The Internal Revenue Service has a comprehensive strategy in place to combat abusive tax shelters and transactions. This strategy includes guidance on abusive transactions, regulations governing tax shelters, a hotline for taxpayers to use to report abusive technical transactions, and enforcement activity against abusive tax shelter promoters and investors.
There are substantial penalties that the IRS can impose for failure to disclose “reportable transactions,” that is, transactions identified by the IRS as having a potential for tax avoidance or evasion. Reportable transactions are divided into five categories, discussed below.
The penalty for failure to disclose a reportable transaction is 75% of the decrease in tax as a result of the transaction. The maximum penalty for each such failure to disclose a “listed transaction” on the appropriate tax return is $100,000 for an individual and $200,000 for other taxpayers. The maximum penalty for failure to disclose any other reportable transaction is $10,000 for an individual and $50,000 for other taxpayers. The minimum penalties are $5,000 for an individual and $10,000 for other taxpayers. [IRC Sec 6707A(b)]
In addition to IRS penalties, certain states have adopted similar disclosure requirements and large penalties for failure to comply.
For a complete list of reportable transactions, please visit www.irs.gov/Businesses/Corporations/Abusive-Tax-Shelters-and-Transactions.
Five Categories of Reportable Transactions:
Listed Transactions – To date, the IRS has identified 36 listed transactions which are summarized below. Each transaction has a link to the IRS Notice or other ruling naming the transaction as a “listed transaction” and providing details about it.
Transactions of Interest – To date, the IRS has identified six transactions of interest which are also summarized below and include a link to the applicable IRS Notice.
Confidential Transactions – Transactions that are offered to you or a related party (as described in section 267(b)) under conditions of confidentiality limiting what you can disclose about the tax treatment or structure of the transaction and for which you or a related party paid an advisor a minimum fee. The minimum fee for a transaction is $250,000 for corporations (excluding S corporations) and or partnerships or trusts in which all of the owners or beneficiaries are corporations (excluding S corporations) and $50,000 for all other taxpayers.
Transactions with Contractual Protection – Transactions for which you, or a related party (as described in section 267(b) or 707(b)), have the right to a full or partial refund of fees if all or part of the intended tax consequences are not sustained. These also include transactions for which fees are contingent on your realization of tax benefits from the transaction.
Loss Transactions – Transactions resulting in losses under IRC Sec. 165 for individuals, partnerships, S corporations and trusts that are at least $2 million in any single tax year or $4 million in any combination of tax years. The thresholds for C corporations (and partnerships with only C corporations as partners) are $10 million in any single tax year or $20 million in any combination of tax years. In addition, the threshold for individuals or trusts with losses arising from certain foreign currency transactions is $50,000 in any single taxable year.
Listed Abusive Tax Shelters and Transactions
- Revenue Ruling 90-105 – Certain Accelerated Deductions for Contributions to a Qualified Cash or Deferred Arrangement or Matching Contributions to a Defined Contribution Plan (transactions in which taxpayers claim deductions for contributions to a qualified cash or deferred arrangement or matching contributions to a defined contribution plan where the contributions are attributable to compensation earned by plan participants after the end of the taxable year (identified as “listed transactions” on February 28, 2000)). See also Rev. Rul. 2002-46, 2002-2 C.B. 117 (result is the same, and transactions are substantially similar, even though the contributions are designated as satisfying a liability established before the end of the taxable year), modified by Rev. Rul. 2002-73, 2002-2 C.B. 805.
- Revenue Ruling 2002-46- §401k Accelerators
- Revenue Ruling 2002-73-modifies RR 2002-46 for taxpayers electing to
change method of accounting.
- Notice 95-34 (Voluntary Employee Beneficiary Association) – Certain Trusts Purported to be Multiple Employer Welfare Funds Exempted from the Lists of §§ 419 and 419A (certain trust arrangements purported to qualify as multiple employer welfare benefit funds exempt from the limits of §§ 419 and 419A of the Internal Revenue Code (identified as “listed transactions” on February 28, 2000)). See also § 1.419A(f)(6)-1 of the Income Tax Regulations (10 or more employer plans)).
- ASA Investering Partnership v. Commissioner -Transactions similar to that described in the ASA Investering litigation and in ACM Partnership v. Commissioner, 157 F.3d 231 (3rd Cir. 1998) (transactions involving contingent installment sales of securities by partnerships in order to accelerate and allocate income to a tax-indifferent partner, such as a tax-exempt entity or foreign person, and to allocate later losses to another partner (identified as “listed transactions” on February 28, 2000)).
- Treasury Regulation § 1.643(a)-8 – Certain Distributions from Charitable Remainder Trusts (transactions involving distributions described in § 1.643(a)-8 from charitable remainder trusts (identified as “listed transactions” on February 28, 2000)).
