Can I deliberately structure my companies to avoid being associated for tax purposes?

Legitimate structuring to avoid association is possible, there are genuine ways to arrange ownership and control, such as issuing different classes of shares with carefully considered voting rights, or ensuring there's truly no common control or related-person connection between corporations, that can keep separate businesses from being associated under the Income Tax Act. This is different from simply moving names around on paper while control stays the same in substance.

Where this gets risky is when a structure is put in place specifically, and primarily, to circumvent the associated corporation rules without any other real business purpose, CRA scrutinizes arrangements that look designed purely to multiply access to the small business rate, and broader anti-avoidance provisions can potentially apply in more aggressive cases where the structure has no purpose beyond the tax result itself. A structure built for genuine business reasons that happens to also avoid association is in a very different position than one built with no purpose except avoiding it.

Because the line between legitimate structuring and an arrangement CRA will challenge isn't always obvious from the outside, getting proper professional advice before implementing any structure aimed at managing association status is far safer than assuming a particular arrangement will automatically be respected.