Rosen & Associates Tax Law

08/18/2026

🏒💼 When does a signing bonus become taxable employment income?

The Tax Court of Canada is hearing a high-profile case involving John Tavares and the CRA, with millions of dollars at stake and potentially significant implications for cross-border tax planning, employment contracts, treaty interpretation and future free agent acquisitions.

This case is a reminder that the substance of a payment, not just its label, can have major tax consequences.

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Canada Revenue Agency regards $15M signing bonus as income, but Tavares says it was an "inducement" to be taxed at a much lower rate.

08/13/2026

Last week, R&A was excited to welcome our 2026–2027 Articling Cohort, along with two new associates joining the team!

We’re thrilled to have them with us and look forward to supporting their journeys, celebrating their accomplishments, and watching them grow throughout the year. Here’s to an exciting year ahead!⚖️

08/12/2026

Is CRA Automation Really Making Canada’s tax System Simpler?

The CRA is increasingly turning to AI, automated filing and data-driven audits. But with taxpayer complaints rising 27% and only about one-third of Canadian tax returns considered suitable for reliable automation, there are growing questions about what technology can, and can't solve.

This Canadian Accountant article looks at CRA automation, AI-driven audits, taxpayer rights and the growing need to simplify Canada’s tax system.

📰Read the full article to learn what's ahead.
https://hubs.li/Q04sQNg10

08/05/2026

An Ace of an Evening! 🎾

Yesterday our team enjoyed an exciting evening at the National Bank Open, courtesy of our Health & Wellness Committee. Watching Aryna Sabalenka defeat Moyuka Uchijima made for an unforgettable night filled with great tennis and even better company.

08/03/2026

Our office is closed today in observance of the Ontario Civic Holiday.

We'll be back and ready to assist you tomorrow, Tuesday, August 4. Wishing everyone a safe, relaxing, and enjoyable long weekend!

07/24/2026

The Department of Finance is proposing a wide range of tax reforms, and they're now open for public feedback.

The draft legislation includes measures to simplify certain tax rules, strengthen compliance, expand eligibility for some tax incentives, and introduce technical amendments across Canada's tax system.

With consultations running until September 4, now is the time to understand what's being proposed.

📖 Read the full article for all the details.
https://hubs.li/Q04qKLHh0

07/22/2026

A recent Tax Court of Canada decision serves as an important reminder that re-contributing funds in the same calendar year can trigger costly overcontribution penalties if you don't have sufficient contribution room.

Even though the taxpayer was simply re-depositing money that had previously been withdrawn, the Court confirmed that the Income Tax Act's TFSA rules are strict, and intention alone isn't enough to avoid the 1% monthly tax on excess contributions.

Before making your next TFSA contribution, take a moment to confirm your available contribution room. A simple mistake can become an expensive one.

Have questions about your TFSA or a CRA assessment? Our team is here to help.

07/20/2026

🚲🍻 Our team traded the boardroom for the bike this Friday as we took on a Pedal Pub adventure through the city!

It was a great afternoon to unwind, enjoy some fresh air, and spend time together outside the office. Building strong relationships isn't just important with our clients, it's something we value within our team too.

Thanks to everyone who joined and made it such a fun event. Here's to creating great memories together!

07/16/2026

Congratulations to Matthew Po***ck on his promotion to Managing Associate at Rosen & Associates Tax Law.

Since joining the firm more than six years ago, Matthew has grown into a highly respected advocate, leader, and mentor.

Beyond his legal achievements, Matthew has played a key role in our firm’s growth through mentorship, recruitment, process improvement, and steadfast support of our team. He exemplifies the values we cherish most: leadership, integrity, continuous learning, collaboration, and a genuine commitment to helping others succeed.

We are grateful for Matthew’s many contributions and look forward to seeing him thrive in this new leadership role.

Congratulations, Matthew!!

https://hubs.li/Q04pPS8y0

07/07/2026

⚠️ AI can be a helpful tool, but it can't replace legal expertise

A recent Tax Court decision is a powerful reminder that while AI can be a valuable tool, it isn't always accurate. After a self-represented taxpayer relied on AI-generated court cases that didn't exist to challenge the CRA, the Court dismissed the submissions and warned that fake citations can have real consequences.

With reports of AI-generated fake case law on the rise in Canadian courts, this decision highlights the importance of using AI responsibly and always verifying its output.

Learn how this Tax Court decision reinforces the importance of accurate legal research and professional judgment: https://hubs.li/Q04nLLcj0)