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Internal Revenue Code Section 409(p) (Section 409(p)) imposes significant obligations on S corporation Employee Stock Ownership Plans (ESOPs) with severe penalties for noncompliance. A violation of Section 409(p) can result in a 50% excise tax, deemed distributions to participants, potential loss of tax qualified ESOP plan status, and termination of the company’s S corporation election. Despite the severity of these penalties, Section 409(p) is frequently overlooked or forgotten about as the ESOP lifecycle continues. This article provides an overview of how the Section 409(p) test works, what triggers a failure, and practical strategies for maintaining compliance.

Background and Purpose of Section 409(p)

There are significant tax benefits for ESOP-owned S corporations. Because S corporations are pass-through entities and ESOPs are funded through tax-exempt trusts that are not subject to unrelated business income tax (UBIT) on S corporation income, no federal income tax is paid at either the corporate or shareholder level until ESOP distributions are paid to participants. This allows a 100% ESOP-owned S corporation to retain and reinvest earnings on a fully tax-deferred basis until participants receive distributions, potentially decades later. However, this beneficial tax treatment comes with a catch. An ESOP that holds S corporation stock must comply with the strict anti-abuse rules under Section 409(p).

Congress was concerned that the tax benefits provided to ESOP-owned S corporations could result in abusive structures that disproportionately benefited executives over rank-and-file workers. What was intended to be a broad-based retirement plan granting stock to all employees could become a tax-advantaged vehicle for the few, contrary to the general purpose of an ESOP. To prevent concentration of ESOP ownership among select executives, Congress enacted the Section 409(p) anti-abuse rules for ESOPs that hold S corporation stock.

The Section 409(p) Basics

Under Section 409(p), no portion of an ESOP’s assets attributable to, or allocable in lieu of, employer securities may accrue, or be allocated, directly or indirectly, for the benefit of a “disqualified person” during a “nonallocation year.” That general rule alone is a lot to unpack, but as a gating item this requires S corporation ESOPs to conduct the 409(p) analysis in two steps: (1) identify the “disqualified persons” and (2) determine whether there is a “nonallocation year.”

Step #1: Identify Disqualified Persons

An ESOP participant is a “disqualified person” if:

• The individual owns 10% or more of “deemed-owned shares” (individually); or
• The individual and their family members (such as spouses, children, and parents) own 20% or more of the “deemed-owned shares.”

“Deemed-owned shares” include (a) shares allocated to the participant’s ESOP account, (b) a pro rata share of unallocated shares held in a suspense account (applicable for leveraged ESOPs), and (c) synthetic equity. Notably, deemed-owned shares do not include shares that an individual owns outside the ESOP that are not synthetic equity.

Perhaps the most challenging aspect of Section 409(p) compliance is the breadth of the “synthetic equity” definition. The regulations cast a deliberately wide net that includes the following as various types of synthetic equity:

• Stock options and warrants
• Restricted stock and deferred issuance stock rights
• Stock appreciation rights (SARs)
• Phantom stock units
• Nonqualified deferred compensation (even if not tied to stock value)
• Split-dollar life insurance arrangements
• Rights to acquire stock or assets of a related entity

Step #2: Determine Whether There Is a Nonallocation Year

A “nonallocation year” occurs if disqualified persons collectively own at any time 50% or more of (1) the outstanding shares (including “deemed-owned shares”), or (2) the sum of the outstanding shares, the deemed-owned shares, and the synthetic equity owned by disqualified persons. This calculation also includes shares held by the disqualified persons’ family members, such as parents, children, and spouses.

Note that the Section 409(p) test must be met every day of the plan year to avoid a “nonallocation year.” For this reason, it is important that ESOP-owned S corporations always consider any Section 409(p) impact before creating new potential synthetic equity arrangements or when there may be changes to those arrangements or ESOP participant make-up (including due to employee terminations and other ESOP-related distributions). Keeping Section 409(p) top of mind for the company (and its board and management) and asking the “What about Section 409(p)?” question to your advisors early and often when there may be changes in compensation structures, new hires, or departures is key.

