Canada held the spotlight during the last worldwide economic downturn in 2008, leading a local highrise construction boom fueled by market globalization. The number of tower cranes populating the Toronto skyline was unprecedent. Canada Rising was a favorite topic of discussion at industry events like those organized by the Council for Tall Buildings and Urban Habitat (CTBUH). This building boom was not limited to highrise residential buildings but also included institutional and major infrastructure expenditures, including hospitals and universities. The boom continues anew; entire city block developments, major commercial towers (some targeting net-zero), and experimental neighborhoods embracing resilience goals and benefiting from emerging technologies are gaining worldwide attention. Local design and construction teams active in these projects reflect on recent experiences and share thoughts on challenges of the emerging future.