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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 questions:
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🪙 Q2 estimated taxes are due June 15. Here’s how to not guess wrong.
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🏕 Summer camp might be tax-deductible. Day camp, specifically.
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💍 You got married. Congrats. The IRS has follow-up questions.
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Follow us for even more great tips, tricks, and deadline reminders. Facebook | Instagram | LinkedIn
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Tax Strategies
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🪙 The June 15 deadline nobody’s ready for
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Image from Envato
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The June 15 quarterly tax deadline is coming up and I have no idea how much to send. Is there a simple way to figure it out so I don’t owe a penalty?
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First, take a breath. You are not the only business owner staring at June 15 on the calendar and feeling a low-grade existential dread. Quarterly estimated taxes are one of those things everyone knows they’re supposed to do and almost nobody feels confident about.
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The simplest method is the prior-year safe harbor. Find last year’s Form 1040, line 24. That’s your total tax liability. Divide it by four. Send that amount. If your adjusted gross income was over $150,000 ($75,000 married filing separately), multiply line 24 by 110% first, then divide by four. That’s it.
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If you pay at least that amount each quarter, you will not owe an underpayment penalty, even if your actual 2026 bill is significantly higher. You may owe a balance in April, but a balance is just tax. A penalty is extra money for being late, and the safe harbor eliminates it.
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The alternative is estimating your current-year liability and paying 90% of it across four installments, but that requires projecting your income for the rest of the year, which is essentially fortune-telling with a spreadsheet. If your income dropped significantly from 2025, this method keeps you from overpaying. Otherwise, the safe harbor is simpler and safer.
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Pay through IRS Direct Pay at directpay.irs.gov — no registration, no fees, confirmation in seconds. And make a calendar reminder for Sept. 15. Q3 comes faster than you think.
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PRESENTED BY DEXT
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June 15 is staring you down and you have no idea what you spent this quarter. Dext captures every receipt automatically — snap, done, synced to your accounting software. No shoebox required.
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👉 Try Dext free
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Money Moves
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🏕 The summer camp tax break hiding in plain sight
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Image from Envato
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I’m sending my kids to summer day camp so I can keep working. Is any of that deductible?
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Not deductible, exactly, but potentially worth a tax credit, which is better. The Child and Dependent Care Credit covers expenses you pay so you can work, and day camp for kids under 13 qualifies.
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Day camp counts. Overnight camp does not. The IRS draws the line at whether the care is enabling you to work during the day, and apparently believes that once s’mores and bunk beds are involved, it stops being childcare and becomes a vacation. Agree or disagree, that’s the rule.
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The credit covers up to $3,000 in expenses for one child or $6,000 for two or more, and the credit itself ranges from 20% to 35% of those costs depending on your income. For most families, that’s a credit of $600 to $1,050 for one kid, or $1,200 to $2,100 for two. It’s not going to pay for the whole summer, but it’s real money.
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Both parents must have earned income (or be full-time students or disabled) for the credit to apply. If one parent stays home, it doesn’t qualify regardless of how many camps are involved. And you’ll need the camp’s name, address and tax ID number when you file, so grab that information at registration while it’s easy to find rather than in February when it isn’t.
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Report it on Form 2441. Your tax software will walk you through it, but the setup is: enter the camp info, enter the cost, enter your kid’s name, and the form does the math.
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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 for business owners, from quick intros to full deep 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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Filing Made Simple
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💍 You said “I do.” The IRS says “noted.”
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Image from Envato
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I got married last month. Do I need to tell the IRS now, or does it wait until I file next year?
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Congrats! You don’t need to call the IRS to announce your nuptials. There is no form for “I got married,” no notification requirement and no mid-year filing status update. The IRS finds out when you file your return, and what matters is your marital status on Dec. 31 of the tax year. If you’re married on Dec. 31, 2026, you’re married for the whole year as far as the IRS is concerned, even if the wedding was on Dec. 30.
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That said, there are a few things worth doing now rather than at tax time.
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Update your W-4. Marriage can change your withholding, especially if both spouses work. The IRS Tax Withholding Estimator at irs.gov can tell you whether your current withholding will leave you with a surprise bill or a giant refund. Neither is ideal. Five minutes now can save you a headache in April.
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Decide how you’ll file. Married couples can file jointly or separately. Joint is almost always better — lower rates, more credits, higher deduction thresholds. Filing separately makes sense in a few narrow situations: income-driven student loan repayment, one spouse with significant medical expenses, or one spouse who doesn’t want to be liable for the other’s tax situation. If none of those apply, joint is your default.
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Update your name with the Social Security Administration if you changed it. The name on your return has to match what the SSA has on file. A mismatch can delay your refund, and a delayed refund is a terrible wedding gift from yourself.
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