Consequences of a Section 409(p) Violation

If there is a nonallocation year, any S corporation stock held in a disqualified person’s ESOP account is an impermissible accrual, even if the stock had been allocated to the account in a prior year. In other words, under most circumstances, there is a Section 409(p) anti-abuse violation once a nonallocation year occurs resulting in severe penalties, including:

Prevention Strategies

Because there is no formal correction program for a Section 409(p) failure, prevention is the only remedy. The following strategies can help avoid a nonallocation year:

• Internal Revenue Service (IRS) Preferred Method. The plan sponsor may transfer S corporation stock from the disqualified persons’ accounts to a non-ESOP portion of the plan or another qualified plan, such as the 401(k) plan. Notably, this preventative method results in the transferred shares being subject to UBIT, so it is often reserved for situations where action must be taken immediately.
• Fail-Safe Plan Language. ESOP plan documents often include provisions that automatically redirect allocations away from disqualified persons or potential disqualified persons when testing approaches threshold levels.
• Exclude Allocations to Highly Compensated Employees Who Would Otherwise Become Disqualified Persons. The ESOP plan document can be amended to make highly compensated employees who are disqualified persons ineligible for additional allocations of employer stock. Because the amendment negatively impacts highly compensated employees only, there are no nondiscrimination or anti-cutback issues.
• Expand Allocations to Non-Disqualified Persons Who Are Not Highly Compensated Employees. The ESOP plan document could be amended to broaden eligibility or increase compensation-based allocations if those amendments do not otherwise result in nondiscrimination testing issues.
• Expand Diversification. The ESOP plan document could be amended to expand diversification beyond the statutory requirement to offer diversification to “qualified participants” (age 55 with 10 years of ESOP participation), subject to the expanded diversification provision passing nondiscrimination testing.
• Accelerate, Reduce, or Eliminate Synthetic Equity. The disqualified persons’ synthetic equity (e.g., stock appreciation rights or deferred compensation) will be subject to a plan document and/or award agreement that may need to be amended with the disqualified persons’ consent before accelerating, reducing, or eliminating their synthetic equity. Importantly, if the synthetic equity is “deferred compensation” subject to Section 409A, all or a portion of the synthetic equity may be accelerated if done in accordance with the Code Section 409A regulations. Companies should consider the Section 409(p) impact when creating potential synthetic equity arrangements as protective language should be built into the plan or agreement at the outset to allow flexibility to adjust or reduce awards automatically to address Section 409(p) issues.

Practical Takeaways

• Test early and often. Be proactive in seeking advice for any Section 409(p) impacts related to potential changes in synthetic equity arrangements or key hires/departures. Do not wait for year-end plan administration to discover a potential failure.
• Know your employees’ family relationships. The expanded attribution rules are a frequent source of an unexpected disqualified person status.
• Track all synthetic equity, including nonqualified deferred compensation. Ensure incentive compensation arrangements are not inadvertently “deferred compensation” that should be included as synthetic equity in the Section 409(p) analysis.
• Monitor stock value changes. Declining valuations can increase the deemed share count of synthetic equity (e.g., cash awards that are not tied to the company’s stock value), which can change the Section 409(p) test results.
• Build fail-safe language into the ESOP plan document.
• Coordinate annually among the third-party administrator (TPA), ESOP legal counsel, valuation advisor, and executive compensation advisors. Lenders to ESOP-owned companies also regularly require plan sponsors to provide Section 409(p) test results on a periodic basis.
• Remember that there is no correction for a failed Section 409(p) test. Prevention is the only cure.

Conclusion

Section 409(p) compliance is essential for all ESOP-owned S corporations, including companies that intend to adopt an ESOP. For additional information on common issues affecting mature ESOPs, please see our prior article Those Unpredictable Teen Years: A Practical Guide to Considerations for Maturing ESOPs.

Section 409(p) is one of the most consequential and least forgiving compliance requirements in the ESOP space. The common pitfalls include: the need to comply with Section 409(p) at all times during the plan year, the expansive family attribution rules, and the broad synthetic equity definition. Together, these create ongoing risks that demand proactive management and ongoing awareness of how changes to the business, synthetic equity arrangements, and underlying ESOP participation and distributions can impact Section 409(p) compliance. Companies that integrate Section 409(p) testing and advanced planning into their governance processes can enjoy the substantial benefits of the S corporation ESOP structure with confidence. Those that do not may find themselves facing penalties that can be catastrophic.