- Notice 99-59 (Corporate Distributions of Encumbered Property (BOSS)) – Transactions involving the distributions of encumbered property in which losses claimed for capital outlays have been recovered (aka BOSS transactions) (transactions involving the distribution of encumbered property in which taxpayers claim tax losses for capital outlays that they have in fact recovered (identified as “listed transactions” on February 28, 2000)). See also § 1.301-1(g) of the Income Tax Regulations.
- Treasury Regulation § 1.7701(I)-3 – Fast Pay or Step-Down Preferred Transactions (transactions involving fast-pay arrangements as defined in § 1.7701(l)-3(b) (identified as “listed transactions” on February 28, 2000)).
- Revenue Ruling 2000-12 – Debt Straddles (certain transactions involving the acquisition of two debt instruments the values of which are expected to change significantly at about the same time in opposite directions (identified as “listed transactions” on February 28, 2000)).
- Notice 2000-44 – Inflated Partnership Basis Transactions (Son of Boss) (transactions generating losses resulting from artificially inflating the basis of partnership interests (identified as “listed transactions” on August 11, 2000)). See also § 1.752-6T of the temporary Income Tax Regulations and §§ 1.752-1(a) and 1.752-7 of the proposed Income Tax Regulations.
- Notice 2000-60 – Stock Compensation Transactions (transactions involving the purchase of a parent corporation’s stock by a subsidiary, a subsequent transfer of the purchased parent stock from the subsidiary to the parent’s employees, and the eventual liquidation or sale of the subsidiary (identified as “listed transactions” on November 16, 2000)).
- Notice 2000-61 – Guam Trust (transactions purporting to apply § 935 to Guamanian trusts (identified as “listed transactions” on November 21, 2000)).
- Notice 2001-16 – Intermediary Transactions (transactions involving the use of an intermediary to sell the assets of a corporation (identified as “listed transactions” on January 18, 2001));
- Notice 2008-111 – (12/01/2008) – Clarifies Notice 2001-16 (2001-1 C.B. 730) that identified and described the intermediary transaction tax shelter as a listed transaction and supersedes Notice 2008-20 (2008-6 I.R.B. 406). The Notice defines an intermediary transaction in terms of its plan and of more objective components. Also, the Notice specifies when a person is engaged in a transaction as part of a plan and clarifies that a transaction may be an intermediary transaction for one person and not another.
- Notice 2001-17 – §351 Contingent Liability (transactions involving a loss on the sale of stock acquired in a purported § 351 transfer 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 (identified as “listed transactions” on January 18, 2001)).
- Notice 2001- 45 – §302 Basis-Shifting Transactions (certain redemptions of stock in transactions not subject to U.S. tax in which the basis of the redeemed stock is purported to shift to a U.S. taxpayer (identified as “listed transactions” on July 26, 2001)).
- Notice 2002-21 – Inflated Basis “CARDS” Transactions (transactions involving the use of a loan assumption agreement to inflate basis in assets acquired from another party to claim losses (identified as “listed transactions” on March 18, 2002));
- Notice 2002-35 – Notional Principal Contracts (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 (identified as “listed transactions” on May 6, 2002));
- Notice 2002-50– Partnership Straddle Tax Shelter (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 (identified as “listed transactions” on June 25, 2002)); Notice 2002-65, 2002-2 C.B. 690 (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 are substantially similar to transactions described in Notice 2002-50); and Notice 2003-54, 2003-33 I.R.B. 363 (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 are substantially similar to transactions described in Notice 2002-50 and Notice 2002- 65);
- Revenue Ruling 2002-69, Lease In / Lease Out or LILO Transactions (transactions in which a taxpayer purports to lease property and then purports to immediately sublease it back to the lessor (often referred to as lease-in/lease-out; or LILO transactions) (identified as listed transactions on February 28, 2000).
- Revenue Ruling 2003-6, Abuses Associated with S Corp ESOPs (certain arrangements involving the transfer of employee stock ownership plans (ESOPs) that hold stock in an S corporation for the purpose of claiming eligibility for the delayed effective date of § 409(p) (identified as “listed transactions” on December 17, 2002)).
- Notice 2003-22 – Offshore Deferred Compensation Arrangements (certain arrangements involving leasing companies that have been used to avoid or evade federal income and employment taxes (identified as “listed transactions” on April 4, 2003)).
- Notice 2003-24 – Certain Trust Arrangements Seeking to Qualify for Exception for Collectively Bargained Welfare Benefit Funds under § 419A(f)(5) (certain arrangements that purportedly qualify as collectively-bargained welfare benefit funds excepted from the account limits of §§ 419 and 419A (identified as “listed transactions” on April 11, 2003)).
