Do the experiences that children and youth face early in life impact their mental health differently across immigrant generations? And do these associations vary by ethnicity and gender? My thesis addresses these significant and critical questions, as immigrants have been a large contributor to Canada’s population and are expected to grow in the next couple of decades. Research on the complexities of the social environments that shape and contribute to a child and youth’s mental health has been well documented in literature throughout the years. However, current research on immigrant children and youth that have examined the healthy immigrant effect across immigrant generations (immigrants versus. Native-born) in Canada have been sparse as there have been relatively few studies on this topic. Moreover, the studies on the healthy immigrant effect of children and youth immigrants in Canada have been inconclusive if immigrant children and youth have this initial health advantage. My study contributes to the understanding of how children and youth can experience similar life events (e.g., having parent-child educational aspiration discrepancies and sense of community belonging) but can impact their mental health differently based on immigrant status as well as ethnicity and gender. I use data from the Hamilton Youth Study (HYS) (2013) that has a representative sample of first-, second-, and native-born children of children and youth living in Hamilton, Ontario, Canada to examine parent-child educational aspirations and mental health across immigrant generations along with gender. I also use data of the Canadian Community Health Survey-Mental Health (2012) along with the Census data to examine the association of how South Asian and Chinese youth living in similar ethnic neighborhoods contributes to their sense of belonging and impacts their mental health across generations. To test out these associations, I conducted Ordinary Least Squares regression for chapters 2 and 4 and Hierarchal Linear Modelling (HLM) techniques for chapter 3. These three papers contribute to the discussion of the healthy immigrant effect of children and youth by suggesting that children and youth that experience the same events earlier in life can impact their life to a greater extent more than others based on immigrant status, as well as ethnicity and gender. / Thesis / Candidate in Philosophy