Can a taxpayer claim a capital loss when a stock plummets in value and then is delisted from the Toronto Stock Exchange? I bought a small amount of a mining stock a while back and it’s now worthless, but I didn’t sell the stock and so I assume I am out of luck when it comes to claiming a capital loss.

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Good news: Even though you didn’t sell the shares before they were delisted, you still may be able to claim a capital loss – either now or in the future – depending on the status of the company.

According to Section 50(1) of the Income Tax Act, there are three scenarios in which a loss can be claimed:

• the company went bankrupt during the year
• the company is insolvent and subject to a “winding-up order”
• the company is insolvent; it no longer carries on business; the fair market value of the shares is nil; and “it is reasonable to expect that the corporation will be dissolved or wound up and will not commence to carry on business.”

If one of the above three situations applies, the investor can deem to have disposed of the stock at the end of the year “for proceeds equal to nil and to have re-acquired it immediately after the end of the year at a cost equal to nil,” the Income Tax Act states.

Why the bit about reacquiring the shares for nil?

Well, if the shares happen to increase in value at a later date (unlikely, but not impossible), the investor could potentially realize a capital gain and have to pay tax.

According to a TD Waterhouse bulletin, because there is no form for making a Section 50(1) election, investors should attach a signed letter to the tax return stating that they want Section 50(1) to apply to the shares. “For returns that are electronically filed, all elections and supporting documentation must be submitted in writing,” TD Waterhouse says in the bulletin (available at tinyurl.com/kpoy2sg).

Your broker may be able to facilitate an even simpler solution. For investors holding delisted (and presumably worthless) stock, some financial institutions will agree to purchase the shares for a token amount (a penny per share, for example) and then charge the client a nominal fee so that the net cost to both parties is zero.

“This allows the client to use the transaction slip from the sale for tax purposes,” TD Waterhouse says.

“It is important to understand the potential downside of utilizing this procedure: If the ‘worthless security’ ever revives itself and becomes relisted and tradable, you would have given up all ownership rights by selling the shares to the financial institution.”

When I asked my own discount broker, BMO InvestorLine, about its procedure, I was told that delisted shares can be disposed of using a “deed of gift” form. Essentially, the client agrees to give the broker the worthless shares and the disposition appears in the client’s transaction history with a value of zero. This provides a record that can be used to claim the loss for tax purposes.

BMO’s deed of gift form states that it is the investor’s “responsibility to determine whether the gift of the securities constitutes a disposition within the Income Tax Act (Canada) which would allow the donor(s) to realize a capital loss.”

So take heart: If the company you own goes bust, you can still claim a loss on the shares even if there is no market for them.

If I may leave you with one other piece of advice: Try to invest only in stable, profitable companies with a history of paying dividends. That will reduce the chances of finding yourself in a similar situation again.

Follow John Heinzl on Twitter: @johnheinzl