Many readers of this blog contact me directly with questions and comments. While often the responses are very specific to a particular circumstance, occasionally the subject matter is general enough that it might be of interest to others as well. Accordingly, I will occasionally post a new "MailBag" article, presenting the question or comment (on a strictly anonymous basis!) and my response, in the hopes that the discussion may be useful food for thought.

In this week's MailBag, we look at a question about what are 831(b) Captive Insurance Companies (CICs), whether they are a legitimate planning strategy or just an insurance scam, and what to watch out for and consider.

Comment/Question: I just had a client stump me yesterday by asking what I thought about him forming an 831(b) Captive Insurance Company. I didn’t feel too stupid because his corporate attorney had never heard of such a thing either.  I've since done some research on it, and found this apparently reliable source online from the NY Times, but was wondering if this is a strategy you have ever come across or evaluated for your clients?

Indeed, the 831(b) captive insurance company (CIC for short) is definitely a legitimate strategy, though CICs have generally been the domain of much larger businesses and are only more recently coming “downstream” in the past few years. That NYTimes article does a very good job covering them, and Jay Adkisson (cited heavily in the article) is a very high quality and credible source on the subject.

As the article notes, the basic concept of a CIC is pretty straightforward - instead of paying premiums to an insurance company to cover your risks, you pay the premiums into your own "captive" insurance company instead. The premiums may not be any different, but to the extent that you don't have any claims (and/or the claims are less than the premiums), the excess profits flow back to you as the owner of the CIC, instead of the shareholders of a publicly traded insurance company. In some cases, the CIC might be owned by the next generation as a way to indirectly transfer money/value to them from an estate planning perspective. In other scenarios, it's simply a way for profits of the main business to be redirected to the CIC and then distributed from the CIC as a dividend (which may be more favorable than drawing the profits directly from the original business, especially if it's a pass-through entity subject to ordinary income tax rates), or maintained in the CIC in a more asset-protected manner. And small CICs with less than $1.2M in premiums have some tax preferences of their own to mitigate the impact of double-taxation of the CIC (once at the corporate level and again as a dividend). Sometimes a CIC is simply a way to try to insure a risk that can't otherwise be insured in the marketplace.

The primary challenge to these in mind my is simply the acknowledgement that ultimately, all you’re doing is setting aside your own money to pay your own claims. That’s only insurance in the loosest sense of the word. As a business owner, I can put aside $100,000/year (or whatever amount I want) into my “emergency reserves” or into my CIC, but the fact remains that if I have a $100,000 expense/claim because something bad happens, whether I liquidate my emergency reserves or take a claim from my CIC, all I’m doing is spending my own money. And with CICs, they're often billed as a way to "save" on insurance premiums, but there can be a risk that, for serious events, the CIC might not have enough in premiums set aside yet to even cover the claim, in which case the client is in serious trouble with what is essentially an undercapitalized insurance company (at least if the CIC didn’t reinsure, and while reinsurance can often be obtained at cost-effective rates for the risk, it's yet another cost that reduces the relative efficacy of the strategy). In general, be very wary of tax schemes that do nothing more than help people pay their own expenses with what would have been their own money in the first place. Yes, you can make deductible contributions to the CIC and receive the claims tax free, but the net is that may ultimately be the exact same result as just keeping the money and using it in a deductible manner for the business expense (that was paid as a claim) anyway.

The appeal for larger organizations is that insurance is generally run on a for-profit basis, has some administrative costs, and can be reasonably predictable in large numbers – those are situations where a larger company having a CIC becomes appealing. In the very small business owner context, I’m still largely unconvinced. I rarely find the tax savings – which ultimately is just tax deferral, and maybe converting some income from ordinary to qualified dividends – is really worthwhile, unless literally the business already pays hundreds of thousands (or millions?) in insurance premiums for various risks (which is true for a 100-person company but not a 5-person small business and certainly not a sole proprietor). As the NY Times article notes, a lot of these are pitched from a pure tax perspective, and most I find don’t hold up at all once the math is really scrutinized, unless it’s a business with many millions in revenue (by the time there's a million+ in insurance expenses already the math starts to get interesting). The fatal flaw is the setup and ongoing costs of the insurance company (which the NY Times article notes can be $25,000 up front for setup and $36,000 annually to maintain!), often to just get a tax deduction that the business would have gotten just by keeping the money and spending it on future needs anyway - again, unless the business is sizable, administrative costs can be managed, and claims can get reasonably predictable.

