Assessment of parenting frequently relies on parent self-report despite well-documented discrepancies between this methodology and observational measures. In the current study, we investigated patterns of disagreement between self-reported and observational measures of positive parenting and negative parenting with 102 dyads of parents and 4–6 year-old children. Specifically, we tested whether differences in parent distress and family socioeconomic status (SES) moderated the association between self-reported and observed parenting. Results showed significant interactions with less agreement between self-report and observational measures among parents reporting higher levels of distress and among families from lower SES backgrounds. Effects were more pronounced in models of negative parenting than those of positive parenting. Findings suggest that two factors relevant to parenting quality, emotional distress and SES, predict meaningful differences in manner of parent-report relative to observational measures. We discuss implications for the extant literature and for future efforts regarding effective and efficient parenting measurement.