Objectives: Experiencing an immigration-related arrest of a family member adversely impacts youth well-being, yet the role of parental documentation status for exacerbating adverse mental health outcomes following these arrests has not been investigated. Method: Using a general population sample of Latino 7th-grade students in an urban public school district in the south-central United States (N = 611), we examined the relationship between an immigration-related arrest of a family member and depressive symptoms as well as the moderating associations of perceived parental documentation status. Results: Using ordinary least squares regression, findings indicate that experiencing or witnessing an immigration-related arrest of a family member is significantly associated with higher rates of depressive symptoms. Moreover, parental citizenship status has a moderating effect; depressive symptoms are magnified among youth who report that both of their parents have undocumented legal status. Conclusions: The study findings suggest that there are significant consequences for youth well-being when a family member is arrested for immigration-related violations. Further, among youth whose parents are both undocumented, there appears to be a compounding effect on mental health. Immigration policies, programs, and schools need to consider the emotional needs of youth who have undocumented parents, particularly in the context of elevated immigration enforcement.