The health care domain is experiencing a shift from traditional hospital-based care to care delivered in a patient's home setting. Although home health care provides many benefits, it creates new challenges and difficulties for professional caregivers (e.g., registered nurses) who are performing complex medical tasks without the support often present in a health care environment. In addition to performing these tasks themselves, registered nurses are also responsible for training patients to perform many of these tasks, which may include using medical devices and managing complex medication regimens. The purpose of this research was to identify and systematically categorize the issues facing registered nurses (RNs) when training older adult patients. Eight RNs participated in individual structured interviews wherein they were asked to describe the difficulties and frustrations associated with training older adult patients to use medical devices and manage medication independently. The data were categorized as patient-related, RN-related, or situation-related issues. The results highlight the complexity of training device use and medication management, as well as the needs of RNs for forms of additional support in training older adult patients.