The strawberry industry is facing the reality that it has been built on an unsustainable foundation. with dependencies on fumigation, plastic, pesticides, fertilizers, diminishing groundwater, undocumented labour and fuel for transportation. This chapter offers a case study of the impact of that market expectations have had on the US strawberry industry. After an introductory survey of the history of strawberry production in the United States, the chapter examines the development of an annual strawberry production system with the capacity to provide fruit to consumers year around. The chapter looks at the impact of shifting market expectations on the sustainability of strawberry production and examines the challenges of maintaining the high levels of inputs required for annual strawberry production in just a few favourable locations. Finally, the chapter looks ahead to potential solutions to current challenges.