Although numerous studies have examined the factors influencing problematic Internet use (PIU), few studies have investigated the interactions between inappropriate physical and mental health (e.g., cyberbullying, Internet pornography, and Internet fraud) as factors facilitating PIU and examined the moderating effect of community bond. Thus, this study analyzed the moderating role of community bond in the relationship between cyberbullying, Internet pornography, Internet fraud, and PIU. Using a cross-sectional survey, adolescents were surveyed through self-report questionnaires. A total of 5,211 responses were received from participant students at 60 senior high schools in Taiwan. Statistical analyses were performed using structural equation modeling. The results indicated that cyberbullying, Internet pornography, Internet fraud, and community bond have significant positive effects on PIU. Community bond has a significant moderating effect in the relationship between cyberbullying, Internet fraud, and the PIU of adolescents. Parental Internet attitude and behavior were found to significantly moderate the relationship between inappropriate physical and mental health, community bond, and PIU. The results suggest that public health and education policies should focus more on adolescents who require additional assistance. Furthermore, school policies could be more informed in regard to relevant psychosocial variables and patterns of Internet use. Finally, this study may serve as a reference for parents, schools, and government education authorities.