For most business owners, the next federal tax date is October 15, 2026. That's when extended individual returns and extended calendar-year C corporation returns are due.
Next come fourth-quarter estimated payments on January 15, 2027. W-2s and 1099-NECs follow on February 1, 2027, because January 31 lands on a Sunday. If you know which of those apply to you and have your numbers ready a few weeks early, most of the stress goes away.
Tax deadlines are easy to lose track of when you're busy running a business. The dates don't change much from year to year, but your business does. A new hire, a big contract, a switch to S corp status, or a new state you're selling into can change what you owe and when.
It depends on how your business is set up. If you filed an extension this spring, your return is due October 15. One thing trips people up: the extension moved your filing date, but your payment was still due in April.
The IRS has been charging interest on any unpaid balance since then. If you missed the April deadline without an extension, the failure-to-file penalty is 5% of the unpaid tax for each month you're late, up to 25%. Filing on time, even if you can't pay in full yet, keeps that penalty from growing.
S corporations and partnerships on extension had to file by September 15. If you missed it, file now, since the late-filing penalty for S corps and partnerships grows every month.
If you're self-employed, own a pass-through business, or have income without withholding, you probably pay quarterly estimated taxes. The last 2026 payment is due January 15, 2027, right after the holidays, when most owners are thinking about anything but taxes.
The IRS's safe harbor rules help here. You generally avoid an underpayment penalty if your 2026 payments cover 100% of last year's tax, or 90% of this year's. If your prior-year adjusted gross income was over $150,000, that first number goes up to 110%. If your business had a much better year than last year, look at your fourth-quarter payment before the holidays so a January bill doesn't catch you off guard.
This one affects almost everyone who pays contractors. The One Big Beautiful Bill Act raised the reporting threshold for Form 1099-NEC and 1099-MISC from $600 to $2,000, starting with payments made in 2026, and that number will be adjusted for inflation each year beginning in 2027. The $600 threshold had been in place since 1954.
That means fewer forms for smaller jobs. You'll still want a W-9 on file for every contractor, though, because you won't always know in March who will pass $2,000 by December.
If taxes feel like they're always in the back of your mind, you're in good company. Xero's 2026 survey of U.S. small business owners found that financial pressure, fatigue, and avoidance cost owners an average of 33 working days of productivity a year, with about eight hours a week consumed by worry. That's a lot of energy going to something that could be planned for.
Start with books reconciled through the most recent month. Add your prior-year return, payroll reports, and a list of every contractor you've paid this year with their W-9. Pull receipts for any large purchases, like equipment or vehicles, since those can change your tax picture a lot. If those records live in a few different places, getting them into one shared folder now will save you hours in January.
You don't have to be the person tracking every date and every form. A lot of business owners already have a bookkeeper or financial partner in their corner, and taxes fit naturally into that same relationship. Your financial lineup works better when the people handling your books also have eyes on your tax calendar.
If you'd like help staying ahead of your next deadline, BELAY Tax Services matches you with a dedicated U.S.-based CPA who tracks the calendar with you all year. Explore BELAY Tax Services.
This article is for general information only and isn't tax advice. Talk with a qualified tax professional about your specific situation.
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The most useful year-end tax planning happens before December 31. After that, most of your options are gone. Start by projecting your full-year profit. Then look at the timing of big purchases, retirement contributions, owner pay, and contractor records. Two or three hours with your books in November can save you real money and a lot of stress in April.
Planning before December 31 lets you shape the result while the year is still open. Planning is your chance to shape the result while the year is still open.
Take your year-to-date numbers and estimate the rest of the year. Include the invoices you expect to collect and the bills you'll pay in December. This one number drives almost every other decision on this list. If you're headed for a much bigger year than last year, you'll want to know now, not when your return is being prepared.
If you've been thinking about new equipment or vehicles, the rules are generous right now. For 2026, the Section 179 expensing limit is $2,560,000, and 100% bonus depreciation is permanent for qualifying property acquired after January 19, 2025. For many small businesses, that means you can deduct the full cost of qualifying purchases in the first year.
The catch is timing. To count for 2026, the equipment has to be bought and placed in service by December 31, meaning it's set up and ready to use, not just ordered. A laptop still sitting in its box on New Year's Eve counts toward next year.
Buy only what your business actually needs, though. A deduction still comes from real money spent.
