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Category: 55(2)

Deliberate triggering of 55(2) and the GAAR

Posted on: August 22, 2026 Last updated on: August 21, 2026 Written by: John Loukidelis
The CRA accepted that the pre-2024 GAAR did not apply where subsection 55(2) was triggered deliberately. Will the amended GAAR apply to such planning? The authors point out that the economic substance test in subsection 245(4.1), if it applies, is…
Continue reading “Deliberate triggering of 55(2) and the GAAR”…

Subsection 55(2) can be good actually

Posted on: June 6, 2026 Last updated on: June 5, 2026 Written by: John Loukidelis
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”…

55(3.01)(g) butterflies

Posted on: January 19, 2024 Last updated on: January 11, 2024 Written by: John Loukidelis
The authors describe a scenario where Aco and Bco own 85% and 15% respectively of Opco. Opco cannot spin-off its real property to Realco where Aco and Bco become direct 85/15 shareholders of Realco. 55(3)(a) will not apply because Bco…
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Part IV and 55(2) confusion

Posted on: April 21, 2023 Last updated on: April 19, 2023 Written by: John Loukidelis
Consider the situation where subsection 55(2) applies to a dividend because it is paid as part of a series that includes the refund of the Part IV tax that was payable on the dividend. Ottawa Air Cargo Centre Ltd. v…
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Safe income again

Posted on: March 9, 2023 Last updated on: March 6, 2023 Written by: John Loukidelis
A corporation must reduce the safe income of its shares by contingent liabilities and reserves, if they reduce the “inherent gain” of the shares. “The safe income is reduced by actual and potential cash outflows”. APFF 2022 Conference question 1,…
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Safe income determination time

Posted on: March 6, 2023 Last updated on: March 6, 2023 Written by: John Loukidelis
If Aco is incorporated to purchase the assets of Bco and then purchases the assets, Bco’s safe income is not increased by any gain realized on the sale if the incorporation of Aco triggers the safe income determination time. The…
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RDTOH and safe income

Posted on: February 17, 2023 Last updated on: February 17, 2023 Written by: John Loukidelis
The CRA accepts that, if refundable tax contributes to the gain on a share immediately before its disposition, it can also contribute to the safe income of the share. In the example, a corporation with a December 31 year-end, sells…
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GAAR and 55(2)

Posted on: November 9, 2022 Last updated on: November 7, 2022 Written by: John Loukidelis
3295940 Canada Inc. v R, 2022 TCC 68 considered a taxpayer who had wanted to sell shares of 329, which had a high tax cost, to an arm’s length purchaser. The purchaser would not buy the shares for commercial reasons.…
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Dividend ordering

Posted on: August 12, 2022 Last updated on: August 12, 2022 Written by: John Loukidelis
Holdco owns all of the shares of Opco, which are worth $5 million. The Opco shares have safe income of $1 million. Opco has GRIP of $1 million and NERDTOH of $70,000. Opco can pay a $1 million eligible dividend…
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55(2) and T5s

Posted on: July 18, 2022 Last updated on: July 18, 2022 Written by: John Loukidelis
Opco pays a dividend to Holdco, and part of the dividend is re-characterized as a capital gain under subsection 55(2). Does that affect the amount of the dividend reported on the T5 for the dividend? I have not been able…
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Pleading away privilege

In One York Street Inc. v 2360083 Ontario Limited, 2026 ONCA 176, the Court held that, by putting in issue its state of mind on signing a lease where the state of mind was based in part on legal advice,…
Continue reading “Pleading away privilege”…

Resigning as a director

According to the author, Stevens v R, 2026 TCC 76, is an important reminder of the importance of “objective” evidence for a director’s resignation. Having a resignation witnessed, ensuring that the corporation has updated its records and ensuring that the…
Continue reading “Resigning as a director”…

