High-rise towers characterize Toronto across a low-rise landscape. These towers represent a unique form for North America, and bring a series of challenges for future sustainability targets. Following storms in 2013, the topic of resilience has emerged as an important aspect of long-term sustainability. Storms are increasing in severity making them more difficult to resist. How can residents in high-rise buildings prepare for an uncertain future and demonstrate resilience in the face of hazards? What do condominium boards and apartment managers need to have prepared to mitigate the damage caused by a disaster? This paper analyzes existing literature of high-rise sustainability and desirability, recognizing these as important foundations for social cohesion (Uzzel, Pol, & Badenas, 2002) under the assumption that engagement and partnerships are central to community resilience (Chandra et al., 2011). The final product is a discussion guide for groups aiming to assess and develop their respective community’s resilience.