Globally, more and more cities are affected by the Urban Heat Island Effect (UHI). This phenomenon describes urban areas’ increased air and surface temperatures as compared to surrounding suburban or rural areas. The UHI was first observed and analyzed in the early nineteenth century, but only in recent decades has it attracted greater attention from policymakers due to the UHI’s increasing magnitude and widely recognized environmental and health consequences. Increasing awareness among residents about the UHI has further amplified the pressure on city governments to implement mitigation strategies. This chapter explores the strategies and policy ideas emerging in cities around the world aimed at mitigating the UHI. Two major forms of interventions are distinguishable. First, there are measures that specifically and directly target the UHI. Second, there are broader climate change adaptation strategies that involve using tools that indirectly address the UHI problem. Each policy initiative described in this chapter is analyzed with a focus on regulatory strategy – specifically, what are the successful regulatory measures UHI mitigation policy strategies employ? More particularly, what is the correct balance between classical regulation, which relies on imposing obligations and sanctions, and more innovative, flexible, and less directive tools that often encourage autonomous and voluntary citizen engagement in implementing public policy objectives? This chapter will show that what some may consider unorthodox UHI mitigation policies can serve as inspirations for other public intervention strategies targeting climate change.