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Category: TOSI

TOSI and a power of attorney

Posted on: August 18, 2025 Last updated on: August 14, 2025 Written by: John Loukidelis
Son is the owner of 10 out of 100 issued Common Shares in the capital of Opco, which are the only issued shares of the corporation. Son grants a power of attorney to his father to exercise all rights to…
Continue reading “TOSI and a power of attorney”…

Deduction for TOSI under 20(1)(ww)

Posted on: December 1, 2023 Last updated on: November 27, 2023 Written by: John Loukidelis
A taxpayer can deduct an amount under paragraph 20(1)(ww) even if the taxpayer must include a taxable capital gain in income that is subject to TOSI but he or she can offset the gain with an allowable capital loss. STEP…
Continue reading “Deduction for TOSI under 20(1)(ww)”…

More good times with TOSI

Posted on: February 11, 2023 Last updated on: February 10, 2023 Written by: John Loukidelis
The CRA confirmed that multiple businesses run by a husband and wife where they work fewer than 20 hours per week in each business would not be “excluded businesses” under the “bright line test” for substantial involvement. The CRA wrote…
Continue reading “More good times with TOSI”…

82(3) elections and TOSI

Posted on: February 14, 2022 Last updated on: February 14, 2022 Written by: John Loukidelis
This articles review the interaction of the subsection 82(3) election and the TOSI rules. “n the CRA’s view, the correct method of applying the two provisions is to allocate receipt of the dividends in accordance with subsection 82(3) and then…
Continue reading “82(3) elections and TOSI”…

TOSI and digital downloads

Posted on: October 19, 2020 Last updated on: October 19, 2020 Written by: John Loukidelis
In technical interpretation 2019-0833181E5 (March 15, 2020), the CRA considered when the sale or licensing of digital products could be considered to generate income from a service for the purposes of the TOSI rules. According to the CRA, the download…
Continue reading “TOSI and digital downloads”…

TOSI and foreign affiliates

Posted on: March 2, 2020 Last updated on: March 2, 2020 Written by: John Loukidelis
The TOSI rules don’t just apply to dividends from Canadian private corporations. The rules can apply to dividends from foreign private corporations as well, and the tax results are potentially horrendous. Stan Shadrin, Manu Kakkar and Alex Ghani, “FAPI and…
Continue reading “TOSI and foreign affiliates”…

TOSI and business reorganizations

Posted on: March 2, 2020 Last updated on: March 2, 2020 Written by: John Loukidelis
In a technical interpretation (TI 2019-0814181E5, August 19, 2019), the CRA confirmed that the five-year test to qualify for the “excluded business” exception under the TOSI (tax on split income) rules should take into account all taxation years in which…
Continue reading “TOSI and business reorganizations”…

Capital gains and excluded shares

Posted on: October 15, 2019 Last updated on: October 15, 2019 Written by: John Loukidelis
The CRA believes that taxable capital gains are “income” for the purposes of paragraph (c) of the “excluded shares” definition in the TOSI rules. The CRA also states that the gains in question should be computed on a gross basis,…
Continue reading “Capital gains and excluded shares”…

Five-year test when no related individual

Posted on: July 13, 2019 Last updated on: July 13, 2019 Written by: John Loukidelis
An employee who works in a business on a full-time basis (ie more than an average of 20 hours per week) for five or more years will not be subject to TOSI even where the years occurred before the TOSI…
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TOSI and rental income

Posted on: July 10, 2019 Last updated on: July 10, 2019 Written by: John Loukidelis
Mr X owns the voting shares of Holdco that owns a rental property. His two kids own non-voting shares that on which Holdco pays dividends. Does the TOSI apply to dividends paid to the kids? Is the rental operation a…
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Related siblings under section 55

At the 2025 APFF conference, the CRA stated that the sisters in the following scenario would be related as per subparagraph 55(5)(e)(i): Sister A and Sister B each owned 100 percent of the shares of their respective holding corporations, whose…
Continue reading “Related siblings under section 55”…

