For those in poor health who face potential estate taxes and have a large IRA, a popular tax strategy is the so-called “deathbed Roth conversion” where the IRA owner converts to a Roth before death as a means to pay the income taxes up front and reduce the size of his/her estate. For large estates (and large IRAs), the tax savings can be significant.
However, the caveat of the deathbed Roth conversion strategy is that in most cases it is unnecessary, thanks to the availability of the so-called “IRD” (Income in Respect of a Decedent) tax, which provides IRA beneficiaries an income tax deduction for any estate taxes paid by the original IRA owner. In fact, the whole purpose of the IRD deduction is to eliminate any need for deathbed conversions (or liquidations) of pre-tax assets, by aligning the tax deductions to ensure that the beneficiaries will be no worse off (nor any better).
On the other hand, it’s notable that while the IRD deduction does shelter against Federal estate taxes, deathbed Roth conversions can still be relevant to protect against state estate taxes. Though in either case, the greatest driver of the outcome is not actually the IRD deduction or minimizing state estate taxes at all, but trying to shift the timing of when the IRA is recognized for tax purposes, so that the income taxes are paid at whichever rate is lower – either the IRA owner now, or the rate the beneficiaries would pay by simply inheriting the pre-tax IRA and stretching it out in the future!