January 31st is swiftly approaching! If you’ve paid contractors, freelancers, or vendors this year, the 1099 filing deadline should already be on your radar. Don’t panic—but don’t procrastinate either. Here’s your survival checklist for getting it right.
Start NOW: Your Pre-Filing Action Items
Pull your payment records. Review all payments made to non-employees throughout 2025. Look through your accounting software, bank statements, and credit card records. You’re looking for anyone you paid $600 or more for services.
Collect missing W-9 forms. This is the number one mistake that trips up small business owners. You need a completed W-9 from every vendor before you can file their 1099. Missing information means you can’t file, and missing the deadline means penalties. Reach out now to anyone who hasn’t provided one.
Identify which forms you need. Not all vendors get the same form. Understanding which 1099 to use prevents costly filing errors.
Know Your 1099 Forms
1099-NEC is for payments to independent contractors and freelancers totaling $600 or more. This includes your graphic designer, bookkeeper, marketing consultant, or anyone providing services who isn’t your employee. Due January 31st to both the recipient and the IRS.
1099-MISC reports other types of payments like rent ($600+), prizes and awards ($600+), or royalties ($10+). The deadline is February 28th for paper filing or March 31st for electronic filing.
1099-K is issued by payment processors like PayPal, Venmo, or Stripe. For 2025, you’ll receive one if you processed $20,000 and had 200+ transactions through these platforms. Be careful not to double-count this income if you also receive a 1099-NEC from the same client.
1099-INT reports interest income of $10 or more from business accounts or investments.
Who Doesn’t Get a 1099?
This is where many small business owners get confused. Generally, you don’t issue 1099s to corporations (S-Corps or C-Corps). However, attorneys are the major exception—they get a 1099 regardless of their entity structure if you paid them $600 or more.
LLCs can be tricky. Some are taxed as corporations, some aren’t. This is exactly why you need that W-9 form—it tells you how the LLC is taxed and whether a 1099 is required.
The Real Cost of Getting It Wrong
Let’s talk penalties, because they add up fast. If you’re 1-30 days late, it’s $60 per form with a maximum penalty of $232,500 for small businesses. Miss the deadline by 31 days to August 1st? That jumps to $130 per form with a $664,500 maximum. File after August 1st and you’re looking at $330 per form with a $1.3 million cap.
Intentional disregard? That’s $660 per form with no maximum penalty. The IRS doesn’t mess around with this.
Your Action Plan for the Next Two Months
Review your vendor list this week and identify everyone who needs a 1099. Send requests for W-9s immediately to anyone you’re missing. Verify that LLCs and other entities have provided accurate tax classification information. Set up your filing method—if you’re filing 10 or more forms, electronic filing is required. Mark January 31st on your calendar in red ink, and consider having everything ready by mid-January to avoid last-minute chaos.
Don’t Navigate This Alone
Think of 1099 filing as a narrow trail with steep drop-offs on either side—one misstep and you’re dealing with penalties and IRS notices. At Lightening the Load, we help small business owners get their 1099 filing right the first time. We’ll review your vendor payments, identify who needs forms, verify your information, and handle the filing to ensure you meet all deadlines without the stress.
The January 31st deadline isn’t flexible, but your approach to it can be. Start now, and you’ll file with confidence instead of panic.
Let us lighten your load.
