According to the Canada Revenue Agency (CRA), A Capital Gain/Loss is registered when you have been considered to have sold property. Therefore for each buy-and-sell pair of transactions, the capital gain/loss must be reported. Say for example - You bought and sold a stock 2 times, and then bought again (and have yet to sell for the third time) you will still have to report your capital gain/loss of those 2 times, even if you are still holding the security.
For more information, check out: Canada Revenue Agency (CRA) - Capital Gains
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