TAX DECISIONS RARELY STAND ALONE
The value of year-end planning lies in modelling how transactions interact, then coordinating the order and timing of execution.
Let’s start with a hypothetical scenario where an investor has a concentrated equity position with substantial unrealized gains, declining value in investments that led to realization of portfolio losses, and a planned charitable donation at the same time as when the sale of shares in a privately held business is under consideration.
Each of these situations presents a decision to make regarding the potential tax-planning opportunity. And the order, timing and interaction of those transactions could produce very different outcomes.
Impact Of Policy Clarity On Decision-making
One significant source of uncertainty in recent years has been resolved. In March 2025, the federal government cancelled its proposed increase in the capital gains inclusion rate from one-half to two-thirds. The general inclusion rate therefore remained 50%.¹
The increase in the Lifetime Capital Gains Exemption for qualifying small business corporation shares and qualified farming or fishing property was retained, with indexation resuming in 2026. The amount and eligibility conditions should be confirmed against current guidance for any contemplated transaction.
These developments provide a clearer policy setting for investors and business owners. However, they do not determine the best timing of a sale, the treatment of investment losses or how a charitable contribution fits within a wider financial plan.
When One Tax Decision Changes Another
Tax-loss harvesting provides a useful example. Investors with unrealized losses in non-registered accounts may consider selling certain holdings to offset realized capital gains. Net capital losses can generally be carried back three years or forward indefinitely, subject to applicable rules.²
Selling a security at a loss and immediately repurchasing identical property may trigger the superficial-loss rule, potentially denying the immediate deduction. The rule can also apply when an affiliated person or entity acquires the identical property within the relevant period and continues to hold it 30 days after the sale.
Charitable giving introduces another interaction. Donating eligible appreciated publicly traded securities directly to a qualified donee can result in a zero capital-gains inclusion rate for regular income-tax purposes and may generate a charitable donation tax credit.³
The Alternative Minimum Tax (AMT) calculation treats the same transaction differently. Under the rules applicable in 2026, 30% of the accrued gain on donated publicly listed securities is included in adjusted taxable income; only 80% of the donation tax credit is recognized. The AMT calculation also includes 100% of other capital gains and permits only 50% of capital losses carried forward from prior years to be deducted.
These differences mean that realizing a significant gain, using carried-forward losses and making an in-kind charitable gift in the same year can produce an AMT liability even when each transaction appears tax-efficient under the regular calculation.
AMT doesn’t necessarily represent a permanent additional cost. An amount paid can generally be carried forward for seven years and applied against future regular tax when regular tax exceeds AMT. Recovery depends on the investor’s future taxable income. Scenario modelling should therefore consider both the current-year liability and the likelihood and timing of recovering any AMT paid.
Another constraint is liquidity. Even if AMT can eventually be recovered, it may create an immediate cash requirement. The investor must determine whether the remaining portfolio can support anticipated tax payments and other financial commitments after the transactions are completed. If private-company shares are involved, eligibility for the Lifetime Capital Gains Exemption and the sequencing of legal or corporate steps could also affect timing.
Comparing a base case with alternative transaction sequences can reveal which approach supports the investor’s objectives without introducing avoidable financial or tax consequences.
A Coordinated Process For The Final Quarter
Having a coordinated and staged process keeps tax efficiency in its proper place. Begin by assess the current position on projected income, realized and unrealized gains, available losses, investment holdings, expected obligations and planned transactions.
The investment advisor, accountant and legal counsel can then evaluate how each scenario affects regular income tax, AMT, portfolio exposure, liquidity and any corporate or trust arrangements. Their roles remain distinct, but the analysis should use the same assumptions and transaction sequence.
And remember, in-kind charitable donations, private company transactions, legal reorganizations and securities transfers can require documentation and processing well before December 31. So, an execution calendar should identify dependencies, professional approvals and operational deadlines, along with decisions that require further analysis or are better deferred.
Exhibit: Year-End Planning Process
|
Stage |
Focus |
|
Assess the Current Position |
Income, gains and losses, holdings, obligations and planned transactions |
|
Compare Scenarios |
Regular tax, AMT, liquidity and portfolio implications |
|
Coordinate and Execute |
Donations, transfers, legal and corporate steps, approvals and deadlines |
Year-end planning is most effective when decisions are considered together rather than as a collection of individual tax saving strategies. As you enter the new year, do so with a clearer understanding of how investment choices, tax obligations, liquidity and longer-term objectives fit together, supported by an execution plan that reflects those connections.
Sources
1. Government of Canada, press release
2. Canada Revenue Agency, Capital Losses
