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Captive Insurance Risk Alert

Captive Insurance Risk AlertTax practitioners should be cognizant of the Internal Revenue Service (“IRS”) increasing and focused activity related to micro-captive insurance companies (hereinafter referred to as Captive Insurances. Captive Insurance Risk Alert

Additional scrutiny and skepticism may increase the professional liability risk of a CPA firm. CPA firms with clients who have established, or are considering establishing, a Captive should pay special attention to this Risk Alert.

IRS Audits Micro-Captives

IRS Audits Micro-Captives IRS Audits Micro-CaptivesShortly after the Internal Revenue Service once again warned taxpayers to steer clear of unscrupulous promoters selling abusive micro-captives. It is part of the IRS annual Dirty Dozen listing. The IRS Large Business and International (LB&I) Division touted the success of its partnership with the Small Business/Self-Employed Division in carrying out the micro-captive campaign.

The US Tax Court handed the IRS its third straight victory involving a small captive structure in Syzygy v. Commissioner. Six days after the Syzygy opinion was issued, LB&I announced the initiation of a “Captive Services Provider Campaign” aimed at ensuring US multinational companies pay their captives no more than arm’s-length prices.2 The IRS is clearly moving quickly to address tax compliance issues in the captive world.

The IRS has now obtained victories in cases involving both forms of small captives electing tax-exempt status under § 501(c)(15) and captives electing to be taxed only on investment income under § 831(b). With each victory in court, the IRS has succeeded in highlighting problematic program design features and implementation missteps. Going forward, IRS revenue agents and appeals officers will likely look to the deficiencies identified in the case law in resolving captive controversies.

Lance Wallach receives hundreds of calls annually to help people fight the IRS and get their money back from the promoters of these scams. As an expert witness, Lance’s side has never lost a lawsuit. Google Lance Wallach and your advisor, who do you trust?

+1 516-236-8440

Wallachinc@gmail.com

Micro Captive Insurance audit deal from IRS

Micro-captive Insurance Schemes

Micro-captive insurance schemesIRS expands enforcement focus on abusive micro-captive insurance schemes.

WASHINGTON — With the October 15 filing deadline quickly approaching, the Internal Revenue Service today encouraged taxpayers to consult an independent tax advisor if they participated in a micro-captive insurance transaction.

The IRS encourages any taxpayer who has continued to engage in an abusive micro-captive insurance transaction to not anticipate being able to settle its transaction with the IRS or Chief Counsel on terms more favorable than previously announced. Any potential future settlement initiative that the IRS may consider will require additional concessions by the taxpayer.

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IRS to Settle with some under audit for micro-captive insurance plans

IRS Gathers Information on Taxpayers

IRS Gathers Information on Taxpayers, Micro-captive, IRS Dirty Dozen listSince the time when micro-captive insurance companies were placed on the IRS Dirty Dozen list of tax scams, it has also been identified as a transaction of interest.

The IRS continues to expand its enforcement efforts of what it views as abusive micro-captive insurance arrangements.

The IRS gathers information on taxpayers and institutes a new virtual currency compliance program.

Excerpt from one of their notices; We have information that you have or had at least one account containing virtual currency. Yet may not have properly reported your transactions involving virtual currency, which may include cryptocurrency and/or non-crypto virtual currencies.

A new IRS Notice 6174-A which states that the IRS clearly sees noncompliance on virtual currency transactions as a threat to the tax system.

As if the onslaught of recent losses in Tax Court was not enough, investors in syndicated conservation easements now have more to worry about.

The Senate Finance Committee released a bipartisan report condemning syndicated conservation easements as abusive and therefore encouraging the IRS to take further action to ferret out such abuse.

Lance Wallach has received hundreds of calls in order to help citizens fight the IRS on this subject and help sue the promotors of easement, captive, and cryptocurrency plans.

Your advisor! Who do you trust?

wallachinc@gmail.com

CIC Services LLC v. IRS

micro-captive transactions, CIC Services LLC v. IRS, micro-captive transactions

A lawsuit arguing that taxpayers are permitted to challenge a Treasury Department reporting requirement without first violating it defies a measure Congress took to protect tax collection, the U.S. Solicitor General’s Office told the U.S. Supreme Court.

The office made that argument in a Wednesday court filing urging the justices against taking up a case testing the reach of the Anti-Injunction Act. The act blocks lawsuits aimed at restraining officials from assessing or collecting taxes, which some interpret as shielding the department from early legal challenges to regulatory actions.

In the new filing, the government insisted that the reporting requirement is directly tied to tax collection.

