NW Croppped

Natalie Worsfold

Partner, Tax Litigation

Natalie’s excellence in tax litigation protects against CRA overreach.  

Since 2008, Natalie has dedicated her practice exclusively to resolving tax disputes, providing trusted expertise to private company CEOs and high-net-worth individuals.  

Natalie consistently devises innovative litigation strategies, and she has achieved highly favourable outcomes for numerous clients.  

Natalie has:

  • Overturned a CRA assessment for a $20 million investment portfolio from business income to lower-tax capital transactions;
  • Protected the personal interests of corporate directors by shielding them from more than $13 million in HST charges following a corporate merger;
  • Successfully challenged CRA reassessments that were denying SR&ED credits and ensured the recognition of similar SR&ED credits for the long term, a vital component of the business's long-term strategy and feasibility;
  • Dismantled the CRA's valuation of a property and protected the taxpayer from a $1.7 million tax liability;
  • Overturned the CRA's classification and valuation of mining equipment and supplies, leading to savings of over $3 million;
  • Demolished CRA's allegations of $10M+ of unreported income and taxable shareholder benefits;
  • Overturned the CRA's reassessment and attempt to use the anti-avoidance rules to nullify a legitimate tax planning strategy connected to a low-tax jurisdiction.
Natalie calculated the financial impact of every outcome, kept us informed of the progress, and explained the route that would lead to the best return on our legal fees.

- Jim & Yvonne Schunk, Private Business Owners

Peter's and Natalie's deep and unique expertise and disciplined approach carved out a competitive edge for us during our tax dispute. We recommend Counter to any mid-sized company facing a significant tax dispute.

- Yuriy Tiraspolskiy, President , Consagro Inc.

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

Natalie regularly presents on tax matters and contributes articles, sharing her expertise in tax avoidance, shareholder benefits, and various tax issues. She also offers her insights on different methods to create advantages in tax disputes. And she has developed courses to teach tax litigators about early case assessment, strategy in litigation, and decision science. 

Natalie also offers mentorship and coaching to litigation lawyers and rising stars outside of Counter’s team, fostering growth and litigation excellence within the broader legal community. 

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Insights

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...

The Three Critical Inflection Points in CRA Challenges

The Three Critical Inflection Points in CRA Challenges

September 07, 2025 - Peter Aprile, Senior Counsel at Counter LLP, describes three inflection points that define how CRA challenges develop and are resolved. The framework reflects insights drawn from years of...

Mutual Fund Trust Disputes: When Form Without Execution Collapses

Mutual Fund Trust Disputes: When Form Without Execution Collapses

August 21, 2025 - Key Takeaways Benefit without cost invites scrutiny: Courts scrutinize tax structures that offer benefit without tradeoff, and when they find this gap, they side with the CRA and uphold the...

Surplus Cash and the Active Asset Test: Lessons from Ehresman

Surplus Cash and the Active Asset Test: Lessons from Ehresman

August 14, 2025 - Key Takeaways No inference of intent: Courts rejected the claim that surplus cash was earmarked for decommissioning in the absence of contemporaneous reserves, allocations, or disclosures. ...