Abstract: A system and method of providing care annuities that guarantee provision of actual, appropriate custodial care to individuals. The care annuities are priced based on an estimated cost of providing anticipated, appropriate custodial care for an anticipated time period, such as a Medicaid lookback time. Some or all of the calculations involved in pricing and providing the care annuity, including estimating the type, length and cost of custodial care appropriate for an individual, may be made using a suitably programmed computer. A suitably priced care annuity will guarantee the individual actual, appropriate custodial care for as long as actually required and make business sense to the seller of the annuity. The risk of a possible difference between the estimated and actual cost of providing care may be factored into the price in a statistical manner so that the risk can be spread over a pool of care annuities.