Distance learning in response to the COVID-19 pandemic presented tremendous challenges for many families. Parents were expected to support children's learning, often while also working from home. Students with Attention Deficit Hyperactivity Disorder (ADHD) are at particularly high risk for setbacks due to difficulties with organization and increased risk of not participating in scheduled online learning. This paper explores how smartwatch technology, including timing notifications, can support children with ADHD during distance learning due to COVID-19. We implemented a 6-week pilot study of a Digital Health Intervention (DHI) with ten families. The DHI included a smartwatch and a smartphone. Google calendars were synchronized across devices to guide children through daily schedules. After the sixth week, we conducted parent interviews to understand the use of smartwatches and the impact on children's functioning, and we collected physiological data directly from the smartwatch. Our results demonstrated that children successfully adopted the use of the smartwatch, and parents believed the intervention was helpful, especially in supporting the development of organizational skills in their children. Overall, we illustrate how even simple DHIs, such as using smartwatches to promote daily organization and task completion, have the potential to support children and families, particularly during periods of distance learning. We include practical suggestions to help professionals teach children with ADHD to use smartwatches to improve organization and task completion, especially as it applies to supporting remote instruction.