The frequency and intensity of hot weather events are expected to increase globally, threatening human health, especially among the elderly, poor, and chronically ill. Current literature indicates that emergency preparedness plans, heat health warning systems, and related interventions may not be reaching or supporting behavior change among those most vulnerable in heat events. Using a qualitative multiple case study design, we comprehensively examined practices of these populations to stay cool during hot weather (“cooling behaviors”) in four U.S. cities with documented racial/ethnic and socio-economic disparities and diverse heat preparedness strategies: Phoenix, Arizona; Detroit, Michigan; New York City, New York; and Philadelphia, Pennsylvania. Based on semi-structured in-depth interviews we conducted with 173 community members and organizational leaders during 2009-2010, we assessed why vulnerable populations do or do not participate in health-promoting behaviors at home or in their community during heat events, inquiring about perceptions of heat-related threats and vulnerability and the role of social support. While vulnerable populations often recognize heat's potential health threats, many overlook or disassociate from risk factors or rely on experiences living in or visiting warmer climates as a protective factor. Many adopt basic cooling behaviors, but unknowingly harmful behaviors such as improper use of fans and heating and cooling systems are also adopted. Decision-making related to commonly promoted behaviors such as air conditioner use and cooling center attendance is complex, and these resources are often inaccessible financially, physically, or culturally. Interviewees expressed how interpersonal, intergenerational relationships are generally but not always protective, where peer relationships are a valuable mechanism for facilitating cooling behaviors among the elderly during heat events. To prevent disparities in heat morbidity and mortality in an increasingly changing climate, we note the implications of local context, and we broadly inform heat preparedness plans, interventions, and messages by sharing the perspectives and words of community members representing vulnerable populations and leaders who work most closely with them.