Reportable Transactions

The American Jobs Creation Act of 2004 (2004 Jobs Act) imposed new penalties on taxpayers who fail to adequately disclose “reportable transactions” to the IRS. Before the 2004 Jobs Act, taxpayers were generally only penalized for not disclosing a reportable transaction if the IRS was successful in challenging the transaction. Accordingly, many taxpayers were not overly concerned about disclosing these transactions, especially if the tax benefits of the transaction were clearly legitimate and/or there was little chance of a successful IRS challenge.

In an attempt to curb the use of abusive tax shelters, the 2004 Jobs Act enacted new, stiff penalties for failure to adequately disclose a reportable transaction to the IRS on a return due after October 22, 2004 (the date the 2004 Jobs Act was signed into law). Under the 2004 Jobs Act, natural persons who failed to disclose a reportable transaction to the IRS were subject to a $10,000 penalty. Other nonreporting taxpayers were subject to a $50,000 penalty. The penalties increased to $100,000 and $200,000, respectively, for natural persons and other taxpayers who failed to disclose a reportable transaction that is a listed transaction.

In an effort to achieve proportionality between the penalty and the tax savings resulting from the reportable transaction, the 2010 Small Business Act revised the penalty structure for all reportable transaction penalties assessed after December 31, 2006. Under the Small Business Act, a participant in a reportable transaction who fails to disclose is subject to a penalty equal to 75 percent of the reduction in tax reported on the participant’s tax return as a result of participation in the transaction. Regardless of the amount determined under the general rule, the penalty for each such failure may not exceed $10,000 in the case of a natural person and $50,000 for all other taxpayers. For listed transactions, the maximum penalties are increased to $100,000 and $200,000, respectively, for natural persons and other taxpayers. The Small Business Act also establishes a minimum penalty with respect to failure to disclose a reportable or listed transaction. The minimum penalty is $5,000 for natural persons and $10,000 for all other taxpayers.

If a reportable transaction is not disclosed and results in an understatement of tax, an additional penalty in the amount of 30 percent of the understatement may be assessed.

If the reportable transaction is disclosed, taxpayers are still subject to a 20 percent penalty on the understatement of tax. In addition to the penalties, the statute of limitations is suspended for any listed transaction that is not disclosed.

Unlike most other penalties, the law significantly limits the IRS’s ability to rescind or abate these penalties for reasonable cause or other reasons. Accordingly, taxpayers should be extra vigilant in identifying and disclosing these transactions. Taxpayers should not fall into the trap of thinking reportable transactions are limited to abusive tax shelters. The definition of a reportable transaction is very broad and includes many transactions that are routine and perfectly legitimate.

The IRS has additional information available on its website (including Treasury Regulations discussed herein).

Reportable Transactions Defined

Reportable transactions are defined by Treasury Regulation Section 1.6011-4 and generally include the following categories of transactions. Many times these transactions are perfectly legitimate; however, the government requires disclosure.

Confidential Transactions

These are transactions offered under conditions of confidentiality and for a minimum fee of $250,000 for corporations or partnerships or trusts wholly owned by corporations and $50,000 for all others. Some tax professionals or investment promoters require clients to sign agreements stipulating the client may not disclose a tax strategy to others. Sometimes this is because the professional or promoter does not want competitors to find out about the strategy, but sometimes it is because the professional or promoter does not want the taxing authorities to find out.

Transactions with Contractual Protection

These are transactions with the right to a refund of fees or investment if the transaction’s intended tax consequences do not occur. They also include most contingent fee transactions. Sometimes the promoter of an investment will provide for a refund to the investors if promised tax benefits fall short. The IRS apparently views such a transaction as the sale of a tax benefit.

