Although automobiles remain the transportation of choice for older adults, late life cognitive impairment and dementia often impair the ability to drive safely. There is, however, no commonly utilized method of assessing dementia severity in relation to driving, no consensus on the assessment of older drivers with cognitive impairment, and no gold standard for determining driving fitness. Yet, clinicians are called upon by patients, their families, other health professionals, and often the Department of Motor Vehicles (DMV) to assess their patients' fitness-to-drive and to make recommendations about driving privileges. Using the case of Mr W, we describe the challenges of driving with cognitive impairment for both the patient and caregiver, summarize the literature on dementia and driving, discuss evidenced-based assessment of fitness-to-drive, and address important ethical and legal issues. We describe the role of physician assessment, referral to neuropsychology, functional screens, dementia severity tools, driving evaluation clinics, and DMV referrals that may assist with evaluation. Finally, we discuss mobility counseling (eg, exploration of transportation alternatives) since health professionals need to address this important issue for older adults who lose the ability to drive. The application of a comprehensive, interdisciplinary approach to the older driver with cognitive impairment will have the best opportunity to enhance our patients' social connectedness and quality of life, while meeting their psychological and medical needs and maintaining personal and public safety.