Few studies have examined whether maternal caregiving representations are associated with maternal reflective functioning (MRF), especially when MRF is evaluated longitudinally beginning in pregnancy. This study addresses this gap by evaluating whether prenatal and postnatal MRF are associated with mothers’ caregiving representations assessed at 7 months postpartum, and by exploring theoretically unexpected MRF scores in each of the representational categories. Forty‐seven mothers were recruited during their last trimester of pregnancy from an obstetrics clinic at a university hospital located in a large mid‐western city in the United States. During pregnancy, mothers completed the Pregnancy Interview, and at 7 months postpartum they completed the Parent Development Interview (PDI) and the Working Model of the Child Interview. Results indicate that higher prenatal and postnatal MRF increased the odds of being classified as balanced versus disengaged. At 7 months, MRF also increased the odds of being balanced vs. distorted. Ten mothers who were classified as balanced or distorted had unexpected prenatal MRF scores, and six mothers had unexpected MRF scores when representations were assessed concurrently. Mothers classified as balanced with low MRF scores tended to have a low level of education, whereas mothers classified as distorted with high MRF scores had responses that were hostile, helpless, and role‐reversed.