This quantitative, correlational, and transversal study was performed with a sample of 482 participants from an urban community at the Historic Centre of Porto (HCP). Participants answered to an enquiry designed to collect information about (dis)satisfaction with the police and its performance, with sociodemographic, victimisation, criminal, environmental, social control, and community variables as potential predictors. Findings revealed that the community was mainly satisfied with the police in its efforts to guarantee security, and there was no relationship between those variables, and sociodemographic and some community variables (e.g., years at the HCP, willingness to collaborate in security measures, and strength of attachment to HCP). On the other hand, there were relationships of (dis)satisfaction with the police and being the victim of crime, and some criminal and environmental variables (e.g., perception of increased criminality, conditions promoting crime, and incivilities). Regression analyses found that the perception of increased criminality and the need to adopt improvement measures were significant predictors of dissatisfaction with the police. This study promotes further discussion on factors that can be improved to increase satisfaction with the police and the connection of community–institutions to promote community security.