Roth IRA Conversion: How to Convert Without Losing Money or Paying Taxes

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Just about anyone who understands the benefits of a Roth IRA, will want to convert their traditional IRA money to a Roth IRA if they can, but the income tax consequences of the conversion can be significant. Thankfully, there are a couple of ways to work the conversion that will prevent you from losing money from a Roth IRA conversion. Not all of them are available to everyone, but all options are worth some investigation.

The Benefits of a Roth IRA Conversion

The benefits of converting a Traditional IRA to a Roth IRA are numerous, so here’s a quick refresher:

  • Your distributions in retirement will be completely free of income tax
  • The tax-free distributions will lower your overall income, protecting more of your Social Security benefits from taxation too
  • You will completely eliminate the possibility of facing higher taxes in retirement than you are paying now (which will be entirely possible if you will have multiple retirement income streams)
  • Roth IRA’s are almost unique among tax-sheltered retirement plans in that they don’t require RMDs (required minimum distributions), that are required on other qualified plans; that means you can preserve more of your retirement capital for your later years, allowing them to grow even larger

The Cost of Doing a Roth IRA Conversion

The downside of doing a Roth IRA conversion is that the amount of your IRA funds that are transferred to a Roth IRA will become taxable in the year of conversion. That will include all investment income earned on the traditional IRA, plus plan contributions on which you received a tax deduction in the year taken.

The only portion of the converted balance that won’t be subject to income taxes are any contributions to the traditional IRA that were not tax-deductible when made. However, you don’t get to pick and choose which amounts you transfer either (i.e., declaring that the amount converted was comprised entirely of nondeductible IRA contributions).

The IRS requires that you apportion any amount converted. You have to take the amount of your non-deductible IRA contributions, and divide it by the total amount of all of your IRA accounts.

For example, if you made $20,000 in nondeductible IRA contributions to your plan, but you have $200,000 in IRA account balances from all IRAs, then only 10% ($20,000 divided by $200,000) of any amount converted to a Roth IRA will escape income taxes in the year of conversion.

If you want a helping hand, you can use Personal Capital and its free Roth IRA conversion calculator to estimate how much you'll owe in taxes by converting some or all of your accounts into an IRA.

Personal Capital Roth IRA Conversion calculator

How to Not Lose Money on a Roth IRA Conversion

So how do you not lose money on an IRA conversion? There are a couple of ways.

Converting Non-Deductible IRA Funds

The easiest way to escape paying taxes on an IRA conversion is to make traditional IRA contributions when your income exceeds the threshold for deducting IRA contributions, then converting them to a Roth IRA.

If you’re covered by an employer retirement plan, the IRS limits IRA deductibility. For 2019, if you’re single, an IRA contribution is no longer deductible when your income reaches $74,000. If you’re married filing jointly, the limit is $123,000.

In order to be able to contribute directly to a Roth IRA, your income can’t exceed $137,000 for singles and $203,000 for married filing jointly. However, there’s no income limit on Roth IRA conversions.

If you’re married and you make more than $123,000 (the IRA deductibility limit) you can make a contribution to your traditional IRA, then roll it over to a Roth IRA. If you do this immediately — as in before the traditional IRA has a chance to accumulate investment income — the rollover will take place without any income tax consequences, as long as you have no other traditional IRA balances.

What if you do have existing IRA balances? You can try to make them go away…

Leveraging Your 401(k) Plan

Some employer 401(k) plans will allow you to roll your traditional IRA accounts over into the plan. If they do, you can convert your existing IRA accounts to your 401(k). In doing so, you will no longer have IRA money, and you will no longer be required to apportion your Roth rollovers based on a percentage of your nondeductible IRA contributions. All-new, non-tax-deductible traditional IRA contributions can then be converted into Roth IRAs without tax consequences.

But what if your employer 401(k) doesn’t permit IRA rollovers?

If Your 401(k) Doesn’t Permit IRA Rollovers

The insurance industry has rolled out new products in recent years in order to make their annuities more competitive with other investment vehicles. One that is particularly interesting in connection with IRA conversions is the bonus annuity. These are annuities that pay you an upfront bonus of between 2% and 10% of the amount of the annuity.

Much like IRAs, annuities have the advantage of being tax-deferred. A bonus annuity can offset the taxes paid on a partial IRA conversion.