If your business uses cash-basis accounting, when you get paid and when you pay bills affects which year they count toward. Paying a January expense in December, or sending a late-December invoice in early January, can shift income between years.
Whether that helps depends on where you expect your income to be next year, so this is a good one to talk through with your tax advisor instead of guessing.
Retirement accounts are one of the simplest ways to lower taxable income while saving for your own future. Some deadlines are tighter than people expect, though. With a Solo 401(k), for example, the employee deferral generally has to be elected by December 31.
A SEP IRA gives you more room, since contributions can usually be made up until your return's due date. Know which kind of plan you have before the calendar turns.
S corporation owners who work in the business need to take a reasonable salary through payroll. If you've mostly paid yourself through distributions this year, fix that before your final payroll run in December. The IRS watches closely for S corp owners who take little or no salary.
Year-end is the right time to make sure every contractor has a current W-9 on file. Starting with 2026 payments, you'll only need to issue a 1099-NEC or 1099-MISC when a contractor's total reaches $2,000 for the year, up from $600. Run a report of who you've paid so far so you know who's likely to cross that line. Chasing tax ID numbers in late January is nobody's idea of a good time.
Your last 2026 estimated payment is due January 15, 2027. If your profit projection came in higher than expected, adjust that payment now so the extra tax doesn't all come due in April.
A lot of year-end planning comes down to having someone look at your numbers early and ask the right questions. If you already trust someone with your books, it can make sense to have that same team help with your taxes, too.
Before the year wraps up, talk with BELAY Tax Services about year-end planning with a dedicated U.S.-based CPA, and walk into 2027 knowing where you stand.
This article is for general information only and isn't tax advice. Talk with a qualified tax professional about your specific situation.
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To start the new year ahead on taxes, close your December books in the first couple of weeks of January. Make your last 2026 estimated payment by January 15, 2027, and send W-2s and 1099s by February 1, 2027. Then put all four of your 2027 estimated payment dates on the calendar before February. Owners who handle January well usually have a much calmer spring.
The first month of the year is when last year's loose ends and this year's habits overlap. Here's how to handle both.
Everything else in January depends on clean December numbers. Reconcile your bank and credit card accounts, categorize the last few weeks of transactions, and chase down any missing receipts while they're still easy to find. If you use a bookkeeper, ask when they expect December to be closed so you can plan around it.
If you pay quarterly estimated taxes, the fourth payment for 2026 is due January 15, 2027, and it’s admittedly easy to miss because it shows up right after the holidays. If your December was stronger than expected, check whether this payment needs to be bigger than you planned.
Employers need to send W-2s to employees and file them with the Social Security Administration by February 1 this year, since January 31 falls on a Sunday. The same date applies to 1099-NECs for contractors.
This is also the first filing season under the new 1099 rules. For tax year 2026, you only report payments on a 1099-NEC or 1099-MISC once a contractor reaches $2,000, and the Form 1099-K threshold for payment apps and marketplaces went back to $20,000 and 200 transactions.
One caution from the other side: contractors still have to report all their income, even amounts that never show up on a 1099. If you're a contractor yourself, keep your own records instead of waiting for forms to arrive.
Once 2026 is wrapped up, put your 2027 estimated payment dates on the calendar: April 15, June 15, and September 15, 2027, with the fourth payment due in mid-January 2028. Add your business return due date too. That's March 15 for S corporations and partnerships and April 15 for most sole proprietors and C corporations.
Then decide how much to set aside from each month's revenue for taxes. A separate savings account just for tax money makes a big difference. When the payment comes due, the cash is already sitting there instead of coming out of this month's operating budget.
Tax stress piles up when everything waits until spring. In Xero's 2026 survey, 81% of U.S. small business owners said their work had been more stressful than in previous years, with rising costs as the top contributor. You can't control costs or the tax code, but a steady routine takes a lot of the unknown out of it. A 30-minute review of your books each month makes your quarterly payments easier to estimate and makes year-end planning much less painful.
If last year felt like you were always catching up on taxes, this is a good time to change that. Having one trusted team handle your books and your tax calendar means fewer dates to track on your own.
If you want to start 2027 prepared, see how BELAY Financial Solutions can help with your taxes this year.
This article is for general information only and isn't tax advice. Talk with a qualified tax professional about your specific situation.