With the 2025 CRA tax filing season now recently behind us for most Canadian taxpayers, this is an excellent time for wealthy investors, family offices, business owners and their professional advisors to start looking ahead. For most individuals, 2025 Canadian personal tax returns and balances owing were due April 30, 2026, while self-employed individuals generally have until June 15, 2026 to file, although any balance owing was still due April 30, 2026, according to the CRA filing dates page.
My team and I are not CPAs, and we do not provide tax advice. However, we work very collaboratively with our clients’ tax professionals, estate advisors and other professional advisors. We are highly conversant with many of the tax-advantaged strategies available to affluent families, entrepreneurs and private investors—investors should always seek independent professional tax advice before implementing any tax strategy.
1. Employee Ownership Trust (EOT) business succession planning
For qualifying private business owners, the Employee Ownership Trust (EOT) regime may now be one of the most significant Canadian tax planning opportunities available. The 2026 federal Spring Economic Update proposed making permanent the exemption from tax on up to $10 million of capital gains realized by individuals, other than trusts, on certain sales of a business to an Employee Ownership Trust (EOT) or worker cooperative corporation, subject to conditions, according to the Government of Canada’s 2026 tax measures.
2. Lifetime Capital Gains Exemption planning
For owners of qualifying small business corporation shares, the Lifetime Capital Gains Exemption can be a meaningful wealth preservation tool. The CRA states that, under proposed changes, the 2025 lifetime capital gains exemption limit is $1,250,000 for qualifying property, with a maximum capital gains deduction of $625,000 based on the 50 percent inclusion rate, according to the CRA capital gains deduction page.
The art of taxation consists in so plucking the goose as to obtain the largest possible amount of feathers with the smallest possible amount of hissing.
Jean-Baptiste Colbert
3. Section 85 in-kind rollover and exchange strategies
Section 85 planning can allow eligible property to be transferred to a taxable Canadian corporation on a tax-deferred basis. The CRA says subsection 85(1) and 85(2) elections can defer all or part of the income that would otherwise arise on transfers of certain eligible property to a taxable Canadian corporation, provided the required conditions are met, according to CRA Interpretation Circular IC76-19R3.
4. Estate freezes and succession planning
Estate freezes can help shift future growth to the next generation or to a family trust while allowing the founder or owner to retain control, preferred shares, or fixed-value economics. Trust planning should be reviewed carefully, as Budget 2025 proposed broadening anti-avoidance rules related to indirect trust-to-trust transfers under the 21-year deemed-disposition regime, according to the Budget 2025 tax measures.
5. Structured flow-through share investments
The aforementioned tax measures website outlines that structured flow-through share strategies may offer significant deductions for suitable high-income investors with the right risk tolerance. Budget 2025 described Canadian exploration expense deductions at 100 percent and Canadian development expense treatment generally on a 30 percent declining-balance basis, while also extending the 30 percent Critical Mineral Exploration Tax Credit to March 31, 2027.
6. Corporate surplus and holding-company planning
For incorporated business owners, corporate surplus planning can be a major source of Tax Alpha™. Passive investment income can affect access to the small business deduction, since passive income above $50,000 can grind down the small business deduction and passive income at $150,000 can eliminate it, according to Wolters Kluwer’s CCPC passive income analysis.
7. Tax optimization, tax overlay and tax loss harvesting
Tax optimization and tax overlay strategies can add meaningful after-tax value for taxable investors. The CRA states that net capital losses can generally be carried back three years and forward indefinitely to reduce taxable capital gains, while superficial loss rules can deny losses when identical property is reacquired within the specified 30-day window, according to the CRA capital losses guidance.
8. Charitable giving with appreciated securities
For philanthropic investors, donating appreciated publicly traded securities can be more tax-efficient than donating cash after selling securities. The CRA states that eligible gifts of publicly traded securities to qualified donees can receive a zero capital-gains inclusion rate, according to CRA guide P113 on gifts and income tax.
9. Corporate-owned life insurance planning
Corporate-owned life insurance can be relevant for business owners seeking estate liquidity, tax-efficient corporate asset transfer, key-person coverage, or shareholder-agreement funding. In the right structure, it may help address estate taxes, equalization among heirs and business continuity—subject to review by tax, insurance, legal, and estate professionals.
10. Post-mortem and estate tax planning
For ultra-high-net-worth families post-mortem planning can help reduce double-taxation risks after death. The CRA states that a graduated rate estate can exist for up to 36 months after death if conditions are met, according to the CRA T3 Trust Guide.
11. Individual Pension Plans
Individual Pension Plans can be attractive for incorporated professionals, executives and business owners with T4 income. IPPs are generally designed for business owners and key employees;they can help reduce corporate taxable income while building retirement assets, according to Hylton Financial’s IPP overview.
12. Capital gains timing and realization planning
Tax Alpha™ often comes from controlling when gains are realized. The CRA has stated that it reverted to administering the currently enacted one-half capital gains inclusion rate after the government cancelled the proposed capital-gains inclusion-rate increase, according to the CRA’s 2025 capital gains update.
13. Prescribed-rate loan strategies
Prescribed-rate loan planning can support income-splitting within families where properly structured and maintained. For the second quarter of 2026, the CRA lists the prescribed interest rate used for taxable benefits from interest-free and low-interest loans as 3 percent, according to the CRA prescribed interest rates page.
