This article is featured in the KROST Industry Financial Services Magazine Volume 5, Issue 1, titled “Section 1244 Stock Demystified: Maximizing Benefits for Small Business Investors” by Randall Poe.

Understanding the various provisions of the tax code can provide valuable insights to investors. One of which is Section 1244 of the Internal Revenue Code, which offers unique benefits to small business investors.


Section 1244 stock refers to shares issued by a domestic small business corporation that meet specific requirements outlined in Section 1244 of the Internal Revenue Code. The purpose of this provision is to incentivize investments in small businesses by offering potential tax advantages to shareholders in the case of loss.


The primary benefit of Section 1244 stock is in the tax treatment of losses. If an investor incurs a loss from the sale or worthlessness of Section 1244 stock, they can treat the loss as an ordinary loss rather than a capital loss. This is significant because ordinary losses can be deducted against ordinary income, resulting in potentially higher tax savings. In comparison of capital gain losses, only $3,000 can be deducted as an ordinary loss each year.

While the ordinary loss treatment under Section 1244 is subject to certain limitations, the deductions significantly outweigh capital gain losses. The maximum amount of ordinary loss an individual can claim in a single year is $50,000, $100,000 for joint returns. Additionally, the stock must have been acquired directly from the corporation in exchange for money or other property. The stock cannot be acquired via another shareholder.


These several conditions must be met:

Domestic Small Business Corporation: The issuing corporation must be a domestic small business corporation at the time of stock issuance. Small businesses are defined as corporations with aggregate capitalization (including stock and debt) of $1 million or less when the stock is issued.

Stock Issued for Money or Property: The stock must have been acquired directly from the corporation in exchange for money or property. It cannot be acquired through stock options or other forms of compensation.

Original Issuance: The stock must be issued directly by the corporation as an original issuance. It cannot be acquired from another shareholder in a secondary market transaction.

The corporation’s assets must consist primarily of assets used in an active trade or business. This requirement ensures that the corporation is engaged in active business operations rather than being primarily an investment company.


While Section 1244 stock offers potential tax benefits, investors should be wary of potential risks. Here are some key considerations:

Investment Risks: Investing in small businesses inherently carries higher risks compared to established companies like blue chip stocks. Investors should thoroughly research the company, its management, financials, and growth potential before investing.

Qualification Criteria: Investors should ensure that the stock they are purchasing qualifies for Section 1244 status. Failure to meet any of the qualifying conditions may result in the disallowance of ordinary loss treatment.

Tax Planning: Investors should consult with tax professionals to understand the implications of Section 1244 stock on their individual tax situations. Proper tax planning can maximize the benefits of the provision while complying with the necessary requirements.

Diversification: It is generally prudent to diversify investments across different asset classes and sectors. Investors shouldn’t solely rely on Section 1244 stock investments which may expose investors to concentrated risks.

Section 1244 stock provides an opportunity for investors to potentially receive favorable tax treatment in the event of losses incurred from small business investments. However, it is essential to understand the qualifying criteria, investment risks, and engage in appropriate tax planning.

Contact Randall at, he can help investors make informed decisions and leverage the benefits of Section 1244.

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KROST Industry Magazine is a digital publication that highlights some of the hot topics in the accounting and finance industry. Volume 5, Issue 1 highlights some of the hot topics in Financial Services including the Silicon Valley Bank collapse, Section 1244, Section 1256, virtual currency, and more.