"If you have the money buy $5000 of new shares for the TSFA." This is good advice if you have the free cash.

Otherwise there is a trade-off - you lose your tax loss but you can get more shares in the TFSA if you contribute at a lower price. Right now you can get about double the number of shares into the TFSA as opposed to waiting for the share price to reach $2.40 before contributing - about 4000 shares as opposed to 2000 shares.

If NOT were to rise to $10.00 and you had 4000 shares of NOT in a TFSA you would have $40,000. in the TFSA (tax-free).

If NOT were to rise to $10.00 and you had 2000 shares in the TFSA plus 2000 additional shares outside the TFSA you would have $20,000 in the TFSA (tax-free)and 2000 shares outside the TFSA with a taxable capital gain of about $15,000. The actual tax would be in the order of $2000. depending upon tax brackets etc. So if NOT rose to $10.00 you would be out about $2000.00 if you waited for NOT to rise to $2.40 before contributing. This presumes that you do not have off-setting tax losses on other shares.

Now of course this is dependent upon NOT rising to $10.00. Don't forget if you do transfer shares into your taxfree account you are giving up the right to claim the tax loss forever; so to some extent you are speculating that NOT will go up enough to offset the potential benefit from any tax loss in NOT shares (claimable against capital gains in other stocks, etc.).

I decided to transfer shares with a loss into my TFSA based upon the above scenarios. I don't think there is any hard and fast rule here though if you are very optimistic about NOT going forward you should probably put as many NOT shares as possible into the TFSA.

I am not a tax expert; do your own DD.