This paper argues that, as Canadian Higher Education campuses embark on large scale Universal Design for Learning (UDL) implementation, it is essential for them to take the time to strategically consider inherent institutional challenges before pushing ahead. As a result, it is argued that ecological theory will represent a unique and powerful lens in this process of implementation. The first section of the paper examines two inherent dangers being perpetuated in current UDL drives on the vast majority of Canadian campuses that have embarked on this adventure: (i) overreliance on disability service providers, and (ii) a conceptualization of UDL work in silos. The second half of the paper focuses on solutions, and on the idea of developing a strategic approach to UDL integration framed around ecological theory. The paper draws on an analysis of phenomenological data emerging from the author's own lived experience as a consultant responding regularly to the needs of post-secondary campuses with regards to the institutional adoption of UDL.