“I assume I should report this on my tax return. I received a 1099-like form from the investment bank (called a T5008; its a Canadian investment firm). The same amount appears in both the cost/book value box and the Proceeds/Settlement box. Would I simply report these amounts on my tax return?”---> I guess so; as Box 21 is for Proceeds of disposition or settlement amount , you need to report the total proceeds received by or credited to you, a recipient, in exchange for the securities. Amount deposited to your account is reported on box 21.