A history of trauma can have a significant negative impact on the functioning of a student in the school environment. Check & Connect, a school engagement and dropout intervention program, has been found to have positive effects on student school engagement and decrease the likelihood of dropping out of school. However, a review of the Check & Connect literature and trainings indicates that several adaptations could increase the effectiveness of Check & Connect for students at risk for school dropout that have a history of trauma. This study examined the implementation of Trauma-Informed Check & Connect, a school engagement and dropout intervention integrating motivational interviewing and elements of trauma-informed care with the current Check & Connect procedures. The study participants were ninth grade students at a high school with a history of trauma who were experiencing disengagement and at-risk for dropping out of school. The study utilized a basic A-B single case design to evaluate the initial implementation of TICC and its impact on student functioning. The extent to which students perceived their relationship with the mentor as helpful and the intervention as socially valid and/or trauma-informed was also examined and a cost analysis completed to understand the costs of implementing TICC in a high school. Results indicated TICC did not have any significant effects on the studied variables. However, students indicated the relationship with the mentor as helpful and viewed TICC as trauma informed. Future research should aim to implement TICC for a longer period to understand if it can significantly impact student functioning and engagement in a positive manner and foster a positive mentor student relationship long-term. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]