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Category: 55(2) (page 2)

CRA problems with 55(3)(a) butterflies

Posted on: February 11, 2022 Last updated on: February 11, 2022 Written by: John Loukidelis
The CRA might apply the GAAR to a 55(3)(a) butterfly if A + B > C where A is the ACB of the remaining shares in the capital of DC after the butterfly B is the ACB of the DC…
Continue reading “CRA problems with 55(3)(a) butterflies”…

CRA and relationship breakdowns

Posted on: August 23, 2021 Last updated on: August 23, 2021 Written by: John Loukidelis
My very first butterfly was undertaken pursuant to 55(3)(a) for a couple who were divorcing after many years of marriage. I recall looking carefully at whether their divorce would be treated as part of the series of transactions that included…
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Safe income and trust allocations

Posted on: October 19, 2020 Last updated on: October 19, 2020 Written by: John Loukidelis
In technical interpretation 2019-0833061E5 (January 27, 2020), the CRA stated that, where a trust receives a dividend of $2,500, $1,000 of which is ‘safe’, it cannot designate the safe portion to a corporate beneficiary and the rest to an individual…
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55(3)(a) purpose test?

Posted on: June 29, 2020 Last updated on: October 2, 2020 Written by: John Loukidelis
The CRA believes that a dividend otherwise exempt under paragraph 55(3)(a) of the Income Tax Act (Canada) will be subject to GAAR if one of the purposes of the dividend was to increase the cost of property contrary to the…
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Safe income accrual

Posted on: August 6, 2018 Last updated on: August 6, 2018 Written by: John Loukidelis
From Henry Shew, “Safe Income May Vary Within Shares of the Same Class” 8:3 Cdn Tax Focus (August 2018): Assume that Holdco purchases 100 shares of Opco for $10 (“the old shares”). These shares earn $1 per share of safe…
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55(2) ‘double taxation’

Posted on: November 3, 2017 Last updated on: November 3, 2017 Written by: John Loukidelis
In 101139810 Saskatchewan Ltd. v R, 2017 TCC 3, an individual owned all of the shares of DC, which held some shares of Targetco. The individual undertook a series of transactions that ended with the sale of Targetco shares to…
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More s 55 nonsense

Posted on: June 6, 2017 Last updated on: June 6, 2017 Written by: John Loukidelis
Tax Interpretations has translated a technical interpretation (2017-0683511E5) in which the CRA states that using a redemption of shares to avoid s. 55(2.1)(b) is potentially GAAR-able. I have another translation: the government needs to invoke GAAR to cooper up its…
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55(2) Gone Bad

Posted on: April 17, 2017 Last updated on: April 17, 2017 Written by: John Loukidelis
Michael Welters “Results Test in Subsection 55(2)” Canadian Tax Highlights 25:3 (March 2017) discusses 101139810 Saskatchewan Ltd. v R, 2017 TCC 3. The court applied 55(2) to intercorporate dividends paid to two holdcos even though the individual who owned them…
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S 55(2.1)(b)(ii)(B) and cash

Posted on: December 3, 2016 Last updated on: December 3, 2016 Written by: John Loukidelis
According to the CRA, cash is property for the purposes of the application of s 55(2.1)(b)(ii)(B). 2016 CTF Roundtable Q8. S 55(2.1)(b) reads as follows: (b) it is the case that (i) one of the purposes of the payment or…
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More s 55 hocus pocus

Posted on: December 3, 2016 Last updated on: December 3, 2016 Written by: John Loukidelis
Holdco owns all of Opco’s issued shares. Both corporations have calendar year-ends. Opco doesn’t have any safe income, but it has $383,333 of RDTOH. Opco pays a $1 million dividend to Holdco, which pays a $1 million dividend to its…
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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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