As social technologies become more integrated into students’ lives, new means of communication have emerged, along with novel problem behaviors with significant consequences for students’ well-being. One of these is the sending of sexualized images via cell phone, referred to as “sexting”. An understanding of how and why some students choose to sext is important for schools to appropriately prepare for sexting-related incidents. This study explored some of the personal and environmental correlates of the behavior, including gender, thrill-seeking, impulsivity, perceived school experience, and related attitudes about the normalcy and risk of the behavior. Participants were college undergraduates from a large urban university, retrospectively reporting about their high school experience. Results indicated that the majority of students did not send sexts in high school. However, of those who did, students who sexted exclusively with romantic partners had significantly more positive engagement in school. Students with lower feelings of connectedness, academic motivation, and social belonging in high school tended to sext in riskier ways. Additionally, recent high school graduates were asked if and how schools should effectively educate students about the risks of sexting. These perspectives were assessed through survey questions and a focus group discussion session. Results suggested that students do recognize the potential consequences of the behavior, regardless of what teachers tell them. They feel that, rather than using “scare tactics”, school personnel should try to understand the social and relational context in which the behavior occurs. Limitations of this research are discussed, along with implications and recommendation for practice and future research. / School Psychology