Transactions with contractual protection involving the following tax credits are exempt from the reportable transactions disclosure rules:

  • Work opportunity and welfare-to-work credits
  • Indian employment credit
  • Low-income housing credit
  • New markets tax credit
  • Empowerment zone employment credit
  • Renewal community employment credit
  • Employee retention credit

Loss Transactions

These are transactions resulting in a loss under Internal Revenue Code 165 (wagering, theft, capital, worthless securities, casualty, disaster, insolvent financial institution and certain other losses) of at least:

  1. $10 million in any single taxable year or $20 million in any combination of taxable years for corporations or partnerships wholly owned by corporations
  2. $2 million in any single taxable year or $4 million in any combination of taxable years for all others
  3. $50,000 in any single taxable year for individuals or trusts related to foreign currency transactions

The IRS requires disclosure apparently because some of the tax shelters it deems abusive were set up to manufacture large losses of these types.

A loss is not subject to the reportable transactions disclosure rules if all of the following are true:

  • The basis of the asset is a “qualifying basis”
  • The asset is not an interest in a pass-through entity
  • The loss from the sale or exchange of the asset is not an ordinary loss from foreign currency transaction
  • The asset has not been separated from any portion of the income it generates
  • The asset has never been part of a straddle

A qualifying basis, in general, is one equal to the amount paid in cash for the asset, plus improvements, or acquired in certain tax-free corporate reorganizations, inheritance, gift or a like-kind exchange.

Transactions of Interest

These are transactions that the IRS believes have potential for tax avoidance or evasion, but for which it lacks enough information to determine whether they should be identified specifically as tax avoidance transactions, i.e., listed transactions. The IRS has additional information available on its website.

Listed Transactions

These transactions (and those substantially similar) are identified by the IRS as potentially abusive and are required to be disclosed. These transactions are complex, and the IRS guidance is technical. Summarized below are various Listed Transactions. For detailed information, see the IRS guidance on its website at https://www.irs.gov/businesses/corporations/article/0,,id=97384,00.html

Transactions Involving Tax-exempt Entities

The Tax Increase Prevention and Reconciliation Act of 2005 also imposed new rules on taxable entities that participate in a reportable transaction involving a tax-exempt entity. Taxable entities must disclose to tax-exempt entities that the transaction is a reportable transaction. Failure to do so subjects the taxable entity to the same penalties as if it fails to disclose a reportable transaction to the IRS.

The Tax Increase Prevention and Reconciliation Act of 2005 added new sanctions and disclosure rules for tax-exempt entities and their managers who participate in “prohibited tax shelter transactions.”

The new rules potentially affect charities, churches, state and local governments, Indian tribal governments, benefit plans and individual retirement accounts (IRA) and managers of these entities. For this purpose, an entity manager is defined as the person with authority or responsibility similar to that exercised by an officer, director or trustee and, with respect to any act, the person having authority or responsibility with respect to such act. For benefit plans and IRAs, the term means the person who approves or otherwise causes the entity to be a party to the prohibited tax shelter transaction; however, an individual beneficiary or owner of the plan may be liable as an entity manager if he/she has broad investment authority.

A prohibited tax shelter transaction is any listed transaction or any prohibited reportable transaction. Prohibited reportable transactions include confidential transactions and transactions with contractual protection.

The new rules impose excise taxes on a Non-Plan Entity (basically, an exempt organization other than a benefit plan or IRA) that is a party to a prohibited tax shelter transaction. The amount of the excise tax can be as much as the greater of (1) 100% of the entity's net income with respect to the transaction or (2) 75% of the proceeds received attributable to such transaction.

The new rules also impose a $20,000 excise tax on an entity manager who approves the exempt organization as a party, or otherwise causes the entity to be a party, to a prohibited tax shelter transaction and knows or has reason to know that the transaction is a prohibited tax shelter transaction.

Any tax-exempt entity, including a benefit plan or IRA, that is a party to a prohibited tax shelter transaction is required to disclose to the IRS that it is such a party and the identity of any other party or parties to the transaction. Failure to comply can result in a penalty of $100 per day of noncompliance up to $50,000 per failed disclosure. For a Non-Plan Entity that fails to disclose such a transaction, the penalty is assessed against the entity. For a Plan Entity (basically a benefit plan or IRA) that fails to disclose, the penalty is assessed against the entity manager.

