This chapter illustrates the reasons and circumstances that have led in Italy to the decline of traditional comprehensive planning and to the emergence of new approaches to general planning based upon informal tools. It presents a case-study of Milan that was chosen not only because it has always been the most economically dynamic area of the country, but also because many interesting innovations in planning practices have been attempted in the city although not always with positive results. The metropolitan area of Milan contains between 4 million and 10 million inhabitants depending on where one decides to draw the boundary; it is in fact one of the most densely populated and lively areas of the European continent. The chapter focuses on the deeper movements in Italian society that explain and give sense to these events. It draws some general conclusions for the new role of planning in contemporary society.