Converting to a Roth IRA: Key Considerations and Estate Planning Opportunities

Converting to a Roth IRA: Key Considerations and Estate Planning Opportunities

Until now, the option of contributing to a Roth IRA was limited to those individuals with modified adjusted gross incomes below roughly $176,000 (for married taxpayers filing jointly) or $120,000 (for single taxpayers or those filing as head of household).[1]  While these limits remain in place for direct contributions to Roth IRAs, 2010 has brought a new opportunity for taxpayers at all income levels to establish Roth IRAs by converting traditional IRAs into Roth IRAs.  This offers an important possibility for tax savings, and in some cases estate planning, for many individuals.

This article provides an overview of the basic rules and tax implications of Roth IRA conversions, as well as the key considerations for individuals considering this option.  Particular attention is devoted to the potential tax savings and estate planning opportunities that this development presents for many individuals with relatively high net worth.  As set forth below, this article concludes that the potential extended tax-free growth offered by a Roth IRA conversion is generally most advantageous for individuals who (i) are able to pay the income tax resulting from the conversion with non-IRA assets, (ii) are likely to be able delay or avoid lifetime withdrawals from the IRA, (iii) are relatively young, and/or (iv) do not expect to be in a significantly lower tax bracket when funds are withdrawn.

Tax Treatment and Advantages of Roth IRAs

Before exploring the mechanics and tax implications of a Roth conversion, it is important to understand the basic tax treatment of Roth IRAs.

Unlike some contributions to traditional IRAs, direct contributions to Roth IRAs are not tax deductible.  Accordingly, where contributions to a traditional IRA were tax deductible and any portion of the IRA is subsequently converted to a Roth IRA, the converted amount is treated as taxable income.[2]  (The timing of such income inclusion is discussed in greater detail below.)  The advantages of a Roth IRA, however, in some cases far outweigh the drawback of this upfront tax.

First and most important, qualified withdrawals from a Roth IRA are free of income tax.  This means that unlike a traditional IRA, in which gains are taxed as ordinary income as they are distributed, all gains on a Roth IRA are tax-free as long as only qualified distributions are made from the account.  For a Roth IRA withdrawal to be excluded from taxable income, (i) the account owner must be at least age 59½ and (ii) at least five years must have elapsed since the owner's first contribution to any Roth IRA.  (These rules apply to lifetime withdrawals by the owner; as discussed below, different rules apply where an IRA is distributed to beneficiaries upon the owner's death.  Special exceptions also apply under certain circumstances such as the owner being permanently disabled.)  In addition, traditional IRAs converted to Roth IRAs are subject to a five-year waiting period that is calculated separately based on the conversion date of the applicable IRA; withdrawals made before this five-year waiting period are subject to a 10% penalty tax.  Thus, assuming that these basic requirements are met, Roth IRAs offer the benefit of entirely tax-free growth following the initial contribution or conversion.

Second, Roth IRAs offer more flexibility than traditional IRAs with respect to required minimum distributions or "RMDs."  Under the rules of a traditional IRA, the owner must begin annually withdrawing 4-5% of the account balance upon reaching age 70½ (increasing to over 6% per year at age 81) in order to avoid substantial tax penalties.  Thus, even where an individual does not currently need the assets in his or her traditional IRA, he or she is essentially forced to make annual withdrawals from it - thereby losing the benefit of holding the assets in the IRA - after reaching age 70½.  The holder of a Roth IRA, on the other hand, is not required to make any withdrawals from the account during his or her lifetime.  Thus, a Roth IRA's tax-free compounding may continue throughout the owner's lifetime, or at least until he or she needs the assets.

Roth IRAs, like traditional IRAs, are subject to RMDs if the owner dies without exhausting the funds, leaving the Roth IRA to beneficiaries.  (An exception is made where the account beneficiary is the owner's spouse, as he or she may treat the account as his or her own and thereby delay withdrawals.)  Generally, the funds in a Roth IRA are required to be distributed by the end of the fifth year following the owner's death.  However, this time period may be "stretched" over a period not to exceed the beneficiary's expected lifetime if distributions commence the year after the owner's death and the Roth IRA is payable to one or more "designated beneficiaries" (i.e., individuals and/or trusts that meet certain qualifications[3]).  Therefore, especially where a Roth IRA is left to a fairly young beneficiary, its tax-free compound growth may last for many years.