Taxable parties to a prohibited tax shelter transaction are required to notify tax-exempt parties that the transaction is a prohibited tax shelter transaction. Failure to do so subjects the taxable party to the same penalties for failure to disclose a reportable transaction to the IRS.

Transactions of Interest

Basket Contracts

These are transactions designed to defer or change the character of income recognition. They typically involve a taxpayer entering into a notional principal contract, option or forward contract to receive returns based on the performance of a notional basket of assets selected by the taxpayer, including entities trading in hedge fund interests, securities, commodities, foreign currency and similar properties. The issuer of the contract bears little to no risk, as the taxpayer puts down a large upfront cash payment and supplies additional funds to purchase the assets in the basket. The taxpayer has the right to request a change to the assets in the basket at any point while the contract is open and may terminate the contract at any time. At the end of the contract, the taxpayer typically receives the upfront payments—plus any gain or less any loss.

Contribution of Successor Member Interest

This transaction involves a taxpayer who directly or indirectly acquires certain rights in real property or in an entity that directly or indirectly holds real property, transfers the rights more than one year after the acquisition to an organization described in §170(c) of the Internal Revenue Code (IRC) and claims a charitable contribution deduction under §170 that is significantly higher than the amount the taxpayer paid to acquire the rights. See Notice 2007-72 for more information.

Toggling Grantor Trust

This transaction uses a grantor trust, and the purported termination and subsequent re-creation of the trust’s grantor trust status, for the purpose of allowing the grantor to claim a tax loss greater than any actual economic loss sustained by the taxpayer or to avoid inappropriately the recognition of gain. See Notice 2007-73 for more information.

Potential for Avoidance of Tax Through Sale of Charitable Remainder Trust Interests

This transaction involves a sale or other disposition of all interests in a charitable remainder trust (subsequent to the contribution of appreciated assets to and their reinvestment by the trust), results in the grantor or other noncharitable recipient receiving the value of that person's trust interest while claiming to recognize little or no taxable gain. See Notice 2008-99 for more information.

Section 831(b) Micro-Captive Transactions

These transactions involve taxpayers insuring certain risks through an insurance contract with a related company that the parties treat as a captive insurance company. The insured claims deductions for premiums paid for insurance coverage. The related company that the parties treat as a captive insurance company will elect under section 831(b) to be taxed only on investment income and therefore excludes the payments directly or indirectly received under the contracts from its taxable income.

In some cases, the captive insurance company directly enters into a contract (or contracts) with the insured entity. In these cases, the captive insurance company may enter into a reinsurance or pooling agreement under which a portion of the risks covered under the contract are treated as pooled with risks of other entities, and the captive insurance company assumes risks from other entities. In other cases, the captive insurance company indirectly enters into the contract by reinsuring risks that the insured entity has initially insured with an intermediary. See Notice 2016-66 for more information

Subpart F Income Partnership Blocker

In this transaction, a U.S. taxpayer that owns controlled foreign corporations (CFCs) that hold stock of a lower-tier CFC through a domestic partnership takes the position that subpart F income of the lower-tier CFC or an amount determined under IRC §956(a) related to holdings of U.S. property by the lower-tier CFC does not result in income inclusions under §951(a) for the U.S. taxpayer. See Notice 2009-7 for more information.

Listed Transactions

Basket Option Contracts

These are transactions designed to defer or change the character of income recognition. They typically involve a taxpayer entering into an option contract to receive returns based on the performance of a notional basket of actively traded personal property selected by the taxpayer. The issuer of the contract bears little to no risk, as the taxpayer puts down a large upfront cash payment and supplies additional funds to purchase the assets in the basket. The taxpayer has the right to request a change to the assets in the basket at any point while the contract is open and may terminate the contract at any time. At the end of the contract, the taxpayer typically receives the upfront payments—plus any gain or less any loss.

