Product development (PD) is a crucial capability for firms in competitive markets. Building on case studies of software development constructed from fieldwork at a large firm, this paper explores the interaction among the different stages of the PD process, the underlying architecture of the product, and the products in the field. The study corroborates the dynamics of tipping into “firefighting” (Repenning 2001) that follows quality-productivity tradeoffs under pressure. Moreover, we introduce the concept of the “adaptation trap,” where intendedly functional adaptation of workload can overload the PD organization and force it into firefighting because there is a delay in seeing the additional resource need from the field and underlying code-base. Finally, the study highlights the importance of architecture and underlying product-base in platform-based product development, through their impact on quality of new models under development, as well as resource requirements for bug-fixing. Put together, these dynamics elucidate some of the reasons why PD capability is hard to build and how it erodes. Consequently, we offer hypotheses on the characteristics of the PD process that increase its strategic significance and discuss some practical challenges in the face of these dynamics.