Tax Loss Season Info from CRA Is there a deadline?
Yes, and it may be sooner than you think. For a loss to count in the current year, the trade has to settle on or before Dec. 31. Because the settlement date is three business days after the trade date, and because Christmas Day and Boxing Day are statutory holidays, the last day for tax-loss selling of Canadian stocks this year is Dec. 24. If you sell after that date, the loss will be recorded for tax purposes in the following year.
Can I sell and then repurchase the same stock?
You have to be careful here. If you sell a stock and repurchase it within 30 days (before or after the sale date), the Canada Revenue Agency considers it a "superficial loss" and you won't be able to use it to offset capital gains. Furthermore, you can't get around the rule by repurchasing the same stock in a different account such as an RRSP or tax-free savings account (TFSA), or by having your spouse – or a corporation controlled by you or your spouse – repurchase it. The idea is that you can't claim a tax loss if you, or someone affiliated with you, maintains control of the shares. The simplest solution is to wait 30 days before repurchasing the same stock.