If purchased directly by the taxpayer, the assets in the basket would create ordinary income or short-term gain. By investing in a basket option contract with a term longer than one year, the taxpayer defers income recognition until the termination of the contract is terminated or short-term capital gains and ordinary are converted into income into long-term capital gains.

Backdated Retirement Plan Contributions

A transaction in which a taxpayer claims a deduction for contributions made to a qualified retirement plan even though the related compensation is not earned by plan participants until after the end of the taxable year. The transaction is listed even if the employer’s liability to make the contribution is fixed before end of the year.

Purported Multiple Employer Welfare Benefit Funds.

Certain trust arrangements that purportedly satisfy the requirements for the 10-or-more employer plan exemption under IRC §§419 and 419A but where contributions are determined in a way that insulates each employer from the experience of other subscribing employers.

ASA Investerings Partnerships

Transactions involving contingent installment sales of securities by partnerships to accelerate and allocate income to a tax-indifferent partner, such as a tax-exempt entity or a foreign person, and to allocate losses to a taxable partner.

Short-term Charitable Remainder Trusts

Transactions in which a donor contributes highly appreciated assets to a charitable remainder trust that has a short-term and a high-payout rate. The trustee borrows money and sells the assets in the second or third year, i.e., quickly. The borrowed funds are distributed early on, usually in the first year, and efforts are made to characterize these as tax-free distributions.

"BOSS" (Bond-and-Option Sales Strategy)

Transactions involving the distribution of encumbered property in which taxpayers claim tax losses for capital outlays they have in fact recovered. These transactions typically involve taxpayers acting through a partnership to contribute cash to a foreign corporation in exchange for the corporation's common stock. The corporation then borrows money from a bank, giving the bank a security interest in the stock acquired by the foreign corporation that has a value equal to the amount borrowed. The corporation then distributes the security interest to the partnership, and this distribution reduces the value of the remaining stock to zero or to a trivial amount.

Fast-pay Stock Arrangements

Fast-pay stock is stock that is structured so dividends are economically (in whole or in part) a return of the holder's investment, as opposed to on the holder's investment. Stock is presumed to be fast-pay if it has a dividend rate that is reasonably expected to decline, as opposed to fluctuate or remain constant, or if it is issued for an amount that exceeds the amount at which the holder can be compelled to dispose of the stock.

Bull & Bear Note Transactions

Transactions involving the acquisition of two debt instruments that are structured so that value of one debt instrument increases while the value of other instrument decreases. These transactions attempt to recognize loss on the sale of the instrument that decreases in value, while not recognizing gain on the instrument that increases in value.

Son of BOSS

Transactions generating losses by artificially inflating the basis of partnership interests. These transactions typically involve either a taxpayer borrowing money at a premium, with the partnership assuming the debt and the taxpayer contributing proceeds to the partnership, or a taxpayer buying and writing options, and then creating positive basis in its partnership interest by transferring the option positions to the partnership.

Improper Use of a Subsidiary to Satisfy Parent's Stock-based Compensation Obligations

Transactions involving the purchase of a parent corporation's stock by a subsidiary, followed by a transfer of the purchased parent stock from the subsidiary to the parent's employees and the eventual liquidation or sale of the subsidiary.

Guam Trusts

Transactions in which the shareholders of a pre-existing or newly formed S corporation transfer their stock to a newly formed trust that purportedly qualifies as both a domestic trust under U.S. law and a Guam resident trust for purposes of Guamanian law. Promoters claim these trusts are able to pay income taxes to Guam, instead of to the U.S., on income derived from the U.S.-based S corporation. Under certain circumstances, Guamanian law enables the trust to recover all of the taxes paid to Guam.

