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Greetings, Charli25, and welcome. You asked:

My son rolled part of a regular IRA over to a Roth in 1998 and is paying 1/4 taxes each year.

His original investment is now below the conversion, can he reconvert it even though he rolled it in 1998 ?

No, he cannot. Under special rules those who converted in 1998 could recharacterize their conversions back to a traditional IRA provided they acted by December 31, 1999. Conversions made in 1999 or latter must do so by October 15 of the following tax-year. The last date by which your son could recharacterize has long since passed, so those 1998 conversions now stand.

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