Done right, though, the 831(b) captive insurance company strategy is definitely legitimate, and can work. I've seen a number of scenarios for businesses with dozens or a few hundred employees, and a few million of profit (on tens of millions of revenue) where the math worked and it made sense. But for a lot of “mere millionaires” scenarios (i.e., businesses $1M to $5M of value on what may only be a million dollars or less of profits, and not all that much really spent on insurance premiums anyway), it's harder to find scenarios where numbers ultimately hold up and are justified once accounting for the costs and recognizing that the strategy often doesn't save taxes but merely defers them (which isn't worth nearly as much).

For an extended credible source on the subject, I highly recommend Jay Adkisson's "Captive Insurance Companies: An Introduction to Captives, Closely-Held Insurance Companies, and Risk Retention Groups" book. Adkisson also supports an additional database and forum for information on CICs here.

I hope that helps a little?

  • Frederick Dunn

    “But it is a gray area. ‘You’re doing something that is technically in compliance with the law but you’re violating the purpose of the law,’ Mr. Adkisson said.” (from the NY Times article)

    This sort of legal(and clever but not ethical, I assert) behavior is what keeps making the tax regulations so complicated. Now the IRS will have to come back with something to realign the law with the original purpose. And so it goes.

    • Mark Capstone

      I disagree with you. Captive insurance companies are not only legal, they are ethical.

  • Roccy DeFrancesco

    I’m disappointed that you were stumped by a question about the legitimacy of CICs. You’ve been receiving my educational newsletter for years and I’ve done a number of articles on CICs and three different webinars discussing their viability. Maybe my newsletters got caught in your spam box or you didn’t find them worth reading?
    I’m equally disappointed that you are recommending Jay as an “expert.” What Jay’s an expert in is getting himself a lot of press and putting forth his biased view on most topics including CICs.
    There are many risks that are uncovered in a business that could be covered by a CIC. Businesses are self-insuring those risks when they could be paying premiums to a CIC owned by the owners individually or by trusts who have family members as beneficiaries (or some combination thereof). CICs can be one of if not the most powerful risk management tool available that also can turn into a nice wealth accumulation tool with a good claims history.
    There are CIC structures that allow smaller businesses to use them as viable tools where the setup fee is as low as $5,750 per $100,000 in annual budgeted premium with ongoing admin fees as low as 12% of the new premiums paid ever year.
    As most of your readers I’m sure know, you are a very bright guy, but before pontificating on CICs, I recommend doing more research and using more credible sources to obtain your information.

    • Michael Kitces

      Regarding being “stumped” by a question about the legitimacy of CICs, you may wish to re-read the article. The person who was “stumped” was the one who wrote to me and asked the Question/Comment, to which I was responding. Those were the words of the advisor who asked the question that prompted the article.

      Regarding risks that are uncovered in a business that can be covered by the CIC, as long as the CIC is solely funded by the premiums of the business, it’s STILL nothing more than structured self-insuring. The only premiums in the CIC are the ones the business put there, unless it’s some kind of pooled CIC arrangement (which of course risks that the client’s contributions could be depleted by someone else’s claim), or unless it’s reinsured (which may be difficult if the CIC is underwriting already-difficult-to-insure risks). Given that those scenarios seem unappealing for at least most of the CICs we’ve seen, it ultimately still comes down to the client’s own money paying for the client’s own risks, just through a self-created self-funded CIC intermediary. As I noted in the article, that can certainly still be appropriate, if there are savings from the tax treatment of the arrangement (especially if the risks never manifest as claims), or if there are insurance pricing efficiencies, but either way the benefits must still outweigh the hard dollar costs of the strategy.