“Requiring taxpayers and tax professionals to report information (and tax professionals to keep records) about such transactions enables the IRS to ensure that taxes applicable to them are not evaded but are properly assessed and collected”, the Solicitor General’s Office said.

CIC Services LLC, a Tennessee-based company, has argued that the law doesn’t block its challenge to a reporting requirement backed by a penalty in IRS Notice 2016-66 because it’s challenging the burdens of reporting rather than the penalty itself and, in any event, the penalty isn’t a tax.

The case strongly divided judges at the U.S. Court of Appeals for the Sixth Circuit, with a three-judge panel ruling 2-1 in favor of the government and multiple judges weighing in separately when the full circuit declined to rehear that decision.

The IRS notice required CIC Services to report the micro-captive transactions it advised on, which involve small insurance companies that are allowed to pay tax on just their investment income if their premium income doesn’t surpass $2.3 million. The IRS has argued that the arrangements may be tax-avoidance vehicles rather than genuine insurance.

CIC Services has said the notice containing the reporting requirement isn’t legally valid because the IRS didn’t notify the public of its plans for the requirement and respond to comments in advance, which the company says was required by the Administrative Procedure Act.

An attorney for CIC Services LLC didn’t immediately return a request for comment.

The case is CIC Services, LLC v. Internal Revenue Service, U.S., No. 19-930, response brief filed 3/25/20

Micro-captive insurance schemes

Taxpayers engaged in Micro-Captive Insurance Arrangements

Taxpayers engaged in Micro-Captive Insurance ArrangementsTaxpayers engaged in micro-captive insurance arrangements (and re-insurance arrangements) have started receiving correspondence directly from the Large Business and International (LB&I) division of the IRS. The correspondence asks taxpayers to certify whether they have terminated their participation in the arrangement and, if so, to disclose the last tax year they claimed a tax benefit from the arrangement.

For taxpayers still engaged in micro-captive insurance arrangements as a means to self-insure against business risk, the IRS letter may be an occasion to review the captive insurance arrangement.

Background

In Notice 2016-66, the IRS described micro-captive insurance arrangements as “transactions of interest.” Although many taxpayers engage in captive insurance arrangements to legitimately self-insure against business risk, the IRS expressed concern that some arrangements may result in tax abuse. The notice requires taxpayers participating in such arrangements to disclose the transaction on Form 8886—Reportable Transaction Disclosure Statement—and file the form with their current tax return and with the Office of Tax Shelter Analysis.

The notice provided examples of abusive micro-captive insurance arrangements. The IRS describes the potential abusive transaction as one that starts with a taxpayer who deducts premiums paid to a micro-captive insurance company, with the insurance company electing (under section 831(b)) to be taxed only on its investment income (premium income is not directly taxed). The mismatching of the deductible insurance premiums and the insurance company’s election not to be taxed on premium income may lead to potential abuse. This abuse may exist where the micro-captive insurance company insures against implausible risks, the micro-captive insurance company is used as an investment vehicle for its owners, or where there are loans between the micro-captive and related parties.

Notice 2016-66 lists a number of factors used to determine whether a micro-captive arrangement is an abusive tax structure. However, captive insurance arrangements are also widely used to legitimately self-insure against business risk, and micro-captive insurance companies (defined as having annual premiums of less than $2,200,000) are used by many taxpayers in the middle market. The notice recognizes this fact and specifically states:

However, the Treasury Department and the IRS lack sufficient information to identify which § 831(b) arrangements should be identified specifically as a tax avoidance transaction and may lack sufficient information to define the characteristics that distinguish the tax avoidance transactions from other § 831(b) related-party transactions.

IRS correspondence

Last year, the IRS successfully litigated several cases where the micro-captive insurance arrangement was clearly tax abusive. Based on these cases, the IRS sent out the above-mentioned letters to those taxpayers who had previously filed a Form 8886. The letter instructs taxpayers who are no longer claiming deductions or other tax benefits for any of the captive transactions described in Notice 2016-66 to notify the IRS. The notification must be signed under penalty of perjury, and include the date the taxpayer ended participation in the micro-captive arrangement, and the last tax year the taxpayer claimed any tax benefit from the arrangement.

Noticeably confusing in the IRS letter is whether taxpayers still engaged in micro-captive insurance arrangements need to respond at all to the IRS letter. Many taxpayers have established micro-captive insurance companies to insure against legitimate business risk; the captive insurance company manages reserves and pays claims that come due. Under the terms of the IRS letter, these taxpayers may not need to specifically respond to the IRS.

