We have applied space syntax analyses in order to uncover the configurative architectural knowledge into two different, however complementary, scenarios. One scenario, the children constructions of city models with wooden blocks, from 5 to 9 years of age, and in teams of six children, three boys and three girls. The studies show a lot of differences in relation to school, family background and social qualities of places where children live. However, the main differences come from the dialogical qualities of the social interactions among all these factors, and we think that the space syntax analyses are able of measuring these dialogical qualities. The second scenario is urban history scenario in medieval villages in Catalonia and we have analysed thousands of them, and they are deposited in the Catalan National Archive of Catalonia. We use the space syntax analyses to uncover the knowledge of the generation of the urban structures, even if the meaning of them in history has been lost. The forms by themselves can show a lot of information invisible for the users of today. In this paper we will focus our attention into the first of these scenarios: The one related with architectural cognition and with architectural education in childhood. As Bill Hillier has stated: The configurative knowledge of architecture and planning is embedded into building and urban forms in a “generative way”, so we will analyse how this generative and configurative knowledge develops in children.