The moment a system is put into service it begins to lose value as technological and societal changes accrue while the system is frozen in the state it was constructed. System decision makers are faced with the choice of accepting a decline in performance, updating the design, or retiring the system. Each time a decision maker faces these alternatives, the value of the available options must be evaluated to determine the preferred course of action. A design that can adapt to changes with minimal cost should provide more value over a longer period than a system that is initially less costly, but less adaptable. This is especially desirable for systems that have large initial costs and/or a lengthy development cycle. The purpose of this paper is to evaluate the United States Air Force (USAF) B-52 Stratofortress and the United States Navy (USN) F/A-18 Hornet to characterize the changes in desired capabilities and what system attributes allowed them to either successfully adapt or prevented them from adapting. These observations allow the development of heuristics that designers can use during system design to enhance system lifetime value.