If you or a person affiliated with you buys the same stock either 30 calendar days before or after the sale your loss is now a superficial loss.  That means you cannot use the deduction.    Affiliated person means your spouse or common-law partner, a corporation you control, a partnership or a majority interest partner of the partnership, or a trust.  That also includes any registered investment vehicles you have such as an RRSP, RESP, RRIF, TFSA and etc..  Yes, I know their definition of affiliated person includes much more than persons in any normal definition.

If you want to do some tax loss selling make sure to not buy it back within those 30 days on either side of the sale.

You can use that superficial loss rule to your advantage.  If your spouse buys that same stock within the 30 days you have a superficial loss.  This superficial loss is added to the ACB (Adjusted Cost Base) of your spouse’s purchase of the stock.   Make sure your spouse keeps those stocks for at least 30 days.   If your spouse has capital gains this will allow your spouse to use this capital loss.   This is a neat way to transfer losses to your spouse.

Make sure you discuss this with your tax advisor to make sure you do this correctly.

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