The case of an elderly patient with mild dementia and severe depression is reviewed including analysis of the barriers to successful transition that led to readmission. Situations likely to result in failed transitions include poor social support, discharge during times when ancillary services are unavailable, uncertain medication reconciliation, depression, and patients’ cognitive limitations. Evidence suggests deficits in communication by hospital physicians to primary care providers occur commonly but this is only one of many systems barriers to successful discharge. Review of the literature reveals interventions such as involvement of advance practice nurses or family members in the transition may overcome some of the difficulties inherent in discharge of the vulnerable geriatric patient. Weekend discharges present unique challenges and potential solutions are explored. This case offers the opportunity to review the elements necessary for success and insight into the systems limitations which underlie failed transitions.