While recognition of the dangers of extreme heat in cities continues to grow, heat resilience remains a relatively new area of urban planning. One barrier to the creation and successful implementation of neighborhood-scale heat resilience plans has been a lack of reliable strategies for resident engagement. In this research, the authors designed a two-week summer STEM module for youth ages 12 to 14 in Roanoke, Virginia in the Southeastern United States. Participants collected and analyzed temperature and thermal comfort data of varying types, including from infrared thermal cameras and point sensors, handheld weather sensors, drones, and satellites, vehicle traverses, and student peer interviews. Based on primary data gathered during the program, we offer insights that may assist planners seeking to engage residents in neighborhood-scale heat resilience planning efforts. These lessons include recognizing: (1) the problem of heat in neighborhoods and the social justice aspects of heat distribution may not be immediately apparent to residents; (2) a need to shift perceived responsibility of heat exposure from the personal and home-based to include the social and landscape-based; (3) the inextricability of solutions for thermal comfort from general issues of safety and comfort in neighborhoods; and (4) that smart city technologies and high resolution data are helpful “hooks” to engagement, but may be insufficient for shifting perception of heat as something that can be mitigated through decisions about the built environment.