Don't Miss Your Chance for a Roth IRA Do-Over

Roth IRAMost of us stopped worrying about taxes five months ago. But if you were one of the procrastinators who put off getting your taxes done back in April and filed for extension, you're coming up on one month to go until your Oct. 15 deadline.

There's also another thing you may need to consider before mid-October. If you converted your IRA to a Roth IRA last year, you have until Oct. 15 do what's called a recharacterization, which essentially lets you undo the conversion and get a do-over.

The Basics of Roth Conversions

A Roth conversion lets you take money from a regular IRA and move it into a Roth IRA. You'll pay tax on the converted amount, but in return, those investments will grow tax-free as long as they stay inside the account. Unlike regular IRAs, Roth withdrawals are usually free of tax as well.

But if you converted last year and have lost money in your account, you'll still need to pay tax on the higher amount you originally converted rather than on its current lower value.

That's where recharacterization can help you, because for tax purposes, recharacterizing will make all that tax liability disappear. Then, after waiting 30 days, you can convert that money back into a Roth if you want, and you'll only have to pay tax on the lower amount when you file your 2012 tax return.

Cutting Your Taxes

With the stock market setting new five-year highs, the odds are good that you've actually made money in your Roth. But even if that's the case, there may be another reason to recharacterize: if you're in a lower tax bracket.

It's often impossible to tell how much income you'll have when you initially convert to a Roth. But by now, you not only know how much you made last year but also have a good idea of your income for this year. You can therefore make an educated guess about whether you might be in a lower tax bracket this year, and if you are, then recharacterizing could let you take advantage of beneficial tax rates that would otherwise go to waste.

Mechanically, your broker should take care of all the details of doing the recharacterization, so you shouldn't have too much hassle. Given the thousands in taxes that it could potentially save you, considering whether recharacterization make sense is well worth the effort.

Motley Fool contributor Dan Caplinger likes do-overs when he needs them. You can follow him on Twitter @DanCaplinger.

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Be careful about the 2nd five year waiting period that can be applied to CONVERSIONS. A 10% penalty to EARNINGS is described in IRS pub 590.

September 18 2012 at 6:24 AM Report abuse rate up rate down Reply
John Dovak

But.... if you converted to a Roth in 2010 like I prepared for a big tax hit this year unless the Alternative Minimum Tax limit is extended before the end of 2012. Wish somebody had told me this last year that it was a possibility. Sure does lessen the value of converting.

September 17 2012 at 9:34 AM Report abuse +1 rate up rate down Reply