Snowbirds US Expats Radio Podcast

Moving back to Canada: what happens to your 401(k) and IRA? Gerry Scott, host of Snowbirds Expat Radio, swaps seats for this episode and becomes the guest. His friend ,Toronto Mike, steps into the interviewer role and walks him through Chapter 3 of The Great Return, a guide for Canadians moving home from the US that doubles as a first look at Canada for Americans heading north. The book review series was meant to feature a rotating cast of cross-border specialists, but schedules kept getting in the way, so the author took the chair himself. Chapter 3 is about what happens to your money when you cross the border. Gerry explains why a move home feels simple on paper but carries serious tax and regulatory consequences when the wrong people are advising. He covers the most common mistakes, what happens to 401(k)s, IRAs, and regular US investment accounts once you hold a Canadian address, why timing matters, and what a realistic checklist looks like. He also previews the healthcare coverage gap that returning Canadians can fall into, which gets its own deep dive in Chapter 7. The conversation opens with a short tribute to Canadian rocker Sass Jordan, and Gerry closes by explaining why the show has never been a do it yourself podcast: the right team in front of you matters more than any shortcut. What You’ll Learn Why a move home needs a plan for your money as well as your belongings Why so many people skip planning, and why the instinct to save on professional fees costs more later The most common mistake: taking free advice from friends, family, or an advisor licensed in only one country How RRSPs and TFSAs compare to IRAs and Roth IRAs, why they are not interchangeable, and why the tax treaty has not kept pace with the TFSA Why a US advisor generally cannot keep managing your IRA, 401(k), Roth, or non-registered accounts once your statements show a Canadian address Why borrowing a relative’s US address to get around this backfires How forced cash outs create tax consequences on both sides of the border, and why worldwide income must be reported once you are a Canadian resident How mismatched tax slips and residency records create headaches at filing time Why Gerry suggests planning up to five years ahead, and the three professionals to put on your team: a cross-border advisor, an immigration professional, and a cross-border accountant The healthcare gap, including Medicare Parts A and B, provincial waiting periods in Canada, and why the in-between period needs a strategy Resources The Great Return: Canadian’s Guide to Moving Home from the US , available on Amazon. Book page: letsmovetocanada.ca Canadians Heading South for the Winters: What You Don’t Know Will Hurt You , Gerry’s first book. Book page: snowbirdsheadingsouth.com Snowbirds US DayTracker , the travel app for tracking your days across the border: snowbirdsusdaytracker.com Snowbirds Expat Radio , the podcast, with more episodes featuring cross-border accountants, immigration lawyers, and advisors Mike’s podcast : [add link to host’s show]

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 gets, the ones that worry him most come from snowbirds who have fallen in love with an American and are making a permanent move south with their hearts fully invested and their tax plans nowhere near ready. If you missed it the first time, this conversation with Calgary-based U.S. tax specialist Peter Blomfield of Blomfield Tax is the one to catch. Peter walks Gerry through the most common and costly mistakes Canadians make when going from snowbird to U.S. resident, from departure tax to state-level RRSP exposure, from LLC pitfalls to the principal residence trap. What You'll Learn Reporting requirements: Why the IRS's reporting rules catch most Canadians completely off guard, and what the penalties look like when you miss them Two kinds of residency: The difference between immigration residency and tax residency, and why confusing the two can cost you State tax surprises: How state rules vary dramatically, and why Hawaii and California are two states where RRSP holders face a nasty surprise Crystallizing RRSP gains: Why locking in gains inside your RRSP before you leave Canada may be one of the smartest moves you can make The principal residence trap: How the Canadian exemption differs from 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: What every Canadian investor or entrepreneur needs to hear before setting up a U.S. business structure Who builds your 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 Foreign tax credit: How rental income from a Canadian property gets reported once you are a U.S. resident A real-world scenario: Bruce and Susan have $2M in assets, an RRSP, cash, and a principal residence. What does departure planning actually look like? Resources and Links Peter Blomfield, Blomfield Tax: blomfieldtax.com Email Peter: peter.blomfield@blomfieldtax.com Snowbirds US Day Tracker app: https://snowbirdsusdaytracker.com Gerry's book, Canadians Heading South for the Winters: What You Don't Know Will Hurt You : snowbirdsheadingsouth.com

