I questioned the Sales Manager at my dealership at some length about the procedure at the end of the lease if the value of the car is less than the residual. Here is a summary of what he said. If, for example, the residual is $20,000 and the value of the car is $18,000. Chrysler financial, who owns the car, will refuse to sell it to me for $18,000, but will sell the car at auction for $18,000 (or I presume whatever they can get for it) because they have insurance that pays them the difference between the residual and the value of the car if I turn it back to them instead of paying the residual, and that dollar difference can only be established by the auction price for insurance purposes, not by agreement between me and the dealership.
Don't know if what he said was accurate, just reporting what he said.