Parenting sensitivity refers to a caregiver’s ability to perceive, accurately interpret, and respond appropriately to the needs of a child. For mothers of infants, managing depression can impact sensitive parenting, which can be complicated further by individual mental health symptoms such as anger and sleep disturbance and by contextual life stressors. However, links between parenting sensitivity and depression are scarce in parents of toddlers and have yet to be studied in online assessment contexts (e.g., over Zoom). This study examined links between the severity of mental health symptoms (i.e., depression, sleep disturbance, and anger) and parenting sensitivity for mothers meeting clinical criterion for depression and/or anxiety. Recent stressful experience was hypothesized to moderate the association between depression and parenting sensitivity. A secondary objective was to successfully adapt and administer an in-person measure of sensitivity to meet remote assessment needs. The current sample included 141 mothers and their 2-to-3-year-old toddlers in a secondary analysis of baseline data from an intervention for mothers with mental health challenges: the Building Emotional Awareness and Mental Health (BEAM) program. The results of this study indicated both depression, sleep, and recent stressors as unique contributors to sensitive parenting. No significant associations were found between anger and sensitive parenting in this sample. A unique contribution is the use of an online-observed parenting sensitivity assessment. A clinical implication includes the consideration of targeted intervention that addresses both parental mental health and parenting skills.