With the world's highest incarceration rate and an aging incarcerated population, United States correctional facilities must manage the comprehensive healthcare needs of an increasingly medically complex patient population. Transitions of care for complex patients between hospitals and the correctional setting present a particular challenge. Teaching affiliations between correctional health care systems and academic health centers may offer an opportunity to optimize such transitions. In recognition of that opportunity, a team of providers linked by an interdisciplinary student-faculty collaborative clinic (the Crimson Care Collaborative) has undertaken an initiative to improve continuity of care between a large academic health center and a maximum security jail in downtown Boston. The Crimson Care Collaborative is a student-faculty collaborative clinic consisting of medical, nursing, and dental students who provide comprehensive mental health, dental, and medical care to detainees one evening each week. Through prioritization of medically complex patients, interdisciplinary faculty have provided several resources: clinical input on complex patients, improved access to patients' electronic medical information, and direct contact with providers from the acute care setting. Providers have also facilitated transfers of complex patients to and from the academic center and offered continuity visits to detainees admitted there. Faculty have also facilitated communication with academic center subspecialists. Over three months of implementation, all complex patients discharged back to the correctional setting have had at least one adjustment to the care plan because of the system of coordination. Further directions will include codifying key processes and seeking extension to other centers.