Due to the unique characteristics of the online environment, cyberdating abuse (CDA) is a complex phenomenon with very detrimental consequences for the well-being of young people. Research examining romantic attachment systems and their association with CDA highlights the need to consider the heterogeneity of intimate partner violence experiences to better understand this issue and its correlates. From this perspective, the present research study was aimed at identifying gender-specific patterns of CDA in people with anxious attachment as a function of heterosexual script (HS; i.e., stereotypes and gender roles) adherence. In addition, this work was aimed at examining whether digital media constitute an environment where people who are anxiously attached to their partners experience cycles of anxiety and take part in CDA as a result. Across two cross-sectional studies, we found that high anxious attachment was predictive of increased direct cyberaggression to a greater extent in men with high HS adherence (vs. low HS). Furthermore, although high anxious attachment, being woman, and high HS adherence predicted a greater likelihood of exercising cybercontrol, interaction effects were not found among the predictor variables. Additionally, we found that the positive association between anxious attachment and cybercontrol can be explained through increases in electronic partner surveillance and online jealousy. Our research contributes to a better understanding of these issues and may favor the development of CDA intervention programs based on the violence’s characteristics and the problematic use of digital media in relationships.