Guest: Pat Fournier, JPS Accounting Services (Port Coquitlam, BC) You've decided to move back to Canada. You think the hard part is over. Gerry sits down with cross-border accountant Pat Fournier of JPS Accounting Services to walk through Chapter 2 of The Great Return , and the message is clear: leaving the US isn't something that just happens when you cross the border. It's something you have to prove, on paper, to two different tax authorities that don't talk to each other and won't figure it out for you. Pat has seen the mistakes up close, from Canadians who used a BC mailing address to open an investment account while still living full-time in the US, to returning residents who assumed their first year back gave them a free pass on foreign reporting. She and Gerry cover what actually triggers IRS and CRA recognition of a move, what happens to IRAs, 401(k)s, and Roth accounts when you cross the border, and why the T1135 form catches so many people off guard. What You'll Learn There's no punch card for leaving the US. The IRS doesn't automatically know you've gone. Green card holders who surrender their card need to file the appropriate form, and until it's filed, you're still considered a resident with ongoing filing obligations. CRA looks at the facts, not a date you pick. Car insurance, family location, a house purchase, where you're really living, all of it factors into when CRA decides your Canadian residency actually started. The Canadian address mistake. Using a Canadian mailing address to open an investment account while still living in the US can trigger CRA to treat you as a resident and tax your full worldwide income, long before you meant to make that move. The Roth IRA election most people miss. A Roth is tax-free in the US, but that status doesn't carry over automatically. Without filing an election letter with CRA in your first year back, Canada will tax the account's growth. Late elections are possible but not guaranteed. The IRA-to-RRSP "rollover" isn't really a rollover. Moving IRA or 401(k) funds into an RRSP means cashing out and facing US tax first. Pat explains why you need liquid cash on hand to cover the gap, and why some Canadian advisors push this move without fully weighing the cost. Social Security gets taxed differently than people expect. Once you're a Canadian resident, Canada taxes your US Social Security, not the IRS, per the treaty. Pat's advice: stop any voluntary US withholding before you move. The T1135 trap for returning Canadians. New immigrants to Canada get a one-year exemption from this foreign reporting form. Returning Canadians do not. It also covers more than the US equivalent (FBAR), including rental properties, and its reporting threshold is based on cost, not current value. RRSP contribution room doesn't show up on day one. Room is based on the prior year's Canadian earned income, so most people have zero room their first year back unless they're using carryforward room from before they left. Give yourself at least three months. Pat's rule of thumb for how much lead time to build into your planning before an actual move date. Resources & Links Guest: Pat Fournier, JPS Accounting Services , Port Coquitlam, BC Book: The Great Return: Canadians' Guide to Moving Home from the US — Chapter 2 sample now available on Amazon Snowbirds US Day Tracker letsmovetocanada.ca

Guest: Robert Clegg, CanadAmerican Tax Services Host: Gerry Scott Episode Overview A lot of Canadians who built a life in the United States assume that walking away from a green card is as simple as handing it back at the border. It is not. In this episode, Gerry sits down with cross-border tax specialist Robert Clegg of CanadAmerican Tax Services to unpack the U.S. Exit Tax, the rule that can turn a routine move back to Canada into a six-figure tax bill. Robert walks through how the IRS decides who counts as a covered expat, why the 8-out-of-15-year rule catches long-term green card holders off guard, and what really happens at the border when an officer decides your green card has been abandoned. Real client scenarios, including a near miss at the seven-year mark, illustrate just how much timing matters. Whether you are holding onto a green card out of habit, weighing citizenship, or planning your eventual return to Canada, this conversation lays out exactly what to check before you make a move. What You'll Learn What the U.S. Exit Tax actually is, and how it mirrors Canada's departure tax with a mark-to-market calculation on the day you renounce or abandon status The $2 million net worth threshold that determines whether you're a covered expat, and the roughly $800,000 exclusion available against any deemed gain Why deferred compensation, including 401(k)s and RRSPs, faces a 30 percent withholding if you're a covered expat, and why CPP, OAS, and Social Security are treated differently The 8-out-of-15-year rule for green card holders, including how even one day of residency in a given year counts toward the eight Why a green card does not simply expire after ten years for tax purposes, and the official abandonment process required to stop U.S. filing obligations How border officers assess whether you've abandoned your green card by living in Canada, and what filing a Canadian tax return as a resident signals What a reentry permit is and how it protects green card holders who plan to spend up to two years outside the U.S. without losing status Why there's no do-over once a green card is surrendered, and the limited exceptions for U.S. citizen spouses or children The case for taking U.S. citizenship before moving back to Canada if you ever want unrestricted reentry, including the Medicare timing consideration for retirees under 65 Practical consequences of renouncing, from B-2 visitor day limits to firearm import restrictions to how a Canadian DUI or criminal record can bar reentry for former citizens Resources & Links Guest: Robert Clegg, CanadAmerican Tax Services — cross-border personal, corporate, and partnership tax planning IRS Form 8854, Initial and Annual Expatriation Statement USCIS Form I-131, Application for Travel Document (includes the reentry permit for green card holders) USCIS naturalization eligibility tool snowbirdsheadingsouth.com This episode is for educational purposes only and does not constitute individualized tax, legal, or financial advice. Listeners should consult a qualified cross-border accountant, tax attorney, or financial advisor before making decisions about green card abandonment, U.S. citizenship, or a cross-border move.