Intermediary Transactions

These transactions have been used in the sale of a corporate business. Shareholders of a corporation (T) normally face double taxation on the sale of T’s assets. (First, T pays tax on the gain from sale of its assets and then T’s shareholders pay tax on the gain from the liquidation of T). The liquidation proceeds are reduced by the amount of tax T paid on the sale of its assets. This double taxation does not occur if the shareholders sell their T stock. The shareholders pay tax on their gain from the sale, but T has no tax on the sale of its assets. Therefore, corporate shareholders typically prefer to sell stock rather than the assets of the corporation. Buyers, on the other hand, typically prefer to acquire the assets of the corporation, rather than its stock, in order to receive a stepped-up basis in the acquired assets.

Intermediary transactions attempt to satisfy both the buyer and seller through the use of a tax-indifferent third party. Basically, T shareholders will sell their T stock to a third-party intermediary (M). T, now owned by M, then sells some or all of its assets to the buyer (Y). M has a net operating loss, credits or is otherwise not fully taxable on the sale of T assets. The arrangement is such that M makes a profit on the transaction, the old T shareholders purportedly get stock sale treatment and Y gets asset acquisition treatment.

Under one version of this transaction, T is included as a member of the affiliated group that includes M, which files a consolidated return, and the group reports losses (or credits) to offset the gain (or tax) resulting from T’s sale of assets. In another form of the transaction, M may be an entity that is not subject to tax (typically due to net operating losses or credits); and M liquidates T, resulting in no reported gain on M’s sale of T’s assets.

Abusive Section 351 Transfers Using Contingent, Unmatured Liabilities

Transactions involving a loss on the sale of stock acquired in a purported tax-free transfer under §351 of a high-basis asset to a corporation and the corporation's assumption of a liability that the transferor has not yet taken into account for federal income tax purposes.

Foreign Leverage Investment Portfolio (FLIP) & Offshore Portfolio Investment Strategy (OPIS)

Transactions in which a purported redemption of stock owned by a tax-indifferent party, e.g., a foreign party, is treated as a dividend. A variety of devices, i.e., forward open contract, options, puts and calls, are used to enable the redeemed shareholder to claim that it has continuing interests in the entity that is redeeming its stock. Promoters claim that all or a portion of the basis of the redeemed stock can be added to the basis of stock in the redeeming corporation owned by the taxpayer. Then, the taxpayer sells the stock and claims a loss. A variation of the transaction involves the transfer of the stock with a higher basis to an entity in a carryover basis exchange such as a §351 transaction followed by either a sale of the entity interest or a sale of the stock by the entity.

Abusive Basis-shifting Devices Using Loan Assumption Agreements (CARDs)

Transactions involving the use of a loan assumption agreement to inflate the basis in assets acquired from another party to generate tax losses. Generally, these types of transactions have a U.S. taxpayer becoming jointly and severally liable on debt of the transferor of assets, with the debt having a stated principal amount exceeding the fair market value of the assets separately transferred to the taxpayer in consideration for its agreement to pay part of loan. The losses from these types of transactions are not allowable to the extent the taxpayer derives benefit attributable to the basis exceeding fair market value since the parties are liable for loan repayment in accord with their relative ownership of the assets immediately after transfer to the taxpayer.

Abusive Notional Principal Contract

Transactions involving the use of a notional principal contract to claim current deductions for periodic payments made by a taxpayer, while disregarding the accrual of a right to receive offsetting payments in the future.

Abusive Straddles

Three different transactions that are designed to create a permanent noneconomic loss:

  1. Transactions involving the use of a straddle, a tiered partnership structure, a transitory partner and the absence of a §754 election to claim a permanent noneconomic loss.
  2. Transactions involving the use of a straddle, an S corporation or a partnership and one or more transitory shareholders or partners to claim a loss while deferring an offsetting gain.
  3. Transactions involving the use of economically offsetting positions, one or more tax indifferent parties and the common trust fund accounting rules of §584 to allow a taxpayer to claim a noneconomic loss.

Lease-in/Lease-out (LILO) Transactions

Transactions in which a taxpayer purports to lease property and then purports to immediately sublease it back to the lessor.