Finally, in the context of Roth IRA conversions, individuals with sufficient outside assets may pay the tax attributable to the conversion with non-IRA assets.  This in effect enables one to make a substantial additional contribution to the Roth IRA, as the initial amount that is allowed to grow tax-free is never reduced by any income tax.  As discussed later, the benefit of a Roth IRA conversion increases greatly where an individual is able to take advantage of this option.


The mechanics of converting a traditional IRA to a Roth IRA are generally fairly straightforward; an individual normally simply contacts the administrator of his or her existing IRA and arranges to have some amount converted to a Roth IRA with the same administrator.  The determinations of when and in what manner to make a conversion, however, are somewhat more complex.

As noted above, an amount converted from a traditional IRA to a Roth IRA is normally included in the account owner's taxable income in the year of conversion.  A special exception applies to conversions completed in 2010; although the owner may elect normal treatment (i.e., inclusion of the converted amount in 2010 income), inclusion of the converted amount may instead be delayed, with half of the amount included in taxable income for 2011 and half in 2012.  While Roth IRA conversions may be made in later years (barring, of course, a change in the law), this special treatment applies only to those completed in 2010.

Normally, delaying the recognition of taxable income provides at least a modest benefit, as it delays the payment of tax.  In this case, however, the advantage of delayed tax must be weighed against several factors favoring earlier inclusion.  First, tax rates are scheduled to increase beginning in 2011; the tax rate for the highest federal tax bracket, for example, is scheduled to increase from the current 35% to 39.6%.  Second, some experts predict that many assets will appreciate fairly substantially in the near future as the market continues to recover.  Third, the delay in conversion also delays the primary benefit of the Roth IRA: tax-free compound growth.  Therefore, some individuals may wish to convert IRAs this year and treat the converted amount as 2010 taxable income rather than delaying its recognition until 2011 and 2012.  Finally, one should consider the impact of a conversion on his or her tax bracket.  Some might find that splitting the converted amount between 2011 and 2012 prevents them from being pushed into a higher tax bracket for both years, while others might benefit more from having the converted amount included in only one year (thereby limiting the tax-bracket increase to one taxable year); this of course depends on one's other expected income and the amount converted.

In addition to the timing of a conversion and (in the case of 2010 conversions) the timing of income inclusion, an individual must determine the amount(s) to convert and how many Roth IRAs to establish.  Any portion of an individual's traditional IRA(s) may be converted to one or more Roth IRAs.  One interesting - and potentially advantageous, as discussed below - dimension to Roth IRA conversions is that an individual may establish multiple Roth IRAs (even where only one traditional IRA is being converted) and direct different kinds of assets to each account.


Another unique feature of Roth IRA conversions is that they typically may be undone (or "recharacterized") the following year.  Recharacterizations may not be made in the year of conversion, but generally may be made anytime until October 15 of the year after the conversion (i.e., most individuals' extended income tax deadline for the year of conversion).  This gives individuals some flexibility to rethink a conversion, and is particularly useful if the value of a converted amount decreases substantially.  In that case, an individual might elect to recharacterize the amount and try a conversion again later in order to include the reduced amount in taxable income.  A recharacterization entails some risk that the recharacterized amount will increase prior to the next conversion, particularly because the new conversion may not be completed until the later of (i) the year after the recharacterization and (ii) 30 days after the recharacterization.  Moreover, an individual must take into account any expected increases in the applicable tax rate as discussed previously.  However, where an asset depreciates considerably after a conversion, a recharacterization can be advantageous.

These recharacterization rules are structured such that individuals can attempt to maximize the benefit (and minimize the drawbacks) of a Roth IRA conversion.  Because of the timing restrictions set forth above, it may be beneficial to complete a conversion early in a taxable year in order to have almost two years to decide whether to recharacterize the amount.  In addition, most individuals should elect to hold off on a recharacterization until late in the applicable year in order to best gauge the performance of the converted amount(s), as a new conversion will not be allowed in any event until the following year. 

