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Author: John Loukidelis (page 9)

Acting in concert and section 160

Posted on: March 27, 2024 Last updated on: March 21, 2024 Written by: John Loukidelis
In Pillon v R, 2024 FCA 24, the Court upheld a Tax Court finding that the taxpayer “acted in concert” with a tax debtor to whom she was not related so that section 160 applied. The taxpayer and the tax…
Continue reading “Acting in concert and section 160”…

Costs against appellant in “unwinnable appeal”

Posted on: March 25, 2024 Last updated on: March 21, 2024 Written by: John Loukidelis
In Nixon v R, 2024 TCC 4, the Court awarded costs of about $165,000 against the appellant for, among other things, misleading the Court about key facts, refusing to admit key facts and filing “an unwinnable appeal” (paras 20ff).
Continue reading “Costs against appellant in “unwinnable appeal””…

Director due diligence

Posted on: March 21, 2024 Last updated on: March 21, 2024 Written by: John Loukidelis
Jafarnia v R, 2023 TCC 171, restates a hard truth for directors of private corporations: you will not avoid liability for unremitted source deductions if you fail to remit them because you believe the business will turn around and money…
Continue reading “Director due diligence”…

Rectification post-Fairmont

Posted on: January 22, 2024 Last updated on: January 12, 2024 Written by: John Loukidelis
In Slightham et al. v. AGC, 2023 ONSC 6193 (which I also discuss here), the Court granted rectification of two trust deeds where the applicants were able to prove that the deeds did not accurately reflect the intentions of the…
Continue reading “Rectification post-Fairmont”…

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”…

Mandatory disclosure rules (MDR) – CRA guidance

Posted on: January 15, 2024 Last updated on: January 11, 2024 Written by: John Loukidelis
The authors provide notes on the CRA’s updated guidance on the MDR. Taxpayers must report a series of transactions that includes a notifiable transaction if the series straddles the date the transaction is designated as such. The CRA list of…
Continue reading “Mandatory disclosure rules (MDR) – CRA guidance”…

Scams and tax

Posted on: January 10, 2024 Last updated on: January 10, 2024 Written by: John Loukidelis
In an email spoofing attack, an employee of a business might share important financial information with, or send money to a, a fraudster because the employee has received an email from the fraudster masquerading as the employee’s boss. In a…
Continue reading “Scams and tax”…

Employee loans

Posted on: December 27, 2023 Last updated on: December 20, 2023 Written by: John Loukidelis
The CRA has published a document on its website about employee debt.
Continue reading “Employee loans”…

Deans Knight applied

Posted on: December 23, 2023 Last updated on: December 20, 2023 Written by: John Loukidelis
In R v. MMV Capital Partners Inc., 2023 FCA 234, the Court applied GAAR to a scheme where five of the original shareholders of the taxpayer maintained de jure control but an arm’s length party acquired 99% of the corporation’s…
Continue reading “Deans Knight applied”…

Rectification success

Posted on: December 20, 2023 Last updated on: December 20, 2023 Written by: John Loukidelis
In Slightham et al. v. AGC, 2023 ONSC 6193, the Court granted rectification of a trust deed that inadvertently prohibited the allocation of income derived from Opco to Holdco, which was a beneficiary of the trust. The parties had intended…
Continue reading “Rectification success”…
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Amended guidance on third-party penalties

The CRA has amended IC01-1R2 (“Third-Party Penalties”) in light of Guindon v R, 2015 SCC 41, and Ploughman v R, 2017 TCC 64. It has confirmed that “culpable conduct” “is defined with reference to the types of conduct the courts…
Continue reading “Amended guidance on third-party penalties”…

Related siblings under section 55

At the 2025 APFF conference, the CRA stated that the sisters in the following scenario would be related as per subparagraph 55(5)(e)(i): Sister A and Sister B each owned 100 percent of the shares of their respective holding corporations, whose…
Continue reading “Related siblings under section 55”…

Subsection 55(2) can be good actually

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”…

Loans by a partnership to a partner

The CRA has generally held that a loan from a partnership to a partner will reduce the ACB of the partner’s partnership interest because of the “all-encompassing” language in subparagraph 53(2)(c)(v) of the Income Tax Act (Canada). The CRA has…
Continue reading “Loans by a partnership to a partner”…

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”…

Recent Posts

Amended guidance on third-party penalties

The CRA has amended IC01-1R2 (“Third-Party Penalties”) in light of Guindon v R, 2015 SCC 41, and Ploughman v R, 2017 TCC 64. It has confirmed that “culpable conduct” “is defined with reference to the types of conduct the courts…
Continue reading “Amended guidance on third-party penalties”…

Related siblings under section 55

At the 2025 APFF conference, the CRA stated that the sisters in the following scenario would be related as per subparagraph 55(5)(e)(i): Sister A and Sister B each owned 100 percent of the shares of their respective holding corporations, whose…
Continue reading “Related siblings under section 55”…

Subsection 55(2) can be good actually

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”…

Loans by a partnership to a partner

The CRA has generally held that a loan from a partnership to a partner will reduce the ACB of the partner’s partnership interest because of the “all-encompassing” language in subparagraph 53(2)(c)(v) of the Income Tax Act (Canada). The CRA has…
Continue reading “Loans by a partnership to a partner”…

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”…

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Archives

Categories

Recent Posts

Amended guidance on third-party penalties

The CRA has amended IC01-1R2 (“Third-Party Penalties”) in light of Guindon v R, 2015 SCC 41, and Ploughman v R, 2017 TCC 64. It has confirmed that “culpable conduct” “is defined with reference to the types of conduct the courts…
Continue reading “Amended guidance on third-party penalties”…

Related siblings under section 55

At the 2025 APFF conference, the CRA stated that the sisters in the following scenario would be related as per subparagraph 55(5)(e)(i): Sister A and Sister B each owned 100 percent of the shares of their respective holding corporations, whose…
Continue reading “Related siblings under section 55”…

Subsection 55(2) can be good actually

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”…

Loans by a partnership to a partner

The CRA has generally held that a loan from a partnership to a partner will reduce the ACB of the partner’s partnership interest because of the “all-encompassing” language in subparagraph 53(2)(c)(v) of the Income Tax Act (Canada). The CRA has…
Continue reading “Loans by a partnership to a partner”…

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”…

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