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3 tax moves to make October less scary

October 2, 2025
Photo by Vlad Chețan

October traditionally is the scariest month, and I’m not just talking about the terror that strikes when you run out of candy on Oct. 31 while young ghouls and goblins are still roaming your neighborhood’s streets.

There’s also the coming colder weather, which sends a chill along the spines of those like me who prefer warmer weather.

And, of course, there is the absolutely final tax filing deadline to meet by Oct. 15 or face late-filing penalties if you discover you didn’t pay enough when you got the Form 1040 extension.

This year, the tax deadline has an added fear factor thanks to the federal government shutdown that also began on Oct 1, the start of the now unfunded 2026 fiscal year.

So far, the partial closure hasn’t interrupted Internal Revenue Service operations. The IRS says it can operate for five business days during with no disruptions thanks to funds left in the Inflation Reduction Act’s special appropriation for the agency.

But if Capitol Hill and the White House can’t come up with a deal by Oct. 7, nonessential IRS staff will join their other furloughed federal employee colleagues and the tax agency’s operations will slow. That means that if your extended return filing will get you a tax refund, you might not get it as quickly as expected under normal operational status.

File your extended 2024 tax return: The possible (probable) coinciding of the Oct. 15 due date and fewer IRS staff to handle extended filings is why filing your postponed return is the first October Tax Move to make this year.

And yes, you still must do so even when the federal government shuts down, since tax law remains in effect even when the IRS isn’t fully staffed to administer it.

As noted, even if you paid the proper amount when you filed your Form 4868 to get the six-month extension, you still are required by law to file your return on time. This time, that’s by Oct. 15.

And if you find when you finally fill out your Form 1040 that you owe more than you sent with your extension request, the IRS will add penalties to that uncollected amount. You can’t do much now about the ones that will apply from April 15 until when you file, but you can only stop additional fees by filing and paying.

But you can get some financial filing help from the IRS and its Free File Alliance partners. Their Free File option is available through Oct. 15 for taxpayers whose adjusted gross income is $84,000 or less. Eight tax software companies are participating this year.

Check out which new OBBB tax breaks apply to you: Another smart move to make this month is to check out the new One Big Beautiful Bill (OBBB) Act tax law changes that apply to you.

You might be able to save some money on your 2025 filing next year if some of your income comes from gratuities. The IRS has issued a formal list of occupations that qualify for this new, temporary OBBB tax break. More guidance will come later, but it’s good to know now whether the tax benefit will apply to you.

Other new OBBB tax provisions that will show up on your 2025 tax return involve a tax-exemption for some overtime pay, a tax deduction for a new vehicle loan, some added educational expenses that can be paid with 529 plan funds, and increased benefits for families, including the Child Tax Credit and adoption tax credit expenses.

Other existing tax breaks, notably those that offered tax savings for alternative energy projects, also are ending this year. While these tax breaks run through Dec. 31, if you’re interested in making energy-efficient changes to your home, you need to start the process now to ensure you don’t miss the tax credit deadline. If your head is spinning like a possessed person in a Halloween horror movie at the prospect of deciphering just which new tax laws apply to you and how to claim them, then you’ll want to check out the next October tax move.

Find a tax adviser now: Tax professionals are winding down the 2024 tax year by finishing up their clients’ extended returns. But once that Oct. 15 deadline is met, they will have a tad more time.

Take advantage of this welcome, but brief, lull by finding a tax pro now that help you get ready for and file your 2025 return next year.

If you wait until 2026 to start searching for a tax adviser, you could be out of luck. Demand for tax pros will increase once people realize the new OBBB laws mean they need professional help. And tax preparers are only human. They can only handle so many clients. That’s especially true when a tax year means new laws for millions of taxpayers and, depending on just how long federal government offices remain closed, a possibly delayed 2026 filing season.

Don’t Mess With Taxes’ transition update: This October tax moves post originally appeared on the ol’ blog’s Substack page. Back then, and still, I was, and am, working on getting the internet version back up to speed after its original 20-year hosting home shut down on short notice Sept. 30.

Thanks for your support, both here and at Don’t Mess With Taxes’ Substack home, and especially for your patience with the transition.

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The More Tax Posts tab at the top of this page will take you to, well, more tax posts. You also can search below for a tax topic. 

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TO WRAP UP 2026

It’s over! With October’s extended filing deadline behind us, it is now time to focus on year-end moves to reduce your 2026 tax bill. 

You’ll find ways to do just that on the Tax Tips page (see the More Tax Posts drop-down menu at the top of the blog), as well as the separate tax tip pages for each month, notably October through December. If you’re on the Tax Tips page, you’ll find a monthly list at the end of this column. If you’re on another blog page, you can head straight to the October tips; at the bottom of that tips page you’ll find links to all the other 11 months’ collections of tax advice.

Not to spoil what you’ll find in that tax advice, but it does cover such things as tax deductions for charitable donations, investment moves that could reduce tax due, and ways to max out your tax-favored retirement savings. 

Finally, as the year winds down, things get hectic. There are lots of other things to occupy our time, like the much more fun upcoming holidays. But don’t lose sight of taxes, since timing is key. To be of use, most tax moves must be made by the end of the tax year. That’s Thursday, Dec. 31, which also is the last business day of the year. 

So that you don’t miss that final tax year deadline, also keep an eye on the countdown clock below. It will keep you on top of just how much time is left to make important, tax-saving moves. (Note: I’m in the Central Time Zone, so adjust accordingly for where you live.)

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