Background: Internet communication applications have become an important social context for the development of adolescents. The use of Internet is leading to many risk-taking behaviors also. Material and Methods: This study assessed the risk-taking behaviors and related problems among adolescents while using the internet and parental supervision on it. The study followed descriptive cross-sectional research design and the data was collected from 179 school going adolescents through semi-structured interview schedule. Results: About 60% of the respondents belonged to male (M = 14.5, SD = 1.2 years), mean time spent on internet use in the previous week was 6 hours, 41% access to computers at home, and 28% had arguments with their care givers due to their pattern of usage of internet. There was a significant difference in emotional (t = 3.127, df = 177, P <0.01) and personal level risk-taking domains (t = 3.037, df = 177, P <0.01) between male and female respondents, indicating boys were taking more risks than girls. High emotional problems among 8th grade students (M = 1.63, ±1.87) was noted. Significant difference was observed between the number of hours spent on online in a week and arguments with parents (t = 2.517, df = 177, P <0.05). There was also significant difference in emotional problems (F = 3.212, P <0.05) and sex-related risk (F = 4.735, P <0.05) domains between parental filtering and non-filtering group (F = 3.212, P <0.05). Conclusion: Results clearly indicate that there is an evidence of risk-taking behaviors among adolescents those who were in lack of parental supervision. Hence, there is an urgent need to educate parents, teachers, and address this issue on a greater scale including at the policy level.