Finally, a key attractive element of the conversion and recharacterization rules is that the owner may pick and choose which Roth IRA account(s) to recharacterize.  As noted above, an individual may convert a single traditional IRA into a number of Roth IRAs, each with a specific type of investment, thereby "unpacking" a diversified traditional IRA into multiple Roth IRAs with different kinds of holdings.  As most investors are aware, the market does not always perform uniformly; some types of assets may do very well while others depreciate substantially over the same period.  Thus, as one analysis points out, "You can cherry-pick the losing account to get a lower tax cost via recharacterization, while leaving the winners to keep growing and eventually pay out tax‑free profits."[4]

Weighing a Potential Conversion: Primary Considerations

A number of resources provide comparative analysis of the potential outcome of a Roth IRA conversion (as opposed to maintaining a traditional IRA) based on varying factors such as timing of withdrawals, age at conversion, and changes in tax rates.  Bernstein Global Wealth Management's publication entitled Roth to Riches?  Determining Whether a Roth Conversion Makes Sense,[5] for example, provides useful comparative analyses based on varying hypothetical circumstances.  In addition, online tools such as Vanguard's "Roth IRA conversion calculator"[6] provide alternate projections based on one's personal information.  This sort of financial modeling and customized analysis is beyond the scope of this article.  However, a number of trends emerge from these analyses that highlight the following considerations as especially critical when determining whether (or to what extent) to convert a traditional IRA to a Roth IRA.

Although other considerations may come into play, as discussed in the next section, four primary factors generally determine the advisability of a Roth IRA conversion, as well as the extent to which a conversion provides tax savings and estate planning opportunities.

1. Ability to pay the tax attributable to a Roth IRA conversion from non-IRA assets.

One of the most significant advantages of a Roth conversion, as noted above, is the opportunity it affords to effectively make an additional contribution to the IRA by paying the conversion tax with outside assets.  A primary benefit of a traditional IRA is that it allows long-term growth of pre-tax assets, whereas a Roth IRA normally only includes contributions of after-tax assets (but allows all further growth to go untaxed).  By paying the conversion tax with outside assets, an individual is able to take advantage of both of these benefits: the full amount of the pre-tax traditional IRA contributions remains in the account, while all further growth goes untaxed due to the Roth conversion.  Although financial analysis shows that a Roth conversion can still provide tax savings for some traditional IRA holders who pay the conversion tax with IRA assets, the benefit is reduced compared with the substantial tax savings possible when the conversion tax is paid with outside assets and the full IRA account is left intact to grow tax-free.[7]

2. Age.

One need not be 25 to benefit from a Roth conversion.  However, the longer the period of time between the conversion and the commencement of withdrawals, the greater the benefit of the Roth's tax‑free growth.  For individuals who do not expect to make lifetime withdrawals from an IRA (as discussed later), age at conversion is less of a deciding factor because the account will likely have time to grow during the lives of the beneficiaries.  Individuals who expect to withdraw at least some of the account funds during their lifetimes, however, should consider their age at the time of conversion.  Generally, the analyses indicate that an IRA owner who is 55 or younger at the time of a Roth conversion is more likely to benefit from the conversion regardless of other factors such as moderate changes in tax rates or, to some extent, the ability to pay the conversion tax with non-IRA assets.  This is not to say that a 65-year-old who anticipates making lifetime withdrawals should rule out a Roth conversion (particularly if such withdrawals may be delayed at least 5 or 10 years), but simply that he or she must take greater account of the other factors determining the advisability of a conversion.

3. Comparative tax rates.

Whether it is more favorable to pay tax now (upon a Roth conversion) or later (upon withdrawal from a traditional IRA) depends in part on one's comparative tax rates now and in the future.  A traditional assumption is that one's tax rate will decrease upon retirement due to a reduced stream of income, which would weigh in favor of maintaining a traditional IRA in order to pay tax on withdrawals at a future lower tax rate rather than paying tax on a converted amount at one's current tax rate.  However, this may not be the case for wealthy individuals or those who continue to work beyond a traditional retirement age (particularly beyond 70½, the age at which traditional IRAs require minimum annual distributions to commence).  Individuals who expect to retire in another state should also consider whether this will likely increase or reduce their effective tax rate; Florida, for example, currently has no income tax, while California currently has very high income tax rates for higher-income individuals.  Thus, one's personal circumstances can have a significant impact on this factor.

