Educational policies have increasingly promoted parental involvement as a mechanism for improving student outcomes. Few jurisdictions have provided funding for this priority. In Ontario, Canada, the province’s Parents Reaching Out Grants program allows parents to apply for funding for a parental involvement initiative that addresses a local barrier to parent participation. This study categorizes initiatives (N = 11,171) amounting to approximately 10 million dollars (Can$) in funding from 2009 to 2014 and compares them across school settings. Although results show several key contextual differences, parents across settings identify relatively similar needs for enabling parental involvement, emphasizing parenting approaches for supporting well-being (e.g., nutrition, mental health, and technology use) and skills for home-based learning. However, Epstein’s widely used parental involvement typology conceals these prominent aspects of parental involvement. A modified model of parental involvement is presented that may serve as a guide for enhancing parent participation.