Managing retirement payouts generally revolves primarily around securing adequate retirement income and assuring the continuity of such income for as long as the retirees live. Many commentators have suggested that the most efficient strategy to deal with these issues for risk-averse retirees is to annuitize retirement benefits. However, these commentators recognize that relatively few retirees actually choose life annuitization (the so-called “annuity puzzle”). One reason for this is the bequest or inheritance motive which involves using income-tax-favored retirement plans to pass wealth to the heirs (probably children) of the retiree or to charity. This chapter discusses the concepts, strategies, and constraints on using tax-favored retirement plans as wealth transfer devices.