In addition, it is very possible that tax rates will increase in the future due to both scheduled near-term rate increases and long-term revenue requirements.  This could at least partially offset any tax-rate reduction from decreased income in retirement.  Because anticipated changes in the tax rates are naturally speculative, some advisors suggest converting only a portion of one's traditional IRA(s) to Roth IRAs in order to diversify one's retirement portfolio from a tax perspective.[8]  In this respect, the Roth IRA protects against tax rate increases, while the traditional IRA takes advantage of any decreases in tax rates at retirement.

It is important to understand in this context, however, that even if one's tax rates decrease upon retirement, the reduction must be quite considerable in many cases to outweigh the benefits of a Roth IRA conversion if one is able to pay the conversion tax with outside assets; this is particularly pronounced if the conversion is done at least ten years before withdrawals begin, either because the IRA owner converts the IRA well before retirement age or because he or she is able to delay making withdrawals from the account after retiring.  Depending how long the funds are left untouched, a ten or even twenty percentage-point drop in one's tax rate may be outweighed by the benefits of the converted Roth's tax-free growth.[9]  On the other hand, a 65-year-old who expects to begin making moderate withdrawals in the near future is likely to fare better maintaining a traditional IRA (rather than converting it to a Roth) if his or her tax rates will drop even fairly modestly.[10]

Finally, for those planning to use an IRA as a vehicle for transmitting wealth to the next generation, it is relevant to consider the future tax rates of the IRA's intended beneficiaries.  Even if the beneficiaries are expected to be in lower tax brackets than that of the IRA owner, however, this must be weighed against the benefit of a Roth IRA's long-term growth possibilities, as discussed below. 

4. Ability to delay withdrawals.

Finally, the ability to delay withdrawals from an IRA weighs in favor of a Roth conversion-and for some individuals offers an excellent estate planning opportunity.  As noted previously, Roth IRAs have no required minimum distributions during the account owner's lifetime.  For those who must utilize some IRA funds during their lifetimes, the ability to delay the use of these funds - for example until age 70 or 75 - frequently offsets the drawback of making a conversion at a relatively late age such as 65.  The longer one can delay such withdrawals, the greater the benefit of the Roth's tax-free compound growth.

For those who can make modest lifetime withdrawals - or better yet, none at all - a Roth IRA can be a valuable tool for making tax-efficient transfers of wealth to one's heirs.  Although a Roth IRA (like a traditional IRA) is included in one's estate for estate tax purposes, its benefits of income-tax-free growth can extend well beyond one's lifetime.  As noted above, as long as a Roth IRA's beneficiaries are individuals or qualified trusts established for the benefit of individuals, the account generally qualifies for "stretch" treatment.  This means that required minimum distributions may be spread across a beneficiary's expected lifetime, giving the account assets far more time to appreciate free of income tax.

Because of this opportunity to continue tax-free growth, a Roth IRA can provide a far greater financial benefit to beneficiaries than an inherited traditional IRA or cash gift.  As Bernstein's analysis demonstrates, a Roth IRA conversion could still be highly beneficial even for a beneficiary who is age 55 at the time of the account owner's death, and whose tax rate is as much as twenty percentage points below the account owner's at the time of conversion, because required minimum distributions would be spread across a 30-year period following the account owner's death.  Some analysts even assert that the magnitude of this benefit is substantial enough to significantly outweigh any imposition of the generation-skipping transfer ("GST") tax (which is applicable when an individual exceeds his or her $1,000,000 GST tax exemption), thereby making a Roth IRA a potentially attractive asset to leave to grandchildren.[11]

Of course the benefits of delayed required minimum distributions are only applicable to the extent that an account owner and his or her beneficiaries are able and willing to refrain from making account withdrawals.  In this respect, some individuals may find it appealing to establish a trust to hold the Roth IRA in order to prevent beneficiaries from making unnecessarily early withdrawals.  It is critical, however, that such a trust be properly drafted and administered to qualify as a "designated person," as discussed previously, in order to avoid the standard five-year required distribution period following the account owner's death.  (Alternatively, an account owner may establish a "trusteed IRA" for similar purposes.[12])  Finally, it is also essential that an individual refrain from naming his or her estate as the Roth IRA account beneficiary, as an estate does not constitute a designated person and this would trigger the five-year distribution period, thereby preventing the benefit of otherwise delayed distributions.

Additional Considerations

While the above considerations constitute the primary determining factors for most people, some of the following considerations may also be applicable to an individual considering a Roth IRA conversion.

