There are ramifications for the educational loss that comes with student disengagement. Contemporary use of alternative high schools focuses on Tier III responses to intervention for disengaged students at comprehensive high schools. Alternative schools are affiliated with students disenfranchised by traditional educational institutions and are considered a subset of students that are not making adequate progress toward graduation (Lange & Sletten, 2002; Lehr et al., 2009.) Reengagement in an alternative setting is a solution that may be just a one-time opportunity as every attempt is significant to the individual behaviors presented (Cranston et al., 2016; Rittel & Webber, 1973). Staff encountering disengaged students may only have a one-time opportunity to resolve an issue that will reengage the student but, in turn, may open a new series of problems by their attending school. Disengaged students, in this study, are identified as "compliant," students who came to school every day yet failed to make sufficient credit-earning progress. Teachers of chronically disengaged learners can tell you nothing in the research explains how to reengage learners identified as "at-risk." Engagement, according to Sinatra et al. (2015), "is one of the hottest research topics in the field of educational psychology" (p.1). Unearthing the truth about why students disengage from learning and school is one of the most intractable problems of practice that researchers and educators have failed to address adequately. Yet, the front-line teacher must battle learner disengagement minute by minute during any given class period. The behaviors are affected by the lived reality of the individual student, such as adverse experiences that go beyond the present pandemic situation. Lawson and Lawson (2020) point out that disengagement trajectories stemming from adverse experiences can present themselves and create undesirable outcomes that lead to dropping out. The Action Research study applied the narratives of twelve students through the use of Cogenerative Dialogues. These dialogues allowed students to name the disengagement and provide insight into possible reengagement needs for promoting sustainable engagement. Additionally, the study used classroom observations, critical self-reflection, and collaborative conversations of six teachers working to reengage students at an alternative high school. [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.]