With the results of climate change becoming more apparent, sustainability is becoming increasingly popular in all sectors and construction is no different. Whilst larger contractors are leading the way, the same cannot be said for small to medium-sized contractors. The aim of this paper is to uncover the barriers facing small and medium-sized Irish contractors to adopting sustainability within their practices. The lack of research in this area is the motivation behind this study, as there is currently no information available on this topic regarding the Irish sector. This paper commences by identifying themes and underlying barriers identified within the literature. Subsequently, these themes and associated factors are explored in a series of 20 semi-structured individual interviews with small to medium-sized contractors. Five themes and associated factors are identified. First, cost, including cost of materials, cost of training, and cost of practice. Second, lack of understanding along with lack of education, lack of training, and lack of information are also noted. Third, the lack of government legislation is also highlighted, specifically grants, training, and regulation. Fourth, environmental, including materials, training, and practices. Fifth and finally, lack of demand, with a lack of client demand and lack of industry demand being factors. The benefit of this research is that both industry and legislative bodies need to first identify and acknowledge the barriers that result in small and medium-sized contractors not adopting a more sustainable approach, prior to then enacting targeted assistance to address these barriers, as identified within this study.