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Life insurance to secure support obligations – Common problems

Life insurance to secure support obligations – Common problems

There is no silver bullet when it comes to structuring life insurance to secure support obligations.
Personal borrowing and corporate owned life insurance – The gory details

Personal borrowing and corporate owned life insurance – The gory details

Personally borrowing against a corporate-owned life insurance policy is not easy.
An update on legislation in progress and draft legislation not yet introduced

An update on legislation in progress and draft legislation not yet introduced

Here is a snapshot of the various legislative measures we’ve had on our radar.
Interest deductibility and GAAR – Singleton planning is still OK

Interest deductibility and GAAR – Singleton planning is still OK

Where a taxpayer restructures borrowings and ownership of assets to meet the direct use test as Singleton did, interest can be deductible and not GAAR-able.
Another CDA rectification case dismissed

Another CDA rectification case dismissed

The CDA calculation is a cumulative formula often over many years. Errors are costly and seeking rectification won’t help.
Too good to be true – Yep

Too good to be true – Yep

The CRA published a Tax tips 2025 Warning about aggressive tax schemes involving insurance products.
2025 CLHIA Roundtable – CDA Anti-avoidance rule considered

2025 CLHIA Roundtable – CDA Anti-avoidance rule considered

A recent CRA roundtable response involved the interaction of the CDA anti-avoidance rule and the rules upon amalgamation where a CDA balance arose from life insurance.
Bill C-15 – Items of interest

Bill C-15 – Items of interest

Bill C-15 contained a couple of measures relating to life insurance of note.
2025 Federal Budget – Not a lot of new news

2025 Federal Budget – Not a lot of new news

Budget 2025 was all quiet on the insurance front.
2025 Pre-budget musings – Is tax reform on the horizon?

2025 Pre-budget musings – Is tax reform on the horizon?

The Federal budget is coming down next week. Is tax reform on the horizon?
Restoring Trust When Relationships Break: From Brokenness to Belonging

Restoring Trust When Relationships Break: From Brokenness to Belonging

In family enterprises, trust is critical - it shapes not only personal relationships but also how resources, legacies, and responsibilities are shared across generations. Learn how families repair broken trust.
Exemptions from the Trust Reporting rules – What is the value of Life insurance?

Exemptions from the Trust Reporting rules – What is the value of Life insurance?

Touching on one issue specific to life insurance and certain exemptions under the trust reporting rules...
Summer reading of the legislative kind

Summer reading of the legislative kind

The August 15, 2025 package of draft legislation addresses some of the tax legislative back log.
Of interest from the OBBBA

Of interest from the OBBBA

The One Big Beautiful Bill Act (OBBA) is law. From an estate planning perspective, the measures relating to the threshold for exemption from US estate tax are of interest to us.
Stop-Loss Grandfathering – A hidden gem

Stop-Loss Grandfathering – A hidden gem

Stop-loss grandfathering is a hidden gem – no tax to the deceased or the estate on a redemption of grandfathered shares where there is enough CDA. It’s worth asking about.
Intercorporate Dividends, Safe Income and Life Insurance – News and views

Intercorporate Dividends, Safe Income and Life Insurance – News and views

Tax-deductible intercorporate dividends are not as simple as they once were. Safe income calculations are important.
How to Pass the Torch in a Family Business—Without Burning Bridges

How to Pass the Torch in a Family Business—Without Burning Bridges

We are fortunate to partner with Amy Castoro of The Williams Group to guest author our latest TOMPKINSights that provides tips for navigating the tricky handoff between generations.
Wealth and tax – Some developments from around the world

Wealth and tax – Some developments from around the world

We are basking in “tax expenditures”. When will the other shoe drop? Some recent developments relating to wealth and tax from around the world.
Rectification not available for excessive capital dividend

Rectification not available for excessive capital dividend

The use of the remedy of rectification is very limited in the tax context. In this case, involving excessive capital dividends, rectification was not allowed.
Exiting Canada and life insurance – Part II – Common life insurance issues when leaving with private company shares

Exiting Canada and life insurance – Part II – Common life insurance issues when leaving with private company shares

Part II of the mini-series: exiting Canada and life insurance - some of the common questions that relate to life insurance when an individual holding shares of a private company decides to leave Canada.
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ABOUT THE AUTHOR:

Florence is a co-editor of the Canadian Taxation of Life Insurance, currently in its 12th edition and Editor-in-Chief of Insurance Planning, both published by Thomson Reuters. She is a member of the Canadian Tax Foundation, Society of Trust & Estate Practitioners, Estate Planning Council of Toronto, and the Conference for Advanced Life Underwriting. Florence is a frequent speaker and author at these and many other organizations.

If you wish to reach Florence, please email florence@tompkinsinsurance.com