Transportation insecurity causes adverse effects on people’s lives by limiting access to opportunities and resources even in San José. Understanding how people experience transportation insecurity in metropolitan areas may contribute to building a better transportation system. I conducted my research study by interviewing downtown San José residents and analyzing their stories on the effects of transportation insecurity and what they did to cope with the situation to move around San José. I analyzed the contents of the interviews through qualitative data analysis. Findings suggest that people experience transportation insecurity as time infringement through congested traffic, convoluted schedules, and service complications, which causes worry, anxiety, and missed opportunities. People's experiences and reactions allude to what could be improved in San José’s transportation infrastructure.