Two facts decide this, and most buyers only check one of them: what you're buying, and who you're buying it from.
Short answer
Not automatically — but two specific fact patterns will make you liable: buying assets from a related party (or below fair market value), and buying the shares of a company whose own tax history you now own outright. An asset purchase from an unrelated seller at a fair price generally carries none of the seller's tax debt at all.
“Transferee liability” is the mechanism, and it only bites on a specific fact pattern. Income Tax Act s.160(1) provides that where property is transferred to a person not dealing at arm's length with the transferor, “the transferee and transferor are jointly and severally … liable to pay under this Act an amount equal to the lesser of (i) the amount, if any, by which the fair market value of the property at the time it was transferred exceeds the fair market value at that time of the consideration given for the property, and (ii) the total of all amounts … that the transferor is liable to pay under this Act … in or in respect of the taxation year in which the property was transferred or any preceding taxation year.” The Excise Tax Act carries an almost identical rule for GST/HST at s.325(1): the transferee and transferor are “jointly and severally, or solidarily, liable to pay under this Part” on the same value-gap test.
Two features matter more than the headline number. First, the liability is capped at the value gap — pay full price and there is nothing to catch. Second, there is no clock on it: “The Minister may at any time assess a taxpayer in respect of any amount payable because of this section,” so it does not age out the way an ordinary reassessment risk does.
Structure is the whole question. If the asset deal is between related parties or below fair value, s.160/s.325 attach regardless of how careful the paperwork is. If the identical undisclosed liability turns up on an arm's-length asset purchase at a fair price, neither provision reaches the buyer at all — the exposure is zero, not merely capped.
A share purchase is a different question entirely. There is no transferee-liability test to pass or fail, because you are not a transferee — you own the corporation, and every year the CRA can still reassess it travels with the shares. That is a matter of how long the reassessment window stays open, not who the buyer is.
A 30-minute call is enough to tell you which of these facts applies to your deal.
Canadian small-business transaction data is not published anywhere, so most valuations in this country quote an American benchmark. The Deavo–Treadstone Acquisition Index is a daily record of Canadian listings built to replace that: asking-price distributions by province and city are published now, and days on market, departure rates and asking-to-sale spreads follow as the series lengthens. Leave an email and we will tell you as each measure lands.
No pitch, no listings. One email when the first report lands.