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In partnership with
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Every Saturday, we open the mailbag, pour some strong coffee, and tackle the tax questions keeping America awake at 2 a.m. Here’s this week’s question:
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I’m not ready to file by April 15th. What does an extension actually do, and what doesn’t it do?
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Ah, the extension. The great American tax security blanket. Every spring, millions of people request one with the confident relief of someone who just found an extra hour in the day. And every fall, a meaningful portion of those same people discover they’ve been holding the blanket upside down.
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A tax extension gives you more time to file. It does not give you more time to pay.
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Your paperwork deadline moves from April 15 to October 15. Your payment deadline stays exactly where it was, tapping its foot, checking its watch.
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So what does an extension actually buy you?
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Breathing room to get your documents in order, especially useful if you’re waiting on a late K-1, sorting out a complicated situation, or you’ve simply lost the will to live every time you open your tax software. No judgment. We’ve been there.
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Filing an extension also protects you from the failure-to-file penalty, which runs 5 percent of your unpaid balance per month, up to 25 percent. That’s the expensive one. Avoiding it is genuinely worthwhile.
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And what doesn’t it do?
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It doesn’t pause interest. It doesn’t pause the failure-to-pay penalty, which is 0.5 percent per month on whatever you still owe. And it definitely doesn’t make the IRS forget you exist — a fantasy we understand but cannot endorse.
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If you think you’ll owe, the move is to estimate your tax bill and send in a payment by April 15, even if it’s a rough guess. Overpaying slightly means a refund later. Underpaying means penalties and interest on the gap, but a smaller gap is always better than ignoring it entirely.
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The short version: File the extension if you need it — it’s free, it takes about two minutes, and it saves you from the worst penalty on the menu. Just don’t mistake the paperwork reprieve for a payment holiday. The IRS is many things, but flexible about its calendar it is not.
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