This paper presents findings from a funded case study research project conducted in Ontario, Canada during the 2007-2008 school year. Together with the Elementary Teachers’ Federation of Ontario (ETFO), the researchers undertook a qualitative investigation to identify and describe success stories from a diverse sample of 11 Ontario elementary schools working with students and communities affected by poverty. Through school visits, interviews, and document analysis, researchers identified three major findings: schools made connections with parents and the broader community; schools built a sense of collective endeavor and community within the school; and schools struggled with a persistent dilemma regarding students’ social versus academic needs. The project contributes to the Canadian research literature on poverty and schooling and to the practical understanding of how schools can better work with students and communities affected by poverty.