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Also this week: your 401(k) match’s fine print, and filing from abroad.
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In partnership with
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Good morning! Every Saturday, we open the mailbag, pour some strong coffee, and tackle the tax questions keeping America awake at 2 a.m.
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Here are this week’s topics:
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💰 Your 401(k) match already showed up on your pay stub. The IRS has a very specific opinion about when it becomes yours.
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🌍 Moving abroad doesn’t cancel your subscription to the IRS.
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🤝 A loan you never had to pay back sounds like free money. The IRS mostly agrees, with one all-caps exception.
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Money Moves
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💰 Your 401(k) match isn’t taxed yet. Emphasis on “yet.”
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My company match to my 401(k) shows up on my pay stub. Does that count as taxable income to me now?
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Not yet, and for most people, not for decades.
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The default rule
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A standard employer 401(k) match goes into your account pre-tax, same as it always has.
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It’s not included in your W-2 wages and doesn’t show up on this year’s tax return.
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It grows tax-deferred and gets taxed as ordinary income only when you withdraw it in retirement.
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This is true whether your own paycheck deferrals go into the traditional or Roth side of the plan — the match defaults to pre-tax either way.
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The newer wrinkle
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Since SECURE 2.0, employers can let employees elect to receive the match as a Roth contribution instead of pre-tax.
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If you opt in, the match is included in your taxable income for the year it’s made, reported on Form 1099-R (not your W-2).
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In exchange, it grows and comes out completely tax-free in retirement, same as any other Roth money.
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You have to be fully vested to make this election — if you’re still on a vesting schedule, the option isn’t on the table yet.
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Most plans still default the match to pre-tax, and most employees who have the Roth-match option available don’t elect it, because paying tax on money you haven’t touched yet requires a specific kind of optimism about future tax rates. Either way, check your pay stub and your plan statement — “match” and “taxable now” are not the same line item unless your plan and your election say otherwise.
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⚙️ THE TAXSTACHE TOOLKIT
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Still staring at your pay stub, unsure what you’re looking at?
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The 401(k) Match Tax Checker walks through your plan’s vesting and Roth-election setup and tells you plainly: taxed now, or taxed later. No spreadsheet required.
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PRESENTED BY RANGE
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You’re Invited: Investing Moves to Boost After-Tax Returns
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You’ve worked hard to fund your portfolio — your investment strategy should work just as hard to maximize your after-tax returns.
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On September 17, join Range’s CFPs and CPAs live for the practical moves that put more of your returns back in your pocket.
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What we’ll cover:
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Investment moves to maximize your after-tax returns
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How tax-loss harvesting can lower the taxes you owe
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When direct indexing works (and when it doesn’t)
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How to build a diversified portfolio that reduces tax drag.
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Range is all-in-one AI wealth management — tax, investments, retirement, and estate in one place. Bring your questions for the live Q&A. Free to attend, and seats are limited.
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Reserve your spot today
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This webinar is for informational purposes only and does not constitute investment advice or a recommendation to buy, hold, or sell any security. Forward-looking statements involve risks and uncertainties. Past performance is not indicative of future results. Range defines “high earners” as households with income over $300k.
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Tax Strategies
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🌍 Living abroad doesn’t get you off the IRS mailing list
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I’m a U.S. citizen living and working abroad. Do I still have to file a US tax return on foreign income?
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Yes. The United States taxes citizens on their worldwide income no matter where they live, which puts the US in the small club of countries that taxes citizenship rather than residency. Moving to Lisbon doesn’t change your filing obligation; it just changes the view from your desk.
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What counts, and why it matters
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Your income, filing status, and age determine whether you have to file — the same rules that apply domestically apply abroad.
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Wages, self-employment income, investment income, and rental income earned anywhere in the world count toward that determination.
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Everything has to be reported in US dollars, even if you were never paid in them.
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The part that trips people up
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The tax benefits that actually reduce your bill to zero only apply if you file.
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The Foreign Earned Income Exclusion lets you exclude up to $132,900 of foreign earned income for 2026.
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The Foreign Tax Credit lets you offset US tax with tax you’ve already paid to another country.
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Both can wipe out your US liability entirely for a lot of expats.
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Neither one does you any good if you skip the return — they’re claimed on forms attached to a return that doesn’t exist.
