News of Note

Minority shareholders may face challenges in having Opco be connected to their holding companies

It is common for unrelated shareholders of Opco to hold their shares through respective Holdcos in order to access the capital gains exemption on a subsequent sale of their Holdco shares. However, this requires that Opco be connected with Holdco. Assuming that each Holdco would not control Opco, as per s. 186(4)(a), connected status would require either that Holdco own shares of Opco representing more than 10% of the votes and value of Opco (as per s. 186(4)(a)(b)) or (under s. 186(2)) that Holdco, along with any other persons with which it did not deal at arm’s length, own at least 50% of the voting shares of Opco.

It may be difficult for minority shareholders to satisfy these tests. For example, suppose that Opco had two unrelated individual shareholders holding 85%, in the case of the majority shareholder, and 15% in the case of the minority shareholder, of its only outstanding shares, being common shares. Those individuals then exchanged their Opco common shares for frozen voting preferred shares. Each shareholder then established a family trust—the majority trust and the minority trust—which incorporated its own Holdco (“Majority Holdco” and “Minority Holdco”), with each Holdco subscribing a nominal amount for Opco common shares.

Neither Holdco would control Opco, and initially, neither Holdco would satisfy the votes and value test. However, Majority Holdco would not deal at arm’s length with the majority shareholder and, together with the majority shareholder, would own shares representing more than 50% of Opco’s voting rights, so that Majority Holdco would pass the s. 186(2) test.

The minority shareholder, which would deal at arm’s length with the majority shareholder, would fail the s. 186(2) test.

Neal Armstrong. Summary of David Carolin, Marissa Halil, and Manu Kakkar, “Not so connected for the capital gains exemption,” Tax for the Owner-Manager, Vol. 25, No. 4, October 2025, p. 4 under s. 186(4).

Priority Foundation – Federal Court of Appeal finds that Art. XXI(7) of the Canada-US Convention does not require donations made by a Canadian registered charity to a US charity to be treated as made to a qualified donee

Priority Foundation appealed the publication of a notice revoking its charitable registration, made on the basis that it had been using its funds to make donations to entities that were exempted from U.S. taxation under Code s. 501(c)(3) but which were not registered charities and qualified donees. It relied on Art. XXI(7) of the Canada-U.S. Income Tax Convention (the “Convention”):

For the purposes of Canadian taxation, gifts by a resident of Canada to an organization that is a resident of the United States, that is generally exempt from United States tax and that could qualify in Canada as a registered charity if it were a resident of Canada and created or established in Canada, shall be treated as gifts to a registered charity; however, no relief from taxation shall be available in any taxation year with respect to such gifts (other than such gifts to a college or university at which the resident or a member of the resident's family is or was enrolled) to the extent that such relief would exceed the amount of relief that would be available under the Income Tax Act if the only income of the resident for that year were the resident's income arising in the United States.

The numerous reasons of Roussell J.A. for rejecting the submissions of Priority that Art. XXI(7) required its donations to be treated as if made to qualified donees included:

  • Although the current version of Art. XXI(7) notably had been broadened from the 1956 version by replacing a reference to “the computation of taxable income” by a reference to "for the purposes of Canadian taxation," this did not establish “that the phrase ‘for the purposes of Canadian taxation’ was intended to be all-encompassing, such that it would impact the requirements for ongoing charitable registration under the ITA for Canadian registered charities”.
  • If Art. XXI(7) had the effect of deeming a U.S. 501(c)(3) entity to be a registered charity and therefore a qualified donee, this would imply that such a donee was required to keep Canadian records; and It would be “highly unusual that the Minister's powers of revocation mentioned in paragraph 230(2)(a) would extend to U.S. 501(c)(3) entities”.
  • A reading of the U.S. Treasury Technical Explanation and an IRS guidance notice suggested that the drafters of the Tax Convention did not envisage that it would go as far as interfering with each country's authority to determine the statutory requirements a registered charity must meet to maintain its charitable registration; and supported the view that “the purpose of the treaty was to provide relief from the imposition of taxes and not to regulate the conditions an organization must satisfy to maintain its charitable registration in the organization’s resident state”.
  • Furthermore, Priority's submission, if correct, would suggest that a “Canadian resident individual or corporate taxpayer with no U.S. income wishing to donate to a specific U.S. charity to whom Priority made gifts could have circumvented the U.S. income limitation by making the gift to Priority” which “could not have been the result that was intended by the contracting states”.

