During the last decade there has been a dramatic shift in corporate IT infrastructure and how it managed. Gone are the days where IT assets are centrally located and managed only by company employees. Security assessors now have to account for cloud hosting providers, outsourced IT, and 3rd party hosted applications. The problem we are currently faced with is that most of the process that are used to assess the security perimeter of a company are rooted techniques that were developed when IT was centrally housed and managed. This presentation will discuss the problem space and approaches that can be used to obtain objective data to more accurately assess the security posture of distributed corporate IT assets.