For Attorneys & CPAs · Retirement & Benefits
By Brad Caponigro · Founder, Pointer Petroleum LLC · Reservoir engineer
Published · Updated
Traditional IRAs and 401(k)s hold pre-tax dollars. You deducted the contribution when you made it, the dollars have grown tax-deferred, and when you withdraw them in retirement, every dollar of withdrawal is ordinary income. Starting at age seventy-three (rising to seventy-five under current law), Required Minimum Distributions (RMDs) force you to withdraw a minimum each year whether you need the money or not.
Roth IRAs hold post-tax dollars. You paid tax on the contribution, the dollars grow tax-free, and qualified withdrawals are tax-free. No RMDs during your lifetime. Your heirs inherit a Roth that continues to grow tax-free for up to ten years before they must empty it.
A Roth conversion moves dollars from a traditional IRA or 401(k) into a Roth IRA. The converted amount is taxed as ordinary income in the year of conversion. The tax bill is real and must be paid with cash (ideally cash outside the retirement account, to maximize the amount that ends up Roth). In exchange, the converted dollars plus all future growth come out tax-free.
The conversion decision is essentially a tax-rate arbitrage. If your marginal tax rate at conversion is lower than your expected marginal rate in future retirement years — or your heirs' rate, if you are planning multi-generationally — the conversion wins. If your marginal rate at conversion is higher, the conversion loses.
For a typical W-2 retiree with predictable pension and Social Security income, identifying a low-income year for conversion is straightforward. Retire at sixty-five, live off cash savings while delaying Social Security to seventy, and you have five years of relatively low MAGI during which Roth conversions are maximally efficient. After seventy, Social Security plus RMDs push MAGI up and the conversion window closes.
For a royalty owner, the picture is messier. A year with a lease-bonus payment, a completion bonus from a new well, or a ramped-up production profile can land the owner in the 35% or 37% federal bracket with 3.8% NIIT on top — far higher than most retirees would normally see. A conversion executed in that year is taxed at the peak bracket and is almost always a bad idea.
Conversely, a year after the well has declined, before Social Security has started, and before RMDs have kicked in can leave a royalty owner in the 12% or 22% bracket. A conversion in that year, particularly filling up the lower brackets to the point where the next dollar would land in the 24% bracket, can be extraordinarily valuable.
The planning implication: royalty owners need to model tax projections several years forward, identify likely low-income windows, and execute conversions opportunistically. This is not a "set up an annual conversion of $X and run on autopilot" situation. It is specific to each year's royalty trajectory and requires annual coordination with a CPA and ideally a fee-only financial planner.
The most common Roth-conversion strategy is "bracket filling." You identify the top of a tax bracket you are comfortable paying — often the 12% or 22% bracket for a single filer, or the 22% or 24% bracket for a joint filer — and convert exactly enough to fill that bracket without spilling into the next one.
For a couple in a low-income year with, say, $50,000 of other taxable income, the top of the 22% bracket might be around $200,000 of taxable income. That leaves roughly $150,000 of "conversion room" within the 22% bracket. Converting $150,000 at 22% is generally better than leaving those dollars in the traditional IRA to be withdrawn later at potentially 24% or higher.
Two wrinkles for royalty owners. First, the IRMAA thresholds (for Medicare) stack with the tax brackets. Converting up to the top of the 22% bracket may push MAGI past an IRMAA threshold, adding several thousand dollars of Medicare premium two years later that you need to factor into the analysis. Second, ACA marketplace subsidies (if you are pre-Medicare) are far more sensitive to MAGI than the income tax brackets themselves. A conversion that looks efficient on its face may trigger a marketplace subsidy clawback that dwarfs the conversion's benefit.
Modeling with specialized retirement-planning software — or with a fee-only planner who uses such software — is more reliable than eyeballing the brackets. The interactions among federal brackets, NIIT, IRMAA, and ACA are enough to defeat manual optimization in most cases.
A one-shot conversion rarely maximizes lifetime tax efficiency. More often, the right approach is a multi-year program spread across a window where the owner's marginal rate is temporarily low.
For a royalty owner with highly variable income, the program is adaptive. In years where royalties are high, convert little or nothing. In years where royalties are low, convert aggressively. Over a decade of retirement, this approach can shift hundreds of thousands of dollars from traditional to Roth at an average tax cost well below what the dollars would have cost in RMD years or in the hands of heirs.
The end-of-year timing matters. Conversions must be executed by December 31 of the tax year. Royalty income for the year is typically not fully known until after the final 1099s arrive in January or February — which is after the conversion deadline. Sophisticated planners work with projections based on check stubs through November and conservative assumptions for December, then adjust the conversion amount in the final weeks of the year. Smaller, safer conversions executed mid-year can be supplemented with additional year-end conversions once the income picture is clearer.
The SECURE Act of 2019 eliminated the "stretch IRA" for most non-spouse beneficiaries. An adult child inheriting a traditional IRA must generally empty it within ten years — compressing what used to be a decades-long stretch into a much tighter window. For heirs who are in peak earning years when they inherit, this compression can push them into the 35% or 37% bracket on the inherited IRA distributions.
A Roth IRA inherited by a non-spouse beneficiary must also be emptied within ten years, but the distributions are tax-free. For a royalty owner with adult children in or near peak earning years, pre-paying the tax on traditional IRA dollars via Roth conversion — especially at the parent's relatively low retirement marginal rate — can save the family substantial tax on the eventual inheritance.
This multi-generational analysis is where Roth conversion planning gets genuinely interesting for royalty owners. If the parent is in the 22% bracket and the child is in the 35% bracket, every dollar converted at the parent's rate instead of distributed at the child's rate saves the family 13 cents on the dollar. Across a traditional IRA of reasonable size, the savings compound into real money.
Two cautions. First, this analysis depends on the child's actual future tax situation, which is not knowable with certainty. Second, some heirs are themselves in low brackets (retired or not yet earning), in which case the math reverses — conversion at the parent's 22% can be worse than distribution at the child's 12%. The right planning is specific to the family.
You can use any cash you have to pay the tax bill, including royalty income. Ideally the tax is paid with money outside the retirement account — paying tax from inside the IRA being converted reduces the net Roth-value of the conversion. A strong royalty year that provides outside cash is actually a reasonable year to pay conversion tax, even though it may not be the best year to convert (because the royalty income inflates your marginal rate). Timing the conversion for a low-royalty year and using previously accumulated cash to pay the tax is often optimal.
No. You can execute Roth conversions at any age. Conversions after age seventy-three are allowed but interact with RMDs — you must take your RMD for the year before converting any additional amount, because the RMD cannot be converted. For owners with large traditional IRAs who did not convert earlier, post-RMD conversions are still often valuable, they just have this extra ordering rule.
Contributions to a Roth (including converted amounts) can generally be withdrawn after five years of the conversion date without penalty, regardless of age. Prior to five years, withdrawing a converted amount before age 59½ triggers a 10% penalty on the converted portion. For retirees already past 59½, this is rarely a concern. For earlier retirees, staggering conversions to preserve access is worth discussing with a planner.
No — "recharacterization" of Roth conversions was eliminated by the Tax Cuts and Jobs Act in 2018. Once you convert, the conversion is permanent. This makes the decision more consequential than it used to be. If you are uncertain, consider a smaller conversion than you think optimal; you can always convert more later but cannot unconvert.
Primary sources used in writing this article. These are not legal or tax advice — they are the public statutes, regulations, and authoritative materials the article draws from. Consult a qualified attorney or CPA before acting on any of them.
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