The present study aimed at examining the transactional effects between parental styles and adolescent externalizing problems. The total sample included 868 students, 410 preadolescents (M[subscript age] = 10.63, SD = 0.63) attending the last two grades of elementary school and 458 early adolescents (M[subscript age] = 12.65, SD = 0.67) attending the first two grades of high school. Participating schools (N = 15) were purposefully selected to be diverse in terms of urban/rural residence of families they serve, as well as their socioeconomic status, and came from three different Districts of Cyprus. In terms of gender, 451 (52.0%) were girls and 410 (47.5%) were boys. The self-report version of the "Strengths and Difficulties Questionnaire" was used for measuring externalizing problems and the "Parental Authority Questionnaire" was used for measuring parental style. A short-term longitudinal design was used, with the data collected at two points in time having 5-month intervals. By means of a cross-lagged model, and in contrast to prior studies claiming that certain parental styles influence positively or negatively externalizing problems, the current study found that the opposite effect is true. That is, externalizing problems affected positively authoritarian parenting and negative authoritative style. Also, a multigroup analysis revealed that age/developmental phase moderated these relationships. Specifically, T1 authoritarian parenting seemed to be a risk factor for preadolescents, but not for adolescents.