Income Tax Severed Letters - 2025-09-03

Ruling

2025 Ruling 2024-1047551R3 - Multi-wing Split-Up Butterfly

Unedited CRA Tags
55(2), 55(3)(b), 55(3.1), 85(1), 88(2)

Principal Issues: Whether the butterfly dividend is exempt from 55(2) as a result of qualifying under 55(3)(b)?

Position: Yes.

Reasons: Proposed transactions meet the requirements of paragraph 55(3)(b).

Technical Interpretation - External

3 June 2025 External T.I. 2025-1064821E5 F - Related persons

Unedited CRA Tags
251(2), 251(4), 251(5)(a), 251(6), 252(1)
repeated application of ss. 251(2)(b)(ii) and (iii) to relate two corporations

Principales Questions: In the given situation, whether Nouco and Opco are related persons pursuant to subsection 251(2).

Position Adoptée: Yes. In the given situation Nouco and Opco are related pursuant to subparagraph 251(2)(b)(iii).

Raisons: Wording of the Act.

7 June 2024 External T.I. 2024-1006831E5 - Employment settlements and reporting requirements

Unedited CRA Tags
237.3 and 245 of the Act
an employee indemnity, in a settlement agreement with the employer, regarding the employer’s failure to withhold, likely is not contractual protection
employment settlement agreement that provided for non-taxable damages without a legal or factual basis likely would be an avoidance transaction
employment settlement agreement providing legitimate allocation to non-taxable damages likely is not an avoidance transaction under s. 237.3(1)

Principal Issues: Does a settlement agreement containing an indemnification clause and that was signed in the context of an employment termination meet the definition of contractual protection under s.237.3(1)(a)(i)(A)?

Position: Generally, no.

Reasons: A reportable transaction is an avoidance transaction entered into by or for the benefit of a person and that meets one of three legislated hallmarks. In turn, an avoidance transaction exists if it may reasonably by considered that one of the main purposes of a transaction (or a series of which the transaction is a part of) is to obtain a tax benefit. Where principled settlements are negotiated in good faith without consideration to the tax implications and the damages are properly allocated, then generally “one of the main purposes” of the settlement will not be to obtain a tax benefit. To the same extent, the contractual protection hallmark is unlikely to be triggered in light of the indemnity clause in the case at hand.