For example; let’s say you have $200,000 in your IRA, and you want to roll part of it into a Roth IRA. If you move the entire balance of the plan into a bonus annuity IRA that pays a 7% bonus on the balance, that will be $14,000 in “found money”, which can be used to offset the taxes on the portion that will be converted to a Roth IRA.

If you are in the 28% tax bracket, you will be able to convert $50,000 of your IRA into a Roth without losing money. The rollover will result in a $14,000 tax liability ($50,000 X 0.28), but that will be offset by the 7% bonus that you will be paid on the $200,000 rollover to the annuity — which will be $14,000 ($200,000 X 0.07). You still have to pay the tax on the partial conversion, but that is covered by the bonus you receive on the total rollover.

Annuities aren’t the best investment choice for everyone. They do come with certain restrictions and are usually packed with fees. In fact, the primary purpose of a bonus annuity is to cover surrender charges in the event that you decide to terminate your annuity before the contract allows you to do so without penalties. Read more about Annuities as an investment here.

Bottom Line

If you want to do a Roth IRA conversion without losing money to income taxes, you should first try to do it by rolling your existing IRA accounts into your employer 401(k) plan, then converting non-deductible IRA contributions going forward.

The bonus annuity route should only be considered if the 401(k) option isn’t available to you. In either case, be sure to first consult your tax advisor, since the penalties for making a mistake on a Roth IRA conversion can be steep.

Readers: What conversion methods have you tried when attempting to avoid losing money on a Roth IRA conversion?

Kevin Mercadante

Kevin Mercadante is professional personal finance blogger, and the owner of his own personal finance blog, He has backgrounds in both accounting and the mortgage industry. He lives in Atlanta with his wife and two teenage kids.

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  1. I do everything the hard way. I started an IRA in college and funded it each year until I was told it would no longer benefit me when I was also paying into the TSP at work. (Federal employee) I was never matched because I was a CSRS retiree. When I retired in 2010 at age 50 I started trading options in my IRA in which I transferred the TSP account into. Since then I’ve grown the around $50,000 account to around $200,000. I was now looking at converting that traditional IRA to a ROTH so I know longer would have to pay taxes on the trades made inside the ROTH. Is that even doable or feasible? I read where David Tepper traded his ROTH into the millions and I got a bug to find out about it!

  2. I converted $200k from a traditional IRA into a Roth and now I need to pay $60k in taxes. Any idea what I can do?

    1. Hello Rudi

      I would like to know what answer you get ? I am hesitant to do a Roth conversion because of the upfront tax liability, and the later year (post RMD) tax reduction may not be sufficient to off set the upfront tax liability.
      Best Regards

    2. Pay it! That is what I want to do also. I would then have to wait 5 years to reap the benefits of the ROTH but can easily earn the $60,000 back trading options. I’ve averaged between 75-100 thousand in last few years but have to pay 30-40% on withdrawals.

  3. Hello,
    I have an interesting Question about Roth IRA. I know we do not pay taxes when we removed money from it to purchase a home. But how about if I remove some money to purchase physical gold or silver? Do I have to pay taxes on that conversion? After all, it is an investment, and I am not profiting until I either exchange it or sell it.

    I will appreciate your respond

  4. Hi Kevin,
    Thanks for the interesting article. I have some questions! My son is 16 and has a Roth IRA now. I am trying to figure out if it makes sense for him to open a traditional IRA in the near-term just to get it started, or when he starts a ‘real job’ for contributions over what he’d put in his 401k for matching, or not at all assuming he has a job with a 401k. Right now he doesn’t earn enough to owe any taxes.

    Your article makes it seem like it doesn’t make sense to open and maintain a traditional IRA if you don’t already have one. True?

    Also, can you help me understand the “converting non-deductible IRA funds” section. Are you saying to open a new traditional IRA in a given year, fund it, convert to a Roth IRA, then close the traditional IRA AND don’t have any other traditional IRA accounts? (so you don’t have any other traditional IRA balances)

  5. I did not know about the aggregation rule when I did the Roth conversion. I have 200k in my Traditional IRA. So now it looks like most of the $6,500 that I converted will be taxable. Is that true? Is there another way to reduce the tax implication?

    Please advise. Thanks.

  6. Some savers may want to consider a Roth conversion before retirement because of the chance of being bumped into a higher tax bracket after retirement. Some savers have a pension, pick up another job or start a business, their spouse works, etc. so they have a good income. Sometimes, all this income bumps them into a higher tax bracket after retiring from their first career and the tax man visits them with a little surprise.

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