Parental self-efficacy (PSE) captures parents’ beliefs in their ability to perform the parenting role successfully and to handle pivotal issues of specific developmental periods. Although previous studies have shown that, across the transition to adolescence, parents show decreasing levels of PSE while adolescents exhibit increasing engagement in rule-breaking (RB) behaviors, there is a paucity of studies investigating whether and how changes in PSE are related to late adolescents’ RB behaviors across development. The present study examined the developmental trends of PSE among Italian mothers and fathers over seven waves (representing children’s transition from late childhood to late adolescence; approximately from 9 to 18 years old) as well as the longitudinal associations between PSE and RB behaviors during late adolescence. Data were drawn from seven waves of the Parenting Across Cultures (PAC) project, a large-scale longitudinal, cross-cultural study, and included 200 Italian children (MAgeAtTime1 = 9.80, SD = 0.65; 50.5% girls) and their parents (200 mothers; 190 fathers). PSE was measured across all seven time-points (from T1 to T7), while adolescents’ RB behaviors were measured at the first and last assessment (T1 and T7). Results of univariate latent growth models showed a cubic trend of mothers’ PSE, which revealed a decreasing pattern characterized initially by a slight decline, followed by a rebound before continuously decreasing. By contrast, fathers’ PSE followed a linear decrease over time. Finally, our findings evidenced that only the slope of mothers’ PSE negatively predicted adolescents’ RB behaviors at T7, implying that mothers who maintained higher levels of PSE over time had children who later engaged in lower RB behaviors. The study implications are discussed.