An investor short sells the same number of shares as those exercised on the same day as the exercise of the s. 7 options, and donates the proceeds of the short sale to the registered charity. The short position is closed when the shares are received following the exercise of the options. Does the donation of the proceeds of the short sale qualify under ss. 110(1)(d.01) and 110(2.1)? CRA responded:
[T]he taxpayer must, when exercising the option, direct a broker or dealer appointed or approved by the particular qualifying person referred to in that paragraph to immediately dispose of the security and pay all or a portion of the proceeds of disposition of the security to a qualified donee.
In the situation described … those two conditions are not satisfied.