Gerry sits down with Denise Hodgins, a REALTOR® with eXp Realty who specializes in lifestyle-driven moves to Vancouver Island. Together they dig into why Nanoose Bay, Parksville and Qualicum Beach have become such a draw for Canadians heading home and Americans relocating north, and they unpack two of the biggest financial landmines buyers need to understand before they fall in love with a listing: the foreign buyer ban and the speculation and vacancy tax. What They Discussed Denise's background and her focus on lifestyle-driven real estate moves across Vancouver Island Canada's foreign buyer ban, set to expire January 1, 2027, and why industry analysts don't expect lifting it to move affordability much Why Vancouver Island keeps winning people over: pace of life, beach access, year-round golf, and a housing market that still offers relative value The speculation and vacancy tax, which areas are currently exempt (Nanaimo, Lantzville, Parksville, Qualicum, Nanoose, French Creek, Errington, Coombs, Bowser, Deep Bay), and why exemption boundaries can be easy to misread What the tax actually costs: potentially $45,000+ annually for foreign owners, with different rates for Canadian citizens and permanent residents Why buyers need a full cross-border team in place before they fall in love with a house: REALTOR®, immigration lawyer, cross-border tax accountant, and cross-border financial advisor A cautionary story about a client who trusted a charming but unqualified advisor, and what it cost to clean up afterward FIRPTA withholding on the sale of US property, and why the IRS holds back a portion of proceeds until you prove you don't owe tax A tour of Nanoose Bay's Fairwinds community: golf course, wellness centre, marina, and the new Pheasant Glen clubhouse coming this fall Trails and biking in the area, plus planned expansions connecting Top Ridge Park to Coombs Links & Resources Connect with Denise: https://www.bcislandhomes.ca/ The Great Return: Canadian's Guide to Moving Home from the US — letsmovetocanada.ca Canadians Heading South for the Winters — snowbirdsheadingsouth.com Track your cross-border travel days — snowbirdsusdaytracker.com

Most people treat a Canadian-born grandparent as fun family trivia, not a legal pathway to citizenship. But thanks to a change in Canadian law, that old birth certificate could now be the key to citizenship, residency, and a new set of cross-border tax questions. That's the reality cross-border attorney Robert Clegg sees again and again, and it's what he unpacks in this episode. Robert returns from Victoria, BC to talk with Gerry about Canada's expanded "Lost Canadian" citizenship rules. Robert is a U.S. immigration and tax attorney based in Seattle and Victoria with 30+ years of cross-border experience. They dig into who qualifies, how to apply, and the realities of relocating to Vancouver Island. What You'll Learn: The Dec. 2025 rule change: citizenship now extends to grandchildren and great-grandchildren of Canadian-born ancestors. A real case study: how one American traced citizenship through his Alberta-born grandfather. Why 3-4 million Americans may be eligible, with 150,000+ applications filed and ~1 year wait times. Why dual citizenship is required before renouncing U.S. citizenship. How the BC Speculation and Vacancy Tax ties to citizenship status. Popular Vancouver Island landing spots: Victoria, Qualicum Beach, Cobble Hill, Nanaimo, Sydney. Why most renunciations happen after 5-50 years in Canada, not for political reasons. Why the ~$13M U.S. estate tax exclusion means most clients aren't exposed. The overlooked hurdle of rebuilding credit and banking across the border.

