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This study aimed to test the effects of active and restrictive monitoring on youths’ online risky behaviors and the reciprocal effect between youths’ online risky behaviors and parental monitoring. A longitudinal survey was conducted in 28 randomly selected primary and secondary schools in Singapore. The data of 3079 students were analyzed through path analyses across two time points. The results confirmed reciprocal associations between parental monitoring and youths’ online risky behaviors. Active and restrictive monitoring were predictive of lower online risky behaviors, which supports the significant role of parents in online guidance and supervision. Additionally, youths’ engagement in online risky behaviors were also found to result in lower parental monitoring, which implies that parents of youths who engage in online risky activities can also be negatively affected and parenting efforts may decrease as a consequence.