In the urban landscape of Attica, Greece, the safety of delivery drivers is a pressing issue. This study investigates their road safety challenges using a mix of qualitative and quantitative methods. Surveys and interviews with 200 food delivery drivers, alongside traffic safety data analysis, form the core of the research. Drivers responded to scenarios varying in delivery time, accident risk, and profit loss, choosing from three driving behaviour options. Using Multinomial Logistic Regression and Generalized Linear Model (GLM), key influencing factors like delivery time, accident risk perception, profit loss, driver age, fines received, and views on stricter penalties were analysed. These findings deepen our understanding of drivers’ decision-making processes, aiding in devising strategies to improve road safety. This research not only offers insights and recommendations for policy and road safety enhancement but also aims to foster a safer work environment for delivery drivers, contributing to urban road safety advancements.