The purpose of this study is to explore and gain understanding about how Indigenous grandmothers experience their roles as primary caregivers to their grandchildren. Using qualitative research methodologies (Indigenous Storytelling and Interpretive Phenomenological Analysis), six Indigenous grandmothers residing in Prince Albert, Saskatchewan shared their grandmothering stories. Four key themes identified were: Reflecting on the past, It’s not always easy, I love my grandchildren, and What I need. Indigenous grandmothers were willingly taking on the primary caregiver role because of concerns for the well-being of the grandchildren and they did not want to lose them to the child welfare system. This role placed the grandmothers’ own health and well-being at risk and had financial implications. The strain of negotiating with adult children was also difficult on the grandmothers and the grandchildren as their adult children were often struggling with their own addictions and relationship issues. Thus, social workers, and other helping professionals, need to be aware of how colonization has impacted generations of Indigenous families and how these grandmothers are working to end the cycle caused by colonization that has existed for years. However, recognizing that each grandmother’s experience is unique is also key in understanding their needs and providing assistance. There are benefits to all parties when grandmothers take on this primary caregiving role; and they should be respected for this work. Future research in this area may include reviewing the cultural competence of social workers, including increased education about residential schools, the implication of gender roles on this phenomenon, as well as the potential use of two-eyed seeing in social work practice.