      As for CIC structures with lower costs, certainly no disagreement that lowers the bar to breakeven on the benefits. I had not seen any offerings with costs as low as you’re mentioning here, but perhaps our clients have simply been unlucky in the providers offering CIC arrangements to them.

      In terms of Jay Adkisson’s credibility and information, I cannot say I’ve had the same negative experiences you apparently have. When so much of the information coming directly from the CIC providers presents them as though they are the greatest thing since sliced bread (though I’ll grant at least a few give a more balanced view of themselves), I find having an ‘outside’ perspective like Adkisson’s that isn’t being paid to implement the CIC to be very helpful. But you’re certainly welcome to suggest alternative resources in the comments here.

      Overall, though, I have to admit that I’m a bit puzzled by the overall tone of your comment. You would seem to be an advocate for the use of 831(b)s, and I specifically acknowledge that they are an entirely legitimate and reasonable strategy in the article, as long as the size of the risks and premiums and the benefits outweigh the hard costs of setup and maintenance. What exactly are you disagreeing with, short of suggesting that these arrangements have gotten cheaper recently and that they could perhaps go slightly further “down market” than the thresholds I mention in my article here?

      – Michael

  • Lance Wallach

    google lance wallach all over the net for captive problems and audits or

    • Lance Wallach

      Offices of Lance Wallach








      MARCH 26, 2015 ADMIN

      A warning for 419, 412i, Sec.79 and captive insuranceOctober 25, 2010 By: Lance Wallach

      Taxpayers who previously adopted 419, 412i, captive insurance or Section 79 plans are in big trouble.

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

      These plans were sold by insurance agents, financial planners, accountants and attorneys seeking large life insurance commissions. In general, taxpayers who engage in a “listed
      transaction” must report such transaction to the IRS on Form

  • Lance Wallach

    IRS Audits Focus on Captive Insurance Plans

    April 2011 Edition

    Lance Wallach

    The IRS started auditing § 419
    plans in the 1990s, and then continued going after § 412(i)
    and other plans that they considered abusive, listed, or reportable transactions,
    or substantially similar to such transactions. If an IRS audit disallows the § 419
    plan or the § 412(i) plan, not only does the taxpayer lose the
    deduction and pay interest and penalties, but then the IRS comes back under IRC
    6707A and imposes large fines for not properly filing.

    Insurance agents, financial planners and even
    accountants sold many of these plans. The main motivations for buying into one
    were large tax deductions. The motivation for the sellers of the plans was the
    very large life insurance premiums generated. These plans, which were vetted by
    the insurance companies, put lots of insurance on the books. Some of these
    plans continue to be sold, even after IRS disallowances and lawsuits against
    insurance agents, plan promoters and insurance companies.

    In a
    recent tax court case, Curcio v. Commissioner (TC Memo 2010-115), the
    tax court ruled that an investment in an employee welfare benefit plan marketed
    under the name “Benistar” was a listed transaction in that the transaction in
    question was substantially similar to the transaction described in IRS Notice
    95-34. A subsequent case, McGehee Family Clinic, largely followed Curcio,
    though it was technically decided on other grounds. The parties stipulated to
    be bound by Curcio on the issue of whether the amounts paid by McGehee
    in connection with the Benistar 419 Plan and Trust were deductible. Curcio
    did not appear to have been decided yet at the time McGehee was argued.
    The McGehee opinion (Case No. 10-102, United States Tax Court, September
    15, 2010) does contain an exhaustive analysis and discussion of virtually all
    of the relevant issues.

    and their representatives should be aware that the IRS has disallowed
    deductions for contributions to these arrangements. The
    IRS is cracking down on small business owners who participate in tax reduction
    insurance plans and the brokers who sold them. Some of these plans include
    defined benefit retirement plans, IRAs, or even 401(k) plans with life

    In order to fully grasp the severity
    of the situation, one must have an understanding of IRS Notice 95-34, which was
    issued in response to trust arrangements sold to companies that were designed
    to provide deductible benefits such as life insurance, disability and severance
    pay benefits. The promoters of these arrangements claimed that all employer
    contributions were tax-deductible when paid, by relying on the
    10-or-more-employer exemption from the IRC § 419 limits. It was claimed that
    permissible tax deductions were unlimited in amount.

