This paper describes a critical situation for Italy, which is one of the causes of the overall disorganization of settlement growth in the past decades. Using the data extracted from some institutional databases, we show that a large part of the national territory is managed with highly effective decision-making tools (such as municipal town planning schemes in Italy), which are, however, lagging behind in their conception and fulfilment of scientific, cultural, and political requirements deemed essential today for effective and sustainable land transformation. Municipalities with plans dating back to a quarter of a century ago, or without any plans, are 1445 in number (17% of the total) and involve 6,200,000 ha of territory (1/5 of Italy) with almost 10 million residents. The territorial changes in these geographical areas, mainly concentrated in the south, are managed with tools based on mid-20th century concepts and techniques, although a large proportion of these territories are demographically active and transform substantial portions of land. Thus, for at least 15–20 years, these territories underwent transformations disconnected from town plans and driven essentially by one-off measures or managed through numerous exceptional and negotiated procedures provided for by national legislation. Today, it seems necessary for southern Italy to overcome its extensive delay in territorial planning, and the drive can only come from national government. This would help it finally respond to current environmental sustainability, risk resilience, and territorial security requirements, through appropriate and technically advanced management procedures not envisaged in previous planning procedures.