Roth Conversions: When You Should Convert Your IRA or 401(k) to Roth?

Many Americans wonder when they should convert their IRA or 401(k) to Roth? If you have a traditional IRA or 401(k), then that money grows tax-deferred and you pay tax on the money as it is drawn out at retirement. On the other hand, Roth IRAs and 401(k)s grow and come out tax-free at retirement. Who could argue with that? Yet, most Americans have been sucked into traditional IRAs and 401(k)s because we get a tax deduction when we put the money in a traditional account, saving us money on taxes now.

For more on the differences between Roth IRA and Roth 401(k), take a look at the video from my Partner Mark J. Kohler:

The good news is that you can convert your traditional IRA to a Roth IRA, or your traditional 401(k) to a Roth 401(k). The price to make that conversion is including the amount you convert to Roth as taxable income for the year in which you make the conversion. So, if I convert $100K from my traditional IRA to a Roth IRA in 2017, I will take that $100K as income on my 2017 tax return, then pay any federal and state taxes on that income depending on my 2017 tax bracket. Many retirement account owners want to move their traditional funds to Roth, but don’t like the idea of paying additional taxes to do so. I get it. Nobody likes paying more taxes now, even if it clearly saves you more as your account grows and the entire growth comes out tax-free. Here are three cut-and-dry situations of when you should definitely convert you traditional IRA or 401(k) funds to Roth:

  1. Up-Side Investment Opportunity – I’ve had numerous clients over the years convert their traditional funds to Roth before investing their account into a certain investment. They’ve done this because they’ve had a tremendous investment opportunity arise where they expect significant returns. They’d rather pay the tax on the smaller investment amounts now, so that the returns will go back into their Roth IRA or 401(k), where it can grow to an unlimited amount and come out tax-free. These clients have invested in real estate deals, start-ups, pre-IPOs, and other potentially lucrative investments. So, if you have an investment that you really believe in and will likely result in significant returns, then you’re far better off paying a little tax on the amount being invested before the account grows and returns a large profit. That way, the profit goes back into the Roth and the money becomes tax-free.
  2. Low-Income Year – Another situation where you should covert traditional funds to Roth is when you have a low-income tax-year. Since the pain of the conversion is that you have to pay tax on the amount that you convert, you should convert when you are in a lower tax bracket to lessen the blow. For example, if you are married and have $75K of taxable income for the year and you decide to convert $50K to Roth, you will pay federal tax on that converted amount at a rate of 15% which would result in $7,500 in federal taxes. Keep in mind that you also pay state tax on the amount that you convert (if your state has state income tax), and most states have stepped brackets where you pay tax at a lower rate when you have lower income. If you instead converted when you were in a high-income year, let’s say $250K of income, then you’d pay federal tax on a $50K conversion at a rate of 33% which would result in federal taxes of $16,500. That’s more than twice the taxes due when you are in a lower-income year. Now, you may not have taxable income fluctuations. But, for those who are self-employed, change jobs and have a loss of income, or have investment losses where taxable income is lower than normal for a year, you should think about converting your retirement funds to Roth. You may not have a more affordable time to get to Roth.
  3. Potential Need for a Distribution After Five Years – One of the perks of Roth accounts is that you can take out the funds that are contributed or converted after five years without paying tax or the early withdrawal penalty (even if you aren’t 59 1/2). For Roth conversions, the amount you convert can be distributed from the Roth account five years after the tax year in which you converted. The five-year clock starts to tick on January 1st of the tax year in which you convert, regardless of when you convert within the year. So, if you converted your traditional IRA to a Roth IRA in November 2017, then you could take a distribution of the amounts converted without paying tax or penalty on January 2nd, 2022. If you try to access funds in your traditional IRA or 401(k) before you are 59 1/2, then you will pay tax and a 10% early withdrawal penalty even if the amounts you distribute are only the contributions you put in, not the investment gains. Clearly, the Roth account is much more accessible in the event you need personal funds. Keep in mind, you don’t get this perk immediately: You have to wait 5 years from the tax year in which you converted before you can take out the converted amount tax and penalty free.

One final thought to consider when converting to a Roth IRA: The IRS allows you to undo the conversion if you later decide that it was a bad idea (e.g. you can’t pay the taxes and don’t want a payment plan with the IRS). What happens is the converted funds go back to traditional account, and the converted amount is removed from your taxable income. This process is known a Roth Re-Characterization, and you can learn more about it in my prior article here.

IRA Contribution Deadlines: Two Out of Three IRA Types Can’t be Extended

You have until April 18th, 2017 to make 2016 IRA contributions for Roth and Traditional IRAs. If you’re self-employed and are using a SEP, your deadline is determined by your company’s tax filing deadline (e.g. s-corp, partnership, or sole prop). So, if you were an s-corp or partnership in 2016, then your filing deadline was March 15th, 2017. II you are a sole prop, then the deadline is April 18th, 2017. If you extended your company return, that extension will also apply to your SEP IRA contributions. The table below breaks down the deadlines and extension options for Traditional, Roth and SEP IRAs.

