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The research question posed by the study was: have the medium-sized inland cities been the engine of regional growth and the organising structure of the territory, or have they contributed to sucking up population and resources by dismantling the rural spaces they organise? From the methodological point of view, a time-frame has been used to focus attention on what has happened since the beginning of the financial property boom until 2016, differentiating two well-defined periods. The first one in 2000–2008 and the second reflects what happened in 2009–2016. Two main quantitative sources are selected to develop the empirical part of the research: The Municipal Population Register and the Real Estate Cadastre. In order to assess the behaviour of the city outside its administrative boundaries, an analytical space has been generated consisting of a crown with a radius of 30 kilometres from each of the central cities, including the municipalities that have their municipal capital within this radius. Therefore, we have three units of analysis within each of the 22 provinces analysed, the 24 medium cities, the peri-urban crowns and the rest of the rural municipalities that make them up, starting always from the municipal scale. The answers to the research question are neither unique nor simple and seem to depend on the distance at which we move away, on the location of each city with respect to polycentric urban structures, and on the previous level of development and territorial culture of each region.