Every year, I see the same thing:
Business owners scrambling in January to figure out if they need to issue 1099s—and how to do it without getting hit with penalties.

Here’s the deal:
If you paid an independent contractor, attorney, landlord, or prize recipient $600 or more during the year, you may be required to send them a 1099.

It’s not just “good bookkeeping.” It’s a compliance requirement—and skipping it can cost you.

Let’s break it down.

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🧾 Who Should Receive a 1099?

You may need to issue a 1099 if you paid $600 or more to:

• Independent contractors or freelancers for services (use Form 1099-NEC)
• Attorneys, even if they’re incorporated (use 1099-MISC)
• Landlords (if you rent office or warehouse space – 1099-MISC)
• Anyone you gave a cash prize or award (1099-MISC)

Reminder: You generally don’t need to issue a 1099 to C-Corps, S-Corps, or for purchases of goods—but there are exceptions. Attorneys almost always get one, no matter their business structure.

🔗 IRS guidelines: https://www.irs.gov/forms-pubs/about-form-1099-nec
🔗 W-9 instructions: https://www.irs.gov/forms-pubs/about-form-w-9

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📅 1099 Filing Deadlines

There are two forms most commonly used: 1099-NEC and 1099-MISC.

Here are the deadlines that apply every single year (regardless of the calendar):

✅ January 31

• 1099-NEC must be sent to the recipient and filed with the IRS
• 1099-MISC must be sent to recipients (landlords, prize winners, etc.)

Source: https://www.irs.gov/instructions/i1099msc

✅ February 28

• Paper filing deadline for 1099-MISC with the IRS (if not e-filing)

✅ March 31

• E-file deadline for 1099-MISC with the IRS

These dates don’t shift much, and they repeat annually—so just mark your calendar for the same routine every January.

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✅ How to Make It Easier (No More Last-Minute Scrambling)

You don’t need to DIY this every year. Here’s how to simplify it:

📌 Use payroll or contractor software:

Tools like these will file 1099s for you and send copies to your contractors automatically:

• Gusto – Great if you already run payroll or pay contractors regularly
• Patriot – Budget-friendly and handles both payroll and 1099s
• Yearli – A good standalone 1099 filing tool
• Keeper Tax – For self-employed individuals to track deductions and flag income

📌 Collect W-9s from every vendor before you pay them

Make this part of your vendor onboarding. No W-9 = no payment. Period.

📌 Review your vendor payments regularly

We review transactions per vendor monthly for our 1:1 clients and inform them of missing W-9 information

📌 Pay by Credit Card or Payment Processor? You may not need to issue 1099s for those payments

As if this topic couldn’t be any more confusing, if you pay a vendor using a credit card or payment processor, those payments are not factored into your 1099. This is because the vendor will receive a 1099-K from their payment processor. When we work with our clients, our internal software checks for credit card payments and automatically excludes them from the 1099s.

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TL;DR

• If you paid $600+ for services, rent, prizes, or legal work, you likely need to send a 1099
• 1099-NEC is due to the IRS and contractor by Jan 31
• 1099-MISC is due to the recipient by Jan 31, IRS by Feb 28 (paper) or March 31 (e-file)
• Use tools like Gusto or Patriot to automate the process
• Collect W-9s early—don’t wait until it’s a fire drill
• Track payments made via credit card and by check or cash to ensure 1099 accuracy.

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Still unsure if you owe a 1099—or want a system that keeps you in compliance year after year? We walk through this inside Financial Foundations Accelerator, or you can reach out for 1:1 support if you’re managing a high volume of payments and ready to delegate this.

You didn’t start your business to become a tax admin. Let’s make this easy and done—correctly.