If understand all this correctly, when you move funds from your regular IRA to a ROTH IRA, don't you have to pay ordinary income tax on the "withdrawal" from your IRA? I don't know of a tax free roll-over from a rgeular IRA to a ROTH IRA?You are correct. I don't think the original poster was proposing to get pre-tax money into a Roth IRA, only to get more than the "maximum" $2,000 annual contribution into a Roth IRA each year. However, since you have to leave your job to qualify for such rollovers, at many companies you aren't immediately eligible to participate in the 401K plan and it may take even longer to vest in matching contributions, his proposal is at the very least unwise, if not impossible.What may be helpful to those wishing to increase the balance in their tax free retirement accounts, is the Portman-Cardin bill currently in Congress. It would (among other things) create a Roth 401K plus account, that would allow after-tax 401K contributions to be treated like Roth IRA accounts - tax free withdrwals at retirement. For more information on this legislation, see:http://www.passpensionreform.org/housedetails.htm#lang(and be sure to let your legislators know that you support this legislation)
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