Pathological Internet use (PIU) occurs when excessive Internet use results in addictive symptoms that exert detrimental consequences on one's overall functioning and well-being. Poor family functioning has been found to be associated with youths' addictive Internet use, and parental use of active and restrictive mediation has been found to reduce online risk. The current study aims to test if parental active and restrictive mediation strategies are negatively associated with youths' PIU. Additionally, it also tests the effectiveness of these strategies as a function of the broader family environment with measures of parent-child attachment, family communication, and the youth's comfort with living at home. The data of 3,079 students in Singapore were analyzed through a series of logistic regressions. The results revealed that the family environment for students with PIU was significantly less positive. Only restrictive mediation was found to be negatively associated with PIU. This relation was stronger for higher levels of attachment, communication, and comfort at home, implying that the effectiveness of restrictive mediation varies with the degree of warmth and support in the general family environment. The implications are discussed.