What Happens When the CRA Comes Knocking? | Tax Lawyer Dove Whitman

What actually happens when the CRA audits you, and what can you do if you disagree with their decision? In this episode of *The Up Side*, Eli sits down with Dove Whitman, Partner in KPMG Law’s Tax Litigation and Dispute Resolution practice, to unpack what happens when a tax issue turns into a dispute with the government. Dove explains why getting professional help early in an audit can make a significant difference, what the path from an audit to Tax Court can look like, and one of the biggest misconceptions taxpayers have: that challenging the CRA is pointless. They also discuss how to know when an audit may be escalating, when it makes sense to push back, why documentation can become critical years after a transaction takes place, and the mistakes that can make an already difficult CRA dispute even harder. In this episode: • What actually happens during a CRA audit or tax dispute • When to bring in a tax litigation lawyer • Why Tax Court isn’t simply an extension of the CRA • When to cooperate with the CRA and when to push back • Early signs that an audit may be escalating • Why keeping old tax and transaction records matters • What taxpayers should know before taking a dispute further Whether you’re a business owner, investor, or high-net-worth Canadian navigating a complex tax situation, this conversation offers a look at what happens on the other side of a CRA dispute and how to better protect yourself before one begins. ******* 0:00 Meet Dove Whitman 1:36 From Teacher to Tax Lawyer 5:12 Why KPMG Law? 7:35 What a Tax Litigator Actually Does 8:42 When to Get a Tax Lawyer Involved 13:46 The Biggest Misconceptions About Fighting the CRA 14:56 When You Should Push Back on the CRA 17:30 How Far Back Can the CRA Go? 19:52 The Records You Should Never Throw Away 21:29 Warning Signs an Audit Is Escalating 23:29 Why the CRA Is Getting More Aggressive 24:56 What the CRA Is Targeting Right Now 27:27 How the CRA Is Using Data to Find You 31:34 Transfer Pricing & Multi-Jurisdictional Tax Disputes 34:32 Aggressive Tax Planning vs. Abusive Avoidance 37:37 Lessons Learned From the Courtroom 39:50 What Actually Wins a Tax Dispute? 41:34 Managing the Emotional Side of a CRA Dispute 43:23 How to Protect Yourself Before an Audit 44:45 How AI Will Change Tax Disputes 46:58 The Tax Myth Dove Wishes Would Disappear 49:23 How to Connect With Dove