We use the Northeast US Urban Climate Archipelago as a case study to explore three key limitations of planning and policy initiatives to mitigate extreme urban heat. These limitations are: (1) a lack of understanding of spatial considerations—for example, how nearby urban areas interact, affecting, and being affected by, implementation of such policies; (2) an emphasis on air temperature reduction that neglects assessments of other important meteorological parameters, such as humidity, mixing heights, and urban wind fields; and (3) too narrow of a temporal focus—either time of day, season, or current vs. future climates. Additionally, the absence of a direct policy/planning linkage between heat mitigation goals and actual human health outcomes, in general, leads to solutions that only indirectly address the underlying problems. These issues are explored through several related atmospheric modeling case studies that reveal the complexities of designing effective urban heat mitigation strategies. We conclude with recommendations regarding how policy-makers can optimize the performance of their urban heat mitigation policies and programs. This optimization starts with a thorough understanding of the actual end-point goals of these policies, and concludes with the careful integration of scientific knowledge into the development of location-specific strategies that recognize and address the limitations discussed herein.