What happens to your RRSP, your home, and your retirement savings the moment you follow your heart across the border?

Of all the emails Gerry receives, the ones that concern him most come from snowbirds who've fallen in love with an American and are now making a permanent move south with their heart fully invested and their tax plan nowhere near ready. In this episode, Gerry sits down with Calgary-based US tax specialist Peter Blomfield to walk through the most common and costly mistakes Canadians make when transitioning from snowbird to U.S. resident. From departure tax to state-level RRSP exposure, from LLC pitfalls to the principal residence trap, this is the conversation to have before your heart makes the decision for you.

What You'll Learn in This Episode

• Why the IRS's reporting requirements catch most Canadians completely off guard and what the penalties look like when you miss them

• The difference between immigration residency and tax residency, and why confusing the two can cost you

• How state tax rules vary dramatically and why Hawaii and California are two states where RRSP holders face a nasty surprise

• Why crystallizing gains inside your RRSP before you leave Canada may be one of the smartest moves you can make

• The Canadian principal residence exemption vs. the U.S. version and how a tax-free sale in Canada can become a taxable event the moment you cross the border

• The LLC warning every Canadian investor or entrepreneur needs to hear before setting up a U.S. business structure

• Why having a U.S. lawyer set up your investment structure without a cross-border accountant in the room is a recipe for penalties

• The foreign tax credit and how rental income from a Canadian property gets reported once you're a U.S. resident

• A real-world scenario: Bruce and Susan, $2M in assets, an RRSP, cash, and a principal residence. What does departure planning actually look like?

Resources & LinksPeter Blomfield — Blomfield Tax: blomfieldtax.com

Email Peter: peter.blomfield@blomfieldtax.com

Coming Soon: The Snowbirds Expat Radio Book

What happens to your U.S. investment accounts when you move to Canada or vice versa? In this episode, Gerry Scott sits down with returning guest Trent Robinson, a cross-border tax specialist at Buckberger & Partners in Saskatoon, to unpack the most common and costly mistakes people make when holding non-registered investment accounts across borders. From wrong tax slips to CRA audits arriving five years late, Trent breaks it all down in plain language.

What You’ll Learn

• Why holding a U.S. non-registered account as a Canadian resident can trigger serious tax complications

• The key difference between a U.S. “qualified dividend” and a Canadian “eligible dividend” — and why mixing them up is costly

• What happens when your U.S. financial institution doesn’t know you’ve moved to Canada

• The difference between a 1099 and a 1042-S tax slip — and why getting the wrong one creates a mess

• How CRA and the IRS share information — and why the delay can make things worse

• The $2,500/year penalty for failing to disclose foreign investments over $100,000

• Why some people don’t realize they’re U.S. citizens — and what that means for their tax obligations

• How much planning you should do before leaving the U.S. to return to Canada

About the Guest

Trent Robinson is a partner at Buckberger & Partners, a full-service accounting firm based in Saskatoon, Saskatchewan. Trent specializes in cross-border tax for individuals and businesses moving between Canada and the United States, including U.S. tax return filing for U.S. citizens living in Canada, property sales, and dual-country compliance. He has been working in this space since 2008.

Website: www.bbllp.ca

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.

In this episode of the Snowbirds Expat Radio, host Gerry Scott welcomes back cross border tax specialist Sharon Conrod of Hanson Tax LLC for a timely conversation on one of the most misunderstood cross border situations today Canadians living in Canada while working for U.S. employers.

As more professionals take U.S. roles while residing north of the border questions around 401k plans IRAs RRSP room and treaty relief are becoming increasingly common and increasingly complex. Sharon explains how U.S. retirement plans are treated in Canada when deductions are available why tracking basis matters and where many people unknowingly create future tax issues.

The discussion also explores remote work considerations employer matching crystallization strategies state level tax risks and why there is truly no one size fits all solution when families live and work across borders.

What You Will Learn

• How 401k and IRA contributions are treated when you live in Canada

• When U.S. retirement contributions may or may not be deductible in Canada

• Why RRSP room limits matter for cross border commuters

• The role of Form RC268 and why it is critical for Canadians with U.S. plans

• How employer matching works and when it still makes sense to participate

• Why tracking non deductible contributions over time is important

• How crystallizing RRSPs before moving to the U.S. can reduce future taxes

• Why certain U.S. states can complicate otherwise treaty protected plans

• Common mistakes remote workers and employers make

• Why residency and family dynamics matter in cross border planning

Why This Episode MattersCross border work arrangements have grown significantly but the tax rules have not become any simpler. This episode highlights why working with experienced cross border professionals can help prevent costly mistakes both now and in the future.

In this episode of the Snowbirds Expat Radio Podcast, host Gerry Scott welcomes back returning guest Aaron Dawes, a cross-border personal tax expert with Smythe.

While previous conversations focused on Canadians heading south, this discussion flips the script. With shifting economic, political, and lifestyle factors, more Canadians—and Americans—are now moving north, returning to or relocating to Canada despite weather, cost, and lifestyle tradeoffs.

Aaron explains what’s driving this trend and what individuals need to consider before making the move, especially when it comes to cross-border tax exposure.

In this conversation, Gerry and Aaron discuss:

• Why more Canadians are returning home from the U.S.

