Anti-Avoidance – Tompkins Insurance

All Articles Anti-Avoidance

June 24, 2026

CRA guidance for mandatory disclosure rules – Not so honourable mention

The CRA is signalling its displeasure with aggressive planning schemes involving insurance.

Florence Marino

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All Articles Anti-Avoidance

January 7, 2026

Too good to be true – Yep

The CRA published a Tax tips 2025 Warning about aggressive tax schemes involving insurance products.

Florence Marino

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All Articles Anti-Avoidance Estate Freezes

October 2, 2024

CRA Guidance on Mandatory Disclosure – Contingent fees

CRA guidance on mandatory reporting says referral fees in respect of estate freeze transactions and the acquisition of life insurance do not require mandatory reporting. Positive for mainstream non-aggressive tax planning connected to life insurance…

Florence Marino

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All Articles Anti-Avoidance Business Succession Estate Freezes

March 27, 2024

The new GAAR is already getting warmer

More good news from the CRA on the new GAAR. Common tax and estate planning transactions that were not GAAR-able before are not going to be GAAR-able now.

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All Articles Anti-Avoidance Capital Dividend Account Corporate Ownership Life Insurance Tax Pipeline

March 13, 2024

Post-mortem pipelines under the new GAAR are OK

The CRA has confirmed that it does not see post-mortem pipeline planning as a misuse or abuse under the new GAAR and will continue to issue favourable rulings. Life insurance in conjunction with post-mortem pipeline…

Florence Marino

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All Articles Anti-Avoidance Corporate Ownership Trusts

February 28, 2024

Avoiding the 21-year rule? – Be notified

Certain tax planning to avoid the 21-year rule must be reported to the CRA and in their view, subject to GAAR. Consider using life insurance to solve for problems this planning is meant to address.

Florence Marino

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All Articles Anti-Avoidance Business Succession Intergenerational Business Transfers Life Insurance Tax

December 14, 2023

Tax Legislation tabled – Some highlights

Bill C-59 implementing many measures from the 2023 Federal Budget is in progress. Here are our comments on some of the highlights.

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All Articles Anti-Avoidance

November 2, 2023

A new GAAR – Pretty chilly right now

On August 4, 2023, the Department of Finance released revised draft legislation (“the proposals”) that would amend the general anti-avoidance rule (GAAR) in the Income Tax Act (the Act). Given the very short comment period…

Florence Marino

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All Articles Anti-Avoidance Business Succession Capital Dividend Account Corporate Ownership Life Insurance Tax

October 26, 2023

Looking back and looking forward

Over the past 30 years the acceptance and deployment of life insurance within estate and business succession planning has blossomed. In large part, we attribute this increased utilization to a greater understanding of the unique…

Florence Marino

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Anti-Avoidance9

CRA guidance for mandatory disclosure rules – Not so honourable mention

Too good to be true – Yep

CRA Guidance on Mandatory Disclosure – Contingent fees

The new GAAR is already getting warmer

Post-mortem pipelines under the new GAAR are OK

Avoiding the 21-year rule? – Be notified

Tax Legislation tabled – Some highlights

A new GAAR – Pretty chilly right now

Looking back and looking forward

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