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The present study was designed to explore how maternal guidance (i.e., involvement and monitoring) is associated with parent‐level and contextual factors in unstructured and structured tasks. Participants were mothers who had histories of risk and disadvantage (mean age = 30.47) with their preschool‐aged children (aged 2–6 years; n males = 39, n females = 50). Maternal guidance was divided into two categories: directive (i.e., commands and command repetitions) and nondirective (i.e., queries, verbal prompts, and explanations). Results revealed that mothers with more directive guidance had higher levels of parental stress and higher levels of maternal childhood histories of social withdrawal. Furthermore, more nondirective maternal guidance was associated with higher quality of home environments. Taken together, results suggest that parenting practices are best understood in relation to contextual variables. Findings have implications for developing and implementing parenting interventions for at‐risk mothers. Highlights Explored the association between contextual factors (e.g., parent stress, home environment) and maternal guidance (mother's use of commands vs. hints or prompts). Maternal guidance was assessed observationally and commands were associated with more parental stress while hints were associated with a higher quality home environment. Understanding parents as a whole by exploring contextual factors, rather than through isolated parenting practices, may be beneficial in the application of future parenting interventions.