Guaranteeing “certainty” (for governments, business development, society, etc.) is often the goal of state land rights settlements with Indigenous peoples in Canada. Certainty is also often seen as an unequivocally desirable and positive state of affairs. This paper explores how certainty and uncertainty intersect with the challenges of decolonization in North America. I explore how settler certainty and entitlement to Indigenous land has been constructed in past colonial and current national laws, land policies, and ideologies. Then, drawing on data from fieldwork among activists against land rights, I argue that their deep anger about their uncertainty regarding land and their futures helps to reveal how certainty and entitlement underpin “settler states of feeling” (Rifkin). If one persistent characteristic of settler colonialism is settler certainty and entitlement, then decolonization, both for settlers and for jurisprudence, may therefore mean embracing uncertainty. I conclude by discussing the relationship between certainty, uncertainty, and decolonization.