Prior research shows that employees’ work experiences can “spill over” into their family lives and “cross over” to affect family members. Expanding on studies that emphasize negative implications of work for family life, this study examined positive work-to-family spillover and positive and negative crossover between mothers and their children. Participants were 174 mothers in the extended care (nursing home) industry and their children (ages 9–17), both of whom completed daily diaries on the same 8 consecutive evenings. On each workday, mothers reported whether they had a positive experience at work, youth reported on their mothers’ positive and negative mood after work, and youth rated their own mental (positive and negative affect) and physical health (physical health symptoms, sleep quality, sleep duration). Results of 2-level models showed that mothers’ positive mood after work, on average, was directly related to youth reports of more positive affect, better sleep quality, and longer sleep duration. In addition, mothers with more positive work experiences, on average, displayed less negative mood after work, and in turn, adolescents reported less negative affect and fewer physical health symptoms. Results are discussed in terms of daily family system dynamics.