As new technologies are developed to handle the complexities of the Next Generation Air Transportation System (NextGen), it is increasingly important to address both current and future safety concerns along with the operational, environmental, and efficiency issues within the National Airspace System (NAS). In recent years, the Federal Aviation Administration’s (FAA) safety offices have been researching ways to utilize the many safety databases maintained by the FAA, such as those involving flight recorders, radar tracks, weather, and many other high-volume sensors, in order to monitor this unique and complex system. Although a number of current technologies do monitor the frequency of known safety risks in the NAS, very few methods currently exist that are capable of analyzing large data repositories with the purpose of discovering new and previously unmonitored safety risks. While monitoring the frequency of known events in the NAS enables mitigation of already identified problems, a more proactive approach of finding unidentified issues still needs to be addressed. This is especially important in the proactive identification of new, emergent safety issues that may result from the planned introduction of advanced NextGen air traffic management technologies and procedures. Development of an automated tool that continuously evaluates the NAS to discover both events exhibiting flight characteristics indicative of safety-related concerns as well as operational anomalies will heighten the awareness of such situations in the aviation community and serve to increase the overall safety of the NAS. This paper discusses the extension of previous anomaly detection work to identify operationally significant flights within the highly complex airspace encompassing the New York area of operations, focusing on the major airports of Newark International (EWR), LaGuardia International (LGA), and John F. Kennedy International (JFK). In addition, flight traffic in the vicinity of Denver International (DEN) airport/airspace is also investigated to evaluate the impact on operations due to variances in seasonal weather and airport elevation. From our previous research, subject matter experts determined that some of the identified anomalies were significant, but could not reach conclusive findings without additional supportive data. To advance this research further, causal examination using domain experts is continued along with the integration of air traffic control (ATC) voice data to shed much needed insight into resolving which flight characteristic(s) may be impacting an aircraft's unusual profile. Once a flight characteristic is identified, it could be included in a list of potential safety precursors. This paper also describes a process that has been developed and implemented to automatically identify and produce daily reports on flights of interest from the previous day.