In 1994, the U.S. Environmental Protection Agency’s Superfund Program began to develop a paper imaging system known as the Superfund Document Management System (SDMS). SDMS came into being as an attempt to improve management of and access to Agency records. An Agency workgroup composed primarily of Superfund records managers developed functional criteria for the application, and elected an Agency regional office for implementation pilot. At the time of this writing all EPA Superfund regional offices have implemented SDMS. For reasons described in this chapter, even as SDMS achieved institutional acceptance it faced pressures to adapt to internal and external pressures. The emergence of the World Wide Web, the inevitability of electronic records, the rising costs of maintaining large paper collections all combined to produce a niche different in key aspects from that which the system was originally designed to occupy. This chapter discusses how the interactions of two life cycles — records and systems development — affected the fitness of the system to its environment.