Selling the losers in your stock portfolio can help save you tax

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Cite

Wong, C. (2026, October 15). Selling the losers in your stock portfolio can help save you tax. Toronto Star. https://www.thestar.com/business/personal-finance/selling-the-losers-in-your-stock-portfolio-can-help-save-you-tax/article_47f45174-d4a9-5b65-a8b8-ce3aa1a9c301.html

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Toronto Star · collected 2026-10-15 · by Craig Wong

Quick Summary

Experts advise reviewing stock portfolios to identify underperforming investments that can be sold at a loss to offset capital gains and reduce taxes. Kris Kibler from Wealthsimple explains that selling stocks for less than their purchase price generates losses which can be deducted against taxable capital gains, thereby lowering tax obligations. However, it's crucial to adhere to rules such as the superficial loss rule, which prevents claiming losses if identical securities are repurchased within 61 days of sale. Additionally, Julie Petrera from Edward Jones emphasizes that tax-loss selling should complement rather than dictate long-term investment strategies.
Written locally by qwen2.5:14b on 2026-10-15, using this article's own text rather than the other coverage of the same event (that is the story summary below).

AI analysis runs on qwen2.5:14b, locally

Story summary

Nobody likes taking a loss when selling stocks, but experts advise reviewing your portfolio at year-end to reduce your tax bill. On October 15, 2026, Kris Kibler from Wealthsimple explained that selling losing investments can offset capital gains on better-performing stocks, reducing overall tax liability. For instance, if you sell shares purchased for $10,000 at a loss of $7,000, the resulting $3,000 capital loss can be deducted against other capital gains when filing your taxes. However, Kibler stressed that this strategy should not be executed in isolation and must align with broader investment goals to avoid purchasing similar securities immediately after selling them for tax purposes.

Written for “Stock Portfolio Tax Strategies” on 2026-10-15, grounded in this article and the 0 other(s) covering the same event.
Why this leaning score
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No political leaning scored for article 82641 · logged 2026-10-15

Story

📰 Stock Portfolio Tax Strategies
Economy/Business · 1 article(s) covering the same event.

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Signals How these are calculated →

Claims extracted
21
sentences that state something as happening or true
Uncertain
29%
6 of 21 hedged ("reportedly", "may", "according to")
Leaning
not political
takes no side on a contested political question
Publisher signals
63/100
Toronto Star's corrections and hedging, across everything collected from it. Not a measure of accuracy.
Outlets on this story
1
Economy/Business
Same framing elsewhere
1
articles that frame the event the way this one does
Analyzed 2026-10-15 · how these are computed

How this is being covered How these are calculated →

Article leaning vs. publisher reliability
Source leaning vs. consistency

Publisher

Toronto Star · 7344 article(s) · 20 correction(s) detected
Running correction rate · 20 correction(s)
2026-10-07
Correction
2026-09-24
Correction

Who wrote this

Craig Wong
1 article(s) here · 1 carrying a prediction
🔮 Nobody likes taking a loss when selling stocks, but experts say now is the time to look at your portfolio and see if there are any investments that haven’t worked out as you hoped that might help you reduce your tax bill.
The only article under this byline in the corpus.

Topics

CRA Edward Jones OTTAWA Wealthsimple

Subjects

CRA ORG · 3× Kibler PERSON · 2× Edward Jones ORG · 1× Julie Petrera PERSON · 1× Kris Kibler PERSON · 1× OTTAWA GPE · 1× Petrera PERSON · 1× The Canadian Press ORG · 1× Wealthsimple ORG · 1×

Narrative

The superficial loss rules don’t just apply to your account, but also extend to your spouse or common-law partner, corporations you or your spouse control, or what the CRA calls an affiliated person. “What the CRA doesn’t want you to do is get the advantages of the tax-loss harvesting or tax-loss selling strategy in order to get the benefit and then purchase the exact same securities again and continue in the same portfolio,” Kibler said.
framing: mixed · carried by 1 article(s) · first seen 2026-10-15
🔮 Nobody likes taking a loss when selling stocks, but experts say now is the time to look at your portfolio and see if there are any investments that haven’t worked out as you hoped that might help you reduce your tax bill.
2026-10-15 · Toronto Star
Selling the losers in your stock portfolio can help save you tax · mixed framing

Claims (21 extracted, 6 hedged)

Nobody likes taking a loss when selling stocks, but experts say now is the time to look at your portfolio and see if there are any investments that haven’t worked out as you hoped that might help you reduce your tax bill. uncertain
you → like → bill
Reviewing your portfolio and taking a look at what gains you’ve seen and how you might be able to offset them with any losses should be part of your year-end tax planning. uncertain
you → review → planning
Kris Kibler, tax planning lead at Wealthsimple, says if you are selling shares at a loss, that deficit can be used to offset capital gains on better performing stocks, reducing the amount of tax you will owe. asserted
you → say → tax
He explained that if you bought shares for $10,000 and later sold them for $7,000, the $3,000 capital loss could be deducted against capital gains. uncertain
loss → explain → gains
That deduction will reduce the amount of tax you might owe when you file your return next year. uncertain
you → reduce → return
Kibler says it is important that tax-loss selling isn’t done in a vacuum. asserted
selling → say → vacuum
“You don’t necessarily engage in tax-loss harvesting or tax-loss selling in order to just take advantage of the tax implication with disregard for the investment portfolio overall,” he says. asserted
he → engage → portfolio
“This always wants to be kind of done in tandem with your overall investment and financial plan as a whole.” asserted
This → want → whole
It is also important to ensure you don’t run afoul of the rules governing what losses you can claim. uncertain
you → ensure → losses
Tax-loss selling only applies to taxable or non-registered accounts. asserted
selling → apply → accounts
Losses in accounts such as your TFSA, RRSP or RESP cannot be used to offset your taxable gains outside those accounts. asserted
Losses → use → accounts
The losses can only be used to offset any taxable capital gains you have. asserted
you → use → gains
They can’t be deducted from your regular income. asserted
They → deduct → income
If you don’t have any capital gains to offset this year, your losses can be used to reduce your taxable capital gains going back three years or you can carry the losses forward to use in future years. asserted
you → have → years
CRA also doesn’t allow what is referred to as a superficial loss, which prevents you from claiming the loss if the same or identical security is repurchased within a 61-day window starting 30 calendar days before the sale and extending 30 days after the sale. asserted
security → allow → sale
The superficial loss rules don’t just apply to your account, but also extend to your spouse or common-law partner, corporations you or your spouse control, or what the CRA calls an affiliated person. “What the CRA doesn’t want you to do is get the advantages of the tax-loss harvesting or tax-loss selling strategy in order to get the benefit and then purchase the exact same securities again and continue in the same portfolio,” Kibler said. asserted
Kibler → apply → portfolio
Julie Petrera, director of financial planning at Edward Jones, says it is important to remember that tax-loss selling is not an investment strategy. asserted
selling → say → Jones
“It should support your long-term goals but not drive your long-term investing goal,” she said. “I wouldn’t make decisions on what I’m holding in my portfolio just for short-term tax reasons.” asserted
I → support → reasons
Petrera said losses are part of investing at times, but tax-loss selling is the “silver lining” when you have securities that have gone down. asserted
that → say → securities
“While you have lost money on that security or on that investment, the money that you’ve lost could be made up for in tax savings applied to another investment,” she said. uncertain
she → lose → investment
This report by The Canadian Press was first published Oct. 15, 2026. asserted
report → publish → Press
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