Your 1099 Deadline Just Got More Urgent and Expensive

Bookkeeping Tips, Podcast Episodes, Tax Strategies

Last updated September 22, 2026

Danielle Hayden beside bold text reading "The IRS Rules Just Changed" on a CEO Numbers Network episode about 1099 and W-9 compliance

A late 1099 doesn't cost what an on time one does, and that gap only grows the longer it sits.

I bring this up every fall for a reason. It's not because compliance is exciting, it's because the fix is easy if you start early and hard if you wait. This year there's an actual change worth knowing about, and a habit worth building alongside it.

Why This Isn't Really About Paperwork

It's tempting to treat 1099s as a task to squeeze in whenever there's time. But the IRS doesn't treat a late filing the same as one filed on time, and the cost of ignoring it only grows the longer it sits. This is a timing problem, plain and simple. Handle it in the fall, and January is just another month. Wait, and you're the one making the panicked call trying to track down information from someone you haven't spoken to in months.

What Actually Changed For 2026

A contractor, for 1099 purposes, is anyone you've paid for services who isn't your employee, someone operating as a sole proprietor or an LLC. What changed this year is the dollar amount that triggers the requirement. For as long as most of us can remember, that threshold sat at $600. For 2026, it jumped to $2,000, covering payments made by cash, check, ACH, personal Venmo, or Zelle. Cross that number with a contractor this year, and the requirement works exactly the way it always has. Stay under it, and you may not need to file at all.

The W-9, And When To Actually Ask For It

A W-9 is the form your contractor, freelancer, or vendor fills out, and it's on you as the business owner to request it. It doesn't go to the IRS. You keep it on file so you can prepare the actual 1099 in January, and it includes the basics: name, business name, address, taxpayer ID or Social Security number, and an email address so the form can be sent electronically instead of by mail.

The best practice is simpler than it sounds: collect the W-9 before any money ever leaves your account for that contractor. Once the relationship has ended, getting that same information back gets harder every month that passes.

You Don't Have To Carry This Alone

None of this has to sit entirely on your plate. Every fall, our team puts together a list of vendors and contractors likely to need a 1099 based on what's actually moved through your books that year, and we send it over for review. Your part is small and it's on purpose: look at the list, confirm it's complete, and start gathering any W-9s you don't already have. Everything after that, the tracking, the filing, the deadline itself, is ours to carry.