Digital Exclusives 2026

The Premium Roth Conversion: Turning IRA Income Into Tax-Free Wealth

Here’s how CPAs can help clients fund Roth conversions without touching principal or outside savings.
By William Ulivieri

For certified public accountants (CPAs) working with clients who hold substantial qualified retirement accounts, the math of required minimum distributions (RMDs) can be quietly alarming. A client who’s diligently saved $1 million or more in a traditional or rollover individual retirement account (IRA) or 401(k) hasn’t actually saved that amount—at least not in after-tax terms. Instead, the IRS holds a silent ownership stake in every pre-tax dollar, and beginning at age 73, it starts calling in that interest through mandatory annual distributions, whether the client needs the income or not.

The result is a tax liability that compounds alongside the account balance, often arriving when Social Security income, pension payments, and investment distributions may already be pushing clients into higher brackets than anticipated. For clients who inherited IRAs, the situation is more acute because of the Setting Every Community Up for Retirement Enhancement (SECURE) Act’s 10-year mandatory depletion rule, which compresses what was once a multidecade tax deferral into a single decade, often stacking distributions directly on top of peak earning years.

The conventional response to these pressures is a Roth conversion: pay taxes now at today’s income tax rates and move assets into a permanently tax-free environment. The strategy is well understood in principle. What’s less well understood, however, is an approach that makes the conversion largely self-funding by using income the qualified account can easily generate via an options strategy, known as “writing covered call options,” that I feel is a conservative but active strategy that could greatly benefit a portion of a CPA’s client base. Here’s what CPAs need to consider.

The Problem With Standard Roth Conversions

Traditional Roth conversions allow clients to pay the tax bill from outside savings (typically a taxable brokerage account or cash reserves). For many clients, this creates a psychological and financial barrier. Parting with liquid savings each year to fund a tax bill is a difficult ask, even when the long-term math clearly favors doing so.

The result is that many clients who would benefit most from systematic Roth conversions never start, or they start too late. They reach age 73 with multimillion-dollar pre-tax balances, facing RMDs that push them into the highest federal brackets, trigger Medicare surcharges, and create concentrated taxable income events for their heirs.

The Covered Call Strategy: A Time-Tested Approach

The covered call strategy begins with a structural shift in how the qualified account is managed. Rather than holding a passive portfolio of low-cost index funds, the account is invested in a diversified basket of equity exchange traded funds (ETFs) on which the investment manager systematically writes covered calls, selling the right to purchase shares at a specified price and date in exchange for immediate premium income.

This isn’t an unusual strategy. In fact, covered call writing is one of the most conservative and time-tested options strategies available, and it’s permitted inside traditional and rollover IRAs and self-directed 401(k) plans that have received appropriate options approval from their custodian.

What makes my covered call strategy distinctive from others is the location of the underlying assets. When covered calls are written in a taxable account, the premium income is taxed immediately—as short-term capital gains or ordinary income—at the investor’s marginal rate. Written inside a traditional or rollover IRA or self-directed 401(k), that same dollar of premium accrues and compounds tax-deferred within the account. Over time, the difference in the tax-deferred account’s growth trajectory is substantial.

A well-structured covered call program on a $1 million equity portfolio can realistically generate an additional 4% to 12% in annual option premium income—meaning $40,000 to $120,000 in premium accruing tax-deferred inside the account each year, alongside whatever the underlying equities appreciate.

The Mechanics: How the Conversion Is Funded

With the covered call structure in place, the annual Roth conversion follows a straightforward sequence. Consider this example using a 30% effective tax rate:

  1. The traditional or rollover IRA or self-directed 401(k) easily generates enough gross option premium income over the course of the year using weekly expiring options, accruing tax-deferred inside the plan.
  2. Together, the client and CPA request the investment advisor to initiate a $150,000 gross withdrawal, typically at the end of the year from the qualified account, triggering ordinary income tax on the full amount.
  3. The $45,000 tax liability (at the 30% effective rate) is funded by the covered call premium income the account generated over the course of the year. The premium covers the conversion tax—no principal is liquidated, and no outside savings are required.
  4. The remaining $105,000 is contributed to a Roth IRA, where it compounds tax-free at 10% per year, with no RMDs or future tax obligations.

As you can see from this example, the client’s underlying equity portfolio is never touched. Because the gross returns of the plan (8% equity, plus fixed-income appreciation, plus 4% to 12% annual option premium) can exceed the $150,000 annual withdrawal on a $1 million starting balance, the portfolio balance continues to grow over time even as conversions are executed annually.

This is a counterintuitive but important feature of the strategy: The account doesn’t deplete in the way a normal standard Roth conversion scenario might suggest. However, there are a few caveats:

  1. The covered call premiums received vary depending on market volatility. But spread out across three or four different ETFs, the account can still maintain a low-risk profile with high risk-adjusted returns.
  2. Extreme sharp upside rallies can diminish portfolio returns since in-the-money options contracts will need to be “rolled up and out.”
  3. Sequence of return risk can be diminished since sharp market declines typically increase the option premium harvested; rather than liquidating additional investments to fund obligations.

Which Clients Will Benefit Most?

It’s important to know that not every client is a candidate for this approach. The strategy works best where several conditions converge:

  • Pre-RMD window (ages 60-72). The optimal time to execute systematic Roth conversions is in the years after a client’s earned income has declined but before RMDs begin at age 73. During this window, the client’s marginal income tax rate is often lower than it’ll be once forced distributions layer on top of Social Security and other retirement income. Additionally, each year of inaction within this window is a year of Roth conversion opportunity that can’t be recovered.
  • Traditional and rollover IRA or 401(k) balances of $500,000 or more. The strategy requires sufficient assets within the qualified account to generate meaningful options premium since “100 share round lots” are required to sell covered calls against an underlying position. This means that portfolios with assets below $500,000 may not produce enough options premiums to fully cover the Roth conversion tax, requiring some supplemental outside funding.
  • Inherited IRA beneficiaries. Under the SECURE Act, most non-spouse beneficiaries must fully deplete an inherited IRA within 10 years of the original owner’s death. There are no required annual distributions during the first nine years, which means many beneficiaries do nothing for the first several years, then face a massive, fully taxable lump-sum distribution in year 10 stacked on top of their own income. A covered call strategy inside the inherited IRA, combined with a coordinated annual drawdown over the full 10-year period, can substantially reduce the tax consequences.

The CPA’s Indispensable Role

The Roth conversion is a durable tax planning strategy, offering a rare opportunity to pay a known tax liability today in exchange for eliminating an uncertain and potentially larger tax liability in the future. What my covered call approach adds to it is a self-funding mechanism that removes the primary obstacle to execution: The need to draw on outside savings to pay the Roth conversion tax each year.

As CPAs, you’re the first to see a client’s growing pre-tax balance, anticipate the RMD trajectory, or recognize when the 10-year inherited IRA clock has started running. That awareness—and the willingness to surface it as a planning conversation—is often the catalyst that sets the strategy in motion.

For CPAs working with clients who hold meaningful qualified retirement assets, this is a planning conversation worth having. The window is open, the math is compelling, and the potential covered call premium income to fund the strategy is often already there, sitting inside the account, waiting to be put to work.


William Ulivieri is the owner and portfolio manager at Cenacle Capital Management LLC, a state registered investment advisor located in Glenview, Ill. With more than 40 years of experience as a former market maker and options trader, he specializes in options-based portfolio management.

Related Articles