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Cesnick in the G&M today claims you can:
"3. Trigger tax losses. If you're thinking of selling a security that has dropped in value in order to use the capital loss, but you like the future prospects of the investment, consider selling the security outside your TFSA, then contribute the cash to your TFSA and repurchase the investment inside the TFSA. The future growth of the investment will be tax sheltered."

Now my tax knowledge is very old, but still I question this, mainly because I have heard the same advice applied to transfers in kind, or repurchases, to RRSPs. I am not going to look up the exact wording yet again about superficial losses, which I am sure have not changed. It says the loss is denied when there is a transfer to a RELATED PARTY.

Certainly the RRSP owner is related to you and the TFSA owner is related to you. So I can only conclude this not only will not allow the loss, but will make the loss forever lost.

Anyone with up-to-date tax info?
I think Mr. Cestnick is wrong as well. I believe capital loss will be denied under the superficial loss rules if the same security is sold in a taxable account and immediately purchased in a TFSA.
 

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From this post: http://www.canadiancapitalist.com/superficial-loss-rules-regarding-rrsps/

"After March 2004, CRA considers a loss as superficial if “a trust and its majority interest beneficiary (generally, a beneficiary who enjoys a majority of the trust income or capital) or one who is affiliated with such a beneficiary” buys (or has the right to buy) a property during the period starting 30 calendar days before the sale and ending 30 calendar days after the sale."

I think a TFSA would also fall under CRA's definition of a trust with a majority interest beneficiary.
 
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