This article explores intergenerational financial transfers from parents to adult children and grandchildren within a life course perspective. Research on intergenerational financial transfers has been sparse, and little is known about the financial support older Canadians provide to family members or about the meaning of that assistance. Survey data from a convenience sample of older Canadians was analysed to determine the types of financial assistance older persons provide, what motivates them to provide this assistance, and what meanings such transfers have for the older persons themselves. Findings suggest that it is often events and transitions in the lives of adult children that shape the financial assistance that is needed and given within these families. Older parents demonstrate a strong desire to help their children and grandchildren through important or difficult transitions to "build or rebuild secure lives and futures". Parents' assistance is also influenced by their own family history of assistance and their desire to pass on an early inheritance during their lifetime.