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This paper argues that outcomes of school-based parental involvement can be more clearly understood using toolkit theories of culture (Calarco 2014b) as well as theories of inhabited institutionalism (Hallett and Ventresca 2006), both of which can inform how embedded organizational contexts of schools guide social interactions through institutional expectations of school-based parental involvement, while meanings surrounding expectations of parental involvement are also constructed through local interactions. Using data from 129 interviews of school administrators, kindergarten teachers, volunteer leaders of parent teacher organizations (PTOs) and parents of kindergarteners across three distinct public elementary schools, we show that the meaning of what constitutes acceptable types and levels of school-based parental involvement varies widely depending on the embedded environment in which schools are situated and the institutional expectations surrounding whether or not parental involvement within the school is valued. Parents often evaluate their involvement levels more harshly within a school embedded in a predominantly white, upper-middle class community, leading to a “hyper-consciousness” of involvement as parents scramble to measure up to perceived teacher and administrator expectations, whereas parents within a school comprised of more working class and Latino families often evaluate their involvement as meeting or exceeding perceived teacher and administrator expectations. These subjective assessments of parental involvement both shape and are shaped by the value teachers and administrators place on parental involvement within school. These findings suggest that the role and effectiveness of school-based parental involvement in shaping student outcomes is largely situational and cannot be understood by parent characteristics alone.