While the internet provides ample opportunities for children to constructively engage with information and content, there also exist risks that are detrimental to their physical, social and psychological well-being. This study explores children’s self-reported experiences of online risks and their adopted risk mitigation strategies. Using eight focus groups consisting of fifty-one high school students from three communities in Trinidad, children were interviewed about their experiences online and the strategies used to ensure their safety. The results indicate that although it is acknowledged that children are aware of a multiplicity of risks, they only experience certain types of risks. Most children identified strategies and action which they believe allowed them to securely navigate the internet and social networking platforms. Additionally, whilst children did not specify the sources of their risk awareness or recall how they learned their risk management strategies, their behaviours online were mediated by parental concern in the form of parental monitoring. Although parental monitoring can be an effective strategy, the possibility exists that parents are not acutely aware of the plethora of risks that exist and as such are limited in monitoring their children from unknown and unexperienced risks. Consequently, this study questions the ability of children to mitigate unexperienced risks. An examination of parenting styles associated with their willingness to be informed about other potential online risks may be the ideal method that can be used to assist children in successfully mitigating online risks that they may not be aware of and have not yet experienced.