OBJECTIVE: Observations of parents with their children are important for better understanding the critical role that parents play in their children’s adjustment, but resource limitations commonly compromise assessment. A novel online observation tool, Etch-a-Sketch Online (ESO), is introduced that allows resource-efficient observations in the family home. DESIGN: Study 1 was a preliminary, cross-sectional study of 20 mothers with their singleton children (M = 5.96 years). Mothers were observed using both ESO (recorded via Skype) and a traditional Etch-a Sketch task recorded during a home-visit; mothers’ positive and negative parenting was coded from these observations. Study 2 was a longitudinal study of 119 mothers and their young twins. Mothers’ ESO-observed positive parenting and negative parenting at Time 1 (M = 5.51 years) were examined as predictors of children’s disruptive behavior at Time 2 (M = 6.04 years) controlling for mothers’ Time 2 self-reported positive and negative parenting. RESULTS: Study 1 provided preliminary evidence of inter-rater reliability and convergent validity of ESO-observations. Study 2 supported this evidence of inter-rater reliability and ESO’s convergent validity as well as providing predictive validity. ESO-observed parenting at Time 1 was associated with children’s disruptive behavior at Time 2, over and above concurrent maternal reports of their own parenting. CONCLUSIONS: ESO shows promise in providing the means for detailed assessment of parenting processes in the home.