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Category: 55(2)

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…
Continue reading “55(3.01)(g) butterflies”…

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…
Continue reading “Part IV and 55(2) confusion”…

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…
Continue reading “RDTOH and safe income”…

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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Part IV and 55(2) protection

Posted on: April 21, 2022 Last updated on: April 21, 2022 Written by: John Loukidelis
Under the new refundable tax rules, carefully paying dividends can maximize the use of both safe income and Part IV to protect dividends from 55(2). “This tax-planning opportunity requires very specific tax attributes for the payer: a GRIP corresponding to…
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Post-butterfly dispositions gone wrong

Posted on: April 13, 2022 Last updated on: April 13, 2022 Written by: John Loukidelis
The authors note a number of significant issues with 55(3.1)(c): What is a series of transactions? (55(3.1)(c)(i)) What is considered the ordinary course of business? (subclause 55(3.1)(c)(i)(A)(I)) How is the 10% allowable threshhold determined? (pre- and postamble to 55(3.1)(c) and…
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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”…

Limits on CRA demands for information

In Canada (National Revenue) v Cohen, 2025 FC 2012, the Court dismissed a Crown application for a compliance order because the taxpayer had demonstrated, on a balance of probabilities, that he had done everything reasonably possible to obtain the documents…
Continue reading “Limits on CRA demands for information”…

Post-mortem bumps and grandchildren

The bump under ITA paragraph 88(1)(d) could be denied if a “specified shareholder” receives bumped property unless the shareholder was also a “specified person” as defined in paragraph 88(1)(c.2). Grandchildren who receive bumped property could taint the bump if they…
Continue reading “Post-mortem bumps and grandchildren”…

Post-mortem bumps and capital dividends paid from life insurance

Bump room is determined by the ACB of the target corporation’s shares minus the net tax cost of the underlying assets and the amounts in ITA subparagraph 88(1)(d)(i.1), which include taxable dividends and capital dividends. Accordingly, a target corporation that…
Continue reading “Post-mortem bumps and capital dividends paid from life insurance”…

Recent Posts

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”…

Limits on CRA demands for information

In Canada (National Revenue) v Cohen, 2025 FC 2012, the Court dismissed a Crown application for a compliance order because the taxpayer had demonstrated, on a balance of probabilities, that he had done everything reasonably possible to obtain the documents…
Continue reading “Limits on CRA demands for information”…

Post-mortem bumps and grandchildren

The bump under ITA paragraph 88(1)(d) could be denied if a “specified shareholder” receives bumped property unless the shareholder was also a “specified person” as defined in paragraph 88(1)(c.2). Grandchildren who receive bumped property could taint the bump if they…
Continue reading “Post-mortem bumps and grandchildren”…

Post-mortem bumps and capital dividends paid from life insurance

Bump room is determined by the ACB of the target corporation’s shares minus the net tax cost of the underlying assets and the amounts in ITA subparagraph 88(1)(d)(i.1), which include taxable dividends and capital dividends. Accordingly, a target corporation that…
Continue reading “Post-mortem bumps and capital dividends paid from life insurance”…

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Archives

Categories

Recent Posts

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”…

Limits on CRA demands for information

In Canada (National Revenue) v Cohen, 2025 FC 2012, the Court dismissed a Crown application for a compliance order because the taxpayer had demonstrated, on a balance of probabilities, that he had done everything reasonably possible to obtain the documents…
Continue reading “Limits on CRA demands for information”…

Post-mortem bumps and grandchildren

The bump under ITA paragraph 88(1)(d) could be denied if a “specified shareholder” receives bumped property unless the shareholder was also a “specified person” as defined in paragraph 88(1)(c.2). Grandchildren who receive bumped property could taint the bump if they…
Continue reading “Post-mortem bumps and grandchildren”…

Post-mortem bumps and capital dividends paid from life insurance

Bump room is determined by the ACB of the target corporation’s shares minus the net tax cost of the underlying assets and the amounts in ITA subparagraph 88(1)(d)(i.1), which include taxable dividends and capital dividends. Accordingly, a target corporation that…
Continue reading “Post-mortem bumps and capital dividends paid from life insurance”…

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