By shaping our physical surroundings and forming out cultures, buildings are integral to our lives. To serve their many functions -foremost protecting and sheltering occupantsbuildings are complex systems and are elements in the multi-domain network of the built environment. That environment vastly contributes to the global climate crisis but must simultaneously provide protection from its consequences. The expected doubling of building land area by 2060 emphasizes buildings' role in the sustainability and resilience of our environment.Building performance simulation allows the architecture, engineering, and construction industry to analyze building behavior preemptively.However, current industry practice isolates modeling analysis from real buildings, relies on historic data, and excludes future uncertainty. To address these challenges, this dissertation investigates methods of simulating building performance in future scenarios to promote a resilient built environment.Future-aware building simulation requires models accurately describe physical parameters and effectively predict actual building behavior. Extensive prior simulations results indicate that window characteristics, particularly the window-to-wall ratio, strongly influence the energy necessary to maintain comfortable interior conditions.Regression analysis of measured data from actual US buildings reveals window-to-wall ratio to be a statistically significant predictor only in cooling energy, however, the correlation is not as robust in real buildings as in previous model-based studies.Discrepancies between simulated and actual performance are compounded over long building lifetimes.Current practice simulates annual energy use using "typical" exterior conditions assembled from historical meteorological measurements that may be over 40 years old:barely representative of present conditions, nevertheless uncertain future context. To iii predict lifetime performance, future-aware building simulations must incorporate the local effects of projected global climate change. Through the 'morphing' method, climate projections are integrated into simulations with varying attributes, in three time intervals to capture uncertainties. Results show total building energy consumption generally increases with climate change, however, the magnitude of change and effects on individual end-uses depend on location and projected emissions scenario. The interconnection of buildings in larger domains necessitates future-aware simulation to extend beyond the building scale. For example, energy consumed at the building (site energy) is generated from resources (source energy) and transmitted via utility infrastructure. Standard simulation practice defaults to constant national average factors to convert site to source energy, which do not reflect any modification of electricity fuel mixes that evolve across time and by location. New site-to-source conversion factors were calculated and the updated 2018 national factor is 9% lower than the simulation default while subregional f...