Making sure the 1099 box is checked for Contractors

Steph_with_WAVE — Sun, 21 Sep 2025 06:28:45 GMT

Last year I got a notification that 2 of my workers didn't have the "Contractor" box checked so they would not be receiving 1099s from Square on behalf of my business. After talking to support, I realized the only way to fix this was to send them their 1099s separately and amend the report Square automatically files for me with the IRS.

I'm hoping to double check that the box for "Contractor" didn't mistakenly get unchecked for any of my workers BEFORE 1099s are due to send out - but besides going through every single worker individually, I don't see how I can gather that information.

Running a report it shows I've had 237 people work for me in 2023, so I really don't want to have to go through each one and make sure the dang box is checked when I know I checked it when they signed up for direct deposit.

I've got an email into Support, but figured I'd also ask here - how can I make sure every single one of them will get a 1099 this year?

Thanks!

Re: Making sure the 1099 box is checked for Contractors

JJ_ — Tue, 05 Dec 2023 14:33:00 GMT

This sounds like a good question for our Payroll team, @Steph_with_WAVE

They can take a look at your account with you to help shine a light here, as they can look at your account alongside you to confirm how many employees would qualify for this. Please reach out by phone or email when you have a moment by logging into your Square account and heading here.

P.S. Welcome to the Seller Community ✨

thread Making sure the 1099 box is checked for Contractors in Staff & Payroll

Making sure the 1099 box is checked for Contractors

Re: Making sure the 1099 box is checked for Contractors