This dissertation explores how parents engage with school fundraising in the public education system; specifically, it examines parental fundraising at elementary schools in River North School Division (pseudonym), a large public school division in Winnipeg, Manitoba, Canada. Previous research has shown that fundraising allows parents to engage and hold influence in schools, but it also creates inequities between communities of different socioeconomic status and fundraising capacity. However, few explored the question: Why and how does parental engagement with fundraising differ between elementary schools, especially in the prairie provinces of Canada? This dissertation focuses on four major aspects of fundraising: (1) the relationships parent fundraisers have with administrators and staff at their schools, (2) parents’ motivations for getting involved, (3) the resources parents draw from to be successful, and (4) the barriers parents face in their fundraising efforts. Drawing on the theories of Pierre Bourdieu and Annette Lareau, and using a comparative case study approach, data was gathered by interviewing nine individuals associated with River North Division elementary schools, analyzing over 200 documents related to fundraising in these schools, and using Statistics Canada census data to create community profiles for each school’s catchment. While there were some similarities across all River North schools, clear social class differences in fundraising practices emerged. Parental fundraising is becoming an increasingly normalized way for parents to engage with schools in the highest socio-economic communities, allowing them to generate significantly greater resources for their schools. This dissertation argues that more must be done to ensure that community wealth and parental contributions do not determine what resources and supports students can access in the public education system.