There are a number of upcoming paradigm shifts within Information Assurance (IA), to include policy and technical mandates, affecting IA in today's training and simulation systems. Maintaining situational awareness of a system's IA posture has been a challenge DoD wide. Specifically, in the training and simulation community it has been especially difficult given the closed, restricted networks the systems create or may intermittently traverse. A number of DoD wide policies and technical solutions have been developed and procured to ensure a system owner has continuous oversight of their system's IA posture. Over the years the Defense Information System Agency (DISA) has provided tools and solutions to Project Managers (PMs) to easily assess a given systems IA posture at a given time. The most popular example of these tools was the Gold Disk. However, the Gold Disk program was discontinued in 2012. Next came a suite of products much more scalable and robust in capabilities, but also with significant complexity. Assured Compliance Assessment Solution (ACAS), Host Based Security System (HBSS), and Continuous Monitoring and Risk Scoring (CMRS) are a few of the latest DISA licensed Commercial Off The Shelf (COTS) and Government Off The Shelf (GOTS) solutions available to PMs for integration into their systems at no cost. These solutions were designed for an enterprise Information Technology (IT) environment, but must be scaled to integrate with training and simulation systems. This paper will discuss the continuous monitoring requirements, benefits, emerging security practices, implementation concepts, and a training system example. This paper will document how the U.S. Army Program Executive Office for Simulation, Training, and Instrumentation (PEO STRI) is addressing the growing cybersecurity threats through continuous monitoring and improved situational awareness by leveraging DISA licensed COTS and GOTS solutions to secure training and simulation systems. All DISA licensed COTS and GOTS described in this paper are available at no cost to the Government to implement.