Psychopathology poses a risk for optimal parenting. The current study explored antenatal caregiving representations as markers for later risk of nonoptimal maternal behavior among mothers with severe mental illness. Sixty-five mothers diagnosed with psychosis, bipolar disorder, depression (psychopathology group), and nonclinical controls participated in a longitudinal study from pregnancy to 16 weeks after birth. Mental health diagnoses and caregiving representations were assessed during pregnancy. Maternal behavior was assessed during the 5-min recovery phase of the still-face paradigm at 16 weeks. Mothers with psychopathology reported significantly higher levels of “heightened” caregiving representations (i.e., separation anxiety from the child) than did controls. The only significant diagnostic group difference in perinatal maternal behavior was that mothers diagnosed with depression exhibited more overriding-intrusive behavior than did nonclinical control mothers. Regression modeling results showed that antenatal caregiving representations of “role reversal” predicted significantly lower levels of sensitivity and higher levels of overriding-intrusive behavior independent of the effect of psychopathology. The findings can be interpreted in the context of representational transformation to motherhood during pregnancy. The results provide preliminary evidence for the potential of a new questionnaire measure of caregiving representations as a screening instrument for antenatal representational risk.