As systems become more interconnected, the focus of engineering design must shift to include consideration for systems of systems (SoS) e ects. As the focus shifts from singular systems to systems of systems, so too must the focus shift from performance based analysis to an evaluation method that accounts for the tendency of such large scale systems to far outlive their original operational environments and continually evolve in order to adapt to the changes. It is nearly impossible to predict the nature of these changes, therefore the rst focus of this thesis is the measurement of the exibility of the SoS and its ability to evolve and adapt. Flexibility is measured using a combination of network theory and a discrete event simulation, th...