How to Track 1099s and Collect a W9 From a Difficult Contractor or Landlord

You have a vendor who has done the work, the invoice came through, and now they are dodging your W9 request like it is a tax auditor showing up at a family reunion.

Or, alternatively, it’s time to make your annual land lease payment, and your landlord is quick to head out the back door after the Sunday sermon.

Here is the thing: collecting a W9 before you cut a check is not just bureaucratic busywork. It is the difference between staying compliant with the IRS and scrambling in January when 1099 deadlines arrive. If you are running a farm or ranch operation with multiple contractors, the stakes get serious fast.

And, if we’re being real, it’s the difference between writing off an expense – or not.

The IRS Expects You to Know Who You're Paying

Before we discuss the difficult contractor/landlord/vendor, understand why this matters. If you pay someone more than $600 in a calendar year for services (and they are not an employee), you are required to issue them a Form 1099-NEC by January 31st of the following year. The IRS also receives a copy. Without a W9 on file, you do not have their Taxpayer Identification Number (TIN), and the IRS will flag that as incomplete reporting.

The easy fix is simple: do not process payment without a W9. No W9, no check. That is the policy.

What If They Will Not Cooperate?

Sometimes reality is messier than policy. Maybe you did not know about the W9 requirement until after you already paid them, or maybe your landlord is being evasive. Perhaps it is someone you have worked with for years and never thought to request. Life happens.

If you have already paid someone without their W9, you do have options. Ask them directly and be clear about why you need it. Most people understand this is standard business practice. If they still will not provide one, you can file the 1099 with the IRS using their name and address as reported on the invoice or check, using the IRS Individual Taxpayer Identification Number (ITIN) placeholder or leaving the TIN blank. This flags the return as incomplete, but you are still meeting your filing obligation.

If you have not yet paid them, the answer is simpler: hold the payment until they submit their W9. You are being compliant, not difficult.

Make It Easy for Them to Say Yes

Here is where technology helps. If you use QuickBooks Online, your vendors, landlords, and contractors can complete their own profile directly within the system. They complete their information, submit their W9, and the work is done. No back-and-forth emails, no lost forms, and the data flows straight into your records.

Set this up before you need it. Send a link to your QBO vendor/landlord/contractor portal and explain that completing their profile is part of your standard onboarding process. Most will do it immediately, especially if it is easier than filling out a paper form and emailing it back to you.

For those who prefer the old-fashioned approach, keep digital copies of their W9 in a dedicated folder labeled by year. When January rolls around, you will know exactly where everything is located.

The Timeline Matters

Here is what the IRS actually requires: you must issue 1099s by January 31st of the year following payment, with a copy sent to the IRS as well. Miss that deadline and the IRS can assess penalties. They are not huge per-form, but they add up quickly when you are managing dozens of contractors.

The key is staying organized as the year progresses. Do not wait until December to start collecting W9s. Make it part of your contractor onboarding, so the moment someone starts work on your operation, the W9 becomes part of the record.

The Real Policy

Running a farm or ranch means managing people, cash flow, and compliance simultaneously. Setting a clear policy—no W9 on file, no payment—might sound harsh, but it protects you and keeps everyone accountable. 

Those who have been in business understand, and those who have not will soon. 

Keep your records organized, use the tools available to you like QuickBooks Online, and make collection part of your standard process. January 31st comes around every year, and you will be ready.

Running a successful agricultural operation means staying on top of the details that do not make headlines but matter to your bottom line. Whether it is contractor compliance, equipment tracking, or cash flow management, the best operators plan ahead.