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Within any incremental development paradigm, there exists a tension between the desire to deliver value to the customer early and the desire to reduce cost by avoiding architectural refactoring in subsequent releases. What is lacking, however, is quantifiable guidance that highlights the potential benefits and risks of choosing one or the other of these alternatives or a blend of both strategies. In this paper, we assert that the ability to quantify architecture quality with measurable criteria provides engineering guidance for iterative release planning. We demonstrate the use of propagation cost as a proxy for architectural health with dependency analysis of design structure and domain mapping matrices as a quantifiable basis for iteration planning.