This article explores the ways poly-victimized youth (those experiencing multiple different types of victimization over the course of 1 year) use technology to interact with peers. Particular attention is given to the peer harassment victimization and perpetration experiences of poly-victimized youth compared with less victimized and non-victimized youth-both overall and through technology. Data were collected as part of the Technology Harassment Victimization (THV) study; a national survey of 791 youth, ages 10 to 20 across the United States. Study results document the heightened risks that poly-victimized youth experience when interacting with peers. Low and high poly-victimized youth were both at significantly greater risk of being dual victims and perpetrators of peer harassment when compared with non-victimized youth even after taking into account other potentially explanatory factors. This was not found to be the case for less victimized youth. This was true for high poly-victims and technology-involved harassment risk as well. There were indications that poly-victimized youth were interacting with peers in more intense and risky ways in general using new technology. The increase in attention to poly-victimization in recent years has importantly identified the detrimental role that experiencing different forms of victimization have on youth. This study not only adds to that literature but suggests that there is an opportunity to interrupt additional victimization by understanding how poly-victimized youth interact with peers before and during adolescence. Although preliminary, the differences in technology use by poly-victimized youth versus others suggest that more information is needed to understand how they are relating to peers in both positive and risky ways in this environment.