secure digital assets.