Since the 1960s, victimization surveys have attempted to measure the level and extent of fear of crime. Along with the measurement of fear of crime, researchers have tried to develop theoretical models to explain it. These models include variables such as individual and contextual ones. This article presents a study which had the main goal of exploring emotional and insecurity reactions to a set of urban contexts (night, day, rehabilitated and non-rehabilitated neighbourhoods). To measure the impact of emotional and insecurity reactions a questionnaire was constructed and administered to a sample of 99 individuals. The questionnaire included measures of emotional reactions – Self-Assessment Manikin (SAM; Lang, 1980) and the Positive and Negative Affect Schedule (PANAS; Watson & Tellegen, 1985), insecurity reactions, and the importance of contextual features to the level of insecurity and ease of reaction in each urban context. The independent variables were operationalised with eight pictures representing the abovementioned urban contexts. The results showed that both night and non-rehabilitated contexts triggered higher levels of insecurity and negative emotional reactions compared to day and rehabilitated settings. Also, lighting (or lack of it) seemed to be an important contextual cue to perceptions of (in) security in day and night settings. In the non-rehabilitated context the most important spatial cue was the state of conservation of the building. These results will be discussed and the importance of this study for the impact of contextual cues in the fear of crime will be outlined.