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Category: 55(2) (page 3)

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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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…
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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…
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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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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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