Roth Conversions in a Self-Directed Solo 401(k)
2020 may be an opportune time for many investors to consider a Roth conversion. In our first article of this series we discussed how a dip in income, and a corresponding dip in tax rate can reduce the tax cost of performing a conversion. If the cost of conversion is reduced, the long term differential in performance of the conversion will increase.
In this article, we wanted to dive into the mechanics of how the Roth conversion process is executed with respect to a self-directed Solo 401(k) plan. There are several potential routes to performing a Roth conversion that apply to different situations.
A Solo 401(k) Can Hold Both Tax-deferred and Roth Funds
Unlike IRA plans which hold a single type of funds with one tax treatment, a Solo 401(k) can hold both tax-deferred and Roth funds.
As the Solo 401(k) administrator, it is your responsibility to accurately track the value of both tax-deferred and Roth accounts within your plan. Having separate bank accounts for each type of funds is a best practice.
This plan structure gives you a greater range of options when considering Roth conversions than a comparable IRA based plan.
Conversions When Setting Up a New Solo 401(k)
When you establish a new Solo 401(k), you can fund your plan by rolling over funds from a variety of sources.
You cannot, however, rollover an existing Roth IRA into a Solo 401(k). If you are considering converting funds that are currently in tax-deferred status in an IRA or 401(k), do not perform a conversion into a Roth IRA first. You would lock those funds out of your new Solo 401(k) by doing so.
The correct procedure is to first rollover funds from a tax deferred account into your Solo 401(k). Once those funds are in the new plan, you can follow the procedure outlined below for an in-plan Roth conversion.
If you already have a Roth participant account in an existing employer plan like a 401(k) or 403(b), you can directly roll that over to your new Solo 401(k).
In-Plan Roth Conversions
A Roth conversion is accomplished inside your Solo 401(k) via an in-plan Roth transfer.
When you choose to execute a Roth conversion, you move value from the tax-deferred participant account to the Roth participant account and report accordingly.
Roth conversions are a taxable event, so you need to be able to accurately value the portion of your tax-deferred funds being converted. It is, of course, much easier to convert cash than existing investment assets in alternative assets that can be more difficult to value.
Reporting of an in-plan Roth transfer involves:
- Issuing form 1099-R from the Solo 401(k) to yourself indicating the amount converted as taxable
- Filing form 8606 with your personal tax return
If you perform a conversion in the first three quarters of the year, you may need to make estimated quarterly tax deposits based on the tax amount due. Conversions executed after October 1st will simply require full payment of taxes due by April 15th of the next year.
We recommend you work with your licensed tax professional for tax reporting and filing matters.
Converting an Asset In-Kind
While it is easiest to convert cash, it is possible to convert an existing investment from tax-deferred to Roth status.
The challenge is that the asset must be valued in a manner acceptable to the IRS. For real estate, that would mean a formal appraisal. A note can be valued at the open principal balance. With other assets, you will want to seek professional guidance for proper documentation of value.
It is easiest and cleanest to convert an asset in its entirety.
It is possible to convert an asset such as a piece of property in increments over time. You will need to do a fresh appraisal or other form of valuation at each conversion event. You will also need to keep good records related to what percentage is owned by each account and be sure to allocate all expenses and income transactions accordingly.
Fortunately, assets do not need to be re-titled when you perform a conversion. Title is always held in the name of the plan itself, without reference to the underlying plan participant account(s) that may be involved. You just need to retain accurate records relative to ownership by each applicable account.
In Summary
With Roth conversions the best strategy to pursue is always dependent on your specific situation and goals. A Roth conversion is a complex tax matter, and something that should be discussed with licensed council. If you find a conversion makes sense for you, please feel free to reach out and we can assist with the mechanics of implementing your strategy.
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Quick answers to common questions
We’ll take you through a simple, step by step process designed to put your investment future into your own hands…immediately. Everything is handled on a turn-key basis. You take 100% control of your Retirement funds legally and without a taxable distribution.