1. Income tax deductions to offset conversion income.  

A Roth conversion may be especially beneficial for individuals with deductions available to at least partially offset the additional taxable income generated by the conversion.  In this context, it is important to note that conversion income may be offset by ordinary income deductions such as charitable deductions (including "carryforwards" from prior years) and business net operating losses, but not by capital losses. 

Individuals who regularly have ordinary income tax deductions may wish to accelerate them into the year of conversion to the extent possible, such as by incurring business expenses in advance or by making a larger charitable gift in the year of conversion.  Depending on the size of the charitable gift, some donors might wish to make this one-time contribution to a donor-advised fund, which could then make smaller charitable gifts over time based on the donor's ongoing requests.[13] 

The timing of available deductions also could influence the year in which an individual elects to make a conversion and to include the amount in taxable income.  For example, an individual who has a substantial carryforward deduction that will expire in 2010 might wish to complete a conversion in 2010 and to include the converted amount in 2010 taxable income.

2. Estate taxes. 

As many are aware, estate taxes have been temporarily eliminated in 2010 barring further Congressional action.  However, they are scheduled to return in 2011 and most likely will remain part of the tax landscape, whether with the scheduled $1 million exemption or some other amount such as the $3.5 million per person exemption that was applicable in 2009.  Thus, the potential estate tax impact of a Roth IRA conversion is worth considering for individuals who are likely to exceed the exemption amount. 

Where an IRA is used as an estate planning vehicle, some analysts assert that a Roth IRA conversion provides estate tax savings.  This is because paying income tax on the converted amount reduces the owner's taxable estate and saves beneficiaries from paying income tax later (as opposed to traditional IRAs that require beneficiaries to pay income tax on gains as distributions are made).  This benefit is partially offset by the fact that income tax credits are generally available to beneficiaries of a traditional IRA based on the amount of any estate tax paid with respect to the IRA.  However, these credits are phased out for higher-income beneficiaries, and certainly could be eliminated in the future.  Moreover, such credits apply only to federal estate taxes; similar credits would not necessarily be available for any state estate taxes paid on the IRA, so this could weigh in favor of a Roth conversion.

On the other hand, the benefit of tax-free growth with no required minimum distributions during the account owner's lifetime increases the account's size and therefore the owner's taxable estate, presumably increasing the owner's total estate tax liability.  Therefore, it is fairly unlikely that a Roth conversion would afford significant estate tax savings.  It is important, however, for any estate taxes to be paid with non-IRA assets to the extent possible in order to protect the amount that may continue to grow tax-free over beneficiaries' expected lifetimes.

3. IRAs as charitable gifts.  

Traditional IRAs are typically considered excellent candidates for charitable bequests because this avoids any income tax being paid on the account; tax-deductible contributions are made upfront, and (unlike other kinds of beneficiaries) the tax-exempt charity is not required to pay income tax on the distributions.  Where beneficiaries are likely to exhaust an IRA account soon after the owner's death, this still holds true; it is likely best in that case to maintain a traditional IRA to leave to charity, and make cash bequests to beneficiaries.  However, where beneficiaries are likely to leave an inherited IRA largely intact (even over a period of ten or more years, if not over their expected lifetimes) - thereby taking advantage of a Roth IRA's long-term tax-free growth - the analysis indicates that it may be best to make a Roth conversion, leaving the Roth IRA to one's heirs and a cash gift equal to the amount that would have been in the traditional IRA to charity.[14]

4. Risk tolerance. 

Many of the issues involved in the determination of whether to make a Roth IRA conversion - such changes in tax rates, needs in retirement and life expectancy - involve a fair amount of uncertainty.  Most of these factors involve some amount of risk in either direction; one's tax rates could skyrocket, for example, making a traditional IRA far less advantageous than a Roth, or could plummet, potentially making the traditional IRA more favorable.  However, one issue to consider that would drastically alter the analysis herein - potentially making a Roth conversion quite detrimental - is the possibility that the tax treatment of existing Roth IRAs could change.  It does not appear that any such change is on the horizon, and even if tax treatment of Roth IRAs generally were to change, existing accounts could be subject to some sort of "grandfathering" policy that would preserve the tax-free status of future withdrawals from those accounts.  However, there is inherently some risk in electing to pay tax now with the expectation that future distributions will be tax-free in accordance with today's tax rules, as the current benefits of Roth IRAs could be subverted by future legislation.  Individuals who consider this a significant risk may choose not to make any Roth IRA conversions, or at least to maintain a portion of their existing accounts as traditional IRAs.


