Environmental Assessment (EA) is a tool that informs decision making of the potential adverse impacts of proposed development projects. Since EAs deal with future events, uncertainties are unavoidable. It has been found that there are different types and sources of uncertainties in EA and decision making, however; uncertainties are not always being communicated or considered. It is understood that there is a need for more explicit disclosure of uncertainties, yet there is no consensus regarding how uncertainties are perceived, communicated, and considered by those involved in, or affected by, EA, and much less is known about the contextual dynamics of uncertainty disclosure and consideration. This study attempts to better understand the relationship between context and uncertainty practice by exploring uncertainties in a Canadian transport mega project EA, the 407 East Extension in southern Ontario. Transport mega projects are driven by a number of contextual factors, are characterized by high uncertainty, are spatially situated, inherently displacing, and highly visible. This study investigated how elements of the context hindered, supported, or influenced the way uncertainty was communicated and considered by those involved in the EA. In particular, twenty-two (22) semi-structured interviews were performed with key project informants such as project proponents, practitioners, regulators, First Nation representatives, and affected interests. Results demonstrate that uncertainties in the EA are the result of both process and context. In the process, uncertainties were significant in the preliminary and detailed assessment stages. Elements of the environmental and socio-political context were found to contribute to uncertainty as well. In particular, results indicate that location, lack of baseline data, perception, and broader politics, organizational, and regulatory factors worked to influence the way uncertainties were either communicated or considered during the EA. In our study, information about uncertainty was not disclosed in the EA. Uncertainties were minimized or strategically avoided. In order to address these limitations and better inform decision making in EA, we offer a number of recommendations. These are: the development of an uncertainty typology; guidance for uncertainty reporting; stakeholder identification and transparency in trade-offs; uncertainty management commitments; and, more attention on the context within which EA is embedded within and attempting to interact with.