Client discussion

The IRS correspondence received by taxpayers has caused confusion as to how to respond and whether a taxpayer’s micro-captive insurance arrangement will be respected. Taxpayers still engaged in a micro-captive insurance arrangement should consider whether and how to respond to the IRS. Based on concerns raised in IRS Notice 2016-66, questions to determine if the captive insurance arrangement is acceptable may include the following:

  • Does the micro-captive insurance coverage match a business need or risk to the insured?
  • Does the coverage duplicate other insurance coverage already in place?
  • Are premium payments calculated to cover risk based on an analysis consistent with industry standards?
  • Are premium payments consistent with premiums required under commercially available insurance contracts?
  • Is there documentation of insurance coverage?
  • Has the captive insurance company registered as an insurance company with the applicable government agency?
  • If the captive insurance company is an offshore entity, has it elected under section 953(d) to be taxed as a U.S. insurance company?
  • Does the captive insurance company have procedures for the handling of claims?
  • Does the captive insurance company have adequate reserves to cover claims?
  • Does the captive insurance company have assets that significantly exceed the necessary reserves?
  • Does the captive insurance company invest in illiquid or speculative assets?
  • Does the captive insurance company provide loans to related parties?

Although no one factor is dispositive of a bona fide captive insurance arrangement, these questions should be considered by taxpayers to gain an understanding of the micro-captive insurance arrangement and to evaluate their own arrangements. In addition, there is a real concern that the IRS may begin examining taxpayers who are still engaged in micro-captive insurance transactions.

U.S. Department Of Justice Files Suit

U.S. Department Of Justice Files Suit, tax sheltersThe U.S. Department Of Justice Files Suit To Enforce An IRS Summons Against The Delaware Department Of Insurance For Artex Transactions tax shelters.

tax shelters. On June 19, 2020, the Tax Division of the U.S. Department of Justice filed a Petition To Enforce Summons against the Delaware Department Of Insurance, which seeks testimony and certain documents relating to Artex Risk Solutions, Inc. and Tribeca Strategic Advisors, LLC in connection with its promoter audits of those companies. Concurrently with the Petition, the DOJ also filed the Declaration of IRS Revenue Agent Bradley Keltner and the Summons that it is attempting to enforce. Artex/Tribeca is affiliated with publicly-traded Arthur J. Gallagher.

According to the Petition, the IRS is conducting a promoter audit, known as a “6700 audit” from § 6700 of the U.S. Tax Code that creates penalties for the promoters of tax shelters. In this case, says the Petition the IRS is investigating whether Artex and Tribeca marketed and sold so-called “micro captives”, i.e., captive insurance companies qualifying under IRC § 831(b), as tax shelters — which for both Artex and Tribeca is like wading out into the ocean to look for water. The Petition also notes that a class action (Shivkov v. Artex), which I have written about previously, had been brought against Artex and others for not telling their clients that they were entering into an abusive tax transaction.

The Petition goes on to say that the Delaware Department Of Insurance (DDOI) issued 191 insurance certificates to companies associated with Artex, and that the information sought by the IRS might indicate whether Artex made false or misleading statements in organizing those captives. For instance, according to the Petition, there are instances where the DDOI was apparently complicit in backdating Delaware certificates of authority (basically, insurance licenses), such as one was where the certificate was backdated almost two months from February 25, 2013 back to December 31, 2012 — after which Artex then rewarded six

According to the Petition, the DDOI has failed to fully comply with the IRS Summons directed to it, such as failing to produce all the e-mails between the DDOI and Artex (and its predecessor Tribeca).

More juicy facts are found in the sworn Declaration of IRS Revenue Agent Bradley Keltner, including that the DDOI has so far turned over to the IRS over 18,331 pages of documents related to 16 Delaware captives.

ANALYSIS

As shocking as the allegations of backdating and complicity in tax shelter schemes might be to the reader who is unfamiliar with the area of captive insurance tax shelters, this is simply what has gone on for the last decade with the insurance departments of several states that have served as mass outlets for risk-pooled 831(b) captive insurance companies. While the Delaware Department of Insurance may be the first to be caught in backdating documents, I can assure you that they are not the only such department to have done it.

The hard truth is that the so-called micro captive tax shelter industry utilizes a lot of — well, let’s just call them what they are — corrupt co-conspirators. The industry requires actuaries who anticipate huge losses from year to year even though those losses have never actually materialized in any year, underwriters who intentionally draft policies so that nobody can figure out what is actually being covered, accountants who turn a blind eye to numerous red flags, lawyers who write opinion letters of dubious validity, and at the center of it all the captive managers who market, sell and keep the clients writing checks to everybody.

