In two studies, we took a prospect–refuge based perspective to investigate how lighting and other physical attributes (i.e., prospect, concealment, and entrapment) affect people’s judgments of the safety of urban streets during nighttime. Both studies complement existing research, which predominantly use factorial designs, with more ecologically valid correlational research using a large and representative sample of urban streets as stimulus materials. Results from Study 1 corroborate existing research demonstrating that differences in prospect, concealment, and entrapment predicted, to a large extent, variation in the perceived safety of urban streets—thus demonstrating the utility of such environmental information for making safety judgments in real-life settings. Results from a mediation analysis conducted in Study 2 showed that the relation between appraisals of lighting quality and safety judgments was completely accounted for by co-occurring variation in appraisals of prospect and entrapment. Implications for theory and methodology are discussed.