1099 Prep in November: The Four-Week Checklist Before January 31

The W-9 rule is simple: collect it before the first payment. But if you’re reading this in November with contractors already paid and W-9s already missing, the rule doesn’t help you. The checklist does. Four weeks of small tasks, one a week, and the 1099s that are due January 31 go out on time with no January chase.

We run an accounting firm and we file 1099s for our clients every January. The difference between a quiet January and a frantic one is entirely what happened in November. Here’s the sequence.

What is the 1099 threshold for 2026?

$2,000. For payments made in 2026, the reporting threshold for Forms 1099-NEC and 1099-MISC moved from $600 to $2,000, and it’s indexed for inflation after this year. Fewer forms for most small businesses.

The threshold applies to the total you paid a vendor during the year, so a contractor paid $1,500 in June and $900 in November is over it. That’s why the checklist starts with the full-year vendor list, not the recent one.

Week one: the vendor list

Pull every vendor paid this year from your accounting system, with the year-to-date total. Sort by amount. Draw a line at $2,000, and then draw a second line a few hundred dollars below it, because anyone near the threshold in early November will likely cross it by December.

For each vendor above the lower line, answer three questions from the W-9 on file: Is this a corporation? Is it an individual, a partnership, or an LLC taxed as one? Do we have their taxpayer ID and current address? A vendor with no W-9 gets an email this week. Not in January.

Corporations generally don’t get a form. There are exceptions, and the most common one for small businesses is attorneys: legal fees get a 1099-NEC regardless of how the law firm is organized. Medical and health care payments are another exception. If you’re not sure, the W-9 tells you what the vendor is, and your accountant tells you whether that matters.

Week two: payment methods

You only report what you paid by check, ACH, wire, or cash. Payments made by credit card, debit card, or through a third-party payment app that issues its own reporting are the processor’s responsibility, not yours. Including them on your 1099 double-reports the vendor’s income and generates a call from them in February.

This is where most 1099 errors come from, and it’s a bookkeeping problem, not a tax one. If your books record how each vendor was paid, the accounting system can exclude card payments automatically. If they don’t, someone has to go through the vendor’s transactions one by one. Week two is when that gets fixed for the year, and when the books get set up so it doesn’t need fixing next year.

Week three: NEC or MISC, and the exceptions

Two forms, and which one a payment goes on depends on what it was for.

• 1099-NEC is for services performed by someone who isn’t your employee: the subcontractor, the designer, the consultant, the cleaning service, the attorney’s fees. This is the one most small businesses file, and it’s due to both the IRS and the recipient by January 31.
• 1099-MISC is for the other categories: rent paid to a landlord, prizes, certain legal settlement proceeds, and a few others. Rent is the one that surprises people. If you pay your landlord directly by check and they aren’t a corporation, that’s a 1099-MISC. If you pay through a property manager, the manager handles the reporting to the owner.

Week three is sorting the over-threshold list into the right form, and flagging the ones that don’t need one at all: the corporations, the card payments, the reimbursements of expenses that were separately documented.

Week four: TIN match and addresses

A 1099 with a wrong taxpayer ID or a mismatched name produces an IRS notice months later, and a possible penalty for filing an incorrect return. The fix is to run a TIN match in December, before filing, through the IRS matching program your accountant has access to. A mistyped digit gets corrected in an afternoon in December. In March, it’s a corrected form, a notice, and a letter.

Confirm addresses while you’re at it. The recipient copy has to reach the vendor, and a contractor who moved in July won’t tell you.

When should I collect a W-9 from a contractor?

Before the first payment. Every vendor you paid without one this year is the reason this checklist exists, and every vendor you onboard from now on should return a W-9 before a check is cut. Add it to whatever your vendor setup looks like: a checklist, a folder, a required field in the accounting system. The contractor who wants to be paid sends it the same day.

What if a contractor refuses to give me a W-9?

You’re required to withhold 24% from their next payment and send it to the IRS as backup withholding. In practice, telling a contractor that’s about to happen produces the W-9 within a day. It’s the one piece of leverage you have in November that you won’t have in January, when there’s no next payment to withhold from.

The deadline

Forms 1099-NEC, and the W-2s for your employees, are due January 31. In 2027, January 31 falls on a Sunday, so Monday, February 1 is the last day. Most businesses that file ten or more information returns of any kind in total must file electronically, so don’t plan on paper forms from the office supply store. The recipient copies go out on the same schedule.

Done in November, all of that is a formality in January. Skipped in November, it’s the email from your accountant with a list of names and the word “urgently.”

What a CFO does with this number

Once the vendor list is clean, it produces a number worth reading: total contractor spend for the year, by vendor. A fractional CFO looks at it beside payroll.

• Concentration. One vendor at a third of your outside spend is a dependency, and a rate increase from them is a margin problem you didn’t plan for.
• Classification. A contractor paid on a regular schedule, all year, on your terms, with your tools, may be an employee by the state’s definition. The 1099 list is where that shows up first, and converting them on your timeline is cheaper than being required to.
• Real labor cost. Payroll plus 1099 spend, as a share of revenue, is the labor number pricing should be built on. Payroll alone makes most businesses look leaner than they are.

Where we come in

Our monthly close includes a vendor check: anyone paid this month without a W-9 on file gets flagged and chased that month, payment methods are recorded so card payments fall out of the totals automatically, and the TIN match runs in December. Our clients’ 1099s are filed in the second week of January without a single chase email. If your November looks like a spreadsheet and a list of people who aren’t answering, reach out. We’ll pull the vendor list and tell you exactly what’s missing.

Frequently asked questions

When should I get a W-9?
Before the first payment; a contractor who wants to be paid returns it the same day, one paid in April doesn’t.

What’s the 2026 1099 threshold?
$2,000 for payments made in 2026, up from $600, indexed after that.

What if they won’t give one?
You can withhold 24% backup withholding from the next payment; telling them usually produces the W-9 within a day.