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Dec 1991

Utilizing corporate tax attributes following ownership changes.

by Knight, Ray A.

    Abstract- Tax benefits available after corporate ownership changes have been significantly reduced, and even eliminated in some cases, under Internal Revenue Code Sec 382 as modified by the Tax Reform Act of 1986 (TRA 86). Benefits limited by TRA 86 include net operating carryforward and 'net unrealized built-in losses.' Accountants need to understand the modified Sec 382, as well as its relationship to Sec 269 which addresses tax avoidance, for better tax planning for loss corporations considering ownership changes or bankruptcy proceedings.

Passage of TRA 86 served to make these benefits of corporate tax attributes following various corporate transactions difficult to realize. Limitations have been placed on corporate ownership changes greatly reducing or even eliminating the tax benefits associated with this type of transaction. The discussion in this article focuses mostly on net operating losses, and does not discuss attributes limited by IRC Sec. 383. As well, this article does not discuss the consolidated return limitations or attributes.


As modified by TRA 86, Sec. 382 limits the amount of income that may be offset by net operating loss (NOL) carryovers and other tax attributes after an ownership change. This limitation is referred to as the "Sec. 382 Limitation." These attributes may be reduced further or possibly even eliminated if certain requirements are not met.

Change of Ownership Triggers Sec. 382

A change in corporate ownership occurs when a substantial (5% or more) stockholder of a loss corporation has increased their ownership by more than 50 percentage points as of a testing date. This determination is made by comparing the ownership of each 5% shareholder with that shareholder's lowest percentage of holdings during the three-year period ending on the testing date, which is the "testing period." There are many types of transactions that may cause an ownership change: an equity structure shift, an owner shift, or an option transaction.

Equity Structure Shift. An equity structure shift is any tax-free reorganization except "D" reorganizations, which are marked by a division of the loss corporation's business; reorganizations which are only a change in identity, form, or place of organization; and bankruptcy reorganizations. An equity structure shift may also occur when a transaction does not qualify for tax-free status. This prevents a company from structuring a reorganization as taxable to circumvent the Sec. 382 limitation.

Owner Shift. An owner shift involving a 5% shareholder is any change in the respective ownership of stock of the loss corporation. The term "owner shift" is a broad term and is meant to cover almost every kind of stock transaction, i.e., taxable purchases and dispositions, tax-free exchanges through Sec. 351, redemptions and other stock decreases, debt conversions, and stock issuances. For purposes of Sec. 382, all less- than-5% shareholders' ownerships are aggregated and considered one 5% shareholder. In general, the day-to-day trading of stock in a publicly held corporation should not be affected by Sec. 382. However, a public offering, even a small one if added to other stock transfers, may trigger an ownership change.

Option Transactions. An option transaction may result in an ownership change if the option would cause a 50-percentage point increase in the ownership of a 5% or more shareholder if exercised on the testing date. This option can be a new issue by the loss corporation itself or a transfer by or to an existing 5% or more shareholder. If the loss corporation has a corporate shareholder the option transaction takes on broader meaning. Any option transaction involving a 5% or more shareholder of a corporate shareholder of the loss corporation can trigger an ownership change. This portion of Sec. 382 makes it more difficult to avoid an ownership change.

Tax Benefits Limited by Sec. 382

The tax benefits limited by Sec. 382 are those belonging to the loss corporation at the time of ownership change. The most common benefit existing at the time of an ownership change is the NOL carryforward, thus the term "loss corporation." Section 382 limits the ability of a profitable corporation to acquire a loss corporation for the purpose of applying the NOL carryforwards to post-change income.

Other tax benefits limited by Sec. 382 are "net unrealized built-in losses," determined as the amount by which the aggregate adjusted basis of the corporation's assets exceeds their fair market value immediately before an ownership change. Any net unrealized built-in loss is limited in the same manner as NOL carryovers.

The Sec. 382 Limitation Defined

For any tax year ending after an ownership change, the amount of income that can be offset by losses from prechange years cannot exceed the "Sec. 382 Limitation." This limitation is calculated by multiplying the value of the old loss corporation by the long-term tax-exempt rate.