As described herein, Roth IRA conversions offer valuable opportunities for many holders of traditional IRAs to take advantage of long-term income tax savings, during their own lifetimes and potentially even during the lifetimes of their heirs.  These benefits are especially pronounced when the converted IRA is allowed to grow for an extended period of time due to delayed distributions and/or an account owner's relatively early age at the time of the Roth conversion.  In addition, the benefits of a Roth conversion are especially significant in the context of - and sometimes dependent upon - the owner paying the income tax attributable to the conversion with non-IRA assets.  Moreover, changes in tax rates (whether on an individual level or across-the-board) have a significant impact on the financial outcome of a Roth IRA conversion and therefore should be taken into account to the extent possible.

For some individuals, converting to a Roth IRA is clearly an excellent opportunity for tax savings, while the calculation for others involves much more speculation.  In any event, it is important to look closely at one's personal circumstances - preferably with the assistance of a financial advisor who can provide individualized projections - to determine whether a Roth IRA conversion is likely to be beneficial.  In addition, those individuals wishing to utilize Roth IRAs as vehicles for testamentary gifts should consult with their estate planning advisors to ensure that this objective is aligned with their other estate planning objectives and that beneficiary designations - particularly where a trust is involved - are completed in a manner that maximizes the benefits of the Roth IRA conversion.


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Morrison & Foerster's Trusts and Estates group provides sophisticated planning and administration services to a broad variety of clients.  If you would like additional information or assistance, please contact Patrick McCabe at (415) 268-6296 or


© Copyright 2010 Morrison & Foerster LLP. The views expressed in this article are those of the author only, are intended to be general in nature, and are not attributable to Morrison & Foerster LLP or any of its clients. The information provided herein may not be applicable in all situations and should not be acted upon without specific legal advice based on particular situations.


This article is published with permission of Morrison & Foerster LLP.  Further duplication without the permission of Morrison & Foerster LLP is prohibited.  All rights reserved.  The views expressed in this article are those of the authors only, are intended to be general in nature, and are not attributable to Morrison & Foerster LLP or any of its clients.  The information provided herein may not be applicable in all situations and should not be acted upon without specific legal advice based on particular situations.

[1]   These respective amounts reflect the current limits, which have increased incrementally over time under Internal Revenue Code section 408A(c).  These reflect the maximum limits; contributions are phased out at modified adjusted gross incomes of $166,000 and $105,000, respectively.

[2]   Contributions to a traditional IRA that were not tax deductible are not included in taxable income upon a Roth conversion.  However, where an individual has made both deductible and nondeductible IRA contributions, he or she must treat a pro rated portion of any amount converted to a Roth IRA as taxable income, regardless of which IRA account is converted.  This article's analysis assumes that a converted traditional IRA will have been funded with deductible contributions.  However, where non-deductible IRAs are involved, the reduction or absence of a conversion tax weighs in favor of a Roth IRA conversion.

[3]   See U.S. Treas. Reg. §1.401(a)(9)-4.

[4]    Bernstein Global Wealth Management, Roth to Riches? Determining Whether a Roth Conversion Makes Sense (2009) at 11.  See also, e.g., Trytten, Show Me the Money: What's the payoff for converting to a Roth IRA?, 148 Trusts & Estates 9, at 34.

[5]    Id.

[6]   Available at

[7]   See, e.g., Bernstein, supra note 4, at 3.

[8]   Id. at 10.

[9]   See Id. at 4-6.

[10]  Id. at 4.

[11]   See Trytten, supra note 4, at 44-46.

[12]   See Steiner, Before Setting Up a Trusteed IRA and Morrow, Trusteed IRAs: An Elegant Estate Planning Option, 148 Trusts & Estates 9, at 48 and 53.

[13]  Hoyt, Want to Convert To a Roth IRA?, 148 Trusts & Estates 9, at 31.

[14]   Bernstein, supra note 4, at 11.



  • 04-11-2011

This is very helpful blog, I finally understand the IRA's cycles.