There is one more necessary piece to this puzzle, one more group of corrupt co-conspirators for which the entire scheme would fail in the absence of their misdeeds: The state “captive commissioners” and the unit within the state’s insurance department that oversees captive insurance companies. For each and every captive tax shelter relies very heavily on that one sheet of paper — the captive’s license or certificate or authority — without which the shelter would be stillborn. And corruptly conspire they do.

The captive deputies have a powerful incentive to sell as many captives as they can, without regard to the quality of any individual captive. Bigger numbers means more revenue generated by their sections, which leads to bigger staff, greater prestige, and sometimes higher salaries. The departments are themselves frequently willing to turn a blind eye towards what their captive sections are doing, because the department can report to the state legislature a larger number of licenses issued, and thus seek a bigger budget. But between states, the captive insurance marketplace is very competitive: Most of the states have more-or-less the same captive statutes, and if one enacts something better then the rest follow quickly, and most of the states charge about the same for their insurance licenses.

What that leaves is something known as the captive industry as “flexibility”, which means that while most insurance departments are restrained by doing things by the book, have rigorous internal controls, and no backdating a document. A few other insurance departments don’t quite have the same scruples. Instead, some of the captive jurisdictions have earned reputations as being “flexible”. That means that they will bend, break or simply ignore the rules to facilitate the licensure of a new tax sheltered captive. The captives they are licensing don’t make any economic sense but are simply formed for the purpose of cheating Uncle Sam out of a few bucks in taxes. The regulators go along with it because they benefit too. Thus, ignoring or twisting their own rules in the name of “flexibility” as to what constitutes a legitimate captive. These regulators indeed became corrupt co-conspirators too.

Note that “flexibility” is not just in allowing the formation of the captive, but how the captive continues to be regulated in the following years. Here is where the captive deputies really show their complicity in running tax shelters, since they see the same captive managers and same actuaries submitting reporters over and over which predict that losses will be X in the coming year, but it turns out very consistently that the actual losses were actually less than 5% of X. In the real insurance world, consistently missing predicted losses by such a huge margin would be pretty good evidence that false actuarial studies were being submitted, but it is here that the captive deputies know that if they required accurate reporting, then the captives couldn’t charge as much premiums as their clients want for their tax deductions, and everybody would lose business — so the captive deputies simply ignore it all.

This is exactly where the “flexible” insurance departments engage in what cannot be characterized as anything short of tax fraud, i.e., issuing insurance certificates based on actuarial studies that are obviously inaccurate just so that the ultimate taxpayers can generate a false deduction through the vehicle of falsely-inflated premiums. While a tax shelter promoter taking a half-dozen employees of the DDOI to breakfast isn’t exactly the most corrupt quid pro quo, it does illustrate the fundamental coziness between the insurance departments who rely upon the promoters to bring licensure business in, and the promoters who rely upon the insurance departments to issue captive licenses no matter how obviously the application indicates a tax shelter captive.

U.S. Department Of Justice Files Suit, tax sheltersDelaware was one of the first “flexible” jurisdictions, and at captive conferences for years the folks of the Delaware Department of Insurance went out of its way to express to the industry that Delaware was open for “pure tax” captives, so long as application fee checks cleared. Thus, in just a few years, Delaware went from being a state with few captives to being one of the most prolific issuers of captive licenses; 191 to Artex alone as the Petition here states.

Shortly thereafter, two other states, Tennessee and North Carolina, also exploded in the number of their captive licenses issues also because they were holding themselves out as “flexible” — it would frankly surprise me to find out that of each of Tennessee and North Carolina’s hundreds of captive licenses issued, either one has more than a handful of micro captives that are not just tax shelters. Because Delaware is a corporate hub, it probably has a goodly number of legitimate captives, but I would similarly be surprised if less than 90% of its micro captives are not of the tax shelter varietal.

Where Delaware really kicked the sales of tax shelter micro captives into overdrive was in the area of so-called “cell captives” which are organized as Delaware Series LLCs. The idea here was that a tax shelter promoter could form just one parent captive, and then have a bunch of children captives of that parent in which their clients could participate. These cell captives were sold by the bushel to folks who could not afford sufficient premiums to make their own standalone captives worthwhile, such as doctors and other small businesspersons who had high incomes who were looking to shelter income.

Interestingly, the insurance departments of other states quickly replicated this model so that they could also get their piece of the cell captive tax shelter pie by licensing individual cells of Delaware Series LLC in their own states. Tennessee, for instance, licensed a lot of these. The percentage of legitimate captives in these Series LLC programs is very low, probably less than 5%. If a state regulator cross-indexed those captives organized as Delaware Series LLCs against those whose losses were less than 20% of premiums for two consecutive years, the resulting list of captives could safe be put into the “terminate immediately” pile.

