How to actually FILE 1099-NEC forms for contractors my small business paid

Thank you so much! This is already much clearer than anything I've found online. I think I'll try the IRIS portal since we only have 8 contractors to report. Do you know if there's a cost associated with filing through IRIS? And do I need to set up an account way in advance or can I do it now and file right away?

There's no cost to use the IRIS portal - it's free to file directly with the IRS. You can set up an account now and file right away, but don't wait until the last minute as first-time setup might take a little extra time to navigate. You'll need your business EIN and contact information to create the account. Once you're in, you can enter the 1099 information directly or upload a file if you've prepared it in compatible software. Make sure you have all your contractors' correct information (legal name, address, TIN/SSN, and payment amounts) before starting. Setting aside about an hour to get familiar with the system should be plenty for just 8 forms. After submission, you'll receive confirmation that can serve as proof of filing.

Does it handle state filings too? I'm in California and apparently we need to file with the state as well as the feds. Also, can you bulk upload contractor info or do you have to enter each one manually?

I'm a bit skeptical about using third-party services for tax forms. How do you know they're actually submitting everything correctly? I'd hate to find out a year later that something wasn't filed properly and now we're facing penalties.

Yes, it handles state filings including California! That was actually one of my main concerns too since we're also in a state that requires separate filing. The platform automatically routes the forms to both federal and applicable state agencies. Regarding security and accuracy, I was initially concerned too. What convinced me was their confirmation process - you get official filing confirmations directly from the IRS and state tax authorities. You can also download copies of everything submitted for your records, so you have documentation if questions ever come up.

Wait, how does this work? The IRS phone lines are always jammed. Is this just paying someone to sit on hold for you? Or do they have some special line into the IRS? Genuinely curious.

This sounds too good to be true. The IRS is literally unreachable by phone most of the time. I've tried calling dozens of times about a business tax issue and never got through. If this actually works, it would be worth it just for the stress reduction.

It works by using their system to navigate the IRS phone tree and wait on hold for you. When an agent finally picks up, you get a call back immediately and are connected. So yes, they basically handle the hold time for you so you're not stuck with a phone to your ear for hours. They don't have a special line - they're just using technology to solve the hold time problem. When I used it, I got the call back in about 20 minutes and was speaking to someone who could actually help with my 1099 filing questions. Saved me an entire afternoon of listening to hold music.

Do you have a specific organizational system you recommend for keeping track of all these records? I'm filing for the first time and want to set things up right from the beginning.

I create a digital folder for each tax year (e.g., "2024 Tax Filings") with subfolders for each form type. Inside the 1099-NEC folder, I save PDFs of all submitted forms, the confirmation emails, and screenshots of submission confirmations. I also keep a spreadsheet listing each contractor, when their form was submitted, and confirmation numbers. For physical documents, I have a similar system with labeled folders in a fireproof filing cabinet. Everything gets retained for at least 7 years. It might seem like overkill, but the one time the IRS claimed we hadn't filed some forms, I had everything organized and was able to prove we had submitted them within 5 minutes of getting the notice.

We've used TaxBandits for the past two years for about 25 contractors. Overall pretty good experience. The interface is a bit dated but it gets the job done reliably. They handle both federal and state filings, plus distribute forms to recipients. Cost is reasonable too - I think we paid around $2 per form last year.

Thanks for the feedback! That's helpful. The cost seems reasonable for the convenience factor. I'll probably go with them unless I hear any horror stories. My main concern is just making sure everything gets filed correctly since it's my first time handling this.