YES! In 1974, Congress passed the Employee Retirement Income Security Act (ERISA) making IRA, 401(k) and other retirement plans possible. Only two types of investments are excluded under ERISA and IRS Codes: Life Insurance Contracts and Collectibles (art, jewelry, etc.). Everything else is fair game. IRS CodeSec. 401 IRC 408(a) (3)
It’s actually pretty simple. Early on, regulators let the securities industry take the lead in educating the public about retirement accounts. Naturally, brokers and banks promoted stocks, bonds, and mutual funds—giving the impression that those were the only allowed investments. That was never true... and still isn’t. You can probably guess why they kept the rest under wraps.
It is possible to use funds from most types of retirement accounts:
- Traditional IRA
- Roth IRA
- SEP IRA
- SIMPLE IRA
- Keogh
- 401(k)
- 403(b)
- Profit Sharing Plans
- Qualified Annuities
- Money Purchase Plans
- and many more.
It must be noted that most employer sponsored plans such as a 401(k) will not allow you to roll youraccount into a new Self-Directed IRA plan while you are still employed. However, some employers will allow you to roll a portion of your funds. The only way to be completely sure whether your funds are eligible for a rollover is by contacting your current 401(k) provider.
A Solo 401(k) requires a sponsoring employer in the format of an owner-only business. If you have a for-profit business activity – whether as your main income or as a side venture – and have no full-time employees other than potentially your spouse, your business may qualify. The business may be a sole-proprietorship, LLC, corporation or other entity type.
A self-directed retirement plan is a type of IRA or 401(k) that gives you greater control over how your retirement funds are invested. Unlike traditional accounts held at banks or brokerage firms that limit you to stocks, bonds, and mutual funds, self-directed plans allow you to invest in a wide range of alternative assets including real estate, private businesses, precious metals, cryptocurrency, and more.
These plans still follow the same IRS rules and maintain the same tax-deferred or tax-free benefits as conventional retirement accounts. The difference is simply in how and where you choose to invest.
No. Moving to a self-directed IRA or Solo 401(k) does not trigger any taxes, as long as your funds are eligible for rollover.
Self-directed retirement plans maintain the same tax-advantaged status as traditional plans offered by banks or brokerage firms. The key difference is flexibility—our plans are designed to give you greater control and allow for a wider range of alternative investments beyond stocks, bonds, and mutual funds.
A prohibited transaction is any action between your retirement plan and a disqualified person that violates IRS rules and can lead to serious tax consequences. Under IRS Code 4975(c)(1), prohibited transactions include:
- Selling or leasing property between your plan and a disqualified person Example: Your IRA cannot purchase a property you already own.
- Lending money or extending credit between the plan and a disqualified person Example: You cannot personally guarantee a loan your IRA uses to buy real estate.
- Providing goods or services between your plan and a disqualified person Example: You can’t use your personal furniture to furnish a rental property owned by your IRA.
- Using plan income or assets for the benefit of a disqualified person Example: Your IRA cannot buy a vacation home that you or your family use.
- Self-dealing by a fiduciary (using plan assets for their own benefit) Example: Your CPA shouldn't loan your IRA money if they’re advising the plan.
- Receiving personal benefit from a deal involving your IRA's assets Example: You can’t pay yourself from profits your IRA earns on a rental.
If a transaction doesn’t clearly fall within the allowed guidelines, the IRS or Department of Labor may review the situation to determine if it qualifies as a prohibited transaction.
Disqualified persons are individuals or entities that are prohibited from engaging in certain transactions with your IRA or 401(k). Doing so could trigger a prohibited transaction, which may result in taxes and penalties.
Here’s who is considered a disqualified person:
- You (the account holder)
- Your spouse
- Your parents, grandparents, and other ancestors
- Your children, grandchildren, and their spouses
- Any advisor or fiduciary to the plan
- Any business or entity owned 50% or more by you or another disqualified person, or where you have decision-making authority
These rules exist to prevent self-dealing and ensure your retirement plan remains in compliance with IRS regulations.
(Reference: IRC 4975)
Understanding and following these rules can be tricky, but it’s very doable. The best way to stay compliant is to work with professionals who specialize in self-directed retirement plans. They can help you navigate IRS guidelines and avoid prohibited transactions.