One would think that when the IRS issued Notice 2016-66 and listed captives as a “transaction of interest” that such would have put the kibosh on the states aggressively competing for tax sheltered captive sales, but in fact the last several years have seen the rise of a new regulatory player in this sector, albeit not quite a state: Puerto Rico. The captive programs coming out of Puerto Rico take abusive to an entirely new level, and office of the Puerto Rico insurance commissioner seems to welcome that business with open arms.

Meanwhile, captive managers in the “flexible” states continue to market and sell abusive micro captive programs, albeit they are working much harder to try to make it appear (falsely) that they are only selling captives for bona fide insurance reasons. Where many other states that offer captive licenses have significantly backed off taking new micro captive business, there are still a few states out there that are hungry for new business no matter how much it smells. These insurance departments still want to go to their legislatures for bigger budgets, bigger staffs, more prestige, etc., and it that takes complicity in tax fraud then that is what it takes. And they’ll keep getting IRS Summons as here too.

The U.S. Department Of Justice Files Suit To Enforce An IRS Summons Against The Delaware Department Of Insurance For Artex Transactions, tax sheltersFinally, it is hard to figure out why Gallagher continues to hold on to Artex other than maybe blind speculation that Gallagher affirmatively wants to be in the tax shelter business. Otherwise, it makes little sense. Buying Tribeca made little sense to begin with, since it was a notorious tax shelter captive shop that had all the subtlety of a hooker wearing skimpy clothing who waives at cars passing by, and fit nowhere in Gallagher’s traditional business model.

The Artex/Tribeca deal has to go down as one of the singularly worst transactions in Gallagher’s history, and indeed Gallagher now finds itself on the wrong end of a class action suit because of it all. Strange; it seems like maybe Gallagher’s Board of Directors is asleep at the controls on this one. They would be well advised to just totally axe Artex, move its assets and legitimate non-tax business to a new insurance company that doesn’t have any of Tribeca’s taint, and vow never to do anything like this again. But somehow Artex survives. Again, strange.

I have been an expert witness in captive insurance cases. This article is from Jay Adkinson. If you are in a captive you need help NOW.

Captive Insurance Risk Alert, Micro-Captive and the IRS

Micro-Captive and the IRS

Captive Insurance Risk Alert, Micro-Captive and the IRSThe IRS correspondence received by taxpayers has caused confusion as to how to respond and whether a taxpayer’s micro-captive insurance arrangement will be respected.

Taxpayers still engaged in a micro-captive insurance arrangement should consider whether and how to respond to the IRS.

Based on concerns raised in IRS Notice 2016-66, questions to determine if the captive insurance arrangement is acceptable may include the following:

  • Does the micro-captive insurance coverage match a business need or risk to the insured?
  • Does the coverage duplicate other insurance coverage already in place?
  • Are premium payments calculated to cover risk based on an analysis consistent with industry standards?
  • Are premium payments consistent with premiums required under commercially available insurance contracts?
  • Is there documentation of insurance coverage?
  • Has the captive insurance company registered as an insurance company with the applicable government agency?
  • If the captive insurance company is an offshore entity, has it elected under section 953(d) to be taxed as a U.S. insurance company?
  • Does the captive insurance company have procedures for the handling of claims?
  • Does the captive insurance company have adequate reserves to cover claims?
  • Does the captive insurance company have assets that significantly exceed the necessary reserves?
  • Does the captive insurance company invest in illiquid or speculative assets?
  • Does the captive insurance company provide loans to related parties?

Although no one factor is dispositive of a bona fide captive insurance arrangement, these questions should be considered by taxpayers to gain an understanding of the micro-captive insurance arrangement and to evaluate their own arrangements. In addition, there is a real concern that the IRS may begin examining taxpayers who are still engaged in micro-captive insurance transactions. Taxpayers should contact Lance Wallach at 516-938-5007 for any questions or concerns regarding their Captive Investments.


Lance Wallach, CLU, CHFC, CIMC, National Society of Accountants Speaker of the Year and member of the AICPA faculty of teaching professionals is a frequent speaker on abusive tax shelters, Captive Insurance and Conservation Easements. He speaks at more than ten conventions annually and writes for over fifty publications.

Lance Wallach does expert witness testimony and has never lost a case!

irs audit captive

IRS is cracking down on micro-captives

IRS is cracking down on micro-captivesAccording to the IRS, nearly 80% of taxpayers who received a time-limited settlement offer elected to accept the settlement terms. The IRS is establishing 12 new examination teams that are expected to open audits to thousands of taxpayers. IRS is cracking down on micro-captives.

