Urban road-maintenance activities play a central role in sustaining mobility, service reliability, and infrastructure performance in dense metropolitan environments. This study aims to identify significant risks affecting routine road-maintenance operations in Jakarta, a megacity that relies heavily on rapid-response systems driven by citizen reporting. The research adopts a structured risk-identification and evaluation approach based on the ISO 31010 Probability–Impact Matrix (PIM). An initial set of fifty-two risks was identified through literature review and expert interviews, then refined to thirty-six validated risks following expert assessment. These risks were subsequently evaluated using a quantitative survey in which practitioners rated the probability and impact of each risk on a five-point scale. Mean probability and impact values were plotted directly into the PIM adapted from Kaseem and Hamzah (2019), producing a color-coded visualization of risk significance. Ten risks were classified as significant, occupying the red-zones (light and dark) of the matrix. The most dominant risks derive from three primary domains: (1) environmental exposure, notably heavy and extreme rainfall, which severely disrupts workflow and increases defect volumes; (2) resource limitations, including shortages of materials, damaged equipment, and insufficient personnel; and (3) operational challenges related to dense traffic, public non-cooperation, and inaccuracies in citizen-reporting data from the CRM platform. These findings highlight the complex operational landscape of Jakarta’s maintenance ecosystem, shaped by climatic variability, resource constraints, and urban-behavioral factors. The identified significant risks offer a practical basis for prioritizing improvements in resource planning, public engagement, and maintenance coordination. The study contributes empirical insights for enhancing resilience and responsiveness in urban road-maintenance management, with relevance for other rapidly growing cities facing similar infrastructural pressures.