The widespread integration of technology into everyday life has made pedestrians increasingly susceptible to engaging with distractions. Consequently, it is important to understand the factors that drive their use of technology while walking and the associated risky street-crossing behaviors. Given that smartphone and smartwatch use are among the most common technology-related activities in pedestrian behavior, this study aimed to investigate the influence of behavioral and psychological factors, including fear of missing out (FoMO), mindfulness, nomophobia, self-identity, and self-control on pedestrian technology use while walking (i.e., smartphone and smartwatch use) and their propensity for risky street-crossing behavior. Data were collected from an online survey of 2221 participants in different cities of Iran. A structural equation model (SEM) was developed to explore these relationships, drawing on insights from previous theoretical frameworks. To account for the effect of heterogeneity, the relationship between constructs was explored among different individual groups using Multiple Indicator Multiple Causes (MIMIC) models and Multi-Group Analysis (MGA). The results revealed that mindfulness, followed by nomophobia and self-identity, were the strongest predictors of technology use while walking. Technology use while walking was more frequent among males, individuals aged between 18 and 24, those with prior crash experience and in the trips after 4 pm. In addition, individual characteristics proved to pose a moderating effect on pedestrian technology use and its predictors. FoMO emerged to be a more significant predictor of males’ personality factors and their risky behaviour, while nomophobia, mindfulness, and self-identity were stronger predictors of females’ personality factors, technology use, and risky behaviour. The findings of this study contribute to increasing knowledge in the field of pedestrian safety and inform the development of targeted interventions aimed at mitigating risky behaviours and promoting safer urban environments.