The IRS has viewed abusive micro-captives as a threat to tax administration for several years. The transaction has appeared on the IRS “Dirty Dozen” list of tax scams since 2014. In 2016, the Department of the Treasury and IRS issued Notice 2016-66 that identified certain micro-captive transactions as having the potential for tax avoidance and evasion.

The settlement offer followed three U.S. Tax Court decisions holding that certain micro-captive arrangements are not eligible for federal tax benefits. The terms of the settlement required substantial concession of the income tax benefits claimed by the taxpayer together with appropriate penalties.

The IRS is establishing 12 new examination teams that will be working to address abusive transactions and open additional exams. Examinations impacting micro-captive insurance transactions of several thousand taxpayers will be opened by these teams in the coming months. Civil outcomes may include disallowance of claimed captive insurance deductions captive entity and imposition of applicable penalties.

The IRS reminds taxpayers and advisors that disclosure of participation in micro-captive insurance transactions is required with the IRS Office of Tax Shelter Analysis under Notice 2016-66. Failure to properly disclose can result in civil penalties

Written by: Lance Wallach, CLU, CHFC, CIMC, National Society of Accountants Speaker of the year and member of the AICPA faculty of teaching professionals.

IRS audit

Understanding The IRS Settlement Initiative Offer For Targeted Captive Insurance Companies

Understanding The IRS Settlement Initiative Offer For Targeted Captive Insurance CompaniesThe so-called tax shelter captive insurance companies are under scrutiny by the IRS. This happens when the promoter dummies up the insurance policies and the risks, in order for the owners of captive insurances are able to artificially generate large tax deductions.

It’s important to understand that the IRS has extended this offer to only 200 taxpayers. Currently at least 2,000 captive arrangements are under audit. There are probably well over 10,000 captive arrangements that may ultimately come under scrutiny by the IRS as well.

The offer will not be extended to captive arrangements and their owners with pending docketed years under IRS Counsel’s jurisdiction.

IRS audits micro-captives

IRS Audits Captive Insurance Again

IRS Audits Captive Insurance AgainCaptive Insurance, Shortly after the Internal Revenue Service (IRS) again warned taxpayers to “steer clear” of unscrupulous promoters selling abusive micro-captives as part of its annual “Dirty Dozen” listing and the IRS Large Business and International (LB&I) Division touted the success of its partnership with the Small Business/Self-Employed Division in carrying out the micro-captive “campaign,” the US Tax Court handed the IRS its third straight victory involving a small captive structure in Syzygy v. Commissioner.

Six days after the Syzygy opinion was issued, LB&I announced the initiation of a “Captive Services Provider Campaign” aimed at ensuring US multinational companies pay their captives no more than arm’s-length prices. The IRS is clearly moving quickly to address tax compliance issues in the captive world.

The IRS has now obtained victories in cases involving both forms of small captives under the Internal Revenue Code: captives electing tax-exempt status under § 501(c)(15) and captives electing to be taxed only on investment income under § 831(b). With each victory in court, the IRS has succeeded in highlighting problematic program design features and implementation missteps. Going forward, IRS revenue agents and appeals officers will likely look to the deficiencies identified in the case law in resolving captive controversies.

Program Review

Understanding the current state of the law regarding captives in the US Tax Court is important not only for pending IRS controversies but also for current micro-captive owners as they consider what approach to take going forward. While each case stands on its own, a thorough review of the captive program can help establish an informed basis for decision-making both before and during an audit.

To carry out this review, it is important to understand the key issues that will be addressed during a captive audit. Some of the core substantive issues, involving risk distribution and whether a captive program reflects insurance in the commonly accepted sense, are discussed below.

Super Factor: Arm’s-Length Transaction. One of the most important questions in determining whether a captive can survive IRS scrutiny is a simple one: Do the coverages make economic sense? Whether the coverages are “arm’s-length transactions” is important in determining whether there is real risk distribution, as well as whether the arrangement constitutes “insurance in its commonly accepted sense”.

While to date no court has addressed whether this factor might also play a role in resolving whether the arrangement should be set aside under judicial anti-avoidance doctrines, it is certainly possible that the courts could rely on the lack of arm’s-length arrangements as a predicate for applying “substance over form” or the economic substance doctrine.

Risk Distribution

Regarding risk distribution, all three of the Tax Court micro-captive cases referenced above involved the employment of a risk pool established by the captive manager to enable the captive to insure third-party risk and (hopefully) obtain the requisite risk distribution. In each case, after analyzing the risk pool as part of its risk distribution analysis, the court held that the participation in the risk pool did not result in adequate risk distribution for the captive.

