This capstone course is designed as a graduation pathway for MCP students at the University of Cincinnati. It applies the knowledge that twenty-six students have acquired during their two years in the program to a real-world urban challenge: the state of a city’s socio-economic evolution and its dynamic built environment. The report provided here gives an overview of a major, but unique, American city and presents its demography, economy, sectoral composition and environmental issues and problems. A realistic and detailed dataset for San Juan was developed and utilized for discussion  and analysis. Poverty and poverty alleviation, air and water pollution, transportation infrastructure, water management, environmental infrastructure, disaster preparation and relief, and urban design are urban issues were first explored by groups of four or five students, after which sixteen specific studio projects of one, two or three students arising from the research were undertaken to complete the final submission. The project is the centerpiece of the course and requires each student to deal with an urban issue of his or her choosing within the context of the oldest American city and the second oldest city in the Western Hemisphere. Each student’s work, then, culminated in a high quality written and visual product outlining how s/he proposes to improve the urban issue of focus within San Juan, including, in some cases, an actual site-based implementable pilot project.