The chapter develops critical reflections on the relationships between urban planning strategies, urban regeneration, and the vulnerabilities of older adults living in Brescia, a mid-sized northern Italian city. Specifically, it focuses on the dynamics through which local planning logics either support or undermine the right of older adults to autonomously participate in the life of the city. It examines how the definitions of “vulnerable subject” emerging from key planning tools (in) directly create conditions that can be described as “planning-induced dependency” and heightened vulnerability for marginalized residents, including older adults. Drawing on feminist debates in sociology, planning theory, and political philosophy, the chapter critically analyzes urban policies implemented in the city over the past two decades and their effects on ensuring—or hindering—the right of older adults to live dignified and self-determined lives. It also challenges hegemonic definitions of “independence” and “vulnerability” that emerge from the plans and documents orienting local urban governance. By developing critical discussions around the “right to self-determination,” the chapter introduces a developing interpretative framework aimed at comprehensively understanding the contradictions and effects of specific planning logics on the capabilities for self-determination of radically plural subjectivities living in the contemporary city.