Contemporary urban challenges—climate change, rapid urbanization, socio-economic disparities, and disruptive events—exceed the capacity of traditional rational planning paradigms. Planners increasingly confront incomplete information, competing stakeholder values, and unpredictable shocks, necessitating adaptive frameworks capable of managing inherent uncertainty while implementing concrete interventions. This thesis integrates two complementary approaches: the Strategic Choice Approach (SCA), a Problem Structuring Method that incorporates uncertainty into collaborative decision-making (Friend & Hickling, 2005; Lami & Todella, 2019, 2023), and Urban Acupuncture (UA), a design methodology employing small-scale, catalytic interventions to generate systemic urban transformation (Solà-Morales; Hemingway, 2022; Khaing et al., 2024). While SCA provides decision-structuring tools without design guidance, and UA offers design responses without decision structures, their convergence under the paradigm of adaptive planning (Rauws, 2017) creates a framework wherein uncertainties are acknowledged and interventions evolve as adaptive experiments.