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The one break you do get
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If your tax home and residence are both outside the U.S. and Puerto Rico on the regular filing deadline, you get an automatic two-month extension to file — no form required, just attach a statement to the return explaining why you qualify.
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That’s an extension to file, not to pay — interest still accrues on anything owed after the original deadline.
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If you have foreign bank or investment accounts, you may also have a separate FBAR filing requirement with the Treasury Department, with its own penalties for skipping it.
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⚙️ THE TAXSTACHE TOOLKIT
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Filing from abroad and want a straight answer, not a guess?
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The Expat Filing Obligation Checker takes your filing status and worldwide income and tells you whether you’re required to file, plus whether you qualify for the June 15 extension.
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Every Thursday, we go to work.
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The TaxStache Business Edition breaks down the tax and finance topics that actually matter to business owners, from quick intros to in-depth dives. Plus book, podcast, and video recs to keep you sharp, and a weekly download you can put to use right away.
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If you own a business (or you’re building one), this one’s for you.
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Would you like to receive our Thursday Business Edition?
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Businesses & Gigs
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🤝 The loan didn’t have to be repaid. The IRS didn’t want a cut either.
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My business got a PPP-style loan that was later forgiven. Is forgiven debt like that taxable?
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Normally, yes — and this is one of the more counterintuitive corners of the tax code.
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Quick refresher on what a PPP loan actually was
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The Paycheck Protection Program was a Small Business Administration loan program created by the CARES Act in 2020, in the early scramble of the pandemic.
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It let small businesses, sole proprietors, independent contractors, and self-employed people borrow money — no collateral, no personal guarantee — to cover payroll and a short list of other costs during a rough stretch.
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The hook: if you spent the money on the right things within the covered period, the loan didn’t have to be repaid at all. The SBA “forgave” it, and the lender ate the cost, not you.
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The program itself closed to new loans back in 2021, but plenty of businesses are still sorting out the tax consequences of loans that were forgiven well after the fact — hence the question.
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The general rule for forgiven debt
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When a lender cancels debt you owed, the IRS generally treats the canceled amount as taxable income to you.
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The theory: not having to repay $20,000 makes you $20,000 richer, whether or not any cash changed hands.
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Cancel enough debt and the lender issues a Form 1099-C reporting it, and that number is expected to show up on your return.
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PPP loans got a specific, deliberate exception
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Congress wrote the forgiveness of PPP debt out of gross income entirely under the CARES Act.
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The IRS told lenders not to bother issuing 1099-Cs for forgiven PPP amounts, specifically to avoid confusing people into reporting income that was never taxable.
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If your loan was forgiven because you actually met the program’s requirements — payroll, rent, mortgage interest, and utilities during the covered period, no misrepresentations on the application — the forgiven amount stays off your return, full stop.
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The expense fight, resolved in your favor
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The IRS initially tried to disallow deductions for anything paid for with PPP money, calling tax-free forgiveness plus a deduction a “double dip.”
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Congress overruled that in the Consolidated Appropriations Act, 2021: expenses paid with forgiven PPP funds remain fully deductible.
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You get the tax-free forgiveness and the deduction.
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The asterisk, and it’s a serious one
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If a loan was forgiven based on a forgiveness application that included misrepresentations or omissions — proceeds weren’t actually spent on eligible expenses, but the application said they were — the improperly forgiven portion is taxable income.
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The IRS has said plainly that it wants amended returns from anyone in that position.
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If you followed the rules, you’re fine. If your forgiveness application was more aspirational than accurate, that’s a conversation for a tax professional, ideally before the IRS starts it for you.
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If this was a genuinely different type of loan — not PPP itself — the general cancellation-of-debt rule is where you start. PPP-specific relief doesn’t automatically extend to it.
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⚙️ THE TAXSTACHE TOOLKIT
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Got a forgiven loan and a nagging feeling about it?
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The Loan Forgiveness Taxability Checker sorts out whether your forgiven debt is PPP-protected, generally taxable, or somewhere in between.
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ALSO PRESENTED BY COMPOUNDSIGNAL
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Earn up to 10x gains with “Blue Chip Moonshots”
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Trump’s AI nationalization is creating a rare asymmetry in the market that offers up to 10X gains without the risk of tiny speculative stocks.
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Follow us for even more great tips, tricks, and deadline reminders.
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