Do I have to send a 1099 to my contractor?

That includes the photographer who shot your product photos, the person who built your website, the assistant you paid through Venmo, the cleaner who does your studio. If they did work for your business and you paid them $2,000+ total for the year, they get a form. (The line was $600 for years. It moved to $2,000 for payments made in 2026, so if you're catching up on 2025, the old $600 rule still applies to that year.)

Who doesn't get one: corporations (an LLC taxed as an S corp or C corp, or an actual Inc.), and anyone you paid through a card or payment processor like PayPal Goods & Services or Square. The processor sends those people a 1099-K instead. But cash, check, Zelle, Venmo friends-and-family, and CashApp personal payments all count toward your total and need a 1099 from you.

You need their legal name, address, and SSN or EIN. That's what a W-9 is for. Ask for it before you pay them the first time, because asking in January is when people stop answering.

Miss the deadline and the penalty runs $60 to $340 per form depending on how late. Skip it entirely and it's $680 per form. Not filing is the expensive option.