Episode 81: Cross-Border Tax Strategies for Americans in Canada & Canadians Working for U.S. Employers

Host Gerry Scott sits down with Heather Sanders of Tax Junction, a cross-border personal tax specialist who helps U.S. citizens living in Canada and Canadians working for U.S. employers navigate the complexities of filing in two countries at once.

With a practice built around real people in real cross-border situations, not corporations or trusts, Heather brings practical, ground-level insight into the mistakes that happen when employees move countries without thinking through the tax consequences first, and what it actually takes to get it right.

Together, Gerry and Heather unpack some of the most misunderstood rules facing cross-border workers, including why "I just work from my home office" is never as simple as it sounds, and why the payroll question matters more than most people realize.

In this conversation, they explore:

• Why the country where you physically work determines where your payroll must be registered, and the liability risk employers face when it isn't

• The Certificate of Coverage and when Canadians working for U.S. companies can still contribute to CPP

• How 401(k) contributions are treated in Canada and why aligning them with your RSP room is the key to avoiding a surprise tax bill

• Why RSP contributions aren't deductible on a U.S. return, and why that usually matters less than people fear

• The risks of large catch-up RSP contributions for U.S. citizens living in Canada

• How mid-year payroll switches between W-2 and T-4, especially when RSUs are involved, can create reporting nightmares

• Why selling U.S. real estate as a Canadian non-resident requires the right people in your corner from the start

• The foreign tax credit audit that CRA triggers more often than most people expect, and what happens when no one responds

• Why "my situation is pretty straightforward" is almost never true once a border is involved

If you're living in Canada and working for a U.S. employer, considering a cross-border move, or simply trying to understand what compliance actually looks like for internationally mobile workers, this episode offers a frank and practical look at the planning that protects you and the mistakes that are far easier to avoid than to fix.
Cross-border tax doesn't have to be overwhelming. Download the Snowbirds DayTracker app today to connect with specialists like Heather and access the tools and resources you need to navigate your international life with confidence.