Background <p>Disrupted caregiving behaviors are linked to adverse child outcomes, including emotional and behavioral difficulties. However, observational tools for assessing these behaviors are resource-intensive and limited to early childhood.</p> Objective <p>This research developed the Disrupted Caregiving Questionnaire (DCQ), examining its factor structure and associations with maternal history of disorganization and role reversal, maternal internalizing symptoms, and child adjustment.</p> Method <p>Two studies based on samples of Italian cisgender, heterosexual, biological mothers were conducted. Study 1 assessed the DCQ’s factor structure, reliability, and measurement invariance across child gender and developmental stage (<i>N</i> = 1,056; <i>M</i>_<i>age</i> = 41.91, <i>SD</i> = 6.98; age range: 2–18). Study 2 examined convergent and incremental validity through correlations with maternal experiences of disorganization and role reversal with their own mothers, maternal internalizing symptoms, and child adjustment outcomes among 762 mothers (<i>M</i>_<i>age</i> = 44.77, <i>SD</i> = 9.09).</p> Results <p>Confirmatory Factor Analysis supported a three-factor structure (Mother Helpless, Mother Frightened, Maternal Role-Confusion), with good internal consistency. DCQ dimensions were associated with maternal past experiences of disorganization and role reversal, and mental health symptoms. The DCQ was also related to variability in child adjustment outcomes, not accounted for by mothers’ own childhood experiences of disorganization and role reversal.</p> Conclusions <p>The DCQ is a promising measure for assessing disrupted caregiving behaviors in mothers of children aged 2–18, providing a practical tool for research and clinical contexts.</p>