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Unpaid taxes a buyer could inherit

Tax the business should have paid does not disappear when it changes hands. In a share sale it stays with the company you buy, and some unpaid taxes can follow even an asset purchase.
Category
Legal and compliance
Applies to
All business models
Severity
Price it in
Last updated
Author
Loupe editorial
Reviewer
Not yet reviewed

Why it matters

Unpaid tax does not disappear when a business changes hands. Sales tax, VAT or GST, payroll taxes, income or corporation tax, property taxes and customs duties can all be owed for periods before you took over, along with interest and penalties.

In a share sale (a stock sale in the US), the company you buy keeps its full tax history. Any underpayment, late filing or open enquiry stays with it and becomes your problem. Buyers usually protect themselves with a tax indemnity (often called a tax covenant in the UK) and warranties from the seller, and by holding part of the price in escrow or as a holdback. An indemnity is only as good as the seller's ability to pay when a claim arrives, which may be years later.

An asset sale lowers the risk but does not remove it. In many US states, a buyer of business assets can become liable for the seller's unpaid sales and use taxes unless the buyer follows the state's process, which can mean notifying the tax authority before paying, holding back part of the price or obtaining a tax clearance certificate. In the UK, a buyer who takes over the seller's VAT registration number when a business transfers as a going concern also takes on the seller's outstanding VAT. Rules differ by country and by type of tax, so take advice from a tax adviser in each country where the business operates.

Tax problems also say something about the records. A business that has not paid what it owes may also be understating income, treating employees as contractors or keeping cash sales out of the accounts. Loupe's valuation tool reduces the multiple, at its starting settings, by 10% where some legal, tax or compliance issues are known, and by 30% with confidence set to low where they are significant.

Asset sale versus share sale

In an asset sale you buy selected assets of a business; in a share sale (a stock sale in the US) you buy the company itself, with its full history. The choice shapes risk, tax and what needs consent.

Warranties and indemnities

Warranties are the seller's statements of fact about a business in the purchase agreement; indemnities are promises to reimburse specific losses. Together they decide who bears risks that diligence could not rule out.

Escrow

Escrow is an arrangement in which an independent third party holds money until agreed conditions are met. In a business sale it keeps part of the price available to cover claims after completion.

How to spot it

  • Tax balances on the balance sheet keep growing, or the business is on a payment plan with a tax authority.
  • The ledgers show late filing penalties, interest charges or notices from tax authorities.
  • The business sells online into several states or countries but collects tax in only one.
  • Workers are paid as contractors, or staff receive cash payments.
  • The accounts and the tax returns show different figures.
  • The seller pushes for an asset sale with no clearance process, or resists a tax indemnity.

Questions to ask the seller

  • Are all tax returns filed and all taxes paid to date, for every tax and every country?
  • Is the business under audit or enquiry, or in a payment arrangement with any tax authority?
  • Where does the business collect sales tax, VAT or GST, and how was that decided?
  • Have any penalties or interest charges been applied in the last three years?
  • Can you obtain tax clearance or good standing certificates before completion?
  • Would you agree to a tax indemnity, and to part of the price being held back until clearance arrives?

Documents to request

  • Tax returns for the last three to five years, for every tax the business files
  • Statements from tax authorities showing balances, payments, penalties and interest
  • Correspondence with tax authorities, including audit and enquiry letters and payment plans
  • A list of the places where the business is registered for sales tax, VAT or GST
  • Payroll tax filings reconciled to the payroll records
  • Tax clearance or good standing certificates, where the country or state offers them

Sources

  1. Successor liability and clearance certificates (opens in a new tab). Wisconsin Department of Revenue, 16 October 2025.
  2. Bulk sales (TB-ST-70) (opens in a new tab). New York State Department of Taxation and Finance, 17 June 2025.
  3. Transfer a business as a going concern (VAT Notice 700/9) (opens in a new tab). HM Revenue and Customs, 23 May 2025.

Want this checked properly on a real listing?

A dossier checks the listing's figures, registrations and risks, with a source and confidence for every finding. Open a listing in the feed and request a dossier from its page.

  • Tax returns that do not match the accounts

    When the profit in the tax returns cannot be reconciled to the profit in the accounts, you cannot tell which figures to trust, and there may be tax owed.

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  • Unrecorded cash sales

    A seller who says the business takes more cash than the books show is asking you to pay for income nobody can verify, and may be passing on a tax problem.

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  • Contractors who are employees in practice

    Treating people who work like employees as self-employed can flatter profit and build up back taxes and employment claims. Size the exposure and the true cost of labour before you agree a price.

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  • Payables stretched ahead of a sale

    Paying suppliers late before a sale builds up cash the seller can take out and leaves you to pay the bills. A working capital adjustment usually fixes it.

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  • Pending or threatened litigation

    A live or threatened claim can cost a business far more than any damages, and some claims follow the business to a new owner. Find every dispute, understand who carries it after the sale and price or protect against it.

    Severity: price it inLegal and compliance
  • Due diligence: what to check and in what order

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  • Diligence document request list

    The documents to ask for once terms are agreed in principle, grouped by area so the seller can fill a data room in order and you can see what is still missing.

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  • Asset sale versus share sale

    In an asset sale you buy selected assets of a business; in a share sale (a stock sale in the US) you buy the company itself, with its full history. The choice shapes risk, tax and what needs consent.

  • Warranties and indemnities

    Warranties are the seller's statements of fact about a business in the purchase agreement; indemnities are promises to reimburse specific losses. Together they decide who bears risks that diligence could not rule out.

  • Escrow

    Escrow is an arrangement in which an independent third party holds money until agreed conditions are met. In a business sale it keeps part of the price available to cover claims after completion.

  • Holdback

    A holdback is part of the purchase price the buyer keeps back at completion and pays later if no valid claims arise. Unlike escrow, the money stays with the buyer.

  • Cash-free, debt-free

    Cash-free, debt-free is a pricing basis in which the headline price assumes the business changes hands with no cash and no borrowings. The seller keeps the cash, repays the debt and leaves a normal level of working capital behind.

  • See a low, likely and high value from the figures you have, and whether the asking price holds up.

  • Answer about 15 quick questions about a listing to see which areas need checking.

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