• What’s motivating Americans to relocate to Canada

• How lifestyle, stability, and long-term planning factor into relocation decisions

• The tax implications of moving between the U.S. and Canada

• Why cross-border tax planning is critical before you move

• Common mistakes people make when changing tax residency

• How working with a specialist can prevent costly surprises

With decades of experience handling U.S.–Canada personal tax matters, Aaron offers practical insights for snowbirds, expats, and globally mobile families navigating an increasingly complex cross-border landscape.

If you’re considering a move—or a move back—this episode highlights why planning ahead matters more than ever.

Spending time in the U.S.? Take the guesswork out of tracking your days. Download the Snowbirds U.S. Day Tracker app to monitor your stays, stay compliant, and avoid costly surprises at the border.

Connect with Aaron Dawes

What does it really mean to leave Canada — and how do you know when you’ve crossed the line from spending time abroad to officially exiting?

Host Gerry Scott sits down with Jennifer Reid CPA, CGA, TEP and Frank Casciaro of RSM, two cross-border tax specialists who advise Canadians navigating complex international lives — from snowbirds and dual citizens to executives, business owners, and globally mobile families.

With deep experience in international tax and firsthand insight from working with clients before, during, and after a Canadian exit, Jen and Frank break down why leaving Canada is not just a lifestyle decision — it determines how your assets are taxed, what reporting obligations follow you, and where costly compliance mistakes often happen.

Together, Gerry, Jen, and Frank unpack the realities behind some of the most misunderstood rules in Canadian departure planning, including why residency is rarely as simple as counting days or keeping a Canadian mailing address.

In this conversation, they explore:

• Why more than 106,000 Canadians left the country in 2025 — and what’s driving the trend

• The difference between being a factual resident and a non-resident of Canada

• Why spending a few months abroad doesn’t automatically mean you’ve exited

• What departure tax and “deemed disposition” really mean in practice

• Which assets are subject to departure tax — including worldwide holdings, not just Canadian ones

• When deferring departure tax may be possible, and why it’s becoming harder to do

• How the Canada–U.S. tax treaty can help prevent double taxation — and where it falls short

• Why health care eligibility (including OHIP) is not tied to your tax return

• The compliance risks of keeping Canadian bank accounts, investments, or a family address after leaving

• TFSA, RRSP, and withholding tax issues that frequently catch departing Canadians off guard

• Why planning before you leave is far less expensive than fixing mistakes afterward

If you’re living, working, retiring, or investing outside Canada — or considering a permanent move — this episode offers a clear, practical look at what truly defines a Canadian exit and the planning steps that can save you from expensive surprises down the road.

What does it really mean to be a tax resident — and why do so many people accidentally get it wrong when moving between Canada and the United States?

Host Gerry Scott sits down with Nicole Madaisky, a dual-licensed Canadian and U.S. CPA who specializes in complex cross-border lives — from snowbirds and dual citizens to professional athletes and globally mobile families.

With deep experience in international tax and firsthand insight from working with clients on both sides of the border, Nicole breaks down why tax residency is not just a formality — it determines who gets to tax you, how much you owe, and where costly mistakes often happen.

Together, Gerry and Nicole unpack the realities behind some of the most misunderstood rules in cross-border tax planning, including why residency is rarely as simple as counting days or holding a passport.

In this conversation, they explore:

• Why tax residency — not citizenship — often determines which country can tax your worldwide income

• How Canada’s primary and secondary residential ties actually work in practice

• Why the 183-day rule is frequently misunderstood and rarely tells the whole story

• The common ways Americans and Canadians unintentionally trigger tax residency without realizing it

• What snowbirds need to understand about time tracking, treaty rules, and U.S. exposure

• Why buying property in Canada too early can create long-term tax and compliance issues

• How Canadian mutual funds can become a serious problem for U.S. taxpayers

• The foreign reporting requirements that carry steep penalties when overlooked

• Why cross-border planning works best when accountants, advisors, and immigration professionals work as a coordinated team

If you’re living, working, retiring, or even just spending extended time between Canada and the U.S., this episode offers a clear, practical look at the rules that matter most — and the planning steps that can save you from expensive surprises down the road.

Get In touch with Nicole: https://www.nicolemadaiskycpa.com/

Spending time in the U.S.? Take the guesswork out of tracking your days. Download the Snowbirds U.S. Day Tracker app to monitor your stays, stay compliant, and avoid costly surprises at the border.

In this episode of Snowbirds US Expats Radio Podcast, Gerry Scott speaks with Donnie Arnoult, an avid cyclist, local business owner, and passionate advocate for Maui’s natural beauty.

Donnie is the founder of Maui Cyclery, a well-known bike shop in the town of Pāʻia, and a trusted name in Maui’s cycling community.

With decades of experience riding on and off-road across the island, Donnie always dreamed of creating something more immersive — a way to share the untamed beauty of Maui with both visitors and locals in a sustainable, approachable way.

That dream became reality with Emountain Bike Tour Maui: a guided e-bike experience that allows riders of all levels to explore hidden trails, soak in stunning ocean and volcano views, and encounter local wildlife — all while treading lightly on the land.

Donnie’s deep love for Maui and cycling shines through in every tour. His mission is simple: to connect people with the land through the joy of riding.

Spending time in the U.S.? Take the guesswork out of tracking your days. Download the Snowbirds U.S. Day Tracker app to monitor your stays, stay compliant, and avoid costly surprises at the border.