Every January, our phones ring with the same three calls. Someone ordered equipment that showed up too late, someone needs to send 1099s and has no W-9s, or someone meant to set up a retirement plan and never did.

None of those were January problems. They were November decisions that waited too long.

This small business year-end checklist 2026 sorts every task by lead time. You’ll see what to start this week, what has to be done by December 31, and what can wait until January. Forward it to your bookkeeper, print it, or just use the table near the bottom.

What belongs on a small business year-end checklist for 2026?

The short answer: a good year-end to-do list for your small business has three parts, and the order matters more than the items.

• Start now (November): order any equipment you plan to deduct, collect W-9s from contractors, make your retirement plan decision, and verify employee addresses.
• Finish by December 31: get equipment placed in service and run final 2026 payroll, including owner salary and bonuses. Have your year-end planning conversation with your accountant.
• Leave for January: the Q4 estimated tax payment (due January 15, 2027) and W-2s and 1099-NECs (due February 1, 2027).
• New for 2026: the 1099-NEC reporting threshold is now $2,000 per contractor for payments made in 2026, up from $600. Plenty of checklists online still say $600.

What should you start on your year-end checklist this week?

Start your small business year-end checklist for 2026 with the items that have lead time baked in. You can’t speed them up in late December, no matter how motivated you are.

1. Order any equipment you plan to deduct this year

Section 179 and bonus depreciation only count for 2026 if the equipment is placed in service by December 31. In plain English, that means delivered, set up, and ready to use. A signed purchase order doesn’t count. Delivery time does. The IRS lays out the rules in Publication 946.

One Illinois wrinkle: the state doesn’t follow the federal bonus depreciation rules, so your state deduction can look different from your federal one. Any year-end tax checklist for Illinois businesses should include running both numbers before you buy. Our guide to Illinois tax laws for small business owners covers more of where the state parts ways with federal rules.

2. Start collecting W-9s now

You need a W-9 on file to issue a 1099-NEC, and 1099-NECs are due February 1, 2027. For payments made in 2026, you only have to issue one to contractors you paid $2,000 or more. Collect W-9s from everyone anyway. You won’t know who crosses the line until December, and chasing a contractor for paperwork in late January is nobody’s idea of a good week.

3. Make your retirement plan decision

The deadlines depend on the plan and on how your business is set up. Here’s the version without the jargon:

• SEP-IRA: can be set up and funded up to your tax filing deadline, including extensions. The most forgiving option.
• Solo 401(k) for sole proprietors and single-member LLCs: thanks to SECURE 2.0, you can adopt a new plan after year-end and still make first-year contributions. The deadline is your filing date without extensions, usually April 15.
• S-corp owners: your employee deferrals run through payroll. If you want to make them for 2026, the plan has to be in place before your final 2026 payroll. This is the group November matters most for.

IRS Publication 560 has the full rules. Our retirement plans page compares the main options side by side.

4. Verify employee names, addresses, and Social Security numbers

W-2s go out by February 1. A wrong address means a returned W-2 and an annoyed employee. Ask everyone to confirm their details during a November payroll, not the last one of the year. If you run payroll through Payroll Freedom, your payroll specialist can send the request for you.

5. Chase receivables older than 60 days

Old invoices get harder to collect every month. Knowing which ones are actually collectible also gives your accountant a cleaner picture for year-end planning.

What has to be finished by December 31?

These are the December 31 business deadlines that don’t move:

• Equipment placed in service. Delivered and usable, not just ordered.
• Final 2026 payroll. Include year-end bonuses and, for S-corp owners, a reasonable salary that actually ran through payroll.
• S-corp 401(k) deferrals. Taken out of 2026 paychecks, which means before the last payroll of the year.
• Your year-end planning conversation. Planning works with real numbers, and December is the last month you can still change them.

One more to ask about, not assume: prepaying January expenses. Some prepayments are deductible this year and some aren’t. Talk it through with your accountant before you write the check.

What can wait until January?

The last part of a small business year-end checklist for 2026 can wait for the new year:

• Q4 federal estimated tax payment: due Friday, January 15, 2027. Run the number in December so the payment isn’t a surprise. Paying at least 100% of last year’s tax through estimates generally avoids the underpayment penalty. That rises to 110% if last year’s adjusted gross income topped $150,000.
• W-2s and 1099-NECs: due Monday, February 1, 2027. The usual January 31 deadline falls on a Sunday this year.
• SEP-IRA contributions: up to your tax filing deadline, including extensions.
• Solo 401(k) setup for sole proprietors: up to your filing deadline without extensions, usually April 15, 2027.

The small business year-end checklist 2026, at a glance

Screenshot this version of the small business year-end checklist for 2026, or send it to whoever runs your books.

Task	Start	Hard deadline	Watch out for
Equipment purchases (Section 179 / bonus)	Now	Placed in service by Dec. 31, 2026	Delivery and setup time
W-9s from contractors	Now	Before 1099-NECs go out Feb. 1, 2027	$2,000 threshold for 2026 payments
Employee name, address, SSN check	Now	W-2s due Feb. 1, 2027	Ask during a November payroll
S-corp owner 401(k) deferrals	NOw	Final 2026 payroll	Plan must be in place first
Final payroll, owner salary, bonuses	December	Dec. 31, 2026	Payroll provider cutoff dates
Q4 estimated tax payment	Calculate in December	Jan. 15, 2027	Safe harbor: 100% or 110% of last year
SEP-IRA contribution	Anytime	Tax filing deadline, including extensions	None. Most flexible option
Solo 401(k), sole proprietors	Anytime	Filing deadline without extensions (usually Apr. 15, 2027)	Not available to S-corp owners after year-end
W-2s and 1099-NECs	January	Feb. 1, 2027	Jan. 31 falls on a Sunday

What this means for you

If you do three things this week, do these: send the equipment order, send the W-9 requests, and book your year-end conversation. Everything else on this small business year-end checklist 2026 has room to breathe. Those three don’t.

If your accountant doesn’t usually bring this up until after December 31, that’s worth noticing. Year-end planning is part of what tax preparation and planning should mean, not an add-on.

Frequently asked questions

This article is provided for general informational purposes only and does not constitute tax, legal, accounting, or financial advice. Every business situation is different. Before acting on anything you read here, please consult with a qualified advisor — including, we hope, us. Reach out to Accounting Freedom or Payroll Freedom for guidance specific to your situation.

Frank Fiore, CPA, is the Visionary at Accounting Freedom and Payroll Freedom, with offices in Mundelein, Illinois and Grafton, Wisconsin. The firm has helped small business owners across Illinois and Wisconsin with accounting, tax planning, and payroll since 1981. Frank works with contractors, medical practices, restaurants, and family-owned businesses, and he believes year-end planning should happen in November, not April.