The aim of this study was to examine whether mothers who manifest insensitive and disconnected behaviors in interaction with their infants differ in terms of maternal reflective functioning (RF), personality organization, and histories of abuse. A total of 86 mother-infant dyads, 28 of them with histories of abuse, participated in the study. RF was assessed with the Adult Attachment Interview (C. George, N. Kaplan, & M. Main, 1985), and personality organization was assessed with the self-report Inventory of Personality Organization (M.F. Lenzenweger, J.F. Clarkin, O.F. Kernberg, & P.A. Foelsh, 2001; L. Normandin et al., 2002), before the birth of the baby. Maternal behaviors were assessed using the Disconnected and Extremely Insensitive Parenting measure when the infants were 15 to 18 months old. The results of multivariate analyses of covariance indicate that both RF and personality organization were associated with disconnected and extremely insensitive maternal behaviors. Mothers classified as presenting intrusive/aggressive behaviors had significantly lower RF as well as significantly more difficulties in personality organization, including reality testing, identity, and defense mechanisms. Withdrawn and disconnected maternal behaviors were associated with the combination of difficulties in mentalization and personality organization rather than difficulties in one specific area. In sum, the study provides new evidence regarding the importance of a mentalizing stance about early attachment relationships for the modulation of maternal behaviors, especially intrusive/aggressive behaviors.