14. SR&ED and accelerated depreciation planning
Business owners should review whether innovation, technology, manufacturing, or process-improvement investments qualify for tax incentives. Budget 2025 proposed increasing the enhanced 35 percent Scientific Research and Experimental Development expenditure limit to $6 million and introduced immediate expensing for certain manufacturing or processing buildings acquired on or after Budget Day and first used before 2030, according to the Budget 2025 tax measures.
15. Return of Capital (ROC) income strategies
Return of Capital (ROC) can be useful for taxable investors seeking cash flow with tax deferral. The CRA states that Return of Capital (ROC) reduces adjusted cost base, and if the adjusted cost base becomes negative, the negative amount is deemed to be a capital gain, according to the CRA mutual fund tax treatment guidance.
16. Canadian dividend income planning
Canadian dividend income can be attractive in taxable accounts because eligible and non-eligible dividends from Canadian taxable corporations may qualify for the federal dividend tax credit. The CRA states that eligible and non-eligible dividends from taxable Canadian corporations can qualify for the federal dividend tax credit, while foreign dividends do not, according to the CRA dividend tax credit page.
17. Option-writing and covered-call income strategies
Option-writing strategies can create income, enhance yield, or manage entry and exit points for concentrated positions. The CRA’s archived securities transactions bulletin states that covered option gains or losses generally receive the same income or capital treatment as the underlying shares, while naked options are normally on income account unless capital-account treatment is accepted on a consistent basis, according to CRA archived IT-479R.
18. Registered-plan maximization and asset location
Even for ultra-highnet-worth investors, RRSPs, TFSAs, RESPs, RDSPs, and other registered vehicles can contribute to long-term after-tax compounding. The CRA lists the 2026 RRSP dollar limit as $33,810 and the 2026 TFSA dollar limit as $7,000, according to the CRA registered-plan limits page.
19. Alternative Minimum Tax-aware transaction planning
Alternative Minimum Tax-aware planning can be a valuable strategy when large deductions, credits, capital gains, charitable gifts, or flow-through share investments are being considered. The CRA states that minimum tax can limit the tax advantage from certain incentives, including taxable capital gains, capital gains deductions, the federal dividend tax credit, investment tax creditsand capital gains on gifts of publicly listed securities, according to the CRA minimum tax page.
20. Family trust, holding-company, and 21-year deemed-disposition planning
Family trusts and holding-company structures can support estate freezes, asset protection, intergenerational planning, dividend planning, and long-term governance. For families with existing trusts, the 21-year deemed-disposition rule should be reviewed well in advance so that tax liabilities, liquidity needs, beneficiary distributions, and corporate reorganizations can be planned rather than rushed. Budget 2025 proposed amendments aimed at indirect trust-to-trust transfers that seek to avoid the 21-year deemed-disposition rule, according to the Budget 2025 tax measures.
21. Cross-border, residency, and departure-tax planning
Ultra-high-net-worth families are increasingly mobile and that means cross-border planning can be a major source of Tax Alpha™. Families with U.S. persons, foreign property, non-resident beneficiaries, immigration or emigration plans, foreign trusts, or multi-jurisdictional business interests should coordinate Canadian and foreign tax advice before changing residency, selling assets, gifting property or restructuring entities.
Final thoughts
The strategies above can be powerful, but they should be implemented carefully and with proper professional advice. The CRA says the General Anti-Avoidance Rule can deny tax benefits where transactions technically comply with the law but defeat the object, spirit, or purpose of the relevant provisions, according to the CRA GAAR guidance.
For wealthy investors, family offices, business owners, and their advisors, Tax Alpha™ is not about one isolated tactic. It is about coordinating investment management, corporate structure, estate planning, philanthropy, liquidity needs, risk tolerance, and tax advice into one integrated after-tax wealth strategy. After all, it is after-tax results that matter most.
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Thane Stenner Interviews/Articles, Member of Canadian Family Offices.
About Stenner Wealth Partners+
Stenner Wealth Partners+ (SWP+) is an in person/virtual Multi-Family Office/Outsourced CIO Consulting team of financial/wealth specialists with a boutique approach and global perspective. SWP+ serves Canadian and US investors/households with generally a minimum of 10M+ in investable assets or 25M+ net worth. As a CG Wealth Management team, SWP+ is a highly exclusive practice team with one of Canada’s largest independent wealth management firms. Client Range of Net Worths: between $25M To $3B+. They strategically limit new client engagements, onboarding a select number of new key relationships annually to ensure a highly personalized and focused approach. SWP+ is a member of Canadian Family Offices.
*Mr. Stenner’s viewpoints within this interview were submitted to CFO on May 6, 2026. Tax Alpha™ is a trademarked phrase in Canada that Mr. Stenner has been utilizing since 2010.
Disclaimer: This story was created by Canadian Family Offices’ commercial content division on behalf of Stenner Wealth Partners+ at CG Wealth Management, which is a member and content provider of this publication. CG Wealth Management is a division of Canaccord Genuity Corp., member of CIPF and CIRO. Tax & Estate advice offered through Canaccord Genuity Wealth & Estate Planning Services Ltd. Thane Stenner’s views, including any recommendations, expressed in this article are his own only, and are not necessarily those of Canaccord Genuity Corp.