About half of older Americans will need substantial, prolonged help with routine activities. Most people pay out of pocket for these long-term services and supports until they exhaust their financial resources and go onto Medicaid. To show how policy changes could expand insurance’s role in financing these needs, we model several new insurance options. If the primary goal is to significantly increase insurance coverage, mandatory options would be more successful than voluntary versions. If the primary goal is to reduce Medicaid costs, options that cover long-term services and supports relatively late in the disability spell would be most beneficial.