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In 1998, South Africa promulgated a Water Act that is widely regarded as one of the most progressive and enabling pieces of environmental legislation in the world. The environmental aspects of the Water Act are commonly referred to as “resource-directed measures.” These measures attempt to find the right balance between (1) leaving water in the resource (“nonconsumptive use”) to provide ecological goods and services for society and (2) taking the water out of the system for “consumptive” human use. These measures also attempt to ensure that both nonconsumptive and consumptive use is sustainable. This article discusses some of the challenges faced in using the measures to achieve environmentally sustainable ground water use. A major challenge is that misunderstanding still abounds regarding the environmental aims of this legislation. Other major challenges identified included a severe shortage of technical capacity, an inordinately long water use license application process, incorporating adaptive management to deal with uncertainty, incorporating the public participation process, and revising policy implementation processes to accommodate highly localized aquifers. Selecting appropriate scientific methodology—neither too simplistic nor too involved—is a recurring challenge. It is suggested that an important part of addressing these and the other challenges identified is a period of reflection and dialogue between the various sectors involved.