Objective of the study: this article aims to point out and discuss the dilemmas and challenges of urban management that Picos / PI has been facing, considering its current Plano Diretor. Methodology/approach: Methodologically, the construction of the research is guided in two moments: the first, based on theory, among different thinkers, in urban and regional literature. The second, based on a qualitative whose reference is the selection, interpretation and technical analysis of legal documents from the municipality of Picos/PI: the current Plano Diretor and the Lei municipal do Uso do Solo. Originality/Relevance: The urban and regional dynamism that has occurred in many cities located outside the metropolitan areas of Brazil, since the 1980s, has motivated the constitution of a rich academic research stuff, whose direction has been given on the urban management processes and analyzes on the different instruments of urban planning. Many reflections have questioned about this cities future, as they live based on the existence and execution of their Plano Diretor. In this context, Picos/PI appears, a Regional Command City, qualified, for the strong spatial interactions, as well as, for the outstanding capacity, of a Functional Urban Area (FUA), in the hinterlands of Piauí, state of Brazil. Main results: The main dilemma lies in the observation that the analyzed laws have a series of nonconformities with the organicity of the city. In view of this, the great challenge is essentially political: the urgent updating of the Plano Diretor, as well as its effective application, with a view to solving a series of demands, of spatial organization, in the intra-urban context. Theoretical/methodological contributions: Analysis and interpretation of urban roles in the region and spatial impact from the conception of Regional Command Cities.