Skip to main content

BOSTON (

TheStreet

) -- Today is a big day for those scrambling to put some crucial financial affairs in order.

Oct. 15 is the deadline to file income tax returns if you requested an extension. For those with the trickier prospect of overseas assets, today is also the last chance to report undeclared holdings in foreign banks as part of the government's amnesty program. Failure to do so could result in massive fines and even jail time.

As if accountants didn't have enough to do with their procrastinating clients, this is also the annual deadline to undo Roth IRA conversions. If you switched to a Roth in 2008 and wish you hadn't, you can put your money back in a traditional IRA. This maneuver can shrink investors' tax bills and generate interest-paid returns.

Rande Spiegelman, vice president of financial planning at the

Charles Schwab's

(SCHW) - Get Charles Schwab Corporation Report

Center for Financial Research, says investors can reverse a conversion for any reason at any time before the deadline.

"You don't need a reason. You don't need an excuse. You don't need a note from your doctor or your mother. You just want to reverse that thing and make it like it never happened," he says. "Maybe you just changed your mind or your original assumptions were wrong."

Many investors opt to "recharacterize" their IRAs because the upfront tax hit of a Roth IRA proved unpalatable. For example, investors in the 30% tax bracket who converted $100,000 might reconsider the change when they find out they owe $30,000 in taxes next year. It would make sense to move back to a traditional IRA if the investor expects to stay at the same tax bracket in 20 or 30 years, Spiegelman says.

An investor with a traditional IRA might realize at the end of the year that he made too much money to qualify for a tax deduction on his contributions.

TheStreet Recommends

"You can reverse a straight old contribution, not just a conversion from a traditional to a Roth," Spiegelman says

Recharacterization must be done prior to the extended filing deadline for the year in which you converted to a Roth. If you didn't request an extension for your 2008 filing, you will need to file amended state and federal returns to get a refund of the tax paid on conversion income.

Even the do-over can be undone.

"You may want to reconvert at some point," Spiegelman says. "Perhaps you recharacterized because the market went down after you originally converted and now you want to reconvert at a lower level to pay less tax."

To reconvert, you have to wait until the year after the original change or 31 days after the recharacterization, whichever is later. If you converted in 2008 and recharacterized on Oct. 15, you would have to wait until Nov. 15 to reconvert.

Knowing there's an opportunity to do-over a Roth conversion may give peace of mind to those stressing over a conversion.

Traditional IRA contributions are tax-free, but distributions are taxed. With a Roth, contributions are not tax-deductible, but earnings can be withdrawn income-tax-free if you're at least 59.5 years old and have had the Roth at least five years. You also don't need to take required minimum distributions starting at age 70.5, as you do with a traditional account.

Traditionally, you could not convert from a traditional IRA to a Roth IRA if your modified adjusted gross income is over $100,000. Beginning in 2010, that limitation will be lifted.

That conversion opportunity has many wondering whether it is the right move for them.

Those who might benefit from the opportunity, even though they have to pay taxes on the amount converted are parties who think they will be in the same or a higher tax bracket when they withdraw. Others, who don't need to use the money, may want to leave an income-tax-free gift to their beneficiaries.

Spiegelman says there's a danger that investors will blindly jump at the option.

"There are advisors out there saying, 'Wow this is the best thing ever, you have to do this.' Others are saying, 'You've got to be out of your mind to pay a tax before you should. Why would you voluntarily write a check to the government?'" he says. "You need to crunch the numbers and make the decision for yourself."

-- Reported by Joe Mont in Boston.