S Corporation Diligence to Avoid Inadvertent Termination and Loss of Tax Benefits

The S corporation remains a popular entity choice, combining the liability protection of a corporation with many of the tax benefits of a partnership. However, these benefits come at a price: S corporations must comply with strict requirements that limit the number and type of shareholders, prohibit complex capital structures, and impose other restrictions.

Advantages of S Corporation Status

Like a traditional corporation, an S corporation shields its shareholders from personal liability for the corporation’s debts. At the same time, it provides many (though not all) of the tax benefits associated with partnerships.

The most important tax benefit is that an S corporation, like a partnership, is a “pass-through” entity, which means that all of its profits and losses are passed through to the owners, who report their allocable shares on their personal income tax returns. This allows S corporations to avoid the double taxation that plagues traditional C corporations, whose income is taxed at the corporate level and again when distributed to shareholders.

S corporations, unlike partnerships, lack the flexibility to allocate profits and losses among their shareholders without regard to their relative capital contributions. But S corporations have one important advantage over partnerships: Shareholders need not pay self-employment taxes on their shares of the profits, provided they receive “reasonable” compensation.

S Corporation Requirements

To qualify as an S corporation, Form 2553 — Election by a Small Business Corporation — must be filed with the IRS. In addition, the corporation must:

  • Be a domestic (U.S.) corporation,
  • Have no more than 100 shareholders (certain family members are treated as a single shareholder for these purposes),
  • Have only “allowable” shareholders (see below),
  • Have only one class of stock (generally, that means that all stock confers identical rights to distributions and liquidation proceeds; differences in voting rights are permissible), and
  • Not be an “ineligible” corporation, such as an insurance company, a domestic international sales corporation, or a certain type of financial institution.

Allowable shareholders include individuals, estates, and certain trusts. Partnerships, corporations and nonresident aliens are ineligible. A trust is an allowable shareholder if it is domestic and qualifies as one of the following:

  • A grantor trust, provided it has only one “deemed owner” who is a U.S. citizen or resident and meets certain other requirements,
  • A testamentary trust established by a shareholder’s estate plan,
  • A voting trust,
  • A qualified subchapter S trust (QSST) — that is, one 1) that distributes all current income to a single beneficiary who is a U.S. citizen or resident, and 2) for which the beneficiary files an election with the IRS, or
  • An electing small business trust (ESBT) — to qualify, 1) all of the trust’s potential current beneficiaries (PCBs) must be eligible S corporation shareholders or nonresident aliens (NRAs), 2) no beneficiaries may purchase their interests, and 3) the trustee must file a timely election with the IRS. Generally, PCBs are persons who are entitled to distributions or may receive discretionary distributions.

Be aware that grantor and testamentary trusts are eligible shareholders for only two years after the grantor dies or the trust receives the stock.

Among other things, you should:

Continually Monitor the Number and Type Avoiding Termination

  • Preserving S corporation status requires due diligence of shareholders, scrutinize the terms of any trusts that hold shares, and ensure that QSSTs or ESBTs have filed timely elections,
  • Include provisions in buy-sell agreements that prevent transfers to ineligible shareholders,
  • If shares are transferred to an ESBT, make sure all PCBs are eligible shareholders or NRAs, and
  • If shares are held by grantor or testamentary trusts, track the two-year eligibility period, and make sure trusts convert into QSSTs or ESBTs or transfer their shares to an eligible shareholder before the period expires.

Also, avoid actions that may be deemed to create a second class of stock, such as making disproportionate distributions.

Making or Terminating an S Election

To qualify as an S corporation, Form 2553 must be filed within two- and one-half months of formation for newly created corporations. Existing C corporations desiring to convert to S status must file the election by the 15th day of the third month of its new tax year (March 15 for calendar entities). Procedures allowing for late elections under both scenarios exist. However, they should be reviewed for applicability.

S corporations that wish to voluntarily terminate their S elections are required to submit a cover letter along with signed vote(s) by stockholders possessing over one half of the corporation’s stock by the 15th day of the new month of the current tax year.

For existing corporations interested in making or voluntarily terminating an S election, the applicable forms or statements may be filed at any time during the year, to be effective on the first day of the next taxable year.

AAFCPAs advises clients organized as S corporations to monitor shareholders and activities continually to avoid inadvertent termination of your company’s S corporation status. At worst, termination means the loss of substantial tax benefits. At best, it means going through an expensive, time-consuming process to seek relief from the IRS and, if successful, have your S status restored retroactively.

If you have questions, please contact Richard Weiner, CPA, MST at 774.512.4078, rweiner@nullaafcpa.com; or your AAFCPAs Tax Partner.

About the Author

Rich has over 30 years of broad tax experience with a specialty in tax planning and consulting for private and publicly-held businesses. Rich has specific expertise in the Software, Bio-Technology, Medical Device, Life Science, Manufacturing, Retail, Professional Service and Publishing industries, as well as U.S. aspects of international taxation. He works extensively with European companies expanding into the U.S. market. Additional areas of focus include companies and stockholders in transition, including structuring of and planning for Mergers & Acquisitions, planning for changes in ownership and management, and adoption of tax methodologies with a view toward the long term. He is well known in his field and is a frequent speaker on a variety of tax related topics.