Guest Host: Laura Garfield | Co-Founder, Idea Decanter | Guest: Gerry Scott You spent years building a life in the US - a green card, a career, maybe even citizenship. So what happens to your taxes, your investments, and your retirement accounts the moment you decide to move back home to Canada? The tables are turned this episode: Laura Garfield, co-founder of Idea Decanter, steps in as host to interview Gerry Scott about his brand new book, The Great Return: Canadian's Guide to Moving Home from the US. It's the companion to Gerry's first book, Canadians Heading South for the Winters, and this time it's written for the reverse journey - Canadians coming home after years in the US, and Americans making the move north. Gerry and Laura get into why this move feels deceptively easy (same language, similar culture) when in reality it means untangling two completely different tax systems, the CRA and the IRS. They cover exit tax and the difference between a covered and non-covered expat, why cross-border financial advisors can't legally follow clients across the border, and why DIY moves so often lead to expensive mistakes. Laura also shares her own cross-Canada train trip, and Gerry brings up the Lost Canadians genealogy angle for Americans who may already qualify for Canadian citizenship. What You'll Learn Who The Great Return was written for, and why it applies to Americans moving to Canada too Why the CRA and IRS don't line up, even though crossing the border barely feels like leaving home The difference between a covered and non-covered expat, and why it matters for exit tax Why US states like California and Hawaii don't recognize the Canada-US tax treaty Why your US financial advisor can't legally advise you once you move to Canada What happens tax-wise to Roth contributions, employee stock purchase plans, and pensions after the move How the Lost Canadians genealogy path could mean Americans already qualify for citizenship Resources & Links The Great Return: Canadian's Guide to Moving Home from the US — letsmovetocanada.ca Canadians Heading South for the Winters — snowbirdsheadingsouth.com Snowbirds US DayTracker — snowbirdsusdaytracker.com

Nobody wants to think about what happens to their Florida condo or Arizona snowbird home after they're gone. But if you're a Canadian with US property and you haven't planned for it, your family could be facing an audit, a probate mess, and tax consequences that were entirely avoidable. That's the reality cross-border tax attorney Alexey Manasuev sees again and again in his practice, and it's exactly what he unpacks in this episode. Alexey returns to the show from Tampa Bay to talk with Gerry about cross-border estate and tax planning for Canadian snowbirds. Alexey is a US tax attorney admitted in New York and DC, and the founder of US Tax IQ, a boutique firm focused exclusively on US international tax planning, compliance, and structuring. Together, Gerry and Alexey dig into what really happens when a Canadian passes away owning US real estate without a plan in place, and how to make sure that doesn't happen to you. What You'll Learn in This Episode Why proactive planning matters: Alexey explains how problems with US property often surface only after death, when probate alerts the IRS to gaps left decades earlier, turning what should have been a non-issue into an audit. US estate tax exposure for Canadian-owned property: how a Florida, Arizona, or other US property can trigger US estate and gift tax obligations for a Canadian owner, even without US citizenship or residency. Domicile vs. residency: why US estate and gift tax exposure is based on the legal concept of domicile, a facts-and-circumstances test built around intent, not the same as ordinary tax residency. The LLC trap: why an LLC structure that a local US advisor recommends for domestic buyers can create serious problems for Canadian owners on both sides of the border. One will or two: when a single will can work for a cross-border estate, and why a US power of attorney for incapacity and medical decisions is often more important than a second will. The 2026 estate tax exemption threshold: how the $15 million federal base exclusion amount taking effect in 2026 factors into planning decisions. Sell now or hold for the next generation: the shifting trend Alexey is seeing, with some families selling US property as they age while others hold on for the lifestyle and pass it down. Why "campfire advice" is dangerous: why casual, well-meaning tips from friends, neighbors, or a local advisor unfamiliar with cross-border rules can create costly problems, and why a paid consultation with a qualified cross-border tax professional pays for itself. Resources and Links US Tax IQ Snowbirds US Day Tracker App Canadians Heading South for the Winters: What You Don't Know Will Hurt You, by Gerry Scott