If a taxpayer relies on a risk pool, the IRS will request documentation supporting the risk pool structure. This will include documentation setting forth the rights and responsibilities of the taxpayer vis-à-vis the others who similarly rely on the pool. Given the responsibilities of the pool participants, the IRS will look for evidence of security mechanisms that would traditionally be required.

On top of the blueprint for the pooling mechanism, the IRS will want to review how it worked in reality and how it benefited the insured given the insured’s finances and history.

The courts thus far have reviewed captive policies from an objective viewpoint, considering policy metrics (e.g., total cost of risk and rates on line) before and after the implementation of the captive arrangement. After reviewing the various metrics, a court may consider subjective evidence to determine whether there was a rational justification for any expenditures to cover previously unprotected risks through a review of correspondence, marketing materials, etc.

For example, in Syzygy, the court noted that, generally, it is fair to assume a purchaser of insurance would want the most coverage for the lowest premiums. After finding that the coverage and associated premium did not make economic sense, the Syzygy court also considered statements made by the taxpayer (which seemed focused on obtaining large tax deductions rather than putting in place a helpful insurance product), which confirmed the court’s conclusion that there was no true distribution of risk.

Insurance in the Commonly Accepted Sense. In determining whether program transactions constituted “insurance in the commonly accepted sense”, the courts also looked to whether the captive arrangements constituted arm’s-length transactions.

Here, the courts focused on whether the premiums were objectively reasonable. It is probably not much of a stretch for one to conclude that if the captive policies do not make sense (e.g., are duplicative of commercial policies maintained by the taxpayer or that contain coverage that is arguably illusory), the IRS will conclude that the associated captive premiums were likewise unreasonable and thus, not insurance in the commonly accepted sense.

Likewise, if the insured fails to pursue a claim for which the policy appears to provide coverage, the IRS and the courts may view the arrangement as something other than insurance. The Syzygy court reached the conclusion that the premiums were unreasonable with only two sentences’ worth of analysis.6 Despite the existence of a claim on the policy by the insured to the captive, adequate capitalization of the captive, and active regulatory oversight, these insurance-like traits were not enough to overcome alleged late-issued policies with ambiguous language and the lack of an arm’s-length transaction.

Thus, as the arm’s-length nature of the arrangement has been considered by the courts when questioning whether the arrangement involved risk distribution as well as whether a captive provided “insurance in the commonly accepted sense,” it is incumbent on the tax advisor to drill deeply into the facts that would bear on whether the arrangement made economic sense.

Opinion Letters

In an effort to avoid penalties, the taxpayer may produce an opinion letter regarding the deductibility of premiums paid into a captive program. Here, the advisor should review the terms of the opinion as well as all other communications, including marketing materials, that might impact the usefulness of the opinion.

Further, the advisor must be cognizant of the fact that a written tax opinion will not protect a taxpayer from the accuracy penalty imposed with respect to a transaction lacking economic substance, even if the taxpayer relied on that opinion in good faith

Federal Tax Audit

The captive audit may start as a result of audit of another issue and then blossom into a captive audit or may be initiated solely due to the captive deduction itself. Over the last 2 years, after the § 831(b) micro-captive transaction was designated as a “transaction of interest,” the IRS has obtained a wealth of information from captive owners and captive managers, both from required filings regarding reportable transactions (Forms 8886, Reportable Transaction Disclosure Statement, and 8918, Material Advisor Disclosure Statement) and section 6112 list maintenance request to captive managers.

Information Document Requests

A captive audit will often involve intense questioning via Information Document Requests issued to both the captive and the insureds. In some cases, the insured taxpayer may handle responding on behalf of the captive as well as the insured party; in other cases, the captive manager or a third party may respond on behalf of the captive.

Here, it is critical to understand potential ethical issues, as well as the degree of control the taxpayer has over the captive for purposes of consistency in providing the IRS the information it is entitled to receive under the Internal Revenue Code.

If the requested information is not provided, not only will this likely result in summons enforcement proceedings (assuming the taxpayer can actually provide the information), but the taxpayer should also be cognizant that any information not provided (perhaps for strategic reasons) may ultimately have to be produced in subsequent litigation challenging the IRS assessment.

If critical or important documents are withheld and only surface later in litigation, then the taxpayer’s good faith may be put in question.

Ancillary Proceedings

Simultaneous with a tax audit, the advisor must be aware of and address numerous ancillary proceedings, such as issues related to state taxing authorities, civil proceedings involving service providers in particularly weak programs, as well as the exit of a small captive program.

For example, the taxpayer may be interested in civil remedies, joining a class action, or seeking relief in arbitration. Consequently, the advisor will need to carefully review and monitor the flow of information, as it is being requested in different settings, utilized for different purposes, but ultimately for the benefit of the taxpayer client.

