The aim of this study was to investigate the mother-infant relationship in depressive, psychosocial, and cumulative-risk parenting by assessing prenatal and postnatal maternal representations and mother-infant interactions during feeding at 4 months of age. The sample consisted of 167 mother-infant pairs: 41 nonrisk women, 40 depressive-risk women, 40 psychosocial-risk women, and 46 cumulative-risk women. During pregnancy, the women were interviewed about psychosocial-risk variables. Maternal representations and depressive symptoms were evaluated during pregnancy and again when the infants were 3 and 4 months old, respectively. All mother-infant pairs were observed in 20-min video recordings during breast-feeding. Maternal Integrated/balanced representations were more frequent in the nonrisk group whereas the maternal Nonintegrated/ambivalent category was more represented in the cumulative-risk group during pregnancy and after the infant's birth. At 4 months, the cumulative-risk group of mothers and infants showed a lack of reciprocity, conflictual communicative exchanges, and higher food refusal behavior. Moreover, at 4 months, differences between the quality of mother-infant feeding interactions and the quality of prenatal and postnatal maternal representations emerged, showing less adequate maternal scaffolding in the Nonintegrated/ambivalent and Restricted/disengaged women. This study has rich implications for intervention to support the affective and communicative caregiving system and to prevent infant feeding problems and mother-infant relational disturbances in childhood.