Aims & Objectives: Gated communities are systematically seen as safe places to live, especially by an affluent urban middle class. All spatial elements of control such as high walls, porters and guarded gates are seen as strong deterrents of crime and enabling safe live. However, recent reports show that communities became hostages of their own space and security, developing most of their socialization within these places. There is widespread believe that common social rules and laws applied to the city are not applied inside gated places; walls and gates separate them from the outside society’s laws. As a result, young children are allowed to drive cars, which are parked on public spaces, rules and authority is questioned and the dwellers are lenient to transgressions. This article compares American gated communities with Brazilian condominiums showing the similarities and peculiarities of both urban structures. It also investigates the impact of this wide spread new urban configuration on peoples experience of common and public spaces, sense of urbanity, transgression and impunity. Examples of social practices in gated neighborhoods are presented, building up evidence showing the spatial segregation, the lack of social respect, the weak role of administrations and a different concept of community. This paper discusses the effect of experiencing “legal” transgressions of spatial and social rules and norms in gated communities and the emergence of a permissive generation of citizens. Context & background literature: Review the recent literature on gated communities in America, and Latin America. Findings & Conclusions: children and youth being brought up in gated communities are much more lenient towards social transgressions than children experiences city's neighbor.