Value of the Old Loss Corporation

The value of the old loss corporation is the fair market value of all its stock immediately before ownership change, including preferred stock. However, in the event of an ownership change due to a redemption, or certain insolvency reorganizations where there is a reduction in the size of the loss corporation, the value is determined after the transaction has occurred. This will result in a smaller Sec. 382 Limitation.

In determining the stock value, certain capital contributions may be disqualified through the "anti-stuffing" rule. This rule prevents stockholders from inflating the Sec. 382 Limitation by putting new capital into the corporation before an ownership change. Any capital contribution made within the two-year period prior to an ownership change is presumed part of a plan for avoiding or increasing a Sec. 382 Limitation. Furthermore, a capital contribution made anytime when a #not necessarily the principal purpose of the contribution is to avoid or increase the Sec. 382 Limitation will be deducted from stock value on the change date.

Another item that reduces the value of the old loss corporation is non-business assets. The stock value must be reduced by the value of these assets (i.e., assets held for investment) in excess of any unpaid debt on those investments where such assets are at least one third of the total assets of the corporation.

Long-term Tax-exempt Rate. The long-term tax-exempt rate (LT-TE) is used for the calculation of the Sec. 382 Limitation. This rate changes monthly and is published by the IRS in the Internal Revenue Bulletin and was created solely for the use of the Sec. 382 Limitation. The LT-TE rate is the highest Adjusted Federal Long-Term Rate (determined under Sec. 1274(d) with exceptions) among the rates for the month in which the ownership change takes place and the two preceding months. The rate is multiplied by the value of the loss corporation to determine the Sec. 382 Limitation.

Additions to the Sec. 382 Limitation. There are two additional circumstances that can increase the Sec. 382 Limitation. First is the recognition of "built-in gain," within five years of the ownership change. A "built-in gain," or "net unrealized built-in gain," is the excess immediately before an ownership change of the fair market value of the loss corporation's assets over the adjusted basis of those assets. Any recognized amount of that gain in any year during the five- year period will be added to the Sec. 382 Limitation for that year. A second addition to the Sec. 382 Limitation occurs when a gain is recognized in any taxable year because of a Sec. 338 election to treat a stock purchase as an asset acquisition. The amount of the increase is limited to the lesser of a) built-in gains recognized through a Sec. 338 election, or b) the net unrealized built-in gains, discussed previously.

Once the Sec. 382 Limitation has been determined, it must be applied to the year of change. If the ownership change occurred at the beginning of the loss corporation's taxable year, then the full Sec. 382 Limitation amount will apply to offset income in that year. However, if ownership change occurs sometime during the corporation's taxable year, the Sec. 382 Limitation must be prorated daily in proportion to the part of the year after the change date.

Example. Corporation A's stock is acquired by Corporation B, a calendar year taxpayer, on 1/1/89. The value of A on that date is $5 million. The highest long-term tax-exempt rate in effect for November 1988 through January 1989 is 7%. A has an NOL of $1 million. For 1989 the Sec. 382 Limitation imposed on the use of the NOL carryover is $350,000 ($5,000,000 X 7%).

Carryover of Unused Sec. 382 Limitation. Any portion of the Sec. 382 Limitation that cannot be used to offset taxable income after ownership change can be carried over to a subsequent year. The unused portion is added to the Sec. 382 Limitation amount calculated for the following year. Sec. 382 does not extend the NOL carryforward period of 15 years under Sec. 172.

Continuity of Business Requirement In order for net operating losses to survive an ownership change, the loss corporation must meet the "continuity of business" rule. This rule provides that the post-change corporation must carry on the "historic" business of the old loss corporation for a period of at least two years after the change date.

For this requirement to be met, the new corporation must either a) actually carry on the historic business of the old loss corporation, or b use a significant amount of the old loss corporation's assets in the business of the new loss corporation. If the new loss corporation fails to meet this requirement the Sec. 382 Limitation becomes zero. If some pre-change losses have already been deducted, the effect of the Sec. 382 Limitation disallowance is retroactive and the previously deducted losses are therefore disallowed.

Even after the requirements for NOL carryover have been met for purposes of Sec. 382, there is a possibility that these losses may be disallowed. If the principal purpose for an ownership change is for the reason of tax avoidance, Sec. 269 is prepared to disallow the corporation's claims to pre-change losses.


