All moneys that come out of a retirement account are fully taxable.All previously untaxed contributions are taxable when distributed. 401Ks and IRAs allow after-tax contributions. So, the issue is, if one sells an equity in a taxable account at a loss and claims that loss on the tax return, AND, also simultaneously purchases that same equity in a retirement account for which full taxes will be paid at distribution, how would that be a wash sale/purchase. Or, suppose the opposite: sell in the IRA at an investor loss, but not tax deductible, AND, simultaneously purchase in a taxable account. The best approach is to avoid the situation. If you wish to be a test case, that is your choice. Retirement accounts didn't exist when the wash sale rules were inacted. Unless you are willing to take the issue to court, arguments that a Revenue Ruling is incorrect are futile. The Revenue Ruling makes it clear that it the wash sale is one-way. When a wash sale crosses the boundary of a retirement account, the loss can never be used as a tax deduction.
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