Globally, the trend of population aging is accelerating. Taiwan becomes a Super-Aged Society in 2025, with Tainan City identified as one of the most hazardous areas in terms of traffic safety. This study investigates the needs and challenges senior pedestrians face when crossing streets in Tainan, as well as the opportunities and difficulties they may encounter when introduced to smart intersection technologies. The research is based on observation, and media-supported, probe-based contextual inquiry interviews. Elicitation materials (including video clips of problematic intersections, low-fidelity sketches of potential future technologies, and semi-structured interview questions) were used to gather participants’ feedback. Based on the data analysis, we developed a set of design considerations aimed at creating inclusive and safer smart intersections. These considerations are intended to guide policymakers, designers, and researchers in crafting innovative solutions that enhance mobility and safety for aging populations.