Sec. 269 was established in 1943 to help the IRS prevent "trafficking in loss corporations." This section is a tool of questionable utility for the IRS since the determination of its applicability is largely subjective. This is where the concept of "substance over form" is important. A corporate ownership change can fall safely within the provisions of Sec. 382, but if the change, usually an acquisition or merger, was initiated for the purpose of using the NOLs to avoid paying tax, the carryovers are lost. Under tax law, a loss corporation must have two elements for Sec. 269 to apply: 1) a covered type of acquisition and 2) a tax avoidance motive.

Covered Type of Acquisition

A covered type of acquisition must be an acquisition of corporate control (50% of the total voting power and stock) for Sec. 269 to apply. If this control has not been acquired, Sec. 269 does not apply to the ownership change. (Sec. 382 might, of course, operate to restrict the use of the NOL.) Sec. 269 has a broad application and can apply to many acquisitions, some of which include: the incorporation of a new corporation, repossession of corporate stock by default, redemption of stock of fellow stockholder(s), acquisition of stock of a parent corporation, and cancellation of debt in exchange for stock.

Sec. 269(a)(2) can also apply to purchases of assets. The requirements of the application of Sec. 269 in this situation are that the assets must be acquired from a corporation, they must be acquired in an acquisition that calls for a carryover basis, the acquirer must be a corporation, and this acquirer must be a corporation that does not control, indirectly or directly, the transferred corporation.

Tax Avoidance Motive

Sec. 269 applies if the principal purpose of an acquisition was to evade or avoid federal income tax by obtaining NOLs or "built-in" losses that would not otherwise have been available. Sec. 269 gives the IRS the power to disallow the NOL carryover deduction either partially or totally, depending on what portion, if any, is attributable to a "business purpose" acquisition.

In determining a tax avoidance motive, the phrase "principal purpose" means that the tax avoidance purpose exceeds any other purpose in importance. This determination is made at the time of the transaction, unless there are subsequent transactions that appear to be part of a "sequence of events" (i.e., liquidation of an acquired loss corporation within two years) of which the final result is tax avoidance. If tax benefits are acquired and no substantial evidence of a business purpose can be produced, or the value of any tax benefits greatly outweighs the value of business purpose advantages, the principal purpose of the transaction will be considered tax avoidance. Even a taxpayer who incorporates a business for the principal purpose of tax avoidance (i.e., consecutive losses by a sole proprietorship may result in application of the "hobby loss" rule) may have tax benefits disallowed.

Outside the transaction itself there may be other factors that may influence the determination of a principal tax avoidance purpose. Some of the factors that may be considered are whether the taxpayer has prior knowledge of the available tax benefits or the purchase of an entire corporation possessing tax benefits when the indicated objective was to acquire only a specific asset of the corporation.

Related Cases

There are an overwhelming number of cases where the tax benefits have been disallowed for a tax avoidance purpose. One example is that of American Pipe and Steel Corp. v. Comr. (1959). The taxpayer in this case purchased a loss corporation and, within two months of the acquisition, liquidated the loss corporation. That activity, along with the size of the tax benefits acquired from the loss corporation, was enough to convince the courts that the principal purpose was tax avoidance. The tax benefits deducted were subsequently disallowed since the taxpayer could produce no evidence of business purpose.

Another case where the principal purpose was determined to be tax avoidance, is that of Victor Borge v. Comr. (1968). The taxpayer was a professional entertainer who also had an unincorporated poultry business that had sustained losses in excess of $50,000 in each of four consecutive years. The taxpayer, therefore, incorporated the business in year five to avoid the "hobby loss" rule under the 1954 IRC that would disallow further deduction of the losses. The court found that the taxpayer's corporation was formed for the principal purpose of tax avoidance and subsequently disallowed the deduction by the corporation of the pre-existing loss carryover and the deduction of the continuing large losses sustained by the corporation. Disallowance of post- acquisition losses is not addressed by the tax law.

Tax Avoidance Purpose and Post-acquisition Losses

There is generally no dispute of the disallowance of pre-acquisition losses when the court determines that the principal purpose of the transaction is tax avoidance. However, it has apparently been left up to the courts to determine whether disallowance should also apply to losses incurred by the loss corporation after acquisition.