If an IRA holder is found to have engaged in a prohibited transaction with IRA funds, it will result in a distribution of the IRA. The taxes and penalties are severe and are applicable to all of the IRA’s assets on the first day of the year in which the prohibited transaction occurred.
Yes. While self-directed retirement plans allow for a wide range of investments, there are a few important restrictions.
You cannot invest in collectibles or life insurance contracts, and you must avoid prohibited transactions—activities that benefit you personally rather than the retirement plan. These include things like buying or selling property to yourself or family members, using plan assets for personal gain, or self-dealing in any way.
Violating these rules could cause your entire IRA to lose its tax-advantaged status. To protect your account, it’s essential to work with professionals who understand IRS regulations and can help you stay compliant.
This is a common misconception. In many cases, professionals may simply be unfamiliar with self-directed retirement plans, as they fall outside their usual scope of work. CPAs and tax preparers are trained to file taxes, not necessarily to advise on alternative retirement strategies. Financial advisors and brokers often work for firms that focus on traditional investments like stocks and mutual funds—and may not benefit from or support alternative options like real estate or private lending.
Self-directed retirement investing is legal under IRS rules—but like any specialized area, it requires working with professionals who understand how it works.
The IRS has rules in place to make sure your IRA is used only for the exclusive benefit of the retirement account—not for personal gain or to help family members. These rules can get complicated because there are many ways a conflict of interest can occur, even unintentionally.
For example, if your IRA buys a house and rents it to your mother, you might be reluctant to evict her if she stops paying rent. That emotional connection creates a conflict between what’s best for your IRA and your personal relationships, something the IRS aims to prevent.
These rules help ensure your retirement account stays compliant and protected. (See IRC 408)
Yes. Most tax-deferred retirement accounts—such as Traditional IRAs, old 401(k)s, 403(b)s, and TSPs—can be rolled over into a self-directed IRA or Solo 401(k), depending on your eligibility. Roth IRAs cannot be rolled into these accounts.
You can contribute directly from earned income, subject to annual IRS contribution limits. The method and amount depend on the type of plan you have (e.g., Solo 401(k) vs. IRA).
To take a distribution, you'll request funds through your custodian or plan administrator. Distributions may be taxable depending on your account type and age. Early withdrawals may be subject to penalties.
For 2025, the Solo 401(k) max contribution limit is $81,250 if age 60-63, $77,500 if age 50-59 or 69+, and $70,000 if under 50. Traditional and Roth IRAs have a limit of $7,000 ($8,000 if age 50+). Limits are subject to IRS adjustments.
Yes. IRA contributions are typically due by your personal tax filing deadline (e.g., April 15). Solo 401(k) contributions follow your business tax filing deadline, including extensions.
IRS reporting requirements vary depending on the type of self-directed retirement plan you have. Here’s a quick breakdown of what you need to know
Please note: Our team can help you understand what’s required for your specific account, but we don’t provide tax or legal advice. We always recommend working with a qualified tax professional to ensure full IRS compliance.
Self-Directed IRA (Traditional or Roth)
- Form 5498 – Filed by your custodian each year to report contributions, rollovers, and the fair market value (FMV) of your account.
- Form 1099-R – Issued if you take a distribution or move funds out of your IRA.
- Annual Valuation – You'll need to provide updated FMV for any alternative assets held in the account, such as real estate or private placements.
Solo 401(k)
- Form 5500-EZ – Required if your plan assets exceed $250,000 as of year-end. Must be filed annually by the plan participant.
- Form 1099-R – Required if you take a distribution or roll funds out of the plan.
- Contribution Tracking – Keep records of employee and employer contributions. These are not filed with the IRS but may be needed for tax reporting or audits.
SEP IRA
- Form 5498 – Filed by your custodian to report contributions and FMV.
- Form 1099-R – Filed by your custodian. Issued for any distributions.
- Employer Contributions – Must be reported on your business tax return (and on employee W-2s, if applicable).
Health Savings Account (HSA)
- Form 5498-SA – Filed by your HSA custodian to report contributions.
- Form 1099-SA – Filed by your HAS custodian. Issued for any distributions.
- Form 8889 – Must be included with your personal tax return to report contributions, distributions, and how funds were used.
