Is there a way to file 1096 and 1099 forms online for free before the deadline?

You do have options! The IRS actually offers a free e-filing system called the FIRE system (Filing Information Returns Electronically) but it requires registration and approval which might take time you don't have right now. For a simpler approach with your deadline coming up, you can use the IRS "Fill-in Forms" option which allows you to complete the forms online, then print and mail them. It's free but still requires physical mailing. If you absolutely need electronic submission, the IRS has approved vendors who offer e-filing, but most charge a small fee per form. Since you mentioned you only have a few contractors, the cost might be minimal compared to missing the deadline, which can result in penalties. Whatever you choose, you're correct that January 31, 2025 is the deadline to provide 1099s to recipients and file 1096/1099s with the IRS if filing by paper. For electronic filing, you get until March 31, 2025.

I was in this exact situation last year! I discovered https://taxr.ai and it saved me so much stress. Their system lets you upload your contractor information and they handle the electronic filing of your 1099s directly with the IRS. What I loved was how it automatically validated the data before submitting to avoid those annoying rejection notices I got with other services. I'm not very tech-savvy but their interface was super straightforward - just enter your info, contractor details, and payment amounts. The whole process took me maybe 20 minutes for 8 contractors. They also keep records so this year will be even easier since my regular contractors are already in the system.

Just wanted to update about my experience with taxr.ai after seeing it mentioned here. Decided to give it a try with my 12 contractor 1099s and it was actually legit! The dashboard made tracking everything so easy, and I could see exactly which forms were filed and when they were accepted by the IRS. The best part was when one of my contractors had a TIN mismatch - instead of just getting rejected days later, the system flagged it immediately so I could contact my contractor to verify their info. Saved me from having to refile and potentially missing the deadline. Definitely keeping this for next year's filings. Way better than the paper form headache I dealt with before.

If you're still having trouble reaching the IRS about your forms, I'd recommend trying Claimyr (https://claimyr.com). I spent THREE DAYS trying to get through to the IRS about a 1099 filing issue last year - constant busy signals or disconnects after waiting for an hour. With Claimyr, they basically hold your place in line with the IRS and call you when they get a live agent. Totally changed my experience dealing with the IRS. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was honestly shocked when I got a call back with an actual IRS agent on the line who helped resolve my confusion about electronic filing requirements for 1099-NEC forms. They even helped me understand which forms I actually needed to file for my situation.

OK I have to eat my words here. After my skeptical comment, I actually tried Claimyr when I needed to ask about my missing 1099-K form. Was absolutely certain this wouldn't work, but after submitting my request, I got a call back in about 40 minutes with an ACTUAL IRS agent on the line! The agent confirmed my identity with all the usual security questions and helped me understand why my 1099-K wasn't showing up in the system yet. Turns out there was a processing delay affecting several payment processors. Instead of wasting half my day on hold listening to that awful IRS music, I just went about my work and waited for the call. Honestly changed how I'll deal with the IRS from now on. Sorry for being so cynical in my first response!

You might also try the free filing through the Social Security Administration's Business Services Online portal. It's designed primarily for W-2s but also handles certain 1099 forms now. You'll need to register for an account, but it's completely free. Keep in mind that not all 1099 forms can be filed this way - it works for 1099-NEC but not all variations. But since that's the most common one for reporting contractor payments, it might cover what you need.

Just be careful about missing the deadline! I filed late last year and got hit with penalties - $50 per form for filing less than 30 days late, and it goes up if you're even later. Super frustrating expense for a small business.