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[T]he Tax Court judge was also bound to hold that “no part of [the interconnected transaction] can be considered a gift that the appellant[s] gave in the expectation of no return” …. It follows that there was no gift whether the matter is considered from a common law or a civil law perspective. … In response to a further submission that “it is possible to make a ‘“profitable” gift’ due to the favourable tax consequences that some gifts provide” (para. 54), Noël CJ stated (at para 60): [T]the fact that a tax benefit is received as a result of making a gift cannot, in and of itself, invalidate the gift as to hold otherwise would mean that Parliament would have spoken in vain in providing for tax benefits consequential on making qualified gifts. ...

It is also my view that the representations were of sufficient detail such that it could reasonably be considered that a prospective purchaser could deduct the full purchase price of the Software over a two-year period. ... Krumm, IAC and its agents could each be considered to be a tax shelter “promoter”, as defined in subsection 237.1(1) …. ...

He went on to indicate (at para. 49) that in any event, the daughter could be considered to be “subject to tax” (or “liable for tax” to use his preferred translation, and also essentially the phrase considered in Crown Forest): … The income tax legislation … applies to all Canadian residents … because they may, in one year or another, earn business income in Quebec…. ...

CRA considered that there was a requirement to recognize deemed interest income on the notes under Reg. 7000(2)(d) given that, in contrast to the usual equity-linked notes that were available to investors at the time, these notes had “internal puts,” i.e., SLT had the right to terminate the notes at any time, on 367 days’ notice, at the market value of the reference assets. On this basis, it considered that the “the maximum amount of interest thereon that could be payable thereunder in respect of that year” was the difference between the maximum value of the reference assets at the end of the year and the maximum value in the prior years, and assessed accordingly, to treat such annual increase as foreign accrual property income of SLT under element A of the s. 95(1) FAPI definition. ...

The statutory language (quoting for convenience from s. 120.4(5)) relevantly required that an “amount can reasonably be considered to be attributable to a taxable capital gain … of a trust from a disposition of shares … that are transferred, either directly or indirectly, in any manner whatever, to a person with whom the specified individual does not deal at arm's length….” ... [S]ection 766.7.2 can only be interpreted and have meaning when there are two legal transactions related to the shares, namely, first, the disposition of the shares that will subsequently be transferred to generate an amount that could reasonably be considered to be attributable to a taxable capital gain …. ...

This amount can reasonably be considered to be part of the consideration for the disposition of property (the Building) of the taxpayers (the Appellants), and the remainder of this amount can reasonably be considered to be part of the consideration for the disposition of the property of 9118, namely the goodwill and other moveable property of the SR. ...

Canada (Revenue Agency), 2021 FC 1440-- summary under Subsection 220(3.1) Summary Under Tax Topics- Income Tax Act- Section 220- Subsection 220(3.1) a voluntary disclosure planned before, but made after, the audit notification could be considered non-voluntary- but CRA rejection annulled In May 2015, the plaintiff authorized her law firm to represent her in making a voluntary disclosure of her Swiss assets, and in the summer and fall of 2015, various documents were collected and organized to this end. ... However, the (second) decision under review was annulled given that the involvement of the first decision maker in the process for the second review decision “was not minimal” (para. 52), with regard also being had to an internal email from a CRA manager (that “We need to ensure that this VDP is denied as it should not be considered to have been voluntary but rather as a result of audit contact”) “constitute[d] unwarranted interference with the VDP's evaluation of the case” (para. 54) (although there was no evidence that this email in fact interfered with the second decision). ...

This term referred inter alia to a transaction that “is not one that may reasonably be considered to have been undertaken or arranged primarily for a bona fide purpose other than for the purpose of obtaining the tax benefit.” ... To use the language of the provisions, the RVO is a transaction that may reasonably be considered to have been undertaken or arranged primarily for a bona fide purpose other than for the purpose of obtaining the tax benefit. ...

In rejecting such claim that there was no chance of success, Régimbald J stated (at paras. 28, 30, TaxInterpretations translation): [I]t is not clear, in light of sections 125.7(5), 152(3.4) and 164(1)(b), considered together and which are the subject of the application for judicial review, that the ITA does not allow the Minister to accept an amended prescribed form as requested by the plaintiff. … In the absence of a complete and convincing argument demonstrating that sections 152(3.4), 164(1)(b) and 125.7(5) of the ITA, considered together, defeat the interpretation proposed by Lemay based on the Minister having the discretion to accept the filing of an amended prescribed form, the defendant has therefore not discharged its burden of demonstrating that it is clear and obvious that the interpretation proposed by Lemay has no reasonable chance of acceptance …. ...

Furthermore, in TD Securities, the taxpayer was able to demonstrate that it was being treated differently from other fiscally transparent entities, which was considered by Boyle J to be an unreasonable result, whereas here, no unreasonable consequences had been established. ... Allen J stated (at para. 76): As to Boyle J.'s conclusion that TD LLC must be considered to be liable to tax by virtue of all of its income being fully and comprehensively taxed under the U.S. ...