This paper focuses on factors that might influence positive parenting during middle childhood when a parent faces formidable challenges defined herein as "resilient parenting." Data were obtained from 162 families at child age 5 and 8 years. Using an adapted ABCX model, we examined three risk domains (child developmental delay, child ADHD/ODD diagnosis, and low family income) and three protective factors (mother's education, health, and optimism). The outcome of interest was positive parenting as coded from mother-child interactions. We hypothesized that each of the risk factors would predict poorer parenting and that higher levels of each protective factor would buffer the risk-parenting relationship. Positive parenting scores decreased across levels of increasing risk. Maternal optimism appeared to be a protective factor for resilient parenting concurrently at age 5 and predictively to age 8, as well as a predictor of positive change in parenting from age 5 to age 8, above and beyond level of risk. Maternal education and health were not significantly protective for positive parenting. Limitations, future directions, and implications for intervention are discussed.