Writing is a critical foundational literacy skill for preschool and kindergarten and has received increased attention in research and policy as a result. Further, the nature of literacy more broadly is shifting towards more digital forms and formats. Research suggests that children approach tasks with and without technology differently and similarly, other research suggests that young children approach writing differentially depending upon the task context. In a small sample (n = 35) of preschool and kindergarten children at university lab school, this study sought to understand children's writing development in traditional (paper-pencil) and digital (iPad-stimulus/finger) contexts across a variety of writing skills. Results suggest that children have varied writing skills that develop considerably across the school year. Further findings indicate that children's writing products and the ways they take up writing are often different depending on the context (traditional v. digital). Implications for practice are discussed