If you have a Canadian ancestor somewhere in your family tree, you might not need to look very far back. A landmark change to Canadian citizenship law means that for millions of people, especially Americans, that ancestry could now open the door to a Canadian passport. And the person who can help you find that door is a genealogist. This week Gerry sits down with Sheila Hobeck, professional genealogist and founder of Kinalytic, based in Oakville, Ontario, to walk through what Bill C-3 actually means, how to document your Canadian lineage, and why DNA is rewriting family histories that paper records tried to keep buried. What You'll Learn in This Episode What Bill C-3 actually changes: effective December 2025, Canada eliminated the generational limit on citizenship by descent, meaning a Canadian ancestor anywhere in your history, if you can document it, may be enough to claim Canadian citizenship Who counts as a lost Canadian and why historical acts stripped citizenship from individuals through marriage, birth abroad, and other circumstances that Bill C-3 now addresses How to start the process through IRCC, when to bring in a Regulated Canadian Immigration Consultant, and when the situation calls for an immigration lawyer Where genealogists search, from Ancestry and FamilySearch to physical archives and historical societies, and why not everything has been digitized The role of DNA in confirming lineage, identifying unknown relatives, and uncovering what Sheila calls NPEs, non-paternity events, where documents and biology don't match How AI is helping translate old records written in Quebec French, Latin, and paleographic script, and point researchers toward the right archives Why this matters beyond immigration, and what your ancestors' risks and journeys reveal once you start digging Resources and Links Sheila Hobeck, Kinalytic: kinalytic.com IRCC, Immigration, Refugees and Citizenship Canada: canada.ca/en/immigration-refugees-citizenship FamilySearch (free): familysearch.org Ancestry: ancestry.ca GEDmatch: gedmatch.com FamilyTreeDNA: familytreedna.com Track your days across the border with DayTracker: snowbirdsusdaytracker.com Canadians Heading South - Buy the Book: snowbirdsheadingsouth.com

What Canadian Green Card Holders Need to Know Before They Surrender Status Guest: Robert Clegg, CanadAmerican Tax Services | Host: Gerry Scott Episode Overview A lot of Canadians who built a life in the United States assume that walking away from a green card is as simple as handing it back at the border. It is not. In this episode, Gerry sits down with cross-border tax specialist Robert Clegg of CanadAmerican Tax Services to unpack the U.S. Exit Tax, the rule that can turn a routine move back to Canada into a six-figure tax bill. Robert walks through how the IRS decides who counts as a covered expat, why the 8-out-of-15-year rule catches long-term green card holders off guard, and what really happens at the border when an officer decides your green card has been abandoned. Real client scenarios, including a near miss at the seven-year mark, illustrate just how much timing matters. Whether you are holding onto a green card out of habit, weighing citizenship, or planning your eventual return to Canada, this conversation lays out exactly what to check before you make a move. What You'll Learn What the U.S. Exit Tax actually is, and how it mirrors Canada's departure tax with a mark-to-market calculation on the day you renounce or abandon status The $2 million net worth threshold that determines whether you're a covered expat, and the roughly $800,000 exclusion available against any deemed gain Why deferred compensation, including 401(k)s and RRSPs, faces a 30 percent withholding if you're a covered expat, and why CPP, OAS, and Social Security are treated differently The 8-out-of-15-year rule for green card holders, including how even one day of residency in a given year counts toward the eight Why a green card does not simply expire after ten years for tax purposes, and the official abandonment process required to stop U.S. filing obligations How border officers assess whether you've abandoned your green card by living in Canada, and what filing a Canadian tax return as a resident signals What a reentry permit is and how it protects green card holders who plan to spend up to two years outside the U.S. without losing status Why there's no do-over once a green card is surrendered, and the limited exceptions for U.S. citizen spouses or children The case for taking U.S. citizenship before moving back to Canada if you ever want unrestricted reentry, including the Medicare timing consideration for retirees under 65 Practical consequences of renouncing, from B-2 visitor day limits to firearm import restrictions to how a Canadian DUI or criminal record can bar reentry for former citizens Resources & Links Guest: Robert Clegg, CanadAmerican Tax Services - cross-border personal, corporate, and partnership tax planning https://www.canadamericantax.com/meet-us.php IRS Form 8854, Initial and Annual Expatriation Statement: https://www.irs.gov/forms-pubs/about-form-8854 USCIS Form I-131, Application for Travel Document (includes the reentry permit for green card holders): https://www.uscis.gov/i-131 USCIS naturalization eligibility tool: https://www.uscis.gov/citizenship snowbirdsheadingsouth.com

