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Year-end tax-loss selling is better done sooner than later and with an eye on the rules

by Wayne Cheveldayoff, 2004-10-21

When it comes to tax-loss selling, itís better to sell your losing stocks in October or November than to wait for year-end to do it. The reason is quite simple: youíll likely get a higher price for them.

The prices of tax-loss candidates, particularly small cap stocks, usually drift lower right into the deadline (December 24) as most people procrastinate, hoping for a miraculous recovery.

If you sell now, you can buy the same stock back later when a lot of others are selling, usually with a Ďsell at whatever price you can getí mentality.

Of course, nothing is ever certain in the investing world. It is possible that what has been a loser until now can become a winner in the last two weeks of the year.

But if you are thinking of waiting until the last minute, just remember that history and human nature are not on your side. Weak stocks usually get weaker as they get dumped in the days leading up to Christmas.

The reason behind all this is that tax rules allow individuals to deduct their capital losses against capital gains. (This applies only to securities held outside of registered plans like RRSPs, RRIFs and RESPs.)

A capital loss incurred in 2004 can be used to offset capital gains incurred in 2004 or, if there arenít enough gains to use up all the losses this year, in any of the last three years.

This means that investors can save on income taxes for this year or get a tax refund for any year going back to 2001 in which they have reported and paid income tax on capital gains.

Remaining capital losses can be carried forward to offset capital gains anytime in future years.

The capital gains or losses donít have to be from stocks. They can be from selling other securities, such as bonds, mutual funds, exchange traded funds (ETFs), or even real estate.

But be warned that, as with many things related to the Income Tax Act, it is important to follow the rules in how you take and claim your losses.

If you want to be able to claim the capital loss from selling a stock, you (or someone related to you) cannot repurchase the same stock within 30 days of the sale. Your loss could also be denied if you bought more of the stock in the 30 days prior to selling it.

However, the rules donít prevent you from buying another stock in the same sector (for example, selling one insurance company to buy another).

Investors should also check their mutual fund or ETF holdings to see if capital losses can be harvested there.

You can generate claimable losses and still keep your stock market exposure by switching from an equity mutual fund into an ETF replicating the S&P/TSX Composite or visa versa.

Similarly, you could dump a Canadian technology mutual fund and instead buy the iUnits S&P/TSX Canadian Information Technology ETF.

However, it wouldnít be within the rules to sell one index fund based on the TSX Composite Index at one institution and buy an ETF based on the same index or another index fund based on this index from another financial institution. Tax authorities would consider all three of these to be identical property and would reject the claim.

There is another special tax rule that investors may be interested in. If you own shares that have simply lost all value such as from bankruptcy, you donít have to actually sell these to trigger a capital loss. You can claim the capital loss if you attach a note to your tax return explaining the situation and reporting that the shares have been disposed of for no proceeds.

You can claim the loss even if the company hasnít formally declared bankruptcy as long as the company is insolvent, it is no longer carrying on business and is unlikely to in the near future, and the fair market value of the shares is zero.

Of course, since you still own the stock, if a miracle gives it some value again and you eventually sell it, you would have to report a capital gain at that time.

December 24 is the deadline for tax-loss selling for stocks traded on the Toronto Stock Exchange because, with three-day settlement and the exchange closed December 27 and 28 in lieu of the Christmas and Boxing day which fall on Saturday and Sunday this year, it is the last day of the year that you can sell and have your sale registered as occurring in 2004.

Wayne Cheveldayoff is a former investment advisor and professional financial planner. He is currently specializing in financial communications and investor relations at Wertheim + Co. in Toronto. His columns are archived at and he can be contacted at

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©2004 Wayne Cheveldayoff