This is a case study of two elderly, frail women in New York City who were recently rendered homeless. One woman had a massive tumor on her occipital scalp; the other was in renal failure. The obstacles and complexities of providing care to those with double jeopardy--being elderly and homeless--are described. There are enormous difficulties for placement into safe, supportive housing once people become homeless. The process is expensive and labor intensive. This can be complicated by the existence of mental illness. A New York agency that works with mentally ill homeless people is described. There are systemic obstacles as well: One woman loses her Medicaid when she moves from one state to another to be closer to her family. Another, 82 years old, is told to get a job so that she could qualify for Medicare. There are numerous contradictions and unnecessary costs in a fragmented health care system to which the obvious solution is a national single-payer system of care.