If you bought a place in Arizona or Maui twenty years ago and never thought about what happens to it when you sell, or when you die, could it already be too late to avoid a tax shock you never saw coming? This week Gerry sits down with Robert M. Clegg, JD, LL.M, of CanadAmerican Tax Services, a dual Canadian and US cross-border tax specialist based on Vancouver Island, to walk through what really happens when a Canadian sells US real estate. From FIRPTA withholding and ITIN requirements to the currency trap and the long road of selling a property after an owner has died, this is the conversation to have before you let a realtor put the sign on the lawn. What You'll Learn in This Episode - Why your first call should be to a cross-border accountant, not the realtor, and how that single move takes the hidden tax shock off the table before the sign ever goes up - FIRPTA explained: how 10 to 15 percent of your gross sale price gets withheld up front, why California and Hawaii add their own layer on top, and why Arizona, Texas, and Nevada do not - Why each non-resident Canadian spouse must file a separate 1040NR with their own ITIN, and how escrow companies routinely get this wrong by issuing one withholding slip under a single number - The currency trap: how a weak Canadian dollar can turn a 700,000 US gain into a far bigger Canadian one, and why you need the exchange rate at purchase, at sale, and at every renovation - How the foreign tax credit stops you from being taxed twice, why only half your gain is taxable in Canada, and roughly what is left to pay the CRA once the US tax is credited - Why the 1031 like-kind exchange your realtor keeps recommending simply does not work for Canadians - What changes when parents pass away still owning the property, from the US estate return on assets over 60,000 to a clearance certificate that can take two to three years before you can sell Resources & Links Robert M. Clegg, JD, LL.M, CanadAmerican Tax Services: canadamericantax.com FIRPTA Canada, Calgary-based FIRPTA specialists: firptacanada.com Track your days across the border with DayTracker: snowbirdsusdaytracker.com Canadians Heading South - Buy the Book: https://a.co/d/01Ryf45Z Note: the forms, thresholds, and rates discussed are general and reflect the conversation as recorded. Confirm your own situation with a cross-border tax professional and your Canadian accountant before selling.

If you bought a place in Palm Springs or Maui twenty years ago and never thought about what happens when you sell it — or when you die — is it too late to fix that? In this episode, Gerry sits down with Kevin Kirkpatrick of Bordera Tax and Immigration Law — a dual Canadian-US lawyer based in Seattle, with his main office in Calgary — to walk through the estate planning issues that catch Canadians off guard on both sides of the border. From US estate tax thresholds to the 8-of-15 green card rule to FIRPTA withholding on US property sales, this is the conversation to have before you assume your Canadian will is enough. What You’ll Learn in This Episode Why the $60,000 US asset threshold matters — and what counts as “US stuff” when the CRA is done with you How the Canada-US Tax Treaty provides Canadian residents a pro-rated US estate tax credit, and why the current high exemption benefits most Canadians What happens when a US citizen inherits a Canadian private corporation — and why controlled foreign corporation rules create reporting obligations even for family businesses The 8-of-15 rule for green card holders: when you become a long-term resident subject to US exit tax, and a treaty exception that may reduce your exposure Why dual-licensed doesn’t mean one lawyer handles everything — and how Kevin and his partner Asim structure their practice across US and Canadian tax law FIRPTA explained: how 15% gross withholding on US property sales works, why California and Hawaii add their own layer, and what your options are Whether trusts, non-recourse mortgages, or life insurance can still help if you bought your US property decades ago without any planning Resources & Links Kevin Kirkpatrick — Bordera Tax and Immigration Law: bordera.ca FIRPTA Canada (Calgary-based FIRPTA specialists): firptacanada.com Track your days across the border: snowbirdsusdaytracker.com Canadians Heading South - Buy the Book: https://a.co/d/01Ryf45Z

