A unique component of early childhood involves understanding how caregivers and educators promote children's developmental outcomes, with play opportunities being a key avenue for enhancing these skills. Targeted coaching is one type of support that can tap into active family engagement during playful learning. This collective case study examined how remote-based eCoaching could support family-centered practices related to the facilitation of pretend play in caregivers of preschool children in the home setting. Four mother-child dyads of preschool children, with and without a disability, participated in eCoaching focusing on pretend play behaviors. During the implementation of eCoaching, three primary findings emerged related to knowledge acquisition, mothers' facilitation of play with their children, and changes in children's pretend play behaviors. In general, both mothers and children benefited from the eCoaching experience. In addition, mothers' perceptions of eCoaching as a means of family-based support were positive, and all deemed eCoaching easy to engage in and beneficial.