- Notice 2003-47 – Transfers of Compensatory Stock Options to Related Persons (transactions involving compensatory stock options and related persons to avoid or evade federal income and employment taxes (identified as “listed transactions” on July 1, 2003))
- Notice 2003-55 – Accounting for Lease Strips and Other Stripping Transactions (transactions in which one participant claims to realize rental or other income from property or service contracts and another participant claims the deductions related to that income (often referred to as “lease strips”)), modifying and superseding Notice 95-53, 1995-2 C.B. 334 (identified as “listed transactions” on February 28, 2000);
- Notice 95-53 – Lease Strips – Modified and superseded by Notice 2003-55 above
- Notice 2003-77 – Improper use of contested liability trusts to attempt to accelerate deductions for contested liabilities under IRC 461(f) (certain transactions that use contested liability trusts improperly to accelerate deductions for contested liabilities under § 461(f) (identified as “listed transactions” on November 19, 2003)). See also § 1.461-2 of the Income Tax Regulations. See Rev. Proc. 2004-31, 2004-22 I.R.B. 986, for procedures which taxpayers must use to change their methods of accounting for deducting under § 461(f) amounts transferred to trusts in transactions described in Notice 2003-77.
- Lead Executive Memorandum- Advises that settlements will not be offered
on these issues
- TD 9095
- Regulation 136890-02
- Revenue Procedure 2004-31- Change of accounting methods for improper
contested liability trust transactions described in Notice 2003-77.
- Lead Executive Memorandum- Advises that settlements will not be offered
- Notice 2003-81 – Offsetting Foreign Currency Option Contracts (certain transactions in which a taxpayer claims a loss upon the assignment of a § 1256 contract to a charity but fails to report the recognition of gain when the taxpayer’s obligation under an offsetting non-section 1256 contract terminates (identified as “listed transactions” on December 4, 2003)).
- Notice 2004-8 – Abusive Roth IRA Transactions (certain transactions designed to avoid the limitations on contributions to Roth IRAs described in § 408A (identified as “listed transactions” on December 31, 2003)).
- Revenue Ruling 2004-04 (S Corporations ESOP) – Prohibited Allocations of Securities in an S Corporation (transactions that involve segregating the business profits of an ESOP-owned S corporation in a qualified subchapter S subsidiary, so that rank-and-file employees do not benefit from participation in the ESOP (identified as “listed transactions” on January 23, 2004)).
- Revenue Ruling 2004-20 – Abusive Transactions Involving Insurance Policies in IRC 412(i) Retirement Plans (certain arrangements in which an employer deducts contributions to a qualified pension plan for premiums on life insurance contracts that provide for death benefits in excess of 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) (identified as “listed transactions” on February 13, 2004)). See also Rev. Rul. 2004-21, 2004-10 I.R.B. 544, §§ 1.79-1(d)(3), 1.83-3(e) and 1.402(a)-1(a)(1) and (2) of the proposed Income Tax Regulations, and Rev. Proc. 2004-16, 2004-10 I.R.B. 559.
- Revenue Ruling 2004-21
- Proposed Regulation 126967-03
- Revenue Procedure 2004-16
- Notice 2004-20 – 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 to make an election under § 338 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) (identified as “listed transactions” on February 17, 2004)).
- Treasury Department Press Release
- Notice 2004-19- Withdraws
- Notice 98-5
- Notice 2004-30 – S Corporation Tax Shelter Involving Shifting Income to Tax Exempt Organization (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 (identified as “listed transactions” on April 1, 2004)).
- Notice 2004-31 – Intercompany Financing Through Partnerships (transactions in which corporations claim inappropriate deductions for payments made through a partnership (identified as “listed transactions” on April 1, 2004)).
- Treasury Press Release dated 04/01/04
- Notice 2005-13, Sale-In Lease-Out transactions
LILO/SILO Settlement Initiative- On August 6, 2008, IRS Commissioner Douglas Shulman announced that settlements would be offered to taxpayers who participated in Lease-In/Lease-Out (LILO) and Sale-In/Sale-Out (SILO) transactions. IRS sent out letters giving taxpayers 30 days to make a decision on whether to accept the
- Notice 2007-57 – Loss Importation Transaction (IRB 2007-29) (transactions in which a U.S. taxpayer uses offsetting positions with respect to foreign currency or other property for the purpose of importing a loss, but not the corresponding gain, in determining U.S. taxable income (identified as “listed transactions” on July 16, 2007)).