Related Cases

Since the decision of the deduction of post-acquisition losses has been left up to the courts, a conflict is apparent in the decisions of the courts. In R.P. Collins & Co. v. U.S., the First Circuit in 1962 disallowed the deduction of both pre-and post-acquisition losses. The court reasoned that since the principal purpose of the company's acquisition of the loss corporation was to avoid tax, this purpose also "tainted" losses incurred by the loss corporation after its acquisition. The Seventh Circuit also applied Sec. 269 to the losses incurred by the loss corporation after acquisition in Luke v. Comr. (1965). The court found that since the continuation of losses was expected, that expectation warranted the conclusion that the entire acquisition was for the principal purpose of tax avoidance. The Fifth Circuit in 1973 also followed Collins and Luke in the case of Hall Paving Co. v. U.S. Hall Paving Co. was a profitable corporation that acquired five unprofitable corporations and used only the post-acquisition losses to offset income. The court disallowed these losses based on the same reasoning as Collins, where the principal purpose of tax avoidance of the acquisition "tainted" all applicable losses.

However, some of the circuits have disagreed with these findings. In the case of Zanesville Investment Co. v. Comr. (1964), where only post- acquisition losses were at issue, the Sixth Circuit found that post- acquisition losses, standing by themselves, were not under Sec. 269 since the taxpayer claiming the tax benefits actually suffered economic loss. The Third Circuit agreed with the findings in Zanesville and allowed the deduction of post-acquisition losses in Herculite Protective Fabrics Corp. v. Comr. In this case, the court found that even though the examined acquisition was made to avoid tax and the losses existing on that date were disallowed, the post-acquisition losses did, in fact, represent a true economic loss to the acquirer and were not to be disallowed under Sec. 269.

"True" Business Purpose

In the deduction of pre-existing acquired losses, the burden of proof of a bona fide business purpose lies with the taxpayer. The taxpayer must prove that the business purpose of an acquisition was of far greater importance than any tax benefits received, thus, the "principal" purpose. Some of the principal purposes that have been considered "business" purposes in the past include: the merging of several businesses as the first step in creating a conglomerate, the acquisition of a related loss corporation to present a stronger financial picture to prospective lenders who will provide funds to use in rehabilitating the unsuccessful business, the acquisition made to turn the loss corporation around to produce a profit, and the addition of needed manufacturing space. There are other business purposes that may be present which, alone, cannot meet the "principal" purpose requirement. However, these purposes, when combined with other business purposes for the acquisition, may have a greater value than the tax benefits acquired and, therefore, qualify as the "principal" purpose.

Related Cases

The instances referred to as being acceptable business purposes for loss corporation acquisitions, though not so labelled, were actual cases. Since the IRC does not specifically define "business purpose," the taxpayer can only rely on past experiences of others as a guide.

Another instance of a "true" business purpose is the case of Younker Bros., Inc. v. U.S. (1970). In this case, a corporation in the business of operating department stores, acquired a loss corporation that also operated department stores. The acquisition was made for the business purpose of expanding its department store operations into other locations. The business purpose was satisfied and the pre-acquisition losses were not disallowed under Sec. 269.

From this discussion of Sec. 269, it is apparent that there are no specific written guidelines. The IRS and the courts are increasingly applying the rule of "substance over form" in determining proper tax treatments. The determining factor is no longer the fact that certain events occurred, but more importantly, what the taxpayer's reason was for their occurrence. Newly proposed regulations provide some much needed guidelines in the determination of purpose.

SECS. 269 AND 382

Losses incurred by a corporation prior to an ownership change can be disallowed for use by Sec. 269, regardless of whether the losses were limited by Sec. 382. Losses are disallowed under Sec. 269 when the taxpayer fails to provide proof of a bona fide business purpose as the principal purpose of an acquisition. After TRA 86, the relationship of Secs. 269 and 382 remains unclear. Sec. 269 can still disallow losses resulting from a tax avoidance acquisition even if limited by Sec. 382. However, Prop. Reg. Sec. 1.269-7 provides some possible relief to a taxpayer who cannot otherwise provide proof of a bona fide business purpose. This proposed regulation provides that a taxpayer's limitation of pre-change losses under Sec. 382 has some bearing on the determination of a principal business purpose under Sec. 269. In other words, the fact that a corporation willingly enters into a transaction that will limit the immediate deduction of acquired losses, or possibly even completely deny them through Sec. 172 expiration, may be evidence that the taxpayer did not enter into the transaction for the principal purpose of tax avoidance or evasion.