Abusive ESOP/S Corporation Arrangements

Certain arrangements involving the use of an ESOP-owned S corporation(s) to gain the tax advantages of an ESOP without giving employees participation in the ESOP. Typically, the owners of a profitable closely held operating corporation establish an ESOP-owned S corporation management company, which employs only the owners. Earnings of the operating company are stripped out via management fees, and the purported result is tax-deferred income to the owners without the participation of nonowner employees in the ESOP.

Abusive Offshore Employee Leasing Arrangements

Certain arrangements involving leasing companies that have been used to avoid or evade federal income and employment taxes. Typically, an individual taxpayer terminates an existing employment relationship with a domestic corporation and then purports to lease his services back to his former employer through a foreign leasing corporation and then through a domestic leasing corporation.

Abusive Collectively Bargained Welfare Benefit Funds

Certain arrangements that purportedly qualify as collectively bargained welfare benefit funds excepted from the account limits of §§419 and 419A. Promoters of these arrangements usually claim benefits are being provided under a collective bargaining agreement and are currently deductible when paid.

Abusive Option Sales to Family Limited Partnerships (FLPs)/Related Parties

Transactions involving compensatory stock options and related persons to avoid or evade federal income and employment taxes. These transactions purportedly avoid tax on compensatory stock options. The transaction typically involves an individual transferring a compensatory option to a related person through a family limited partnership, which “pays” for the option's value with a long-term, unsecured nonnegotiable note, calling for a balloon payment at end of the note's term. Promoters contend the individual doesn't recognize compensation for the purchase price of the option until the FLP pays the amount due under the note or some other deferred payment obligation.

Lease-stripping

Transactions in which a tax-indifferent participant claims rental or other income from property or service contracts and a taxable participant claims the deductions related to that income. The lease-strip transactions promoted apply not only to tangible property but also to licenses of intangible property, service contracts, leaseholds or other nonfee interests in property and the prepayment, front-loading or retention (rather than assignment) of rights to receive future payments.

Contested Liability Acceleration Strategies (CLAS)

Certain transactions that use contested liability trusts improperly to accelerate deductions for contested liabilities. These transactions claim to allow a taxpayer to deduct a contested liability in a year before the ultimate resolution of liability. However, (1) the taxpayer retains powers over the trust assets; (2) the taxpayer transfers related party notes to the trust indicating the liability is not genuine or there is no intent between the parties to enforce the obligation; or (3) the taxpayer uses the trust for contested tort, workers compensation or other liabilities, for which economic performance requires payment to the claimant.

Abusive Offsetting Foreign Currency Option Contract Transactions

Certain transactions involving offsetting foreign currency option contracts in which a taxpayer claims a loss upon the assignment of a §1256 foreign currency contract with a loss position to a charity but fails to report the recognition of gain when the taxpayer's obligation under an offsetting non-§1256 contract with a gain position terminates.

Abusive Roth IRA Transactions

Certain transactions designed to avoid the limitations on contributions to Roth IRAs. These transactions typically involve a sole proprietorship or a corporation owned or acquired by a Roth IRA. Examples include transactions in which the Roth IRA corporation acquires property, such as accounts receivable, from the business for less than fair market value; contributions of property, including intangible property, by a person other than the Roth IRA, without a commensurate receipt of stock ownership; or any other arrangement between the Roth IRA corporation and the taxpayer, a related party or the business that has the effect of transferring value to the Roth IRA corporation comparable to a contribution to the Roth IRA.

Abusive Use of ESOP/S Corporation Ownership

Transactions that involve segregating the business profits of an ESOP-owned S corporation into a qualified subchapter S subsidiary so that rank-and-file employees do not benefit from participation in the ESOP. The ESOP is the owner of the business in form, but not in substance.

