Hospital discharge planning for older adults is an essential component to successful transitional care and will become increasingly important as hospitals face financial penalties for avoidable readmissions. This study reports a cross-sectional descriptive web-based survey study about challenges to discharge planning experienced by hospitals in the Midwestern state of Missouri. Problems identified by respondents included difficulties finding placement for patients requiring ventilator care, hemodialysis, chemotherapy, radiation therapy, wound vacuums, or who have mental health care needs. In general, urban hospitals reported more problems with finding postacute discharge destinations for patients than did rural hospitals. It is essential that nursing homes, residential care facilities, and home health agencies be adequately reimbursed to manage complex patients. It may be equally important to identify ways to develop critical assessment and care management skills that are needed in postacute staff to increase the likelihood that patients will be accepted at the time of hospital discharge.