    In general, contributions to a welfare benefit fund are not fully
    deductible when paid. Sections 419 and 419A impose strict limits on the amount
    of tax-deductible prefunding permitted for contributions to a welfare benefit
    fund. Section 419A(F)(6) provides an exemption from § 419 and § 419A for
    certain “10-or-more employers” welfare benefit funds. In general, for this
    exemption to apply, the fund must have more than one contributing employer, of
    which no single employer can contribute more than 10 percent of the total
    contributions, and the plan must not be experience-rated with respect to
    individual employers.

    According to the Notice, these arrangements typically involve an
    investment in variable life or universal life insurance contracts on the lives
    of the covered employees. The problem is that the employer contributions are
    large relative to the cost of the amount of term insurance that would be
    required to provide the death benefits under the arrangement, and the trust
    administrator may obtain cash to pay benefits other than death benefits, by
    such means as cashing in or withdrawing the cash value of the insurance
    policies. The plans are also often designed so that a particular employer’s
    contributions or its employees’ benefits may be determined in a way that
    insulates the employer to a significant extent from the experience of other
    subscribing employers. In general, the contributions and claimed tax deductions
    tend to be disproportionate to the economic realities of the arrangements.

    Benistar advertised that enrollees should expect to obtain the
    same type of tax benefits as listed in the transaction described in Notice
    95-34. The benefits of enrollment listed in its advertising packet

    unlimited deductions for the employer;

    could vary from year to year;

    could be provided to one or more key executives on a selective basis;

    need to provide benefits to rank-and-file employees;

    to the plan were not limited by qualified plan rules and would not
    interfere with pension, profit sharing or 401(k) plans;

    inside the plan would accumulate tax-free;

    could receive death proceeds free of both income tax and estate tax;

    program could be arranged for tax-free distribution at a later date;

    in the plan were secure from the hands of creditors.

    The Court said that the Benistar Plan was factually similar to the
    plans described in Notice 95-34 at all relevant times.

    In rendering its decision the court heavily cited Curcio,
    in which the court also ruled in favor of the IRS. As noted in Curcio,
    the insurance policies, overwhelmingly variable or universal life policies,
    required large contributions relative to the cost of the amount of term
    insurance that would be required to provide the death benefits under the
    arrangement. The Benistar Plan owned the insurance contracts.

    Following Curcio, as the Court has stipulated, the Court
    held that the contributions to Benistar were not deductible under § 162(a)
    because participants could receive the value reflected in the underlying
    insurance policies purchased by Benistar—despite the payment of benefits by
    Benistar seeming to be contingent upon an unanticipated event (the death of the
    insured while employed). As long as plan participants were willing to abide by
    Benistar’s distribution policies, there was no reason ever to forfeit a policy
    to the plan. In fact, in estimating life insurance rates, the taxpayers’ expert
    in Curcio assumed that there would be no forfeitures, even though he
    admitted that an insurance company would generally assume a reasonable rate of
    policy lapses.

    The McGehee Family Clinic had enrolled in the Benistar Plan in May
    2001 and claimed deductions for contributions to it in 2002 and 2005. The
    returns did not include a Form 8886, Reportable Transaction Disclosure
    Statement, or similar disclosure.

    The IRS disallowed the latter deduction and adjusted the
    2004 return of shareholder Robert Prosser and his wife to include the $50,000
    payment to the plan. The IRS also assessed tax deficiencies and the enhanced 30
    percent penalty totaling almost $21,000 against the clinic and $21,000 against
    the Prossers. The court ruled that the Prossers failed to prove a reasonable
    cause or good faith exception.

    Other important facts:

    In recent years,
    some § 412(i) plans have been funded with life insurance using face
    amounts in excess of the maximum death benefit a qualified plan is
    permitted to pay. Ideally, the plan should limit the proceeds that
    can be paid as a death benefit in the event of a participant’s death. Excess
    amounts would revert to the plan. Effective February 13, 2004, the
    purchase of excessive life insurance in any plan is considered a listed
    transaction if the face amount of the insurance exceeds the amount that
    can be issued by $100,000 or more and the employer has deducted the
    premiums for the insurance.

