This paper examines the potential of the term ‘settler ally’ to create productive discomfort alongside productive comfort, thereby creating space for positive social change. The setting in which the term is examined is Canada—Alberta in particular—following the release of the recommendations of the Truth and Reconciliation Commission in 2015. The discussion is informed by Megan Boler’s ‘pedagogy of discomfort’ and the work of scholars who’ve considered the potential and limitations of this theoretical framework. The paper argues that discomfort alone may be insufficient when the aim is to create positive social change and that comfort, offered through careful and care-filled language, may support the intended outcomes.