Build Canada announcements

Oslers has a couple of good posts on its website—here and here—about tax-related “Canada strong” announcements. The CRA, when considering advance tax rulings, will prioritize “nation-building projects”, and the Income Tax Act (Canada) will be amended to permit a new…
Continue reading “Build Canada announcements”…

Receipts from fraudulent investment schemes

In Daniel Sze “Receipts from Fraudulent Schemes: When Are They Taxable?” Canadian Tax Focus 16:3 (August 2026), the author gives an overview of cases that have considered the taxation of amounts a taxpayer receives from a fraudulent “investment”. He notes…
Continue reading “Receipts from fraudulent investment schemes”…

Deductibility of professional fees

In Hypertec Systèmes inc. v Agence du revenu du Québec, 2025 QCCQ 6704, the taxpayer, the administrative entity for a corporate group, incurred about $1.3 million of professional fees in respect of a shareholder dispute that included a claim for…
Continue reading “Deductibility of professional fees”…

Recent Posts

Pleading away privilege

In One York Street Inc. v 2360083 Ontario Limited, 2026 ONCA 176, the Court held that, by putting in issue its state of mind on signing a lease where the state of mind was based in part on legal advice,…
Continue reading “Pleading away privilege”…

Resigning as a director

According to the author, Stevens v R, 2026 TCC 76, is an important reminder of the importance of “objective” evidence for a director’s resignation. Having a resignation witnessed, ensuring that the corporation has updated its records and ensuring that the…
Continue reading “Resigning as a director”…

Build Canada announcements

Oslers has a couple of good posts on its website—here and here—about tax-related “Canada strong” announcements. The CRA, when considering advance tax rulings, will prioritize “nation-building projects”, and the Income Tax Act (Canada) will be amended to permit a new…
Continue reading “Build Canada announcements”…

Receipts from fraudulent investment schemes

In Daniel Sze “Receipts from Fraudulent Schemes: When Are They Taxable?” Canadian Tax Focus 16:3 (August 2026), the author gives an overview of cases that have considered the taxation of amounts a taxpayer receives from a fraudulent “investment”. He notes…
Continue reading “Receipts from fraudulent investment schemes”…

Deductibility of professional fees

In Hypertec Systèmes inc. v Agence du revenu du Québec, 2025 QCCQ 6704, the taxpayer, the administrative entity for a corporate group, incurred about $1.3 million of professional fees in respect of a shareholder dispute that included a claim for…
Continue reading “Deductibility of professional fees”…

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Archives

Categories

Recent Posts

Pleading away privilege

In One York Street Inc. v 2360083 Ontario Limited, 2026 ONCA 176, the Court held that, by putting in issue its state of mind on signing a lease where the state of mind was based in part on legal advice,…
Continue reading “Pleading away privilege”…

Resigning as a director

According to the author, Stevens v R, 2026 TCC 76, is an important reminder of the importance of “objective” evidence for a director’s resignation. Having a resignation witnessed, ensuring that the corporation has updated its records and ensuring that the…
Continue reading “Resigning as a director”…

Build Canada announcements

Oslers has a couple of good posts on its website—here and here—about tax-related “Canada strong” announcements. The CRA, when considering advance tax rulings, will prioritize “nation-building projects”, and the Income Tax Act (Canada) will be amended to permit a new…
Continue reading “Build Canada announcements”…

Receipts from fraudulent investment schemes

In Daniel Sze “Receipts from Fraudulent Schemes: When Are They Taxable?” Canadian Tax Focus 16:3 (August 2026), the author gives an overview of cases that have considered the taxation of amounts a taxpayer receives from a fraudulent “investment”. He notes…
Continue reading “Receipts from fraudulent investment schemes”…

Deductibility of professional fees

In Hypertec Systèmes inc. v Agence du revenu du Québec, 2025 QCCQ 6704, the taxpayer, the administrative entity for a corporate group, incurred about $1.3 million of professional fees in respect of a shareholder dispute that included a claim for…
Continue reading “Deductibility of professional fees”…

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