In order to effectively convert an otherwise-expiring non-capital loss to a net capital loss, a CCPC (Aco) sells covered options (Options #1) on shares of a public corporation, thereby realizing a taxable capital gain under s. 49(1)(a) equaling the loss amount, and then purchases offsetting options (Options #2) at the beginning of the following year to close out its option position, thereby realizing a net capital loss. In confirming that this worked as a technical matter, but before noting the GAAR could be engaged, CRA stated:
If it were determined that the gain or loss realized by Aco in respect of Options #1 and #2 was on capital account, we would be of the view that subsection 49(1) would apply in this case to the sale by Aco of Options #1 in the particular taxation year and that, in accordance with our position in paragraph 29 of … IT-479R … the cost to Aco of acquiring Options #2 at the beginning of the taxation year following the particular taxation year would be a capital loss incurred at that time.