Abusive Section 412(i) Plans with Excessive Life Insurance

Certain arrangements in which an employer deducts contributions to a qualified pension plan for premiums on life insurance contracts that provide for death benefits exceeding the participant's death benefit, where under the terms of the plan, the balance of the death benefit proceeds revert to the plan as a return on investment. The IRS holds that a qualified pension plan cannot be an insurance contract plan if the plan holds life insurance contracts and annuity contracts for the benefit of a participant that provide for benefits at normal retirement age exceeding the participant's benefits at normal retirement age under the terms of the plan. Any employer contributions under a qualified defined benefit plan that are used to purchase life insurance coverage for a participant exceeding the participant's death benefit provided under the plan are not fully deductible when contributed but are carried over to be treated as contributions in future years and deductible in future years when other contributions to the plan that are taken into account for the taxable year are less than the maximum amount deductible for the year pursuant to the limits of §404.

Abusive Foreign Tax Credit Transactions

Transactions in which, pursuant to a prearranged plan, a domestic corporation purports to acquire stock in a foreign target corporation and then make an election under §338 (treating the purchase as a purchase of corporate assets rather than corporate stock) before selling all or substantially all of the target corporation's assets in a preplanned transaction that generates a taxable gain for foreign tax purposes (but not for U.S. tax purposes). The purpose of the transaction is to shift foreign tax credits, but not income, to the domestic corporation, which, in substance, is merely a conduit.

Abusive S Corporation Income Shifting Arrangements (SC2)

Transactions in which S corporation shareholders attempt to transfer the incidence of taxation on S corporation income by purportedly donating S corporation nonvoting stock to an exempt organization while retaining the economic benefits associated with that stock.

Abusive Partnership Intercompany Financings

Transactions in which corporations claim inappropriate deductions for payments made through a partnership. Generally, in these transactions, a domestic corporation and a foreign person form a partnership in an attempt to convert interest payments not currently deductible into deductible payments.

Sale-in/Lease-out Arrangements

Transactions in which a taxpayer enters into a purported sale-leaseback with a tax-indifferent person in which substantially all of the tax-indifferent person’s payment obligations are economically defeased and the taxpayer’s risk of loss from a decline, and opportunity for profit from an increase, in the value of the leased property are limited.

Loss Importation Transactions

Transactions in which taxpayers attempt to exploit the entity classification rules in order to claim losses without taking into account the corresponding gains attributable to offsetting foreign currency positions. In such transactions a U.S. corporation acquires control of a foreign entity classified as a corporation for U.S. tax purposes. The foreign entity enters into offsetting foreign currency positions and closes out the positions that generate gain. The foreign entity then elects to be treated as a disregarded entity for U.S. tax purposes, effectively transferring the loss positions to the U.S. corporation.

Abusive Trust Arrangements Utilizing Cash Value Life Insurance Policies Purportedly to Provide Welfare Benefits

Trust arrangements utilizing cash value life insurance policies and purporting to provide welfare benefits to active employees. These are promoted to closely held businesses as a way to provide cash and other property to the owners of the business on a tax-favored basis. These arrangements are sometimes called “single employer plans” or 419(e) plans. Promoters claim that the employers’ contributions to the trust are deductible with no corresponding inclusion in the owner’s income.

Syndicated Conservation Easement Transactions

These transactions are promoted to investors as providing the opportunity to obtain charitable contribution deductions in amounts significantly exceeding amounts invested. The mechanics of the transaction involve a pass-through or series of pass through entities owning real property, an inflated appraisal based on unreasonable conclusions about the use potential of the real property, and a donation of a conservation easement encumbering the real property to a tax-exempt entity. The promoters then syndicate ownership interests in the pass-through entity or tiered entities formed to prospective investors claiming that, upon investing, they may be entitled to a share of a charitable contribution deduction that equals or exceeds two and one-half times the amount of their investment. The investors also place faith in the promoters to hold the real property for a sufficient time to justify applying capital gain treatment to the donation to support the claim of a full fair market value deduction. See Notice 2017-10 for more information.

Distressed Asset Trust Transactions

Transactions in which assets with high basis and low value are transferred to a trust by a tax-indifferent party (e.g., a non-U.S. person who is not subject to U.S. tax or a tax-exempt organization). A U.S. taxpayer acquires an interest in the trust. The trust ultimately sells the assets and shifts the built-in loss to the U.S. taxpayer.