Guest Host: Laura Garfield | Co-Founder, Idea Decanter You’ve been heading south for years and doing everything the same way. So why does it feel like the rules keep changing? This episode is a little different. Gerry’s producer Laura Garfield flips the script and puts Gerry in the hot seat to celebrate the launch of his brand new book: Canadians Heading South for the Winters — What You Don’t Know Will Hurt You. After eight years of fielding the same snowbird questions week after week, Gerry sat down and wrote the guide he’d always wished existed. This episode is the story behind that book — what it covers, why he wrote it, and why he believes no snowbird should be without it. What You’ll Learn Why immigration and tax are two completely separate conversations — and why mixing them up is one of the most common and costly snowbird mistakes What “I’ve always done it this way” actually means at the border — and why it’s no longer a safe assumption How border agents use discretion, and why your travel pattern matters more than your intentions What happens when you’re denied entry — and why you can’t just drive to the next crossing and try again Why the book is designed as a reference guide, not a cover-to-cover read The growing trend of snowbirds selling their U.S. properties — and why it’s a taxable cross-border event most people aren’t prepared for Why Gerry split what started as one book into two — and what the second book, The Great Canadian Return, will cover Where to get your copy: http://snowbirdsheadingsouth.com/ About the Book Canadians Heading South for the Winters — What You Don’t Know Will Hurt You Gerry Scott’s debut book is a practical reference guide covering the 10 most important topics every Canadian snowbird needs to understand before heading south — immigration, tax, healthcare, residency rules, day tracking, border crossings, and more. At 180+ pages, it’s built to sit beside you, not just be read once. Available now at www.snowbirdsheadingsouth.com. Resources Get the book: http://snowbirdsheadingsouth.com/ Track your days: snowbirdsusdaytracker.com

What really happens to your money, your investments, and your tax obligations the moment you leave Canada for the United States? Gerry sits down with Kevin Heath of GTA Accounting to walk through what actually happens when Canadians exit Canada and become U.S. tax residents. From departure tax and deemed disposition to TFSA traps and state-level surprises, this is the conversation to have before your move becomes official on paper. • Why departure tax is triggered when you leave Canada and how deemed disposition forces you to report gains even if you have not sold anything• Which assets are included in departure tax calculations and why Canadian real estate and registered accounts are treated differently• How deferring departure tax works and when the CRA may require security before approving it• Why TFSAs lose their tax-free status in the U.S. and how mutual funds and ETFs inside them can create complex and costly reporting requirements• What PFIC rules are and why holding Canadian funds in the U.S. can trigger higher tax rates and steep penalties• How owning a Canadian corporation creates U.S. reporting obligations under Form 5471 and the penalties tied to getting it wrong• Why RRSPs are treated differently at the federal and state level and how states like California and Hawaii can tax growth inside the account• When it makes sense to liquidate investments before moving and start fresh in the U.S. with cash• How timing your move can impact whether your income or withdrawals are taxed in Canada, the U.S., or both• Why more Canadians are choosing to work in the U.S., from lower tax rates to currency advantages and broader career opportunities Resources and Links: GTA Accounting Snowbird US Day Tracker App: Available on the App Store and Google Play Coming Soon: The Snowbirds Expat Radio Book

Of all the conversations Gerry has about cross-border life, the ones involving Canadians who have quietly become US tax residents without realizing it are among the most urgent. In this episode, Gerry sits down with Karlene Mulraine of Brij Professional Corporation to walk through what Canadian digital nomads actually need to understand about working in the United States. From the rolling three-year calculation that catches even financially savvy Canadians off guard, to the sticky-state problem that can make double taxation impossible to avoid, to the very real cost of trying to file a cross-border return on your own, this is the conversation to have before your wanderlust makes the decision for you. Why the 183-day rule is not the tax shield most Canadians believe it to be, and how the Substantial Presence Test actually works across three calendar years How Form 8840, the Closer Connection Exception Statement, can protect your Canadian tax status even after you have technically triggered US residency Why Canadian employers are almost never equipped to handle US payroll sourcing, and what that means for the employee working from Palm Springs What happens when you file both a 1040NR and a T1, and why the CRA's foreign tax credit review process is where most DIY cross-border returns fall apart Why New York, California, and Hawaii are sticky states, and why working in any of them may leave you exposed to true double taxation that no treaty can fix How treaty tiebreaker positions under Article 4 of the Canada-US Tax Treaty can be used as a planning tool, not just a last resort What a CRA reassessment looks like in practice when a $30,000 foreign tax credit claim gets reversed, and the interest and penalties that follow Why tracking your days across jurisdictions is the single most foundational habit any cross-border traveler or worker can build What You'll Learn in This Episode Resources and Links Karlene Mulraine - Brij Professional Corporation: https://brij.tax/ Snowbird US Day Tracker App: Available on the App Store and Google Play Coming Soon: The Snowbirds Expat Radio Book

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 Matters Cross 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