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Tina Korovilas, Drew Morier, "Non-Corporate Vehicles in the Foreign Affiliate Context", 2018 Conference Report (Canadian Tax Foundation), 20:1 – 114-- summary under Subsection 90(1) Summary Under Tax Topics- Income Tax Act- Section 90- Subsection 90(1) Most pro rata corporate distributions are dividends (pp. 20:16-17) Cangro Resources … held that for the purposes of the Act, “dividend” was to be given its “accepted ordinary meaning” – that is, of a pro rata distribution to all shareholders, other than a formal reduction of paid-up capital or liquidating distribution. … Despite the CRA’s administrative practice, the essence of a dividend, according to the jurisprudence, is a pro rata distribution by a corporation among its shareholders that is not a reduction of capital or a liquidating distribution. ...

Ian Zahra, "The Principal Purpose Test: A Critical Analysis of Its Substantive and Procedural Aspects – Part I", Bulletin for International Taxation, November 2019, p. 609-- summary under Article 7(1) Summary Under Tax Topics- Treaties- Multilateral Instrument- Article 7- Article 7(1) OECD interpretation of “principal purpose” (p. 614) [W]hat is a principal purpose? ... “Notwithstanding the other provisions of this Convention”. … [After referencing view of Danon:] If a purported abusive arrangement can be dealt with by the PPT and a SAAR, the SAAR should prevail, provided that the SAAR does cover the same situation. ... This is evidenced by the fact that a number of examples in the Commentary on Article 29 of the OECD Model (2017), such as Examples A and B … are based on fact patterns of past cases argued on the basis of beneficial ownership clauses. ...

Xiao, "The 88(1)(d) Bump – An Update", 2013 Conference Report (Canadian Tax Foundation), pp.13:1-60-- summary under Clause 88(1)(c.2)(iii)(A) Summary Under Tax Topics- Income Tax Act- Section 88- Subsection 88(1)- Paragraph 88(1)(c.2)- Subparagraph 88(1)(c.2)(iii)- Clause 88(1)(c.2)(iii)(A) Meaning of "significant" in s. 88(1)(c.2)(iii)(A) (pp. 13:46-48) [F]oreign Parent owns Interco, which owns Bidco. ... … Given that the lowest threshold for significant interest in the Act is 10 percent, it is reasonable to argue that the threshold for "significant direct or interest interest" should be no less than 10 percent…. Mitigate s. 88(1)(c.2)(iii)(A) risk by postponing kick-in date of conversion right (p.13:48) One … approach [to mitigate risk in the above scenario] is to ensure that the non-specified person investor, Arm's-Length Investor, does not become a specified shareholder until after the acquisition of control. ...

Kevin Wark, Michael O'Connor, "The Next Phase of Life Insurance Policyholder Taxation is Nigh", Canadian Tax Journal (2016) 64:4, 705 - 50-- summary under Paragraph 148(2)(e) Summary Under Tax Topics- Income Tax Act- Section 148- Subsection 148(2)- Paragraph 148(2)(e) Impact of death benefit on adjusted cost basis of a multi-life policy (pp. 730-1) New paragraph 148(2)(e)…applies to a situation where an insurance death benefit is paid that results in a termination of coverage but not termination of the policy—that is, there are other coverages under the policy that remain in effect. If the fund value benefit [f.n. 109… defined in regulation 1401(3)] that is paid out exceeds the maximum amount permitted in respect of the terminated coverage,[f.n. 110: … regulation 306(4)(a)(iii)] a policyholder with an entitlement to the excess portion is deemed to have disposed of a "part of an interest" for proceeds equal to that excess portion. … Example 4 Corporation A purchases a multi-life policy after 2016 with the following coverages: life-insured 1—$1 million; life-insured 2—$100,000. ... In determining the taxable amount of the proceeds, subsection 148(4) will require an allocation of the ACB of the policy as follows: $80,000 (full ACB) × 100,000/120,000 = $66,667. ...

Hersh Joshi, Jack Silverson, "Understanding and Doing Business with Tax-Exempt Entities", 2018 Conference Report (Canadian Tax Foundation), 29:1 – 35-- summary under Clause 149(1)(o.2)(iii)(C) Summary Under Tax Topics- Income Tax Act- Section 149- Subsection 149(1)- Paragraph 149(1)(o.2)- Subparagraph 149(1)(o.2)(iii)- Clause 149(1)(o.2)(iii)(C) Allocated LP income is income derived from an investment (pp. 29:7-9) [T]he technical notes to section 253.1 implicitly contemplate that a partnership interest would be an “investment” for the purposes of paragraph 149(1)(o.2), and it would be illogical to consider that this conclusion is not valid with respect, specifically, to the investment tests in subparagraph 149(1)(o.2)(iii). … [A]nalysis of the meaning of the word “derive” also demonstrates that when an investment corporation acquires an interest in a limited partnership that allocates partnership income or gains to the investment corporation, the income allocated to the investment corporation is derived from that limited partnership interest. … It is clear that the income allocated to an investment corporation by a limited partnership arises (in other words, has its origin or source) only as a result of the investment corporation’s investment in the limited partnership. ... For example … 2000-0055463 …. ...

