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99% of my entire net worth is denominated in USD, and I only trade in USD stocks & bonds.

Does Canadian capital gains tax only trigger when I attempt to convert those gains/losses into CAD? In other words, can I continue trading indefinitely, year after year, solely in USD without concern for the CRA, and only when I try to convert it into CAD will the capital gains trigger for that particular year?

Can anyone shed some light on how much I am supposed to pay the CRA?

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It doesn't matter what currency you trade in or barter, if you liquidated a position - you recognize the gain. See the CRA guidance here. To handle USD transactions, use this CRA guidance on currency conversions.

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