Background: Emerging findings have shown that high parental monitoring of adolescents’ sexual and reproductive health (SRH) communications between parents and adolescents and good parenting styles prevent adolescents from engaging in risky sexual practices. Objective: The aim of this study was to examine the associations of parental monitoring, parent–adolescent SRH communications, and parenting styles with risky sexual practices among adolescents in Harar, Ethiopia. Designs: This was a cross-sectional study conducted on adolescents aged 13–18 who had sexual initiations. Adolescents who failed to use any contraceptive method and/or condom during last sexual intercourse and who experienced multiple sexual partners in the 12 months prior to the study were taken as ‘at risk’. In view of these, the adolescents risk count ranged from zero to three – greater number indicates higher count of risky sexual practices. Poisson regression model was used to examine the associations and p<0.05 indicated a statistical significance. Results: It was found out that 301 of 633 (47.55%; 95% CI=43.62%, 51.45%) adolescents experienced one or more risky sexual practices. High parental monitoring compared to low decreases the Incidence Rate of engaging in risky sexual practices by 28% (adjusted incidence rate ratio, or IRR=0.72; 95% CI=0.520, 0.986). Those who had a satisfactory level of SRH communications with their parents compared to poor communicators experianced less incidence rate of risky sexual practices which was marginal (adjusted IRR=0.82; 95% CI=0.637, 1.051). Conclusions: A significant proportion of the adolescents engaged in one or more risky sexual practices. Importantly, high parental monitoring decreases the likelihood of these risky practices. Therefore, parents need to be encouraged to keep an eye on their young children.