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Jennifer Mak

Partner, Tax Litigation

Jennifer resolves tax controversies with a holistic view to deliver the best overall result.

Jennifer's practice encompasses all aspects of tax controversy and litigation.

Jennifer has represented clients in appeals before the Tax Court of Canada and Federal Court of Canada.  She regularly works on complex objections and audits for private companies and high-net-worth individuals involving international and domestic issues.  

Jennifer has successfully resolved tax controversies involving residence for tax purposes, GST/HST, applications for judicial review, shareholder and employee benefits. 

Jennifer is a mentor with the Federation of Asian Canadian Lawyers. Each year, she helps two Asian Canadian law students navigate the legal profession.  

Natalie, James and Jennifer have been wonderful to work with for our numerous legal cases. They understand there’s a job to be done and they get it done with minimal fuss and detailed written follow-up.

- Verified Client Feedback for the Legal 500: 2024 Elite Tax Boutique Award

The CRA accepted our submissions and conceded 100% before the hearings. I am so happy with Counter’s representation and the result. Justice has been served and my bruised faith restored.

- Kuldeep Sharma, President, Courtyard by Marriott Toronto/Brampton

There is no ego; just a singular focus on getting the right result. I look forward to continuing to work with the Counter team.

- Vikram Gulati, CPA, CGA

At every step, Counter kept me informed and made practical recommendations. Counter negotiated a settlement that reduced my tax position by 75% and made the Agency drop all the penalties and interest.

- Narinder Seehra, CEO, MSR Holdings Inc.

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The Strategic Choice After Reassessment

Comparing the CRA’s self-adjudication stage with independent oversight in appeal
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Insights

Loss Consolidation Under GAAR: When Interpretation and Judgement Decide the Outcome

Loss Consolidation Under GAAR: When Interpretation and Judgement Decide the Outcome

November 25, 2025 - Key Takeaways Loss consolidation transactions attract CRA scrutiny even when they align with Parliament’s design. The mechanical structure rarely drives the dispute – the interpretive record does.

How Courts Decide When a Transaction Can Be Read Two Ways

How Courts Decide When a Transaction Can Be Read Two Ways

November 24, 2025 - Key Takeaways Penn Ventilator v. HMQ shows how disputes evolve when a transaction supports two viable case theories: one tied to the structure, the other to the business’s economic behaviour. ...

Control and Economic Reality in Cross-Border Dividend Disputes

Control and Economic Reality in Cross-Border Dividend Disputes

November 24, 2025 - Key Takeaways Inconsistent cross-border descriptions created tension between the structure’s design and its economic reality. Risk and benefit flowed to different entities across jurisdictions,...

CRA Audits and Disputes: A New Test of Control and Judgement

CRA Audits and Disputes: A New Test of Control and Judgement

November 03, 2025 - Key Points CRA can now compel sworn questioning. The Income Tax Act authorizes auditors to require oral testimony under oath during audits, bringing executives directly into the record. Early...

When CRA Scrutiny Shifts from Mechanics to Interpretive Requirements

When CRA Scrutiny Shifts from Mechanics to Interpretive Requirements

October 29, 2025 - Key Takeaways CRA challenges often evolve from mechanical to interpretive tests. The decisive factor is not a structure’s mechanics but whether its interpretive elements hold up under scrutiny. ...

Foreign Tax Interest Denied, Tax Court Loss Contained — Bank of Montreal v. HMK

Foreign Tax Interest Denied, Tax Court Loss Contained — Bank of Montreal v. HMK

September 22, 2025 - Key Takeaways The Tax Court confirmed that foreign tax interest is not deductible — BMO lost on the law. The result was predictable, but BMO's strategy maximized potential upside while containing...

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