The rapid assimilation of leading-edge technologies into the modeling and simulation (M&S) tools of today has provided a revolutionary approach for many of DoD's users, particularly within the acquisition, joint training and joint experimentation communities. However, leveraging technology to assist the warfighter w ith the "process of applying incremental review, analysis, evaluation, and testing to M&S products to improve credibility" (Defense Modeling and Simulation Office, DMSO, definition of V&V process) has not kept pace. One area of M&S that has undergone the greatest metamorphosis is the synthetic environment. In the short span of 10 years, what was a paper-like digitized terrain map depicting a flat earth at "high noon" and devoid of weather has evolved into a sophisticated synthetic natural environment. Modern simulation synthetic environments continue to grow in size, geodetic rigor, geographic fidelity, and application domain. The richness of these data sets, while markedly improving their utility and widening their applicability, increases the likelihood of error caused by feature interaction and the sheer complexity of construction techniques. Although our capacity to produce large and complex digital environments has seen great improvement, there has not been an attendant growth in the development of automated tools that can help ensure credible results. This paper addresses V&V of federated synthetic environments. The first section exemplifies classes of digital environment conditions that have proven to contribute to anomalous simulation entity behaviors or incorrect analytical results. We describe a utility to automatically locate such conditions as the first step toward managing inter-simulation interactions within a federation. Then, we discuss a methodology to assess interaction validity of the environmental algorithms and data, across a federation. Finally, we describe this process as an asset for event managers, aiding in the design of scenarios that will avoid unfair fight situations.