Neal Armstrong. Summary of Priority Foundation v. Canada (National Revenue), 2025 FCA 180 under Treaties – Income Tax Conventions – Art. 21.

We have translated 6 more CRA interpretations

We have translated a further 6 CRA interpretations released in January of 2000. Their descriptors and links appear below. These are additions to our set of 3,342 full-text translations of French-language Technical Interpretation and Roundtable items (plus some ruling letters) of the Income Tax Rulings Directorate, which covers all of the last 25 ½ years of releases of such items by the Directorate. These translations are subject to our paywall (applicable after the 5th of each month).

Bundle Date Translated severed letter Summaries under Summary descriptor
2000-01-21 10 January 2000 External T.I. 9908665 F - PROGRAMME IMMIGRANT INVESTISSEUR Income Tax Act - Section 248 - Subsection 248(1) - Small Business Corporation an asset pledged as security for a long-term debt of the business is not in itself considered to be used in that business
10 January 2000 External T.I. 9908925 F - FRAIS DE VOYAGE DU CONJOINT Income Tax Act - Section 6 - Subsection 6(1) - Paragraph 6(1)(a) reimbursement of family’s travel expenses when professor is on continuing education leave, is a taxable benefit
10 January 2000 External T.I. 9917635 F - FRAIS JURIDIQUES-PENSION ALIMENTAIRE Income Tax Act - Section 18 - Subsection 18(1) - Paragraph 18(1)(a) - Legal and other Professional Fees legal fees to modify rather than to enforce support were not deductible
21 December 1999 External T.I. 9928755 F - INDEMNITE DE DEPART-DECES Income Tax Act - Section 248 - Subsection 248(1) - Retiring Allowance retiring allowance paid to beneficiary of deceased employee is a death benefit
Income Tax Act - Section 248 - Subsection 248(1) - Death Benefit retiring allowance paid after death was death benefit
6 January 2000 External T.I. 9929675 F - FUSION - CAPITAL VERSÉ ET PBR Income Tax Act - Section 87 - Subsection 87(4) transfer of individual’s directly held shares to his Holdco at a high elected amount followed by the 2 corporations’ amalgamation reflected in stepped-up ACB of Amalco shares
20 December 1999 External T.I. 9930245 F - COOPERATIVE DE CREDIT ET CAPITAL ACTIONS Income Tax Act - Section 248 - Subsection 248(1) - Share no difference between French and English definition of “share”/ interest in federation fund not a “share”

CRA confirms that the gain on the shares of CFA2 (sub of CFA1) on the continuance of CFA1 (a sub of Canco) to Canada could be taxed again when CFA1 actually disposes of the CFA2 shares

CFA1 (a Country A resident) wholly owned CFA2 (a Country B resident) and was wholly owned by Canco.

Pursuant to s. 128.1(1)(b), at the time immediately before the deemed taxation year of CFA1 arising on the continuance (the “immigration”) of CFA1 to Canada (the “Last FA Year”), CFA1 was deemed to dispose of the shares of CFA2 for proceeds equal to their FMV at that time of $100. The resulting $90 capital gain on the shares of CFA2, which were not excluded property, gave rise during the Last FA Year to FAPI of CFA1 that was included in Canco’s income.

If there subsequently was an actual disposition of the shares of CFA2 by CFA1, CFA1 would be liable to tax of 30% in Country B on the capital gain computed based on the (low) pre-immigration costs of the shares to it of CFA2, thereby likely resulting in the same gain being taxed a second time. In particular, as the ACB of the CFA2 shares of CFA1 would have been stepped-up under s. 128.1(1)(c), on such sale CFA1 would not be subject to tax in Canada on the capital gain accrued prior to the immigration, and would not generate a foreign tax credit under s. 126 for the Country B tax paid on that accrued gain unless it had qualifying income from Country B sources. Further, since CFA1 ceased to be a foreign affiliate of Canco upon the immigration, the Country B tax paid on the actual disposition of the CFA2 shares would not be FAT in respect of Canco.

In addition to the FAPI inclusion under s. 128.1(1)(b) to Canco, s. 128.1(1)(d)(ii) required the inclusion, in computing the FAPI of CFA1 for the Last FA Year, of the amount prescribed under Reg. 5907(13), which would include any undistributed taxable surplus of CFA1, as reduced by its net earnings in respect of the FAPI for the Last FA Year from the deemed disposition under s. 128.1(1)(b). In these circumstances, where the only relevant FAPI was from the gain to CFA1 on the CFA2 shares on the continuance, there would be no net amount to add under Reg. 5907(13).