As an example, a failure to review and monitor communications may lead to tax counsel making statements to the IRS in a tax audit that are wildly inconsistent with statements made by plaintiff’s counsel in pursuing a claim against a service provider. In sum, a captive tax audit may become an incredibly complex process that involves managing numerous moving parts.

irs audits captives

Captive Insurance Audit Settlements

Captive Insurance Audit SettlementsThe Internal Revenue Service announced that the mailing of a time-limited settlement offer for certain taxpayers under audit who participated in abusive micro-captive insurance transactions. Captive Insurance Audit

Taxpayers eligible for this offer will be notified by letter with the applicable terms. Taxpayers who do not receive such a letter are not eligible for this resolution.

Abusive micro-captives have been a concern to the IRS for several years. The transactions have appeared on the IRS “Dirty Dozen” list of tax scams since 2014. In 2016, the Department of Treasury and IRS issued Notice 2016-66 (PDF). Some  identified certain micro-captive transactions as having the potential for tax avoidance and evasion.

Following wins in three recent U.S. Tax Court cases, the IRS has decided to offer settlements to taxpayers currently under exam. In recent days, the IRS started sending notices to up to 200 taxpayers.

Captive Insurance Audit SettlementsTax law generally allows businesses to create “captive” insurance companies to protect against certain risks. Under section 831(b) of the Internal Revenue Code, certain small insurance companies can choose to pay tax only on their investment income. In abusive “micro-captive” structures, promoters, accountants or wealth planners persuade owners of closely held entities to participate in schemes that lack many of the attributes of genuine insurance.

IRS has consistently disallowed the tax benefits claimed by taxpayers in abusive micro-captive structures. Although some taxpayers have challenged the IRS position in court, none have been successful. To the contrary, the Tax Court has now sustained the IRS’ disallowance of the claimed tax benefits in three different cases.

The IRS will continue to disallow the tax benefits claimed in these abusive transactions and will continue to defend its position in court. The IRS has decided, however, to offer to resolve certain of these cases on the terms outlined below.

“Now the IRS is taking this step in the interests of sound tax administration,” IRS Commissioner Chuck Rettig said. “We encourage taxpayers under exam and their advisors to take a realistic look at their matter and carefully review the settlement offer, which we believe is the best option for them given recent court cases. We will continue to vigorously pursue these and other similar abusive transactions going forward.”

The settlement brings finality to taxpayers with respect to the micro-captive insurance issues. The settlement requires substantial concession of the income tax benefits claimed by the taxpayer together with appropriate penalties (unless the taxpayer can demonstrate good faith, reasonable reliance). Taxpayers eligible for the settlement will be notified of the terms by letter from IRS.

Captive Insurance Audit SettlementsThe initiative is currently limited to taxpayers with at least one open year under exam. Taxpayers who also have unresolved years under the jurisdiction of the IRS Appeals may also be eligible, but those with pending docketed years under Counsel’s jurisdiction are not eligible. The IRS is continuing to assess whether the settlement offer should be expanded to others.

Taxpayers who receive letters under this settlement offer, but who opt not to participate, will continue to be audited by the IRS under its normal procedures. Potential outcomes may include full disallowance of captive insurance deductions, inclusion of income by the captive, and imposition of all applicable penalties.

Although taxpayers who decline to participate will have full Appeals rights, the IRS Independent Office of Appeals is aware of this resolution initiative. Given the current state of the law, it is the view of the IRS Independent Office of Appeals that these terms generally reflect the hazards of litigation faced by taxpayers, and taxpayers should not expect to receive better terms in Appeals than those offered under this initiative.

Taxpayers who are offered this private resolution and decline to participate will not be eligible for any potential future settlement initiatives. The IRS also plans to continue to open additional exams in this area as part of ongoing work to combat these abusive transactions. 

irs audits captives

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For the third consecutive year, the IRS places abusive micro-captive insurance tax shelters on its list of “Dirty Dozen” tax scams. IRS takes next step on abusive micro-captive transactions; nearly 80 percent accept settlement, 12 new audit teams established


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IRS Audits Focus on Captive Insurance Plans

IRS Attacks Business Owners that participate in a 419 plan, 412i plan, Section 79 or a Captive Insurance. Under Section 6707A  

lance wallach, IRS Audits Focus on Captive Insurance Plans

By Lance Wallach

Taxpayers who previously adopted any of the following plans, 419, 412i, captive insurance or Section 79 are in trouble.

In recent years, the IRS has identified many of these plans as abusive devices to funnel tax deductible dollars to shareholders and classified these arrangements as listed transactions.