📬 You filed an extension. The IRS wants a word.

The single most common extension mistake is treating October 15 like a finish line you can sprint toward in late September. The whole point of Form 4868 is to give you breathing room. Using all six months of it tends to recreate the exact panic you filed the extension to avoid, just with cooler weather.

Instead, gather your documents now, while April is still recent enough that you remember which 1099s you were missing. Pull together your W-2s, 1099s, brokerage statements, mortgage interest forms, charitable receipts, and anything else that crossed your desk during tax season. Set them in one folder. Future-you will be grateful.

Then, and this is the part that catches people, check whether you owed money. An extension to file is not an extension to pay. If you owed a balance and didn’t send a payment with your 4868, interest is already accruing, currently at 6%, plus a failure-to-pay penalty of 0.5% per month. Six months of that adds up to real money. Sending in even a partial payment now slows the bleeding.

If your situation is more complicated than usual — you sold a house, exercised stock options, had a windfall, started a business — this is also the right moment to find a tax professional. The good ones get booked solid in September. Calling a CPA on October 14 is how you end up missing the extension deadline, which is not fun.

Try to have your return finished by mid-August. That gives you margin for the document you forgot, the question that requires a phone call, and the unexpected complication that always shows up in the last 10% of the work.

Welcome to your kid’s first encounter with the W-2, an experience that has been disappointing teenagers since 1943. There are two separate questions tangled up here, and the answers don’t always go the same direction.

Do they need to file? It depends on how much they earn. For 2026, a dependent is generally required to file a federal return if they earn more than $16,100 in wages (the standard deduction for a single filer), or if they have unearned income (interest, dividends, investment gains) above $1,350. A summer job at the local pool that brings in $3,200 doesn’t trigger a filing requirement.

But they probably should file anyway. If their employer withheld federal income tax, and many do, even on small paychecks, filing is the only way to get that money back. A teenager doesn’t usually owe federal income tax at summer-job income levels. The withholding is often a refund waiting to be claimed.

Have them fill out their W-4 carefully. First-time workers tend to either over-withhold (giving the government an interest-free loan) or check the wrong box and end up owing at year-end. If they expect to earn under the standard deduction, they can usually claim “exempt” from federal withholding entirely. Their employer will need a fresh W-4 to update it.

Can you still claim them as a dependent? Yes, almost certainly. The dependent rules are about residence, support, and age, not about whether your kid earned money. As long as your child is under 19 (or under 24 and a full-time student), lives with you more than half the year, and doesn’t provide more than half of their own support, they’re still your dependent. A summer job doesn’t change that unless they’re earning enough to cover more than half of their own annual living costs, which a lifeguard shift at the YMCA generally does not.

Make sure your kid checks the box on their own return that says someone else can claim them as a dependent. Forgetting that is one of the most common reasons a teenager’s first return gets rejected or amended.

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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.

If you own a business (or you’re building one), this one’s for you.

Congratulations! Your filing status changed the moment the officiant pronounced you married. The IRS considers you married for the entire tax year if you were married on December 31, which means the wedding you had in April (or May, or June) makes you officially Married Filing Jointly or Married Filing Separately for the 2026 return you’ll file next spring.

That feels like a problem for future you. It is not. Several things are worth handling now.

Update your W-4s. Both of you. The default withholding for two married people who haven’t told their employers anything tends to be either way too much or, more often, way too little. The IRS has a free withholding estimator that asks for a few pieces of paper from each spouse and tells you what to put on a fresh W-4. Spending 15 minutes on this in May is significantly more pleasant than discovering in April that you owe $4,200.

Get the name change done with the SSA, not just the DMV. If you changed your name, your tax return needs to match your Social Security record, not your driver’s license. File Form SS-5 with the Social Security Administration. If your return name doesn’t match SSA’s records, the IRS can reject your e-file or hold your refund while it sorts the discrepancy out. This is a small piece of paperwork that creates a large headache when skipped.

Think about the new math. Joint filing usually wins for couples with one significantly higher earner. The lower earner’s income gets pulled into wider tax brackets. It often loses, or at least doesn’t help much, for two high earners with similar incomes (the so-called marriage penalty). Filing separately occasionally makes sense for student loan situations, large medical expenses, or when one spouse has tax issues the other doesn’t want attached to their refund. Most couples should run both scenarios next spring before deciding.

Check your benefits. Marriage is a qualifying life event that opens a special enrollment window for health insurance, HSAs, FSAs, and most employer benefits. Comparing your two plans now, while you can still change them, often saves more money than any tax move you make.

The actual filing change waits until next April. But the moves that make next April easy happen now.

Just got married? Congrats. Now go update your W-4s before you owe the IRS a honeymoon’s worth of penalties next April. Origin connects both your accounts, builds a joint budget from your actual spending, and actually explains the math. One app for your new shared financial life.

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