Type of IRAContribution TypeDeadline Details
Traditional IRATraditional, DeductibleApril 18th, 2017: Due Date for Individual Tax Return Filing (not including extensions). IRC § 219(f)(3); You can file your return claiming a contribution before the contribution is actually made.  Rev. Rul. 84-18.
Roth IRARoth, Not DeductibleApril 18th, 2017: Due Date for Individual Tax Return Filing (not including extensions). IRC § 408A(c)(7).
SEP IRA Employee, DeductibleN/A: Employee contributions cannot be made to a SEP IRA plan.
Employer Contribution, DeductibleMarch 15/April 15th: Due Date for Company Tax Return Filing (including extensions). IRC § 404(h)(1)(B).

As outlined above, you have until the 2016 individual tax return deadline of April 18th, 2017 to make 2016 Traditional and Roth IRA contributions. The deadline for Traditional and Roth IRAs, however, does not include extensions. So, even if you extend your 2016 tax return, your 2016 Traditional and Roth IRA contributions are still due on April 18th, 2017.

SEP IRA contribution deadlines are based on the company tax return deadline, which could be March 15th if the company is taxed as a corporation (“c” or “s”) or partnership, and April 15th if it is a sole proprietorship. Keep in mind that this deadline includes extensions, so if you extend your company tax return filing, you will extend the time period to make 2016 SEP IRA contributions.

Roth IRA Conversion Re-Characterization: One “Do-Over” the IRS Allows

image4144Are you having second-thoughts about your Roth IRA Conversion? Did the value of your IRA decrease after you converted it? Are you unable to pay the tax on the conversion? If so, you’re in luck as you can re-characterize your Roth IRA back to a traditional IRA and you can avoid the taxes due too. Given the ups and downs of investments, this may be an excellent strategy for those whose account has decreased since their conversion in 2016.

If you have converted a Traditional IRA to a Roth IRA in 2016, you can reverse the conversion by doing what is called a Roth IRA conversion re-characterization. Under a re-characterization, the Roth IRA funds and assets are rolled back into a Traditional IRA, and the amounts converted are considered contributed to the traditional IRA and you effectively cancel out the amounts converted. As a result of the re-characterization, the taxes that would have been owed for the Roth IRA conversion are no longer due, and the assets and funds re-characterized go back to a Traditional IRA.

A Roth IRA conversion re-characterization is an excellent strategy in two situations. First, if you do not have the funds to pay the taxes on the conversion. Reversing the re-characterization will remove the tax liability. Problem solved. Second, if the investments in your Roth IRA, following the conversion, did not fare so well and if the account decreased in value you are generally better off re-characterizing the conversion and going back to a traditional IRA and then conducting a new Roth IRA conversions at the lower valuation. If you have completed a Roth IRA conversion re-characterization, you do have to wait until the next year to convert the same amounts back to Roth as the IRS restricts you from immediately re-converting after a re-characterization.

Here are a few keys facts to keep in mind for Roth IRA conversion re-characterizations:

1. You must coordinate the re-conversion with your IRA custodian as they will need to roll the Roth IRA funds back to a Traditional IRA. Your tax return also needs to properly report the re-conversion so that you don’t end up paying taxes on the 1099-R you will have received for the Roth IRA conversion.

2. You can re-characterize up to October 15th of the year following the year you converted. So if you conducted a Roth IRA conversion in 2016, you have until October 15, 2017 to re-characterize the conversion. You have until October 15th even if you did not file an extension and even if you have already filed your tax return for the prior year. If you filed a tax return already and claimed the Roth IRA conversion amounts as income, the tax return will need to be amended.

3. Roth 401(k) or other employer in-plan Roth conversions cannot be re-characterized so once those are reported to the IRS you cannot reverse them as the rules applicable to Roth IRA conversion re-characterizations do not apply to 401(k) or other in-plan Roth conversions.

Because of the re-characterization rules, the decision to convert funds to a Roth IRA isn’t as “taxing” as you’d think as you can later have a change of heart if the odds don’t end up in your favor (e.g. lower investment value, or no personal funds to pay taxes on the conversion).

More details and information can be obtained from an informative FAQ page from the IRS here.

By: Mat Sorensen, Attorney and Author of The Self Directed IRA Handbook.

3 Year-End IRA Tips

vgsgn1482893180It’s the end of the year and many IRA investors are stressing about what they need to do by December 31, 2016. Here’s what you need to know for your IRA as it relates to year-end.

