To reduce emissions to the levels needed to stave off the negative impacts of climate change, emissions from cities, one of the primary contributors to emission totals globally, must be addressed. One avenue for addressing the built environment in cities like Toronto is using deep retrofit projects that target energy and emission reductions within buildings. To further our understanding of the factors that contribute to deep retrofit project approval or rejection, I conducted a literature review and interviews with sustainability professionals in the City of Toronto. The results show that while there are areas of overlap between the findings of existing literature and the lived experience of professionals, the primary area of focus for each is different. The literature skews heavily towards financial factors as the primary drivers and barriers to deep retrofit projects, while sustainability professionals appear to be more focused on non-financial factors. I explore the areas of agreement and disagreement in this paper and provide recommendations for steps sustainability professionals can take to increase the rate of adoption of deep retrofit projects.