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Abstract Cyberbullying significantly undermines adolescent physical and mental health, necessitating effective prevention strategies. Although digital literacy has been proposed as a protective factor against cyberbullying, the dynamic, reciprocal relationship between these factors over time remains unclear because most research relies on cross-sectional designs. This study bridges this gap by examining the longitudinal bidirectional relation between digital literacy and cyberbullying, both in terms of cyberaggression and cybervictimization. A cohort of 679 adolescents ( M age = 14.19 years, SD age = 1.57 years, female = 51.5%) in Hong Kong provided longitudinal data on their demographics and experiences with cyberbullying, both as perpetrators and victims, during the 2018/19 and 2020/21 school years. Performance-based digital literacy was assessed at both time points. Findings revealed that prior digital literacy negatively predicted later cyberaggression ( β = −0.12, p = 0.04), and prior cyberaggression negatively predicted later digital literacy ( β = −0.16, p = 0.03). Prior cybervictimization positively predicted subsequent digital literacy ( β = 0.17, p = 0.02). Adolescents with minimal improvement in digital literacy were more likely to become cyberbullying victims in 2021 ( OR = 0.66, p < 0.001), whereas successfully exiting cybervictimization was associated with significant DL growth ( OR = 1.17, p = 0.03). These findings underscore digital literacy as an indispensable pillar of digital learning for safeguarding adolescents’ physical and mental health. The results also challenge the notion of digital literacy as a static preventative competence by showing that prior digital literacy does not necessarily protect against cyberbullying 2 years later, highlighting the importance of ongoing, developmentally appropriate digital literacy education. Sustained interventions are essential to disrupting cycles of vulnerability, as stagnation in digital competence development may leave adolescents at greater risk for future cyberbullying.