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Plus one costly extension myth and the last-minute mistakes to avoid.
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Happy Tuesday! If you filed a tax extension back in April, congratulations – your six-month reprieve is officially down to 30 days.
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This week, we’re getting you ready with a 30-day gameplan, busting an extension myth that could cost you, and covering the last-minute mistakes you definitely don’t want to make at the eleventh hour.
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This week’s lineup:
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⏱️ You bought yourself six extra months to file your return. Now it’s time to cash them in.
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💰 More time to file? Yes. More time to pay? Absolutely not.
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🚩 Filing your taxes late is sometimes unavoidable. Careless mistakes are optional.
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🏛️ Your tax pro missed a deadline. Guess who pays the penalty.
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Seasonal Tax Alerts
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⏱️ Filed a tax extension? Your 30-day countdown starts now
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The Quick & Bristly: You got the extension. Now the clock is ticking. Use the next 30 days wisely to get your return in by October 15.
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Six extra months to file your tax return seemed like a lot of time back in April. But here we are with 30 days left in the countdown.
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The good news: 30 days is still plenty of time to get this done without making careless mistakes.
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30 days out: Get it together
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Forms (W-2s, 1099s)
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Business income and expense records
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Supporting documents for credits and deductions
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Records for estimated tax and extension payments
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2 weeks out: Know the numbers
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1 week out: Catch the mistakes
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Make sure your income is reported accurately. (Yes, all of it.)
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Check your filing status
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Verify information for yourself and any claimed dependents
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Check all requirements for credits you have claimed
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Double-check deductions (and have the records to back them up)
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Check state filing requirements
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Look for other common mistakes
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48 hours out: Hit submit
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October 15 is here. Now what?
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Submitted? Good. Accepted? Even better. Check that the return was accepted, fix any errors ASAP if your return was rejected, and save your confirmation.
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🧰 TAXSTACHE TOOLKIT
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Open the interactive checklist and track all four phases — from gathering paperwork to hitting submit — so nothing slips through in the next 30 days.
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PRESENTED BY TAXQUOTES
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Behind on taxes? The extension deadline is almost here.
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If you’ve got unfiled tax returns sitting untouched, a free consultation with TaxQuotes is the first step toward getting them resolved. They’ll help you understand where you stand and what it takes to get caught up for good.
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IRS Survival Guide
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💰The tax extension myth that gets expensive fast
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The Quick & Bristly: Filing an extension pushes your return deadline to October 15, but your tax bill was still due in April. If you wait to pay, interest and penalties can start adding up.
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Filing an extension feels a lot like hitting the snooze button on tax season. Six more months? See you in October.
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Except there’s one catch a lot of filers overlook: an extension gives you more time to file your return, not more time to pay your taxes. And if you missed that back in April, it could already be costing you.
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An extension delays your filing deadline, which is great if you’re missing documents, have a complex return, or had a disastrous April. But the IRS still expected payment by April 15. Think of it this way: your paperwork got an extension. Your tax payment did not.
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Now for the expensive part
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For unpaid balances, interest can start accruing from the original due date. The IRS can also add on a failure-to-pay penalty of 0.5% of your unpaid taxes for each month or partial month, up to 25% of your unpaid balance.
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If your plan was, “I’ll deal with it when I file in October,” you may already owe more than you did in April.
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Can’t pay? You still have options.
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If you still owe, pay what you can as soon as you can. If the full amount seems impossible, the IRS offers payment plans. The goal is simple: don’t let the problem get more expensive than it already is.
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The extension bought you time to finish your return, not a six-month break from your tax bill. File by October 15, pay what you can now, and deal with the balance before it costs you more.
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🧰 TAXSTACHE TOOLKIT
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Enter what you still owe and see the penalties and interest that have accrued since April 15, plus what it grows to if you wait until October 15 to deal with it.
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Still haven’t dealt with your tax bill?
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An extension delayed the filing deadline, not the payment one — but that doesn’t mean you’re out of options. The sooner you get clarity, the more room you have to make a plan that actually works. TaxQuotes offers a free consultation to help you take that first step, at your pace.
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Thursday, we go to work.
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The TaxStache Business Edition is built for owners and operators. Quick hits on entity structure, quarterly deadlines, deduction strategy and the IRS rule changes that actually affect your bottom line.
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Would you like to receive our Thursday Business Edition?
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Wacky Tax Tales
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🏛️ Tax preparer missed the deadline? You’re still on the hook
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Image by Andres M.
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The Quick & Bristly: A tax attorney missed the filing deadline, and the taxpayer got the penalty. The Supreme Court’s verdict? You can hire someone to handle your taxes, but the deadline is still your problem.
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You hire a tax professional so you don’t mess up your taxes. Then they make a mistake, and somehow you’re the one footing the bill. Apparently, tax season needed another plot twist.
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In 1985, Robert Boyle found out the hard way that hiring a tax attorney doesn’t get you off the hook when a tax deadline is missed.
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The case: “But my lawyer was handling it!”
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Boyle hired tax attorney Ronald Keyser to handle the tax return for his mother’s estate. He checked in regularly and was told that everything was under control. Famous last words.
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Because of an oversight, the return was filed three months late, and Boyle was slapped with a penalty. He took the matter to court and argued that relying on his attorney should count as reasonable cause for the late filing.
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The decision: Your deadline, your problem
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The District Court and Court of Appeals agreed with Boyle. The Supreme Court, however, had other ideas. The Court’s message was pretty clear: Complicated tax advice can be someone else’s job. Remembering the deadline is still yours.
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In other words, the “My lawyer was supposed to do it” excuse isn’t going to work on the IRS.
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The moral of the story is that hiring a tax professional can make taxes easier, but it doesn’t mean that all responsibility shifts away from you. Know your deadlines, check in often, and make sure your return was actually filed.
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Hire the tax pro. Trust the tax pro. Just keep the deadline on your own calendar.
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The quick (and slightly prickly) stories we didn’t have time to get to:
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🔒 A federal appeals court upheld a ruling blocking the IRS from sharing taxpayer addresses with immigration officials. More than 47,000 records were shared before the policy was stopped, adding, “who has my tax info?” to our list of tax season worries.
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🎓 Lawmakers are taking another shot at passing the SIMPLE Act, which would use IRS income data to enroll some delinquent student loan borrowers in cheaper repayment plans. Even if it passes, changes wouldn’t take effect until 2028, but the idea of one less form to fill out already feels like progress.
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🤖 The American Institute of Certified Public Accountants is pushing back on IRS guidance that suggests tax pros who use AI to save time and money should pass some of those savings on to clients through lower fees. Somewhere, a taxpayer just became very interested in how much AI their accountant uses.
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📅 October 15 is the deadline to file your extended return — but if you owe the IRS, it’s also your last real window to get ahead of the balance before penalties keep climbing. A free consultation with TaxQuotes is where the conversation starts. Take the first step before the deadline (sponsored).
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