A clinical intervention pilot study to improve depression care for short-stay nursing home Medicare-reimbursed rehabilitation patients funded by the National Institute on Aging was conducted. Despite solid theoretical and clinical grounding and the support of a large nursing home company, several roadblocks to implementation were encountered, including involving patients and families, communication between providers, involving community primary care physicians, staff time constraints, and conducting research with short-stay patients. Although frustrating from a research standpoint, these roadblocks closely reflect problems identified by the American Geriatrics Society as impeding the delivery of high-quality transitional care in geriatrics. These research roadblocks are described as they were encountered in the clinical setting, and each is placed within the larger context of challenges associated with care transitions, especially for older persons with complex health needs receiving nursing home rehabilitation. Finally, recommendations are offered for researchers conducting much-needed research within geriatric transitional care settings, including starting early in the care transition chain and assisting patients and families with providing continuity across care settings.