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Category: 55(2) (page 3)

You’d better calculate safe income

Posted on: December 2, 2016 Last updated on: December 2, 2016 Written by: John Loukidelis
The CRA appeared unsympathetic to the idea that detailed calculations of safe income might not be necessary where Opco is wholly-owned by Holdco, and Opco accounting income does not differ greatly from its taxable income. The CRA representative spoke darkly…
Continue reading “You’d better calculate safe income”…

Discretionary dividend shares

Posted on: December 2, 2016 Last updated on: December 2, 2016 Written by: John Loukidelis
Suppose shareholders of Opco hold different classes of common shares on which dividends can be paid at the discretion of the board so that one class can receives dividends to the exclusion of other classes. All common shares participate pro…
Continue reading “Discretionary dividend shares”…

55(2) and creditor-proofing

Posted on: February 15, 2016 Last updated on: February 15, 2016 Written by: John Loukidelis
The new purpose tests in section 55 make creditor proofing problematic. The 55(3)(a) exception remains, however, for deemed dividends. Perhaps it’s possible, then, to achieve creditor proofing by engaging in a 55(3)(a) butterfly. Not so fast. The CRA’s comments at…
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55(2) This Week

Posted on: January 27, 2016 Last updated on: January 27, 2016 Written by: John Loukidelis
Manu Kakkar and Marissa Halil, in “Subsection 55(2): The CRA’s Recent Positions” Tax for the Owner-Manager 16:1 (January 2016), provide a useful summary of the CRA’s pronouncements on 55(2) at the Tax Foundation conference. The CRA is concerned that deliberately…
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55(2) as a tax reduction tool

Posted on: October 26, 2015 Last updated on: October 26, 2015 Written by: John Loukidelis
The CRA accepts that the GAAR will not apply where a taxpayer deliberately triggers 55(2) to reduce tax. Rather than having Opco pay a dividend to Mr A, Mr A could roll his shares of Opco to Holdco and have…
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Safe income and trusts

Posted on: July 13, 2015 Last updated on: July 13, 2015 Written by: John Loukidelis
The CRA accepts that a safe income dividend paid from Opco to a trust-shareholder, which then allocates the dividend to Holdco, one of the trust’s beneficiaries, will be added to Holdco’s safe income. Technical interpretation 2014-0538061C6 dated October 10, 2014,…
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55(3)(a) and GAAR

Posted on: February 20, 2011 Last updated on: February 20, 2011 Written by: John Loukidelis
The CRA has said that GAAR might apply to a deemed dividend otherwise exempt under 55(3)(a) where the purpose is to increase the cost of property (55(2.1)(b)(ii)(B)). Is that right? 55(3)(a) was amended to be applicable only in respect of…
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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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