Young children’s development, is shaped by recurring experiences (i.e., proximal processes) in their immediate environment (i.e., microsystem; Bronfenbrenner & Morris, 2007). Relatedly, psychosocial acceleration theory conceptualizes these early experiences as environmental cues that adaptively shape development to best fit the developing individual to their context (Belsky, Steinberg, & Draper, 1991). Research demonstrates the connection between quality experiences in the home and in the preschool classroom contexts with development (National Research Council and Institute of Medicine, 2000), and compensatory effects on development for children with high quality experiences in one environment, such as the preschool classroom, and low quality experiences in another environment, such as for children living in poverty (e.g., Schweinhart et al., 1993; Ramey & Campbell, 1984; Watamura et al., 2011). Thus, home-classroom (dis)continuity may have implications for development. Using a mixed methods approach, this collaborative dissertation project investigates Head Start home-classroom (dis)continuity. The first two papers use person-centered quantitative analyses to investigate the complex interrelationships between children’s home and classroom environments and children’s development of self-regulation. The third paper uses qualitative data from Head Start parents and teachers to understand their perceptions about the importance of home-classroom (dis)continuity for children’s proximal processes and development. The integrated results of this dissertation offer several contributions to inform research, policy, and practice for Head Start at national and local levels. (author abstract)