One change in ownership occurs in the form of a reorganization. Reorganizations are labelled by "types" (i.e., A,B, C,D,E,F, and G) depending on how the reorganization is structured, and referred to by the letter designation of Sec. 368(a)(1). As stated earlier, tax attributes carried over in a tax-free reorganization are generally subject to the limitations of Sec. 382.

Bankruptcy Reorganization

A bankruptcy reorganization occurs when a corporation transfers all or part of its assets to an acquiring corporation in a bankruptcy case or in a receivership, foreclosure, or similar proceeding in federal or state court. Special rules apply to insolvent thrift institutions.

Type G reorganization transfers are made pursuant to a plan of reorganization that is approved by a bankruptcy court or similar court that has jurisdiction over any party to the reorganization. Under Sec. 381(a)(2), where "substantially all" assets of the insolvent corporation are transferred to the acquiring corporation, the tax attributes are also assumed by the acquirer, subject to the Sec. 382 Limitation.

Limitation of Tax Attributes. To escape the Sec. 382 Limitation, the new loss corporation must meet two requirements: 1) the old loss corporation must have been under the jurisdiction of a court in a Title 11 or similar case immediately after the change of ownership, and 2) the former creditors and shareholders must own at least 50% of the stock of the new loss corporation after ownership change as a result of having been creditors and shareholders. If these two criteria are met, the Sec. 382 Limitation will not apply. However, the tax attributes carried over must be reduced.

Any NOL carryovers must be reduced by the amount of interest payments or accruals on debt for which the creditor received stock in the reorganization plan. This reduction is made for any interest deduction included in an NOL carryover from any of the three years preceding the year of ownership change, and for any interest deduction taken during the year of change prior to the change date.

Furthermore, the loss corporation's existing tax attributes, listed in Sec. 108(b), must be reduced by one half of the amount of debt canceled. This reduction has the same effect as would the requirement of the new loss corporation to take one half the amount of debt cancellation into income. If tax attributes do not exist in a bankruptcy reorganization, no amount of debt cancellation is required to be treated as income.

Since some loss corporations in bankruptcy reorganization may find the special exemption of Sec. 382 to be more limited than being subject to the Sec. 382 Limitation, it is not mandatory. A loss corporation may elect under certain terms and conditions to be excluded from the rules of Sec. 382(1)(5) and, therefore, be subject to Sec. 382(a), like other types of ownership changes. Furthermore, if a second change of ownership occurs within two years of a bankruptcy-protected ownership change, the NOL carryovers are eliminated by the Sec. 382 Limitation becoming zero.

Effects of Sec. 269 on Type G Reorganizations

The rules of Sec. 269 apply to a type G or bankruptcy reorganization where the acquired corporation property has a carryover basis in the hands of the acquiring corporation, if the principal purpose of tax avoidance or evasion exists. Sec. 269 rules disallow the use of any tax attribute existing at the date of ownership change to offset post- change income.

In determining whether a reorganization was undertaken for the principal purpose of tax avoidance, proposed amendments to Reg. Sec. 1.269-3 provide specific requirements that must be met to avoid the rules of Sec. 269. This proposed regulation states that a bankruptcy Sec. 382(1)(5) is considered to be made for the principal purpose of tax avoidance unless a significant amount of active trade or business is carried on, during and after the Title 11 or similar case. Prop. Regs. Sec. 1.382-3 clarifies the continuity of interest requirement of the special Sec. 382 exemption by establishing that a creditor in the Title 11 or similar case cannot be considered a beneficial owner for purposes of Sec. 269 until at least the date of confirmation of the plan of reorganization.

Secs. 269 and 1129(d)

Under Sec. 1129(d) of the Bankruptcy Code, Sec. 269 can play a significant role in bankruptcy proceedings. Sec. 1129(d) provides that, "on request of a party that is a party in interest that is a governmental unit, the court may not confirm a plan if the principal purpose of the plan is the avoidance of taxes...." The statute further provides that in a hearing of this type, the government unit has the burden of proof of tax avoidance. However, disallowance of tax attributes pursuant to Sec. 269 would most likely provide the needed proof of tax avoidance to the bankruptcy court.