Tax-Exempt Entities

The Tax Increase Prevention and Reconciliation Act of 2005 added new sanctions and disclosure rules for tax-exempt entities and their managers who participate in “prohibited tax shelter transactions.”

The new rules potentially affect charities, churches, state and local governments, Indian tribal governments, benefit plans and individual retirement accounts (IRA) and managers of these entities. For this purpose, an entity manager is defined as the person with authority or responsibility similar to that exercised by an officer, director or trustee and, with respect to any act, the person having authority or responsibility with respect to such act. For benefit plans and IRAs, the term means the person who approves or otherwise causes the entity to be a party to the prohibited tax shelter transaction; however, an individual beneficiary or owner of the plan may be liable as an entity manager if he/she has broad investment authority.

A prohibited tax shelter transaction is any listed transactionor any prohibited reportable transaction. Prohibited reportable transactions include confidential transactions and transactions with contractual protection.

The new rules impose excise taxes on a Non-Plan Entity (basically, an exempt organization other than a benefit plan or IRA) that is a party to a prohibited tax shelter transaction. The amount of the excise tax can be as much as the greater of (1) 100% of the entity's net income with respect to the transaction or (2) 75% of the proceeds received attributable to such transaction.

The new rules also impose a $20,000 excise tax on an entity manager who approves the exempt organization as a party, or otherwise causes the entity to be a party, to a prohibited tax shelter transaction and knows or has reason to know that the transaction is a prohibited tax shelter transaction.

Any tax-exempt entity, including a benefit plan or IRA, that is a party to a prohibited tax shelter transaction is required to disclose to the IRS that it is such a party and the identity of any other party or parties to the transaction. Failure to comply can result in a penalty of $100 per day of noncompliance up to $50,000 per failed disclosure. For a Non-Plan Entity that fails to disclose such a transaction, the penalty is assessed against the entity. For a Plan Entity (basically a benefit plan or IRA) that fails to disclose, the penalty is assessed against the entity manager.

Taxable parties to a prohibited tax shelter transaction are required to notify tax-exempt parties that the transaction is a prohibited tax shelter transaction. Failure to do so subjects the taxable party to the same penalties for failure to disclose a reportable transaction to the IRS.

Material Advisors

The 2004 Jobs Act also provides similar penalties for “material advisors” who fail to register any reportable transaction with the IRS or keep investor lists as required. The penalties apply to transactions entered into after October 22, 2004.

Each material advisor is required to file a Form 8918 to register any reportable transaction and maintain an investor list open to IRS inspection.

Generally, a material advisor is a person who receives or expects to receive a minimum fee with respect to a reportable transaction, and the person makes a “tax statement” to or for the benefit of a participant in the reportable transaction. The minimum fee is $250,000 if every person who benefits from the transaction is a C corporation and $50,000 for all others, including partnerships (tiered or otherwise) with an individual partner. The amount is reduced to $25,000 and $10,000, respectively, for listed transactions.

Material advisors who fail to file Form 8918 are subject to a $50,000 penalty per incident. If the transaction is a listed transaction, the penalty is increased to the greater of 1) $200,000 or 2) 50% of the fees received by the material advisor for providing advice to the taxpayer. Material advisors who fail to maintain the list of investors open to IRS inspection are subject to a $10,000-per-day penalty. Plus, the statute of limitations is suspended for any listed transaction that is not disclosed.

It is very important that reportable transactions be adequately disclosed and material advisors timely register transactions as required and maintain sufficient documentation. A breach of these rules can result in significant penalties. If you think you are a participant or material advisor in one of these transactions, contact your BKD advisor immediately.

Jesse Palmer

Partner & Director of Tax Quality Control

Jesse Palmer

Partner & Director of Tax Quality Control

Other

910 E. St. Louis Street, Suite 400
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Springfield, MO 65801-1900 (65806)

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