- Notice 2007-83 – Abusive Trust Arrangements Utilizing Cash Value Life Insurance Policies Purportedly to Provide Welfare Benefits – 2007-45 I.R.B. 1 (transactions in which certain trust arrangements claiming to be welfare benefit funds and involving cash value life insurance policies that are being promoted to and used by taxpayers to improperly claim federal income and employment tax benefits (identified as “listed transactions” on October 17, 2007)).
- Notice 2008-34 – Distressed Asset Trust (DAT) Transaction – 2008-12 I.R.B. 1 (transactions in which a tax indifferent party, directly or indirectly, contributes one or more distressed assets (for example, a creditor’s interests in debt) with a high basis and low fair market value to a trust or series of trusts and sub-trusts, and a U.S. taxpayer acquires an interest in the trust (and/or series of trusts and/or sub-trusts) for the purpose of shifting a built-in loss from the tax indifferent party to the U.S. taxpayer that has not incurred the economic loss (identified as listed transactions on February 27, 2008)).
- Notice 2015-73 – Basket Option Contracts – This notice describes certain transactions involving a contract that is denominated as an option referencing a basket of actively traded personal property. The Basket Option Contract attempts to defer income recognition and convert short-term capital gain and ordinary income to long-term capital gain using a contract denominated as an option contract. This notice was published in the Internal Revenue Bulletin on November 16, 2015. This notice was previously listed under Notice 2015-47 which was revoked.
- Notice 2017-10 – Syndicated Conservation Easement Transactions – This notice describes certain transactions in which some promoters are syndicating conservation easement transactions that purport to give investors the opportunity to obtain charitable contribution deductions in amounts that significantly exceed the amount invested. The promoters identify a pass-through entity that owns real property, or form a pass-through entity to acquire real property. Additional tiers of pass-through entities may be formed. The promoters then syndicate ownership interests in the pass-through entity or tiered entities that owns the real property, suggesting to prospective investors that they may be entitled to a share of a charitable contribution deduction that equals or exceeds two and one-half times the amount of the investor’s investment. The promoters obtain an inflated appraisal of the conservation easement based on unreasonable conclusions about the development potential of the real property. The entity then donates a conservation easement encumbering the property to a tax-exempt entity. Investors then claim a charitable contribution relying upon the pass-through entity’s holding period.
Transactions of Interest
- Notice 2007-72 – August 14, 2007 – Contribution of Successor Member Interest – This transaction involves a taxpayer directly or indirectly acquiring 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, and claims a charitable contribution deduction under § 170 that is significantly higher than the amount that the taxpayer paid to acquire the rights.
- Notice 2007-73 – Potential Abuse of Grantor Trusts – 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.
- Notice 2008-99 – October 31,2008 – 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.
- Notice 2009-7 – Subpart F Income Partnership Blocker – On December 29, 2008 IRS and Treasury identified a new transaction of interest that uses a domestic partnership to prevent the inclusion of subpart F income. 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 section 956(a) of the Internal Revenue Code (Code) related to holdings of United States property by the lower-tier CFC does not result in income inclusions under section 951(a) for the U.S. taxpayer.
- Notice 2015-74 – Basket Contracts – This notice describes certain transactions denominated as an option, notional principal contract, forward contract, or other derivative contract to receive a return based on the performance of a basket of referenced assets (the “reference basket”). The assets that comprise the reference basket may include (1) interests in entities that trade securities, commodities, foreign currency, or similar property (“hedge fund interests”), (2) securities, (3) commodities, (4) foreign currency, or (5) similar property (or positions in such property). The Basket Contracts attempt to defer income recognition and may attempt to convert short-term capital gain and ordinary income to long-term capital gain. This notice was published in the Internal Revenue Bulletin on November 16, 2015.
- Notice 2016-66 – Section 831(b) Micro-Captive Insurance – This notice describes transactions in which a taxpayer attempts to reduce the aggregate taxable income of the taxpayer, related persons, or both, using contracts that the parties treat as insurance contracts and a related company that the parties treat as a captive insurance company. Each entity that the parties treat as an insured entity under the contracts claims deductions for premiums for insurance coverage. The related company that the parties treat as a captive insurance company elects under § 831(b) of the Internal Revenue Code (the “Code”) to be taxed only on investment income and therefore excludes the payments directly or indirectly received under the contracts from its taxable income. The manner in which the contracts are interpreted, administered, and applied is inconsistent with arm’s length transactions and sound business practices.
- Notice 2017-8 – Section 831(b) Micro-Captive Transactions, amends the due date for filing of a disclosure with the Office of Tax Shelter Analysis for Notice 2016-66 transactions.
This information was obtained from the Internal Revenue Service website on January 24, 2023 (The IRS webpage was last reviewed or updated October 3, 2022).