Highly sensitive students are in every classroom, but few educators know of their presence or the problems that they face in the learning environment. This group of children often struggle in silence as twice-exceptional individuals who have both significant gifts but also particular challenges to navigate a neurotypical school environment. Both teachers and parents, often unaware of this trait, can increase stress by "coaching" these children to toughen up and develop thicker skin. As a result, some of our brightest children turn to self-medication to numb their emotions or opt out of education entirely. This multi-case qualitative study was designed to explore and describe the academic experiences of highly sensitive, twice-exceptional adults who managed the stress of school despite mental, emotional, and physical demands. This investigation included perspectives of 13 individuals through the lens of their educational journey, as well as the lived experience in their biological family constellation. Depicting these retrospective narratives of 2e/HSPs illuminated the sometimes secret, subtle struggles of a particular population in our society who "hide in plain sight" in order to survive an intense, toxic school environment of competitive achievement that is consistently critical of their insight, intuition, empathy, and artistic expression--often at extreme cost to the individual. The methods for data collection included the Highly Sensitive Person Scale (HSPS) and 2e Questionnaire, followed by a multi-case study through semi-structured interviews. There were four themes that emerged from this study: family fractures of alienation and isolation, school struggles, misdiagnosis combined with ignored mental health issues, and the struggle for identity midst silent strengths. The impact of this research will help to highlight how our educational system can recognize this unique trait as a strength to celebrate and not a weakness to remediate. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]