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Nature-based-solutions (NBS) pursue a combination of economic, social, and environmental benefits that can meet municipal goals on stormwater and rapid urbanization problems. However, NBS have fallen behind in reaching to the political and legal framework, and with this, to a policy mix for urban stormwater sustainability. When looking closer at NBS, it becomes evident that they are loaded with many barriers, including institutional and political ones, as well as those that exist in the urban area social context. These barriers are also deepened by the lack of policy guidelines and few demonstration projects. In this respect, this paper combines the concepts of urban experiments and the policy feedback cycle (PFC) into a singular assessment tool. It´s goal is to assess Costa Rica’s municipal readiness in the implementation of NBS within the context of policy design and implementation. Therefore, this paper focusses on the first two stages of the PFC of an existing urban experiment to extract its policy insights for the successful replication of NBS projects. This novel method aims to contribute to the ongoing debate with respect to the ability of experimentation to prompt scalability and transferability of results. Hence, the New York City Green Infrastructure plan is considered as an urban experiment that promotes sustainable policy initiatives; while the PFC can identify and (re)formulate these policies initiatives and barriers into an adaptable policy guideline. Results indicate that sustainability policies at the municipal level should incorporate incentive mechanisms policies on (i) community involvement and communication; and (ii) transdisciplinary knowledge transfer between specialists and stakeholders. Finally, this paper suggests the inter-municipal cross-institutional collaboration and the recognition of external trigger events to incentivize a sustainable urban transition.