Subsection 55(2) can be good actually

If subsection 55(2) applies to a dividend, and the cash related to the dividend needs to be paid to an individual shareholder anyway, the shareholder will likely be better off compared to the situation obtained when the subsection does not…
Continue reading “Subsection 55(2) can be good actually”…

Loans by a partnership to a partner

The CRA has generally held that a loan from a partnership to a partner will reduce the ACB of the partner’s partnership interest because of the “all-encompassing” language in subparagraph 53(2)(c)(v) of the Income Tax Act (Canada). The CRA has…
Continue reading “Loans by a partnership to a partner”…

Directors of a dissolved corporation

In 2008, I wrote an article for the Hamilton Law Association Journal that, among other things, addressed the status of directors of a corporation that has been dissolved. I referred to Leger v R, 2007 TCC 322, which held that,…
Continue reading “Directors of a dissolved corporation”…

DAC Investment

The authors discuss R v DAC Investment Holdings Inc., 2026 FCA 35, rev’g 2024 TCC 63. They conclude that, in a GAAR analysis, an overly-broad characterization of a provision or a mere description of its effect will not correctly express its object, spirit and purpose…
Continue reading “DAC Investment”…

Recent Posts

Related siblings under section 55

At the 2025 APFF conference, the CRA stated that the sisters in the following scenario would be related as per subparagraph 55(5)(e)(i): Sister A and Sister B each owned 100 percent of the shares of their respective holding corporations, whose…
Continue reading “Related siblings under section 55”…

Subsection 55(2) can be good actually

If subsection 55(2) applies to a dividend, and the cash related to the dividend needs to be paid to an individual shareholder anyway, the shareholder will likely be better off compared to the situation obtained when the subsection does not…
Continue reading “Subsection 55(2) can be good actually”…

Loans by a partnership to a partner

The CRA has generally held that a loan from a partnership to a partner will reduce the ACB of the partner’s partnership interest because of the “all-encompassing” language in subparagraph 53(2)(c)(v) of the Income Tax Act (Canada). The CRA has…
Continue reading “Loans by a partnership to a partner”…

Directors of a dissolved corporation

In 2008, I wrote an article for the Hamilton Law Association Journal that, among other things, addressed the status of directors of a corporation that has been dissolved. I referred to Leger v R, 2007 TCC 322, which held that,…
Continue reading “Directors of a dissolved corporation”…

DAC Investment

The authors discuss R v DAC Investment Holdings Inc., 2026 FCA 35, rev’g 2024 TCC 63. They conclude that, in a GAAR analysis, an overly-broad characterization of a provision or a mere description of its effect will not correctly express its object, spirit and purpose…
Continue reading “DAC Investment”…

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Archives

Categories

Recent Posts

Related siblings under section 55

At the 2025 APFF conference, the CRA stated that the sisters in the following scenario would be related as per subparagraph 55(5)(e)(i): Sister A and Sister B each owned 100 percent of the shares of their respective holding corporations, whose…
Continue reading “Related siblings under section 55”…

Subsection 55(2) can be good actually

If subsection 55(2) applies to a dividend, and the cash related to the dividend needs to be paid to an individual shareholder anyway, the shareholder will likely be better off compared to the situation obtained when the subsection does not…
Continue reading “Subsection 55(2) can be good actually”…

Loans by a partnership to a partner

The CRA has generally held that a loan from a partnership to a partner will reduce the ACB of the partner’s partnership interest because of the “all-encompassing” language in subparagraph 53(2)(c)(v) of the Income Tax Act (Canada). The CRA has…
Continue reading “Loans by a partnership to a partner”…

Directors of a dissolved corporation

In 2008, I wrote an article for the Hamilton Law Association Journal that, among other things, addressed the status of directors of a corporation that has been dissolved. I referred to Leger v R, 2007 TCC 322, which held that,…
Continue reading “Directors of a dissolved corporation”…

DAC Investment

The authors discuss R v DAC Investment Holdings Inc., 2026 FCA 35, rev’g 2024 TCC 63. They conclude that, in a GAAR analysis, an overly-broad characterization of a provision or a mere description of its effect will not correctly express its object, spirit and purpose…
Continue reading “DAC Investment”…

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