Fundamental to community health and well-being is the capacity to access a sustainable supply of safe drinking water. Small community drinking water systems are the most vulnerable to contamination, and struggle to secure the funds necessary to improve water treatment and delivery systems, and meet increasingly stringent drinking water quality regulations. Little is known of the contextual and cultural differences between communities and the impact this has on regulatory compliance. This study explored the experiences and impact of individual actors within seven small community drinking water systems in locations across Canada. Qualitative, in-person interviews were conducted with water operators, consumers, and decision-makers in each community, and these findings were analysed thematically. Findings from the study show that communities approach and align with compliance challenges in three distinct ways: by adopting regulator-provided or regulator-driven solutions, by adopting an existing improvement framework (i.e. regionalization), or through reinvention to address a new issue or concern. Policy-makers looking to align small communities with appropriate water quality goals may benefit from a consideration of these contextual and cultural differences.