CRA indicates that normal course dividends and loss-shifting transactions generally do not engage the new s. 55(2) rules

Points made by CRA respecting the new s. 55(2) rules include:

• "Normal course" dividends (albeit with a narrow description of the only clear safe harbour) should not be subject to the new rules.
• CRA is willing to issue opinions (and presumably rulings, once the new rules are enacted) on the non-application of s. 55(2.1), although as a purely technical matter they will be somewhat meaningless, as the required representations will beg the (purpose) question.
• Conventional loss shifting transactions (which CRA has already been requiring not to create additional basis) will not be subject to the new rules.
• Where a non-participating discretionary shares has no accrued gain, then a dividend paid thereon which violates the purpose test cannot benefit from safe income. However, where this occurs, CRA is prepared to accept that the safe income on the participating shares of the same corporation will not be affected.
• CRA considers it to be offensive to redeem a share for a note in a s. 55(3)(a) reorganization, with the note being used to generates basis in excess of redeemed shares’ ACB.
• Also offensive is "ACB streaming prior to a reorganization under 55(3)(a) or (b), where the redemption would be of low-ACB shares, while the high ACB shares would be preserved."
• CRA appears to consider creditor-proofing transactions to per se entail a purpose that engages the new rules.

Neal Armstrong. Summary of 24 November 2015 CTF Annual Roundtable, Q.6 under 2015 CTF Roundtable.