<h3>Background</h3> The differential diagnosis of primary or secondary amenorrhea includes obstructive pathologies such as vaginal stenosis. Vaginal stenosis can be acquired as a result of vaginal graft versus host disease (GVHD) in patients who have undergone hematopoietic stem cell transplant (HSCT). The true prevalence of vaginal GVHD is unknown, and young patients in particular are at risk for missed or delayed diagnosis, with the potential for severe complications such as vaginal stenosis and secondary hematometrocolpos. This case report demonstrates the potential for blunt dissection of vaginal adhesions along a tissue plane in cases of vaginal stenosis secondary to vaginal GVHD, and underscores the importance of increased physician awareness of vaginal GVHD in adolescents and increased screening for vaginal GVHD in at-risk adolescent patients. <h3>Case</h3> We report two cases of vaginal adhesions and hematometrocolpos secondary to vaginal GVHD in a 14-year-old patient and a 24-year-old patient, both with histories of allogeneic HSCT. Resolution of hematocolpos was obtained with surgical lysis of vaginal adhesions and temporary vaginal stent placement in both patients, followed by systemic and topical hormone therapy and, in the 24-year-old, dilator therapy. Future vaginal dilator versus surgical therapy is planned for the 14 year-old patient. <h3>Comments</h3> Vaginal stenosis secondary to vaginal GVHD must be considered with patients with a history of allogeneic HSCT who present with primary or secondary amenorrhea. Surgical management may be able to identify a residual plane of the normal vaginal canal, which may avoid the need for vaginal replacement and restore normal anatomy. The use of vaginal stents can facilitate attempts to restore normal anatomy and prevent restenosis, along with adequate postoperative medical and dilator management as appropriate. This complex diagnosis warrants careful treatment and surveillance that are bolstered by a strong physician-patient relationship and patient motivation to participate in care. These cases demonstrate that a tissue plane can be identified even in cases where the vagina appears completely stenotic. As HCST transplant success rates continue to increase, the occurrence of GVHD and vaginal GVHD in adolescents and young adults is anticipated to rise. The increasing incidence of vaginal GVHD and the potential for underdiagnosis supports a need for routine screening and education in adolescent and young adult patients who are at risk for vaginal GVHD.