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If the value then declines afterwards, there is no possibility of ever taking a loss on those. Or is there ? I can't imagine the government letting you have it both ways, not ever taxing you on any Roth gain, but letting you take a capital loss if there is one. Am I wrong ?

Yes, on a couple of fronts. First, in the realm of retirement accounts capital gains/losses are irrelevant from a tax standpoint. If you have after-tax money in an IRA and if you liquidate all your IRAs for less than the total of your after-tax money, you have a Schedule A miscellaneous itemized deduction. See Pub 590.

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