Porter, "Mandatory Disclosure: A Reasonable Balance Between Timely Information and Administrative Burden", Perspectives on Tax Law & Policy, Vol. 4, No. 3, September 2023, p. 4-- summary under Contractual Protection Summary Under Tax Topics- Income Tax Act- Section 237.3- Subsection 237.3(1)- Contractual Protection “Opt Out or Contend with Uncertainty” (p. 5) [P]arties can easily avoid the RT [mandatory reportable transaction] regime by modifying their practices. If a transaction exhibits no hallmark (contingent fees, confidentiality, or CP [contractual protection]), the RT regime is not engaged. … It seems unlikely to us that parties will inadvertently fall into the RT regime. … Thus, only those who choose to undertake (or be implicated in) avoidance transactions linked to a potential hallmark must contend with any remaining uncertainty. … “The Essence of a Hallmark” (p. 5) Hallmarks are intended to identify potentially abusive transactions on the basis that such transactions often exhibit a hallmark. … [H]allmarks do not just exist in the ether; rather, they reveal themselves in circumstances where their presence may influence or cause a party to engage in the targeted riskier behaviour by entering into the potentially aggressive transaction. ...

Marquette, "Hybrid Sale of Shares and Assets of a Business", Canadian Tax Journal, (2014) 62:3, 857 – 79.-- summary under Subsection 84(2) Summary Under Tax Topics- Income Tax Act- Section 84- Subsection 84(2) Description of hybrid transaction using external step-up in basis method (pp. 878-9) [T[he hybrid form of transaction for a corporate business sale utilizes both traditional elements of a business acquisition – the purchase of shares and assets – in order to limit the ultimate tax liability incurred by the vendor and to maximize the cost base of assets for the purchaser…. ... [fn 22: … 2003-0029955 … See also Geransky v. The Queen, 2001 DTC 243…] The CRA has confirmed that in such a situation, subsection 84(2) or 245(2) would not normally apply provided that (1) the vendors and the purchaser deal at arm's length, (2) the vendor shareholders receive a cash amount from the purchaser's own funds in return for shares of the target, and (3) the target's assets continue to be used in an active business by the target, or by another entity within the purchaser's corporate group. [fn 23: … 2003-0029955 …] ...

Rulings on securities issued to pay principal or interest (p. 10) CRA has ruled that subsections 143.3(3) and (4)… would not apply to re-determine the relevant amounts in the context of the issuance of trust units in repayment of principal-and-preferred shares in payment of interest [fn 55: … 2008-0300101R3, 2008-0300102R3 and 2009-0350481R3 ….]…It is…unclear whether the CRA's earlier comment in the context of rebates (i.e., the CRA's view that subsection 143.3(3) would apply such that rebates automatically invested at the issuer's option in common shares would not be deductible by the issuer) continues to reflect the view of the CRA and, if so, how it is to be reconciled with the subsequent rulings [fn 56: … 2006-0176321R3 ….] ... By way of example: paragraph 88(l)(d) refers to "the cost amount to the subsidiary of the property immediately before the winding-up, plus the amount of any money of the subsidiary on hand immediately before the winding-up";…[also citing, ss. 88(1)(d), 87(9), 98(3)(a)(ii), 89(1) – GRIP. 108(1) – cost amount, 132(4)]. ...

Kevin Bianchini, Reuben Abitbol, "Taxation of Stock Appreciation Rights", Taxation of Executive Compensation and Retirement (Federated Press), Vol. 24 No. 8, 2015, p.1655-- summary under Paragraph 6(1)(a); Payment & Receipt Summary Under Tax Topics- Income Tax Act- Section 6- Subsection 6(1)- Paragraph 6(1)(a) Summary Under Tax Topics- General Concepts- Payment & Receipt Safe harbour until SAR vesting (p. 1656) [T]he CRA has taken the position that until the employee has a right to exercise and cash in the SARs, the SDA rules would not apply. [f.n…. 9422835 …] In other words, once the SAR units become fully vested it would have be determined whether the executive is postponing the exercise of the SARs in order to avoid the immediate tax consequences (i.e., the employment income). ... Alternative application of constructive receipt (“CR”) at time of vesting (p. 1657) [I]n the context of the recognition of employment income, the Canadian jurisprudence has yet to develop guidance with respect to the doctrine of CR …[T]he CRA addressed its position with respect to CR in the context of SDAs in… 1999-0007315 …. ...

PWC, "Tax Insights: Cross-border cash pooling arrangements ─ Recent developments", Issue 2018-41, 2 November 2018-- summary under Subsection 15(2.6) Summary Under Tax Topics- Income Tax Act- Section 15- Subsection 15(2.6) CRA expansive view of series in cash pooling context (p.2) 2017-0682631I7 … concluded that transactions occurring as part of a physical cash pooling arrangement are likely to be considered a series of loans and repayments and therefore reductions to amounts receivable would not meet the subsection 15(2.6) repayments exception. Recent CRA audit activity of cross-border cash pooling (p. 2) …The following highlights recent positions the CRA has taken in the course of audits: amounts received by a related non-resident head account holder in a cash pool from a Canadian entity member of the cash pool (as part of a cash pooling arrangement) are subject to the shareholder loan rules in subsection 15(2) of the Act the ordinary business and bona fide arrangement exception is generally not met because: there is a lack of evidence that a Canadian entity loans money to either arm’s length parties or other members in the corporate group … the terms of cash pooling deposit agreements do not generally include a fixed or specific date for the foreign company to repay the loan … [indicating no] bona fide arrangement for repayment the repayments exception is generally not met because the automatic daily cash sweeps are considered to form part of a series of loans or other transactions and repayments …each loan requires a separate [PLOI] election, so if the election is filed late, there can be multiple late filing penalties there will be no refund of the withholding tax paid on the amount of a loan deemed to be a dividend when the loan is repaid if the repayment is part of a series of loans and repayments ...