1. 2016 Contribution Deadline. First, the good news. You don’t have to make your 2016 contributions by year-end. You have until April 18, 2017 to make your traditional IRA, Roth IRA, or SEP IRA contributions for 2016. Check out the “IRS Year-End Reminders for IRAs” here for more details.

2. Roth Conversions. If you are planning to convert traditional IRA dollars to Roth for 2016, then you must make that conversion by December 31, 2016. If you convert in 2016 (by 12/31/16), then the amount you convert will get reported on your 2016 tax return. For those that have a down year or that simply want to start down the path of moving funds from traditional (tax-deferred funds) to Roth (tax-free), you’ve got to jump on this now. Your IRA custodian will typically have a Roth Conversion form that you complete and return to them. If you are converting cash, then the process is pretty simple as the value of the conversion is the cash amount. If you have a self-directed asset such as real estate or an LLC interest, you will need an appraisal or valuation of that asset in order to convert it to Roth. And lastly, if you’re on the fence about doing a Roth conversion because you’re worried about how much it will cause you in taxes, the IRS allows you to un-do the Roth conversion later in 2017, your funds go back to traditional funds, and you don’t have to pay the tax. This is one of the few things the IRS let’s you un-wind. Check out my prior article on Roth re-characterizations here.

3. The Over 70 1/2 Club. For those over 70 1/2 with traditional IRAs, you are required to take required minimum distributions (“RMD”) from your account each year. The deadline for 2016 RMDs is December 31, 2016. There is a 50% excise tax penalty for failure to take RMDs. In other words, if you don’t distribute the money to yourself from your IRA in time, the IRS will just take half of it to penalize you. Those with Roth IRAs need not worry as Roth IRAs are exempt from RMD. I’ve explained the facts and fiction on RMDs in a prior article you can find here.

So, if you’ve got a Roth conversion or RMD to take for 2016, you better get your “IRA” in gear. If you’re wondering about IRA contributions, don’t worry, you’ve got until April 18, 2017 to make them.

Self-Directed IRA Alert: The RISE Act Will Drastically Impact Self-Directed IRAs


6mbve1477367970The Retirement Improvements and Savings Enhancements Act (“RISE Act“) has drastic changes and provisions that effect self-directed IRA investors. From mandatory third-party valuations on all retirement account investment transactions to changing the 50% disqualified company rule to 10%, the bill has some significant changes that will negatively affect your ability to self-direct your account. There are some favorable provisions for IRA owners, however, the negatives greatly outweigh the positives.

The bill sponsor is Sen. Ron Wyden (D-OR) who is the Ranking Member of the Senate Finance Committee and the Joint Committee on Taxation. Here’s a quick run-down of the most troublesome provisions that apply to self-directed IRA investors.

  • Valuation Purchase/Sale Requirement. Mandatory Valuation Requirement for Private IRA (non-public stock market) Transactions. The new proposal seeks to require gifting valuation rules and standards for IRA transactions. This rule will force IRA owners to get a valuation before making any private investment. This valuation would include real estate, private company (e.g. LLC, LP, corporation), and note investments. The gifting valuation rules were created to value gifts where no value is set between a buyer and seller. mandating those same rules on actual transactions between an IRA and another unrelated party is unrealistic and unnecessary to establish actual fair market value.
  • 50% Rule is Reduced to a New 10% Rule. Changes the 50% rule that states a company is a disqualified person to an IRA when it is owned 50% or more by disqualified persons (e.g. IRA owner and certain family). The new rule makes a company disqualified when owned 10% or more by disqualified persons.
  • Roth IRAs Capped at $5M. Roth IRAs will be capped at $5M. Any amount over $5M must be distributed from the Roth IRA.
  • Eliminate Roth Conversions. Traditional IRA funds cannot be converted to Roth IRA funds. Roth IRAs will be allowed only if the account owner makes initial Roth IRA contributions and only when they meet the Roth IRA contribution limits, which restricts high-income earners.
  • Require RMD for Roth IRAs. Roth IRAs are currently not subject to required minimum distribution (“RMD”) rules because the amounts distributed do not result in tax. This rule will change and RMD will apply to Roth IRAs when the account holder reaches age 70 ½.

These proposals will have drastic impacts on self-directed IRA investors. The valuation requirement is perhaps the most dramatic as it will require valuations before an IRA can buy an asset and before it can sell an asset. Not only will this cause administrative issues and increased costs, but it will undoubtedly replace the ability of an IRA buyer or an IRA seller from transacting their IRA at the price and value they determine to represent the actual current fair market value of their investments.

I have written a detailed analysis of the bill which I plan to share with the Senate Finance Committee and the Joint Committee on Taxation. I welcome your input as a self-directed IRA investor and plan to advocate for common-sense rules that help self-directed investors take control of their retirement. My draft bill analysis can be accessed at the link below. Please send your comments to