Neal Armstrong. Summaries of 22 August 2025 External T.I. 2019-0826681E5 under Reg. 5907(13), ITA s. 91(4) and s. 128.1(1)(b).

CRA generally confirms the use of s. 119 to reduce exit tax on CCPC shares by the Pt. XIII tax on their subsequent redemption

On exiting Canada, an individual was deemed, pursuant to s. 128.1(4)(b), to have disposed of preferred shares of a CCPC, which were taxable Canadian property and had a nominal ACB and PUC, for their fair market value, and elected under s. 220(4.5) to defer the payment of the resulting tax years later, the CCPC will now redeem the preferred shares, giving rise to a deemed dividend that is subject to a treaty-reduced withholding rate of 15%. His resulting capital loss will be reduced pursuant to ss. 40(3.7) and 112(3)(b) to nil by the amount of such deemed dividend.

CRA confirmed that, in general, the withholding tax could be credited under s. 119 against the tax payable under s. 128.14(4)(b). In particular, the individual would be allowed under s. 119 to deduct, from his tax otherwise payable for his departure taxation year the lesser of:

  • the amount of tax attributable to the taxable capital gain on the deemed disposition of the shares; and
  • the treaty-reduced Part XIII tax paid by the individual on that amount of the deemed dividend that, pursuant to s. 40(3.7), had reduced the individual’s otherwise determined capital loss from the share disposition.

On satisfying the s. 152(6.3) conditions, he could amend his tax return for the departure year in order to take the s. 119 deduction.

Neal Armstrong. Summary of 11 March 2022 External T.I. 2019-0829251E5 under s. 119.

Elhav – Tax Court of Canada finds that the taxpayer’s son sleeping at the new condo for 2 ½ months satisfied the 1st-occupant test in ETA s. 254(2)(g), but not the intention for a primary place of residence under s. 254(2)(b)

The appellant and his wife agreed in January 2017 with a developer to purchase a still-to-be-constructed condominium unit. They took possession in June 2020 and began renting the unit out in September 2020.

Regarding the appellant’s new housing rebate claim, Friedlander, J. found that a qualifying relation, namely their son (Michael), age 23, had satisfied the first-occupancy test in ETA s. 254(2)(g) given that he had, in fact, slept every night in the condo unit until he decided to return to the family home in Vaughan about 2 ½ months later, and had furnished the unit (albeit, sparsely) while staying there. He was more than “merely ‘camping’” there.

However, the rebate nonetheless was not available because s. 254(2)(b) was not satisfied, i.e., Friedlander, J. doubted that their intention at the time of the purchase agreement was that Michael would use the unit as his primary place of residence. For instance, there was the significant distance between the family home in Vaughan (where Michael was staying until 2020) and the unit’s location in east Toronto, their close family ties, and the absence of any reason to consider that he would work near the condo (and, in fact, he ended up working in the Vaughan area).

Neal Armstrong. Summaries of Elhav v. The King, 2025 TCC 132 under ETA s. 254(2)(b) and s. 254(2)(g).

Income Tax Severed Letters 8 October 2025

This morning's release of three severed letters from the Income Tax Rulings Directorate is now available for your viewing.

Fiducie Historia – Federal Court of Appeal finds that, notwithstanding their agreement somewhat to the contrary, trustees had not delegated their trustee function to others

A discretionary trust received dividend income, which it allocated and distributed to one of its beneficiaries ("Father"). In an attempt to avoid a change in control of the corporation held by the trust due to an associated redemption of shares of the corporation held by family members, the trustees entered into an agreement with two beneficiaries, who were sons of Father, under which the trustees undertook to exercise their powers according to the instructions given by the sons and to not make decisions without their prior consent – and to resign in the event of disagreement with the sons' instructions.

However, this caused CRA to conclude that the trustees had abdicated the exercise of their powers to the sons, so that the sons had become de facto trustees, contrary to Art. 1275 of the Civil Code. This, in turn, signified that the purported trust distributions were void, so that no amount was deductible under s. 104(6).

The Tax Court found that, notwithstanding this agreement, the trustees continued to exercise their powers as trustees and that the sons did not, in fact, act as trustees. Thus, there was no violation of Art. 1275.

Before dismissing the Crown’s appeal, Goyette JA first noted that the terms of the agreement with the sons were ambiguous, and then indicated that the Tax Court was called upon to take the actual facts into account, so that it was entitled to decide based on its finding that in fact their had been no abdication of the exercise of trustee powers. Furthermore, no palpable and overriding error in the Tax Court’s assessment of the facts could be identified.