Although the burden of proof is reversed and the taxpayer must provide evidence of a principal business purpose under Sec. 269, the proposed regulation does not provide the same relief from a bankruptcy court ruling in this situation. In the proposed amendments to Regs. Sec. 1.269-3, new paragraph (e) states that in determining whether an acquisition pursuant to a plan of reorganization under Title 11 was made for the principal purpose of tax avoidance, any determination of non-tax avoidance purpose or the lack of a determination by the court under Sec. 1129(d) has no control over the application of Sec. 269. Therefore, a finding of true business purpose in a bankruptcy court would not have any bearing on the application of Sec. 269.


Sec. 382 can result in a devastating loss of tax benefits as the result of an ownership change.

Although the value of NOL carryovers is not as great as it once was, due to the lowering of the maximum corporate tax rate from 46% to 34%, carryovers still provide an effective way of reducing tax liability. This is especially true for a corporation that has experienced losses in the early years and is now turning a profit. The NOL carryovers provide a way for stockholders who bore losses to recoup those losses through the tax system. To be denied these losses, or limit their expected use, would cause a corporation to pay additional tax that could otherwise be avoided. For this reason, a corporate tax planner must scrutinize the effects of any ownership change whether it be an acquisition, a stock redemption, a reorganization, or other transaction.

An important aspect of tax planning for an ownership change is establishing a "true" business purpose. When tax attributes are passed to a new loss corporation, it is the burden of the taxpayer to establish that the principal purpose of a change of ownership was a business purpose. Any change of ownership for the principal purpose of obtaining tax benefits that would not otherwise be available will result in the elimination of pre-change tax attributes. For this reason, Sec. 382 disallows these attributes where a new loss corporation discontinues the old loss corporation's business in less than two years after the ownership change.

However, if a controlling change of ownership occurs, i.e., acquisition of 50% or more of the stock and voting power of the old loss corporation, additional steps must be taken by the parties to the acquisition to insure retaining the pre-change losses. Establishing a business purpose under Sec. 269 requires more than just the "continuity of business" requirement of Sec. 382. To avoid Sec. 269 disallowance, the corporation must also be able to prove the existence of a business purpose that is of greater importance than any tax benefits received; some examples of possible business purposes were provided in the analysis. In addition, if the acquisition is made in a bankruptcy (Title 11 or similar case) reorganization, the involved parties must make sure that the old loss corporation's creditors and shareholders own at least 50% of the stock of the corporation after ownership change.

Most requirements can be met by careful tax planning. However, establishing a principal business purpose will be the most difficult to achieve where substantial tax benefits are transferred. New regulations may help with tax planning by providing that when an ownership change falls under the limitations of Sec. 382, the willingness to accept that limitation may provide proof of a true business purpose for purposes of Sec. 269.

One additional concern in corporate acquisition tax planning is the possible disallowance of post-acquisition losses when pre-acquisition or pre-change losses were disallowed because the principal purpose of the acquisition was tax avoidance. As discussed, the application of Sec. 269 to post-acquisition losses is not addressed in the IRC and is, therefore, left to the IRS and the courts to determine. In planning a corporate acquisition the taxpayer would be wise to examine previous judgements in its circuits since the courts will follow the precedent set in that circuit. If the taxpayer is under the jurisdiction of a favorable circuit, then a corporate acquisition will most likely not lose a deduction for losses incurred after the change date. However, if a taxpayer is in a circuit where past judgements have disallowed these post-acquisition losses, a corporate acquisition decision may require further consideration since the benefits of the acquisition may be eliminated.

Tax planning for a bankruptcy reorganization is much the same as for a controlling change of ownership. However, one difference may require further consideration.

A tax-free bankruptcy (Title 11 or similar case) reorganization may not be subject to the Sec. 382 Limitation. Provided the "continuity of interest" and "continuity of business" requirements are met, existing tax attributes will be passed to the new loss corporation automatically. Unfortunately, these attributes will be reduced by an interest deduction on creditor debt and by one half the amount of debt canceled. This may eliminate any available tax benefits. The tax planner may, therefore, elect to be subject to the Sec. 382 Limitation. A comparison of the limitations under each option must be made to determine the most beneficial course of action. unkeyable

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