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Research on educational inequality has long emphasized class-based explanations for how families transmit advantage through parenting and school involvement. Yet, how race and ethnicity intersect with class to shape these processes remains understudied, particularly among Latinx middle-class families. Drawing on in-depth interviews with middle-class Latinx parents of elementary school children in San Antonio, Texas, this study examines whether and how class-based resources translate into school-based advantages in a context where schools are well-resourced and Latinx families are numerically prominent. Rather than approaching schools with a sense of entitlement, parents described engaging in what I call strategic niceness: cultivating goodwill with teachers and administrators through relational labor, gift-giving, deference to institutional authority, and the downplaying of their own expertise. Parents framed this approach as both more effective and more morally appropriate than assertive, entitlement-based involvement practices commonly associated with white middle-class parenting. I argue that strategic niceness operates as a racialized class strategy that reflects parents’ anticipation of how schools will interpret their actions. While this strategy sometimes yielded small advantages for children, it also constrained parents’ ability to challenge school practices, potentially limiting the intergenerational transmission of class-based advantage and sustaining within-class racial inequalities in educational outcomes.