One of the most striking pieces of evidence in attachment research is that attachment security is transmitted from 1 generation to the next. Although there has been an enormous advance in the understanding of this process, this area of research suffers from some significant gaps, as for example the transmission across 3 generations when considering the 2 parents as well as the 2 couples of grandparents. The current study was designed to fill this gap in existing literature by investigating AAI attachment representations in the members of 3 generations, belonging to a total of 32 families, each including an adult offspring, both parents and the 4 grandparents (N = 224). Main findings show that the transmission across 2 generations was stronger in the presence of a female caregiver (either mother or maternal/paternal grandmother), and that across 3 generations was confirmed only in the presence of 2 female caregivers (grandmother to mother to offspring). Conversely, the transmissions across 3 generations with only 1 or no female caregiver were not confirmed. Last, experiencing 2 secure parents increased the likelihood of developing a secure state of mind with respect to attachment among offspring, mothers and fathers, 95% confidence intervals [3.52, 1,238.72], [1.67, 31.17], and [1.67, 19.98], respectively. These findings may have important theoretical implications related to the understanding of the factors involved in the continuity and discontinuity of attachment patterns across generations.