Year-end conversations worth having before December 31
Explore the key year-end planning conversations on tax, charitable giving and cross-border exposure before options narrow.
CIBC Private Wealth
Sep. 25, 2026
5-minute read
- Starting before December 31 can give you more flexibility: Thoughtful year-end planning takes time, and starting earlier can help you evaluate options before deadlines and administrative steps begin to narrow them.
- Charitable giving, personal and business tax planning, and cross-border exposure each bring different considerations: Some strategies have hard year-end deadlines, while others may not, but year-end is still a natural time to review what has changed and what may need attention.
- Year-end planning is most effective when viewed as part of a broader financial strategy: Your advisor can help connect these conversations, bring in specialists where needed, and ensure decisions are coordinated around your overall goals.
The window between now and December 31 is one of the most consequential stretches of the financial year — not because of what might go wrong, but because of what’s still possible. Every year-end strategy available to you is still fully open: a charitable gift structured to minimize tax, a conversation about your cross-border exposure, and a decision about how to handle a significant gain. That range of options is at its widest today, and it narrows from here.
We asked three CIBC Private Wealth specialists — Kate Lazier, Director and Lead, Estate Planning and Philanthropy, on charitable giving, Jamie Golombek, Managing Director, Tax and Estate Planning, on tax planning, and Jacinthe Marquis, Director and Lead, Cross-Border Tax Strategist, on cross-border and U.S. holdings — what a well-timed year-end review actually delivers for clients. Their answers were different in detail but consistent in direction: the clients who get the most from year-end planning are the ones who start the conversation early enough to still have real choices.
1. Charitable giving: Kate Lazier, Director and Lead, Estate Planning and Philanthropy
Meeting deadlines is typically the straightforward part of tax planning. What takes time is deciding which causes you want to support and working out whether this is a year to concentrate several years of giving into a single gift. Giving appreciated securities in kind can eliminate the capital gains tax you would otherwise pay on a sale, but it is not a same-day transaction, and a transfer started in late December may not be completed in time to count for this year.
What to consider:
- Whether 2026 is a high-tax year for you, and whether it makes sense to concentrate several years of giving into one gift
- Whether to give cash or appreciated securities, and how long an in-kind transfer takes to complete
- Whether the alternative minimum tax affects the expected result of a significant gift
- Whether a donor-advised fund suits you, and if you want the tax benefit now
- Whether your will reflects your current wishes about a gift from your estate
"When planning a charitable gift, it is important to consider not only how much you give, but also what you give.”
— Kate Lazier
2. Tax planning: Jamie Golombek, Managing Director, Tax and Estate Planning
Tax-loss selling is a well-known strategy, although the timing is tighter than many people expect: the trade has to take place on or before December 30 in order to settle by the December 31 year end. 2026 also brings a deadline that applies only this year, because it is your last opportunity to realize a capital loss that can be carried back to 2023. If you own a corporation, salary and dividend decisions should also be made before year end.
What to consider:
- Whether your 2023 return shows gains worth carrying a 2026 loss back against
- Your salary and dividend mix, if you own a corporation, and the Ontario and Quebec rate changes coming in 2027
- Donating securities in kind, which provides a receipt at fair market value and no tax on the accrued gain
- Whether AMT (alternative minimum tax) applies to a significant 2026 gain, which can sometimes be recovered within the following seven years with advance planning
- Registered plan contributions, deductible fees, and income-splitting opportunities
“Not only do you get a donation receipt for the fair market value of your gift, but you pay zero capital gains tax on the accrued gain.”
— Jamie Golombek
3. Cross-border and U.S. holdings: Jacinthe Marquis, Director and Lead, Cross-Border Tax Strategist
You don’t need to live or work in the U.S. to have cross-border tax exposure. Stocks in a U.S. corporation, a U.S. vacation property, units in a U.S. limited partnership, or a child who has moved south and is a beneficiary of your estate will each create it. Nothing in this area expires on December 31, which causes additional challenge. What can happen instead is that it waits until spring, when it gets handled close to filing deadlines, or worse after you pass away, when little to no option remains available.
What to consider:
- Whether foreign property reporting applies, keeping in mind that the test is based on the cost amount, not market value
- U.S. limited partnership units you own, and whether they create a U.S. tax filing obligation
- Records for any U.S. real estate you sold this year, including withholding documentation
- An updated list of your U.S.-situs assets at current values, measured against your worldwide estate value
- Whether a change in family circumstances has impacted your estate plan
“Many cross-border issues are easy to overlook because they do not arise from straightforward activities such as living or working in the U.S.”
— Jacinthe Marquis
Year-end planning tends to go better when it isn’t compressed into the last few weeks of December
These decisions take time to think through, and several of them reach into more than one area of your financial life at once: for example, a charitable gift that’s also an estate decision or a compensation choice that’s also a retirement one.
Your CIBC Private Wealth advisor can look at the whole picture with you, bring in the right specialist when it matters, and help you work out what applies to you and what to do about it while there’s still time to act.
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