AbstractA strong interest in fare evasion is currently emerging in all proof-of-payment transit systems owing to its severe implications. Recent research has investigated from the passenger perspective how sociodemographic variables, travel behavior, and situational factors affect the intention to evade fares for students, workers, and unemployed passengers. Conversely, testing the demographic segmentation of passengers clustered according to gender and age variables and isolating the key factors related to the intention to evade fares have not yet been addressed. Besides the context of the smart cities’ paradigm, the fight against fare evasion has been little dealt with, also owing to the difficulty in being able to frame such an issue within the classic pillars of smartness. This study covers these gaps using a two-step approach. First, gender and age variables are used to define five demographic segments: male, female, young, middle-aged, and older passengers. Next, crucial determinants are detected for each segment using statistical models. The analysis revealed that the intention to evade fares increases for males who travel a lot during the day and for females who are dissatisfied with the service and know the fine amount. Moreover, it increases for young, middle-aged, and older passengers that make short trips, often travel, and use various transit systems, respectively. Finally, the intention to evade fares increases for each segment when passengers have a history of fare evasion. The overall findings may help bus operators plan tailored countermeasures against specific segments.