An Overview of Tax Liability Insurance
POSTED 6.18.19 Insurance, M&A

With any merger or acquisition, tax liability is a major concern because when you buy a company you assume its tax obligations. And you can bet the IRS is keeping close tabs on every transaction for taxable events, not to mention state tax authorities.

Not paying attention to tax treatments that apply to acquisitions could cost a Buyer significantly, and perhaps negate any advantage they had in the deal at all. For example, say a Buyer purchases because they think it has favorable tax deals, but the taxing authority disagrees. Then they’re on the hook for the tax bill.

But for a low premium, tax insurance, with policy terms generally set at six years, would protect against that disastrous event. Think of tax insurance as an “add-on” to Representations and Warranty insurance, kind of like you add earthquake or hurricane coverage to your homeowner’s policy.

That might be putting it too lightly, actually. Tax insurance protects a taxpayer (in this case, the acquiring company) if there is a failure of tax position arising from an M&A transaction, as well as reorganizations, accounting treatments, or investments.

A few examples of where tax liability insurance would be applicable (thanks to RT ProExec Transactional Risk’s recent white paper for this info and other helpful tips in this post):

  1. Historic tax positions of a target entity in an M&A transaction
  2. Investment in clean energy (e.g. solar), new market, rehabilitation, and other investor tax credits
  3. Real Estate Investment Trusts (“REIT”) and their representations as to their REIT status in an acquisition
  4. Foreign tax credits
  5. Preservation of (or availability of exceptions to any limitations to) net operating losses and other tax attributes following a transaction
  6. Transfer pricing
  7. Tax treatment of reorganizations, recapitalizations and/or spin-offs
  8. Debt v. Equity analysis
  9. Capital gain versus ordinary income treatment
  10. Deductibility of expenses (as opposed to capitalization)
  11. Excessive compensation
  12. Deferred compensation
  13. Whether withholding taxes are imposed
  14. Whether distributions constitute a “disguised sale”
  15. Valuation risks
  16. S Corporations and 338(h)(10) elections

Checking tax status is, of course, part of any Buyer’s due diligence. An outstanding tax bill is easy to find. But certain tax treatments the Seller insists are correct and up to standard, may not be. The Buyer, relying on its tax attorney’s specialized tax expertise, can insist those issues be taken care of pre-sale because they are exposures.

In the past, Sellers could go to the IRS and ask, “Is this an exposure?” and get a Private Letter Ruling okaying the request. But with the IRS swamped these days, they’re not really issued anymore.

Where Tax Insurance Comes In

When there are tax issues that come up for debate during due diligence for an M&A transaction, both sides bring in tax attorneys and each side makes the best determination in their opinion if this is a taxable transaction or not. They could take a light touch or be very conservative.

The Buyer will likely insist that a portion of any tax liability goes to the Seller, whose expert says they don’t agree with that determination. If there is a disagreement – get tax insurance.

Underwriters will get letters from tax attorneys from both sides outlining their arguments, along with supporting documents. It’s quite simple underwriting.

Underwriters want to see:

  • Name and address of the insured.
  • Covered tax descriptions of detailed descriptions of the underlying transaction and the relevant tax issues.
  • Draft opinion from a tax advisor.
  • The tax backgrounds of the Buyer and Seller.
  • Limit of liability the insured would desire.
  • A potential loss calculation, including additional taxes, interest, penalties, claim expenses, and gross-up.

It generally takes the Underwriters about three to four days to deliver a preliminary response.

In some cases, M&A transactions can become tax-free transactions or tax-free exchanges. Of course, the IRS can always disagree and insist on back taxes and fines.

Some things to keep in mind:

When Underwriters aren’t confident about a specific tax position, they may set retention at where they think the tax authority would settle. When they are more confident, they will be okay with minimal retention by the insured or none at all.

If a tax memo convinces them that the IRS agrees that it is not a taxable event – good. If not, the IRS triggers an inspection.

The insurance will pay the legal costs to fight the IRS, as well as taxes, penalties, and fines if they lose. And, get this. If your insurance win was, let’s say, $5 million and the IRS says, “You just made $5 million in income,” the insurance will pay tax on that as well. That is known as a “gross-up.”

Tax liability insurance is more expensive than R&W (it generally costs between 3% to 6% of the limit), but it makes sense as the stakes are higher. So it should be an important part of any M&A transaction.

If you’d like to discuss how to protect yourself with tax liability insurance and how it coordinates with R&W coverage (because R&W does not include a Seller’s identified or disclosed tax risks), please call me, Patrick Stroth, at (415) 806-2356 or email me at, to further discuss this vital insurance protection.