    A 412(i) plan in
    and of itself is not a listed transaction; however, the IRS has a task
    force auditing 412(i) plans.

    An employer has
    not engaged in a listed transaction simply because it is a 412(i) plan.

    Just because a
    412(i) plan was audited and sanctioned for certain items, does not
    necessarily mean the plan engaged in a listed transaction. Some 412(i)
    plans have been audited and sanctioned for issues not related to listed

    Companies should carefully evaluate proposed investments
    in plans such as the Benistar Plan. The claimed deductions will not be
    available, and penalties will be assessed for lack of disclosure if the
    investment is similar to the investments described in Notice 95-34. In
    addition, under IRC 6707A, IRS fines participants a large amount of money for
    not properly disclosing their participation in listed, reportable or similar
    transactions; an issue that was not before the tax court in either Curcio
    or McGehee. The disclosure needs to be made for every year the
    participant is in a plan. The forms need to be properly filed even for years
    that no contributions are made. I have received numerous calls from
    participants who did disclose and still got fined because the forms were not
    filled in properly. A plan administrator told me that he assisted hundreds of
    his participants with filing forms, and they still all received very large IRS
    fines for not properly filling in the forms.

    IRS has targeted all 419 welfare benefit plans, many
    412(i) retirement plans, captive insurance plans with life insurance in them
    and Section 79 plans.

    Lance Wallach, National Society of Accountants
    Speaker of the Year and member of the American Institute of CPAs faculty of
    teaching professionals, is a frequent speaker on retirement plans, financial
    and estate planning, and abusive tax shelters.
    He speaks at more than ten conventions annually and writes for over
    fifty publications. Lance has written numerous books including Protecting
    Clients from Fraud, Incompetence and Scams published by John Wiley and
    Sons, Bisk Education’s CPA’s Guide to Life Insurance and Federal
    Estate and Gift Taxation, as well as AICPA best-selling books, including Avoiding
    Circular 230 Malpractice Traps and Common Abusive Small Business Hot Spots.
    He does expert witness testimony and has never lost a case. Mr. Wallach may be
    reached at 516/938.5007,, or at or

    The information provided herein is not intended as legal,
    accounting, financial or any type of advice for any specific individual or
    other entity. You should contact an appropriate professional for any such

  • Lance Wallach



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    Section 79, Captive Insurance, IRS Audits and Lawsuits
    By Lance Wallach, CLU, CHFC

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    Section 79 and captive insurance plans with life insurance in them are being looked at by the IRS. We have received calls from people that are being audited. – The dangers of being “listed” – A warning for 419, 412i, Sec.79 and captive insurance. Accounting Today: October 25, 2010, By: Lance Wallach

    Taxpayers who previously adopted 419, 412i, captive insurance or Section 79 plans are in big trouble.

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

    These plans were sold by insurance agents, financial planners, accountants and attorneys seeking large life insurance commissions. In general, taxpayers who engage in a “listed transaction” must report such transaction to the IRS on Form 8886 every year that they “participate” in the transaction, and you do not necessarily have to make a contribution or claim a tax deduction to participate. Section 6707A of the Code imposes severe penalties ($200,000 for a business and $100,000 for an individual) for failure to file Form 8886 with respect to a listed transaction.

    But you are also in trouble if you file incorrectly.

    I have received numerous phone calls from business owners who filed and still got fined. Not only do you have to file Form 8886, but it has to be prepared correctly. I only know of two people in the United States who have filed these forms properly for clients. They tell me that was after hundreds of hours of research and over fifty phones calls to various IRS personnel.

    The filing instructions for Form 8886 presume a timely filing. Most people file late and follow the directions for currently preparing the forms. Then the IRS fines the business owner. The tax court does not have jurisdiction to abate or lower such penalties imposed by the IRS.

    Many business owners adopted 412i, 419, captive insurance and Section 79 plans based upon representations provided by insurance professionals that the plans were legitimate plans and were not informed that they were engaging in a listed transaction.

