It is not unheard of to find over 20,000 different applications once you consider all of the processes associated with executables under the hood. With that kind of scale, the task of going through all of those applications to identify the working white list is a monumental first step. This paper examines how to manage beyond the established white and black lists and offers a mechanism that keeps user productivity unimpeded while the automated trusted sources and ranking decision-makers look closely into those 50 shades of gray.