The discretionary nature of the development management process in the UK makes the relationship between the plan and the decision on individual development projects especially important. Drawing on empirical research with professional planners in England and Scotland, this chapter explores some of the key dilemmas of contemporary planning practice. Development Management has long been neglected by planning scholars, but within a public sphere increasingly shaped by austerity, outsourcing and deregulation, the challenges for everyday practice are manifold. This chapter considers the issues against a background of an appreciation of the importance of good-quality planning.