Neal Armstrong. Summaries of The King v. Fiducie Historia, 2025 CAF 177 under s. 104(6) and s. 171(1).

We have translated 6 more CRA interpretations

We have translated a further 6 CRA interpretations released in February and January of 2000. Their descriptors and links appear below.

These are additions to our set of 3,336 full-text translations of French-language Technical Interpretation and Roundtable items (plus some ruling letters) of the Income Tax Rulings Directorate, which covers all of the last 25 ½ years of releases of such items by the Directorate. These translations are subject to our paywall (applicable after the 5th of each month).

Bundle Date Translated severed letter Summaries under Summary descriptor
2000-02-04 5 January 2000 Internal T.I. 9931817 F - TRANSFER D'UNE POLICE D'ASSURANCE-VIE Income Tax Act - Section 15 - Subsection 15(1) s. 15(1) benefit on distribution of life insurance policy to shareholder
2000-01-21 17 January 2000 External T.I. 9930235 F - ALLOCATION AUTO, CHANTIER PARTICULI Income Tax Act - Section 6 - Subsection 6(1) - Paragraph 6(1)(b) - Subparagraph 6(1)(b)(v) attending to union employees’ grievances was re the application of the contract (the collective agreement) rather than its negotiation
Income Tax Act - Section 6 - Subsection 6(6) - Paragraph 6(6)(a) - Subparagraph 6(6)(a)(i) 3-year “insecure” assignment was not temporary
11 January 2000 External T.I. 9930695 F - VETEMENTS D'AVOCATS Income Tax Regulations - Schedules - Schedule II - Class 8 barristers’ gowns were Class 8 property
Income Tax Act - Section 18 - Subsection 18(1) - Paragraph 18(1)(h) clothing must be acquired specifically for income-producing purpose
17 January 2000 External T.I. 9932865 F - ACTION APPROUVÉE - FONDS DE TRAVAILLEURS Income Tax Act - Section 127.4 - Subsection 127.4(1) - Approved Share - Paragraph (b) exclusion in para. (b) does not apply if the Taxation Act (Quebec) granted a tax credit to any taxpayer for the acquisition of shares
12 January 2000 External T.I. 9910105 F - PRIS PAR DES PERSONNES/HUMAN CONSUMP Income Tax Act - Section 67.1 - Subsection 67.1(1) wine tasting was a human consumption activity
11 January 2000 External T.I. 9916595 F - FRAIS MEDICAUX-CONSEILLERS GENETIQUES Income Tax Act - Section 118.4 - Subsection 118.4(2) genetic counsellor did not qualify as a medical practitioner

Laurie – Tax Court of Canada finds that a taxpayer had failed to establish due diligence re a repeated failure to file T1135s

The taxpayer filed a voluntary disclosure regarding her failure for her 2012 to 2014 taxation years to file T1135 returns reporting her foreign investments, which the CRA accepted. In the course of preparing her 2021 taxation return, she realized that she had failed to file T1135 returns for her 2019 and 2020 taxation years. CRA refused a second voluntary disclosure, and she appealed the imposition on her of s. 162(7) penalties.

Graham J. found that the jurisprudence had established that a due diligence defence was available under s. 162(7). In rejecting a Crown submission that Parliament had turned its mind in s. 233.5 (respecting due diligence in seeking unavailable information) regarding the only relevant circumstances in which due diligence could be a defence, Graham J. stated (at para. 8):

I cannot see how, in providing a due diligence defence for information returns under sections 233.2 and 233.4 that were filed on time but were incomplete, Parliament could in any way be said to have indirectly precluded a due diligence defence to the late filing of all information returns covered by subsection 162(7).

However, he went on to find that in these (repeat mistake) circumstances, the taxpayer had failed to establish that she satisfied the Résidences Majeau due diligence tests.

A somewhat analogous issue arises, regarding the s. 245(5.1) GAAR penalty, as to whether the extremely narrow statutory defence under s. 245(5.2) implies that there is no Résidences Majeau due diligence defence (although the analogy is perhaps complicated by the availability of the alternative defence for voluntary disclosure under s. 237.3). The final version of the Explanatory Notes on s. 245(5.2) notably added a statement that:

It is not intended to replace any other defences that may be available under applicable law.

Neal Armstrong. Summary of Laurie v. The King, 2025 TCC 130 under s. 162(7).