Strawberries are produced in much of the world with practices that many consider unsustainable. These include soil fumigation, the use of plastic, a high water requirement, and dependency on pesticides to produce high quality fruit. In addition, strawberry fruit quality is inconsistent in the marketplace, and the product is often unaffordable to poorer segments of the population. Many of the problems inherent in our production systems simply reflect an absence of design around certain guiding principles. No one set out to deliberately design an input-intensive, environmentally expensive production system for strawberries, it just evolved as growers and researchers responded to problems with short-term solutions. Researchers are now challenged to design and build strawberry production systems that follow certain guiding principles that include the use of renewable and recyclable resources, the use of products and practices that do not cause environmental damage, practices that do not harm communities of people, and systems that are economical. Eight critical questions are presented that, when answered, will help provide the building blocks for a more sustainable design. Our legacy as a worldwide community of researchers could be one of entrenchment as we fine-tune current production systems, or it could be one of creative design as we develop and introduce novel production systems that sustain soils, farms, communities, and the environment far into the future.