In this episode of Canadian Investing in the US, Glen Sutherland sits down with returning guest Tim Miron, founder and president of Pursuit CPA, to discuss what investors should do when they receive an unexpected tax bill. Tim explains that the most important step is to file your taxes on time, even if you cannot immediately pay the balance. Filing late can trigger significant penalties—such as Canada’s 5% late filing penalty plus additional monthly interest—which can quickly increase the amount owed. Instead of avoiding the issue, Tim encourages investors to determine the exact amount owed as early as possible so they can create a plan to deal with it. The conversation also explores practical strategies for managing a surprise tax bill, including using lower-interest financing (such as a line of credit or refinancing), negotiating payment arrangements with tax authorities, and exploring taxpayer relief programs if extraordinary circumstances caused the issue. Tim emphasizes the importance of proactive tax planning, recommending that investors review their tax strategy in mid-year so there’s still time to make adjustments before year-end. Glen and Tim also highlight the value of communicating with your accountant before making major financial decisions—like buying vehicles or structuring business expenses—so that investors can deploy their money in the most tax-efficient way possible.