    Upon audit, these taxpayers were shocked when the IRS asserted penalties under Section 6707A of the Code in the hundreds of thousands of dollars. Numerous complaints from these taxpayers caused Congress to impose a moratorium on assessment of Section 6707A penalties.

    The moratorium on IRS fines expired on June 1, 2010. The IRS immediately started sending out notices proposing the imposition of Section 6707A penalties along with requests for lengthy extensions of the Statute of Limitations for the purpose of assessing tax. Many of these taxpayers stopped taking deductions for contributions to these plans years ago, and are confused and upset by the IRS’s inquiry, especially when the taxpayer had previously reached a monetary settlement with the IRS regarding its deductions. Logic and common sense dictate that a penalty should not apply if the taxpayer no longer benefits from the

    Treas. Reg. Sec. 1.6011-4(c)(3)(i) provides that a taxpayer has participated in a listed transaction if the taxpayer’s tax return reflects tax consequences or a tax strategy described in the published guidance identifying the transaction as a listed transaction or a transaction that is the same or substantially similar to a listed transaction. Clearly, the primary benefit in the participation of these plans is the large tax deduction generated by such participation. It follows that taxpayers who no longer enjoy the benefit of those large deductions are no longer “participating ‘ in the listed transaction. But that is not the end of the story.

    Many taxpayers who are no longer taking current tax deductions for these plans continue to enjoy the benefit of previous tax deductions by continuing the deferral of income from contributions and deductions taken in prior years. While the regulations do not expand on what constitutes “reflecting the tax consequences of the strategy”, it could be argued that continued benefit from a tax deferral for a previous tax deduction is within the contemplation of a “tax consequence” of the plan strategy. Also, many taxpayers who no longer make contributions or claim tax deductions continue to pay administrative fees. Sometimes, money is taken from the plan to pay premiums to keep life insurance policies in force. In these ways, it could be argued that these taxpayers are still “contributing”, and thus still must file Form 8886.

    It is clear that the extent to which a taxpayer benefits from the transaction depends on the purpose of a particular transaction as described in the published guidance that caused such transaction to be a listed transaction. Revenue Ruling 2004-20 which classifies 419(e) transactions, appears to be concerned with the employer’s contribution/deduction amount rather than the continued deferral of the income in previous years. This language may provide the taxpayer with a solid argument in the event of an audit.

    The information provided herein is not intended as legal, accounting, financial or any other type of advice for any specific individual or other entity. You should contact an appropriate professional for any such advice.

    ABOUT THE AUTHOR: Lance Wallach
    Lance Wallach, National Society of Accountants Speaker of the Year and member of the AICPA faculty of teaching professionals, is a frequent speaker on retirement plans, financial and estate planning, and abusive tax shelters. He writes about 412(i), 419, and captive insurance plans. He speaks at more than ten conventions annually, writes for over fifty publications, is quoted regularly in the press and has been featured on television and radio financial talk shows including NBC, National Public Radio’s All Things Considered, and others. Lance has written numerous books including Protecting Clients from Fraud, Incompetence and Scams published by John Wiley and Sons, Bisk Education’s CPA’s Guide to Life Insurance and Federal Estate and Gift Taxation, as well as AICPA best-selling books, including Avoiding Circular 230 Malpractice Traps and Common Abusive Small Business Hot Spots. He does expert witness testimony and has never lost a case.

    Copyright Lance Wallach, CLU, CHFC
    More information about Lance Wallach, CLU, CHFC

    Disclaimer: While every effort has been made to ensure the accuracy of this publication, it is not intended to provide legal advice as individual situations will differ and should be discussed with an expert and/or lawyer. For specific technical or legal advice on the information provided and related topics, please contact the author

  • Michael Kitces

    Using CICs is not a gray area of the law. The “gray area” Jay was referring to were those who are trying to invest the money inside of CICs in life insurance and use that money to pay a death benefit outside of the estate.

    That’s a separate messy matter from just the standard approach of using CICs (which is not gray).

    But yes, there are definitely some aggressive and shady and “gray” versions of complex CIC strategies out there.
    – Michael

Michael E. Kitces

I write about financial planning strategies and practice management ideas, and have created several businesses to help people implement them.

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